EVERY SPOKEN WORD
90 min read · 17,765 words- 0:00 – 6:15
Why job searching feels awful—and why you shouldn’t do it solo
- AGAakash Gupta
Why should you never search for a job alone?
- PTPhyl Terry
Job searching sucks. It really sucks, especially right now in this tough economy. And we're gonna give you the tools to find the best job you can find today and set yourself up to succeed, and a bunch of tactics. I really wish people would do this. Do not send me cold introductions. If you send me a cold introduction, it is a person I do not want to speak to. We all hate networking, right? I, I do too, by the way. I want you to negotiate the things that will set you up to succeed, to deliver on the OKRs that you have discussed already. Okay? One SaaS company had about $10 million in technical debt and the other had $20 million.
- AGAakash Gupta
Because there was such a greater demand for PMs in New York City-
- PTPhyl Terry
Yes, product management isn't for everyone. It's a great... I love it, but it's not for everyone. And by the way, if anyone listening is a recruiter, we need more recruiters.
- AGAakash Gupta
The number one book that they bring up that has helped them is Never Search Alone. So we have Phyl Terry. Phyl Terry has helped over 30,000 job seekers get jobs. If you've ever been interested in how to handle the emotional and tactical aspects of a job search, if you wanna learn more about Phyl's bestselling book, Never Search Alone, if you wanna learn more about candidate market fit or even negotiation and how to negotiate so that you succeed in a role, this episode is for you. Really quickly, I think a crazy stat is that more than 50% of you listening are not subscribed. If you can subscribe on YouTube, follow on Apple or Spotify podcasts, my commitment to you is that we'll continue to make this content better and better. And now on to today's episode. I talk to job seekers every day, and the number one book that they bring up that has helped them is Never Search Alone. So we have Phyl Terry here today. It's an honor. Thank you so much.
- PTPhyl Terry
Glad to be here. Thank you for inviting me.
- AGAakash Gupta
So I really wanna start with the title itself, Never Search Alone.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
Why should you never search for a job alone?
- PTPhyl Terry
Yeah. So let me answer that by saying, and I'll, I'll come right back to it. There's three big ideas in the book, right? The first is the title, Never Search Alone. I'll answer your question. The second is candidate market fit, which of course resonates really strongly in the product community where both of us come from. And then third is what I call, uh, w- playing to win-win, how you negotiate, how you interview. Um, in terms of the title, why should you never search alone? Here's the surprising thing, Aakash, and many people don't believe me when I'm, when I say what I'm about to say, and then they get into a job search council, which is what I propose, and we'll talk about that in a moment, and they experience it, and it kind of blows them away. No matter how smart you are, Aakash, no matter how fantastic your resume might be, maybe you were the VP of Product at Google, right? Maybe you were the chief product officer who built, you know, so, uh, uh, some great AI application or are doing that today. No matter who you... Maybe you are CEO of a publicly traded company. No matter how smart and experienced you are, when you are in the job search, you feel anxious, nervous, and insecure, and everyone feels this way [laughs] . And, and people don't believe me. They think, "Oh, it's only me who feels this way," you know? "If I were X, I wouldn't feel this way." Well, as you know, Aakash, I started running product councils in, in '03, so quick background. You know, was involved in the early internet, was a part of the first company that Amazon bought, then built a company called Creative Good. We were leaders in customer experience and product management. We were so early that Marty Cagan was one of our clients, by the way. [laughs] This is how I know Marty, going back 25 years, whatever. And when I started the councils, you know, I brought, you know, Google and Amazon and all these folks together. Now I've had 2,500 senior leaders go through this program from every company in Silicon Valley. And every single one of them, okay, when they get into that next phase of either leaving the job, they've left the job, or they're thinking about leaving, they feel that insecurity and anxiety that everyone feels. It is the sort of the great leveler, and the only thing that I have found that addresses that is if you put people together in a support group, what I call a job search council, and you ask them to be open and vulnerable with each other, right? So that they actually share, "Oh, I'm feeling anxious." [laughs] And when you're sitting around the room, you know... So you know, one, one of, um... We did a, we do these LinkedIn Lives every couple weeks with job seekers, and one of the ones we did last year was prominent guy at Google who left and, uh, ended up taking a job, uh, at Capital One. Great guy. Uh, and he, you know, when he got into that job search council, it was the same for him, everybody else. You open, you're like, "Oh, I'm feeling insecure." Like, you hear that around the room and you're like, "Oh my God, okay. I'm not alone." And it actually flips the experience emotionally from insecurity and anxiety and fear to hope and motivation, accountability and confidence. These are the four things you really need in a good job search. And on the other hand, if you're feeling that anxiety that everyone feels, it can really undermine your search. It can undermine how you show up in interviews. It can undermine what you think you're qualified for. It can, you know, it can take you in all kinds of directions that don't actually help you get to that next stage.So, you know, it's, it's kind of crazy. I feel bad that it took me so long to sort of figure this out. [laughs] Like, this is clearly what we should've been doing in the job search for a very long time. I'm glad we're doing it now.
- 6:15 – 8:32
What a Job Search Council is (and Aakash’s real-world results using one)
- AGAakash Gupta
Yeah. I actually used the book hooks you up with a matching service, which you can apply for and get a job search counsel. So I used one of those actually-
- PTPhyl Terry
Wow
- AGAakash Gupta
... in measles in a successful job search. So-
- PTPhyl Terry
Wow.
- AGAakash Gupta
Yeah. Well-
- PTPhyl Terry
Well, there you are. You're a walkie-talkie testimonial. So what was that experience like?
- AGAakash Gupta
Yeah. So one of the coolest things is, like, the people who I was matched up with, they weren't exactly going for VP of Product at a unicorn, but they had very similar life circumstances.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
One was a really senior technical program manager caught up in the layoffs at Meta.
- PTPhyl Terry
Oh.
- AGAakash Gupta
Another one had been a sales engineer at a whole bunch of really high-profile companies-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... now is working at Databricks, you know, one of the hottest-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... companies out there. Like, all of us ended up landing really awesome jobs.
- PTPhyl Terry
Wow.
- AGAakash Gupta
And the cool thing was meeting weekly, tracking progress, seeing techniques that were working for one person that-
- PTPhyl Terry
Yes
- AGAakash Gupta
... potentially applying to me.
- PTPhyl Terry
Right.
- AGAakash Gupta
Yeah.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
And so there was so much sharing that was happening, but as you emphasized, a lot of it is the mental part as well.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
Because when you go into that job search, you're feeling so anxious [laughs] and you're not... You don't have a... There's never been a course, right, that we took. We didn't take a college course, job searching 101.
- PTPhyl Terry
No- nobody teaches us this, no.
- AGAakash Gupta
Yeah.
- PTPhyl Terry
No one said, "Aakash, listen, you're really smart. You're really capable." It's so helpful for your audience to hear that you felt that anxiety too, right?
- AGAakash Gupta
Exactly. I mean, I was just even worried to... At the beginning, one of the things the counselor helped me do is just advocate for myself and speak up for how much experience I did have. I did have 15 years of PM experience. You know, sometimes you're even scared to put that label on yourself.
- PTPhyl Terry
Right.
- 8:32 – 12:08
The free matching program, volunteers, and the cultural mission
- PTPhyl Terry
You've really, uh, done a great job. A lot of people respect you, deservedly so. So even Aakash, folks, you see what we're talking about? People... Someone, someone as smart and qualified, who understands product as well as you do, you were, you were reluctant to sort of step forward in a certain way, right? And your counsel helped you do that. I'm so thrilled to hear that. So you mentioned, so just so your audience knows, we run a free program that's volunteer-driven, where if you go to phyl.org, that's Phyl with a Y, you can sign up, and we will match you. And, uh, and then you will go through this experience together like you did. And we have met... We have put together now almost 4,000 of these, Aakash, of these job search counsels. More than 100,000 hours of volunteer time have gone into building this. And people say to me, "Why aren't you charging?" And it's not like I'm against charging. You know, I charge for other things, whatever, and I've, uh, I've made some money. But it's, um, we're really looking to drive a cultural impact here, Aakash. We want this to be big. We want this to be as ubiquitous as something like AA is, right? Like, this becomes the standard way to look for a job. And, uh, you know, the, the, the volunteers have been amazing. I mean, people are putting in thousands of hours to help make this work. And, uh, and, uh, you know, the product community has really taken this on. Marty Cagan wrote a lovely forward for me. And, um, it's just, it's just been great to see the product world, uh, you know, take this on and embrace it. And what I... And people... Sometimes people say, "Is this only for product people?" No, no, it's certainly for product people. They understand it the best because of the methodology. But it's, it's kind of like what I like to tell people, this is, this is what the product community has done to reinvent the job search, right? This is... We- we've taken the product mindset to reima- and then we're giving it to the world. And I've, I really hope that we can help many, many people.
- AGAakash Gupta
Hey, let me take a quick break to talk about something that's completely changed my product management workflow, Linear. As a PM, I was drowning in tools, one for planning, another for issue tracking, roadmaps and sheets, and jumping between Slack, Intercom, and app reviews just to piece together customer feedback. Sound familiar? I was spending more time keeping systems in sync than actually building product. Every time development kicked off, my carefully crafted plans would immediately need updating. I was the human API between all our teams, constantly chasing updates and translating between tools. That's why I love Linear. I can capture customer feedback, shape product ideas collaboratively, quarterback cross-functional teams, and monitor development progress in one place. It cuts through the maze of disconnected systems that were complicating my life. Product teams at OpenAI, Vercel, Brex, and Cash App all use Linear. If you're tired of spending your days keeping different tools and teams in sync, check out Linear at linear.app/partners/aakash. That's linear.app/partners/aakash. Today's episode is brought to you by Maven. The problem with most courses online, like Udemy, is there's no live component, and the instructors aren't experts in their fields, they're professors. At Maven, you get direct live access to experts and operators from the world's best tech companies. You can't get that access anywhere else, in any university, and you usually can't find them on YouTube either. I've featured so many of Maven's experts in the newsletter and podcast for that reason. To help you out, I've put together a collection of courses I recommend at maven.com/x/aakash. This includes courses like AI Prototyping for PMs-Product sense for PMs and getting an AI PM certification. Visit it
- 12:08 – 15:15
Why small groups work: belonging, motivation, and accountability
- AGAakash Gupta
now at maven.com/x/aakash. Yeah. The roles that it helps is definitely not just product management. As I mentioned, there were program managers, engineers, sales. It can really apply broadly, but it is the core product skill set. Even the job search council itself, I think it kind of replicates the product trio that we're used to or the product team meeting. You have a designer, you have an engineer, you have a PM. Everybody's talking about how we solve the same problem, and it's, it's part of the way probably humans were brought up. We like to, to discuss our problems across-
- PTPhyl Terry
That's right
- AGAakash Gupta
... the campfire. [laughs]
- PTPhyl Terry
So that's exactly right. And, and as you know, in the b- there's a Stanford psychologist named Irvin Yalom, who I quote in the book, and, uh, he's done a lot of work on why small groups are so powerful. And he talks about, yeah, he thinks it's baked into our DNA from thousands of years. Uh, you know, we were w- as a species, we grew up in small groups, and it, it creates this motivation and, and sense of belonging that is just really, really powerful. We're tapping into some sacred impulses here that we didn't create. We're just trying to create the environment that makes that possible for the, for the insecure job seeker, which everyone is, to, to do something different. Now, you laid out, hey, there's ... We provide a whole ... We provide all this structure, right? You know, all these agendas. We've got this methodology for candidate-market fit, which we'll talk about in a moment, methodology for networking and also for interviewing and negotiating, all of which, you know, is really important. But the core is, hey, let's get these folks together into, into a support group and have them meet weekly or even twice a week if they like. And these have been ... These are going on all over the world. And just to the point of, you know, it's not, not just product. It's also, like, a, a woman who was the CEO of a major financial institution in Europe joined a job search council. Like, you know, [laughs] we're talking about somebody who is making a salary of $20, $30 million probably, right? And, uh, and so this is the whole gamut. And she just wrote to me. She's just got a great new CEO job, and she loved her council, and they're all gonna stay in touch, you know. Uh, one of the side benefits, Aakash, I don't know if you saw this, is, is friendships, right? You, you build a friendship with these folks, and that's such an important part. Did, d- have you stayed in touch at all with the folks you were part of or how-
- AGAakash Gupta
The two of the five who are, like, regularly attending every week, we're ... So three of us basically are regularly, uh, in touch. And I think that the magical part of it is that, uh, that's exactly what we're lacking in this era. [laughs] As we become increasingly more just being working from our desk, working in front of a laptop, we've actually been s- trading off and sacrificing those relationships. And it's f- it sounds kinda soft, I think, when you're going into, "This is how you get a job. You control your emotions." But actually I think it's, it's one of the most powerful insights once you really put your mind around it.
- 15:15 – 16:46
Candidate–market fit: treating your career like product-market fit
- PTPhyl Terry
Yeah. Cool. You wanna talk about candidate-market fit?
- AGAakash Gupta
Yeah. This is my second favorite concept. I just recently wrote an entire newsletter ar-
- PTPhyl Terry
I know. You did
- AGAakash Gupta
... about-
- PTPhyl Terry
By the way, you asked me about ... Do you wanna show your visual? 'Cause I think you put together a great visual on it, didn't you?
- AGAakash Gupta
Yeah, I did put together some visuals. Let's pull those up. So this is my take on your concept of candidate-market fit here. [laughs]
- PTPhyl Terry
I lo- I l- I love your dictionary pronunciation piece there, by the way. That was great.
- AGAakash Gupta
[laughs]
- PTPhyl Terry
Uh, it's nice. Yeah, and that's what we're looking for is that intersection, uh, between candidate and market. And, you know, it's ... Aakash, how c- how ... You know, if you ... Not your book, but ... 'Cause I know you also have a book that you've written, uh, which is terrific. Um, but many career books, they act as if there's no market, as if it's just you, the candidate, and what do you want, and let's do some self-reflection. You know, it's like, it's the same mistake of building products without any understanding of the customer or the market that you're putting them out in, right? It's insane. How did we do that for so long, right? [laughs] Now, I do want you to understand what you want, and that is radical for many, many people, that they don't even take the time to think about what they want, right? Let- let's, let's talk about, you know, the equivalent of the waterfall me- meth- in, in, in other words, the conventional way, in this case, of looking for a job versus building a product, and that's spray and pray. Just
- 16:46 – 25:06
The Mnookin Two-Pager + Listening Tour: discovery before execution
- PTPhyl Terry
you quickly get out and just send your thing out, your, your, your LinkedIn or your resume out to as many people as possible. It's a terrible way to go, right? It'd be like, you know, creating a product blind and just throwing it in the marketplace and seeing if it lands somewhere, right? We would never do that. Well, why would you do that here? You know, so, so first of all, think about what you want. And we have this tool. We call it the Mnookin Two-Pager. It's a f- named after my dear friend Alison Mnookin. She was a longtime collaborative game product council member. She came up through Intuit and then eventually ran one of their divisions, spun it out, and became the CEO of an independent company. And then now today she sold that, and she's at, uh, Harvard Business School on the faculty. She's absolutely terrific. But about 15 years ago when she was at a crossroads and thinking about her career, we sat down and created what it- we now call the Mnookin Two-Pager, which is just a really simple tool of saying, "What do you like? What don't you like?" And in fact, we start with what don't you like and e- and even what do you hate? [laughs] 'Cause that's always easier for people to access than what it is that they want. And then we go to what do you want and, you know, how are you thinking? And it's a draft. Doesn't have to be perfect. Some people go overboard, and they make it so perfect and whatever. No, no. It's, it's a talking point. And we'll come back to your, to, to your diagram in a moment. And, um, it's a talking point because what I really want you to doIs, you know, I want you to do some discovery.
- AGAakash Gupta
[laughs]
- PTPhyl Terry
What I call a listening tour, right? I want you to go out and talk to people and get their point of view on you, your skills and experience, and on the market, right? And where there might be a fit. And, uh, Aakash, a number of people, they get very nervous about doing this, like, "Oh, no, what are people gonna tell me?" But there's a lot of love out there, and you do this thoughtfully, you get... It's, it's so powerful. Did, did you do that? Did you go out and do a listening tour?
- AGAakash Gupta
Yeah. It was at... So the greatest thing, right, is the job search council kind of facilitates this, 'cause there's the lead person who also kept us ours. He was very good at keeping us accountable-
- PTPhyl Terry
Sure
- AGAakash Gupta
... making sure we knew exactly what we needed to do-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... on any given week. And so I thought this, to me, for people who don't understand the concept, is, you know, I know you do 360 review feedback, but let's be honest, right? We're all political in those. We generally wanna be nice to our friends.
- PTPhyl Terry
Right.
- AGAakash Gupta
We're not actually getting the real feedback. So after your... As you start your job search, you go and ask people y- these questions, like, "What am I good at? What did I do really well? When did you see me really energetic and happy at work?" And-
- PTPhyl Terry
Right
- AGAakash Gupta
... they're, they have a perspective on you that you don't even have. It's gonna open your mind-
- PTPhyl Terry
Right
- AGAakash Gupta
... to think bigger about, oh, you know, maybe I have done X for my entire career, but now I have an opportunity to evaluate.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
Is that exactly what gives me joy? And I saw people in my group say, "Okay, I've been X title, now I'm gonna shift to Y." And that's how you make these pos- decisions, is through that reflection.
- PTPhyl Terry
And get that input. Like, I just, I got this great email recently, and look, it's, it is challenging out there in tech world, it has been for a couple of years, and, uh, and product management is going through some changes, as you know. And, uh, this, this person wrote to me, they're on job search council, and they had this epiphany through their listening tour that they're really not a product manager, that they really need to go in a different direction. And I thought that was terrific. It's... Product management isn't for everyone. It's a great... I love it, but it's not for everyone, and it's really important to figure out what is it that you wanna do and, and what you're, and what you're a good fit for, right? And, um, I, I consider that a win. Like, they would have spun their wheels for maybe a year and a half trying to get product roles, maybe not getting them. Maybe even worse, they got one, but they were unhappy and it didn't work out, and then they lost that job, and you know what I mean? We've seen people go on that treadmill. It's really tough. So we want you to go out there, want you to think about what you want, for sure, and then, like you said, go out and talk to people you worked with before. I call those reverse exit interviews, [laughs] just as you described. But also people in your broader network, and even recruiters. Now, people don't often realize recruiters have great insight about candidate-market fit, but we don't often ask them, right? We just say, "Hey, get me a job. Can you get me a j- I want this job. Why can't you get me this job?" Instead, "What do you think I'm a fit for?" And if... It's so important, and now I will tell you, many of your audience, 'cause many people in the world, not just in your audience, may not have preexisting recruiter relationships, Aakash, and this is a challenge. So after we launched the free community, actually one of my collaborative game council members, a chief product officer, volunteered to set up and run a recruiter network. So we now have recruiters who volunteer to help people who are in job search councils do those recruiter interviews, right? If they don't-
- AGAakash Gupta
Mm-hmm
- PTPhyl Terry
... have those recruiter relationships already. And by the way, if anyone listening is a recruiter, we need more recruiters. Please go to phyl.org or get in touch with me over LinkedIn. We'd love to have you join and volunteer and help these candidates. And you also mentioned, I'll just switch gears, you mentioned there's a moderator or lead for the job search council who kind of... They're a, they're a job seeker. They volunteer to do that role. If anyone in your audience is gonna sign up for a job search council, and all of you are welcome, now or at any point in your career, please be a moderator. We need more moderators. It's actually the thing, it's the limiting factor. It's what... If we had more moderators, we could launch more councils more quickly. We're always working to... And it's not a hard job. It's, it's, it's, we give you a lot of support, and it's a great experience. You don't have to have any background in moderating, facilitating, or in this method to do it. So I just wanted to, I wanted to put that plug out there. But, um, [laughs] in terms of candidate-market fit, do you wanna throw that, throw that slide back up again?
- AGAakash Gupta
Yeah.
- PTPhyl Terry
Thank you, and I appreciate you putting this together.
- AGAakash Gupta
Of course.
- PTPhyl Terry
Maybe in a future copy of the book I'll, I'll put it in and credit you, uh, with that if you, uh, if you're open to that. Um-
- AGAakash Gupta
Definitely.
- PTPhyl Terry
So I love this. So it's really that intersection, right? There's a marketplace, so what do you want, but what does the market want, and what does the market see you as a fit for today? And I just wanna pause, Aakash, and say we all contain multitudes. We all have all kinds of skills, right? That's not the question. The question is, what does the market see you as credible for? So I always have people say to me, you know, "I could be a VP of product." And I say, "I, I'm sure you could be a VP of product, but if the market is telling you that today..." And this is important, because Aakash, let's be clear, three years ago, okay, if you were a director or senior director of product, you could get a VP of Product role pretty easily. There was a ton of hiring happening. Everyone, from Meta and Google to the smaller firms, everybody was hiring. And so that in- that sort of inflated candidate-market fit for a lot of people, which is amazing. In a down market, though, it deflates candidate-market fit. It has nothing to do with you, right? Now, if today you're a director or senior director of product, depending on your skills and experience, depending on your background, the brands you've worked with, the kinds of case studies you can talk to, et cetera-You may not be able to get a director role. You may have to look at a senior manager role. You may even have to look at an IC role, right? Again, this is not an in- indictment of you or your skills. This is a reflection of supply and demand marketplace, right? And that's the other thing that's... I, I think people tell me that they love about candidate market fit, there's almost a therapeutic quality to it in the sense of, oh, you know, 'cause i- otherwise, we always feel like if we're... if people don't want us for this job or that job, that it's some terrible thing about us. No, no, it has nothing to do with you in the sense that, uh, you know, the market conditions, you need to factor that in and understand it and see how, see how you're playing for this market today, right? So...
- 25:06 – 40:39
Market realities: location, AI-era reinvention, and “stale” candidate fit
- AGAakash Gupta
It's so powerful. So I was talking to somebody who, she had moved from Florida to Philadelphia.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
So she understood that market mattered, and yet she wasn't getting PM interviews.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
So we said, "Okay, you know what? You're gonna move again. You're gonna move to New York City." And I kid you not, one month later she was employed because there was such a greater demand for PMs in New York City-
- PTPhyl Terry
Yes
- AGAakash Gupta
... than Philadelphia or Florida.
- PTPhyl Terry
Right.
- AGAakash Gupta
And so where you are matters, and I think that in 2025, unfortunately, most PM jobs, most jobs these days, they're looking for hybrid. So they care about that address that you're at. There's some lucky few remote jobs out there, and go figure if you can, although they're hyper-competitive. But these hybrid jobs, they care about that address. And so thinking about, what is my market [laughs] and how am I judged in this market? Because how she's judged in New York City is actually probably different than San Francisco, too. San Francisco, it's way easier to go up a level because there's crazy demand and not many people wanna live in that high cost of living. New York, actually, everybody wants to live there, so it's a little bit harder. It's-
- PTPhyl Terry
It's hard. It's harder-
- AGAakash Gupta
Really hard
- PTPhyl Terry
... to market than San Francisco, but better than Philadelphia, and I'm, I'm really glad that you brought this up. So we're talking about the market in general, but we also have to keep in mind that local market, right? Not just the market, but the market that you're in today. And if you're in San Francisco, by the way, it is a better market, but you better have some AI skills. Like, you know. So I will give you an example, and I ta- So we had a guy go through Never Search Alone. You know, this is somebody who'd been a PM for, for, you know, 15-plus years, right? Had been a VP of Product, had been in e-commerce companies, um, and you know, 15 years ago was right on the cutting edge, but frankly got complacent. And one of the most difficult things about living in a capitalist system is this thing called creative destruction, right? It's this economic concept. Now, it's the reason the PM role exists, by the way [laughs] . It's because creative destruction is the thing that creates the conditions for new products and services to emerge and old things to go away, right? It's literally our job, in a way. At the same time, though, you could be a good PM in a particular era, and if you don't keep reinventing yourself, which is hard to do, Aakash. It's not like... You know, especially if you rise up and you get into a more senior level, you know. It's like, "Okay, I'm a VP now. I'm busy. I'm busy at home. I'm busy at work," whatever. And he just did not keep that reinvention happening. So now he looks like an e-commerce, like, 1.0-type guy and has a terrible candidate market fit for the world that we're in today. And, uh, you know, my heart goes out to him. And so what do you do in a situation like that? Well, you do everything you can do, right? You take classes. You know, you, you see if you can advise startups at no cost and get some connection. You know, build an app yourself or get together with some friends and build an app. Who cares if it goes anywhere? But give yourself some experience with gen AI or at least machine learning, you know, and have some way to talk about that, right? And so you have to keep reinventing, otherwise your candidate market fit goes stale. And it's a hard message. I, I, you know, I wish... In a way, I wish it weren't true. On the other hand, it's what makes our economy dynamic and it's why we have Silicon Valley and the jobs, most of the jobs we have today. By the way, let's, let's be clear, all the PM jobs today in the world that we talk about PM, not like, you know, brand product management for Frito-Lay or something like that, but software tech product management. These jobs did not exist 25 years ago. Every single one of them, right? So what's gonna exist 25 years from now that doesn't exist today, and are you going to keep reinventing yourself? I'm pretty sure, by the way, PM will be there, but it's gonna, it's gonna continue, it's gonna continue to look different, and you have to, you have to keep your eyes open on that. It's tough. It's tough. And that's also why you need... You need a support group and a job search counsel, but it's also why you need a support group in the job. So my next book, which people are like, "When is it coming out?" It's like, I don't know, a year or two away. It's like, it, it's basically the follow-on. It's I helped you get a job the last book. Uh, the next book I'm gonna help you keep that job [laughs] and reinvent yourself, you know, for this world of AI that we're moving into.
- AGAakash Gupta
One of the most powerful things I find about candidate market fit that you mentioned was the story of the guy who decided he wasn't gonna be a PM anymore.
- PTPhyl Terry
Yeah.
- AGAakash Gupta
If you're getting a signal from the universe-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... that, hey, I've been laid off from my last three jobs, it's now an opportunity to kind of look back and say, "Was, were those jobs a fit for me?" Today's episode is brought to you by Amplitude. Building great digital products is hard. You know that better than anyone. Getting teams aligned, measuring what matters, and scaling your product strategy isn't easy. But what if you had a clear framework to guide your next steps? That's exactly what Amplitude built. They studied the best product teams to understand what really drives impact.And turn those insights into the Digital Experience Maturity Assessment. In two minutes, you'll be able to see where your team stands and what you can improve to build better products faster. Click the link in the caption to take the free assessment and get a clear path to product growth
- PTPhyl Terry
That's right. And this, and this... So, you know, what he discovered is that, you know, he, the market didn't see him as a credible PM, but guess what? He also didn't love it. He didn't love it. He didn't ha- He, he almost, he- I don't know, he had this idea that he should want that job, right? And I get it. It's a g- I love PM. It's a great job, but it's not for everyone, right? There's a lot of people for whom this is not the right job, and for him, it was, like, a huge relief, Aakash. It's like, oh, like, just being honest. "Okay, this, this ain't for me, but there is something else for me, and let me go find that." Or one of the stories I tell in the book... So, you know, there's so many different stories, but... So, a woman, she was a, she was a chief data officer at a large company, and she wanted a CTO role, okay? And she went out there, and she did it on her own. She spun her wheels for, like, a year. Nothing was happening. We talked, and I said, you know, "Get, get thee to a job search council and figure out your candidate market fit." So she did that, and she went and she spoke to a recruiter, and it was like, bingo. The recruiter said, "Look, you are not a fit for the conventional CTO role, which is what you've been looking at. But there are new CTO roles that are emerging that are data-centric CTO roles. Holy hell, are you a great fit for that." She's like, "What?" You know, she didn't even realize that, right? And so then she, she did everything... And this is what I say in the book. Once you figure out that candidate market fit, and we're, we're gonna talk about this more, because it's the narrower and the more specific, the better, right? We're PMs. We know that about product market fit, right, Aakash? [laughs] You... Don't tell me your product market fit is everything, right? Give me that very focused fit. Well, the same is true here. So she figured out she was a great fit for a regional bank that wanted that data-centric CTO role. So she tuned her, her LinkedIn to that, her resume, the whole thing, and I sw- I swear, three weeks later, had three serious offers and then two that fully came through and she could choose between, after a year of spinning her wheels because she wasn't thinking about the fit correctly and she was just kind of broadly looking at CTO roles. When we talk about candidate market fit, there's a really important piece of human psychology, Aakash, that I want your listeners to understand, which is that we humans can be expansive. Meaning, if I give you a really clear, specific fit, I'm looking for a data-centric CTO role in a regional bank, right? So it's specific to the financial services industry, but not just anything, a bank. And not just any bank, a regional bank. And not just any CTO role, but a data-centric one, right? So you can see how clear and specific that is. Well, we humans, we can be expansive. We hear that... First of all, we can remember it, which is a really important point. But also, we can... Like, if we hear of something, oh, a data-centric CTO role, uh, in a healthcare company, that's not financial services, but it's regulated me- And they'll think of you for that. On the other hand, if you say, "Hey, I'm looking for any kind of CTO role," no, no one's gonna think of you because we can't be reductive. We can be expansive from a narrow-focused thing that we'll remember and is clear, but we can't be... We can be expansive from that, but we can't be reductive from a general statement. Another way that I say it is you can catch a job not with a net, jobs flow through a net, but with a spear, with a really clear focus, right? This is hard for people. It is counterintuitive, Aakash. When you're in that job search and you're, like, feeling that nerves, and you're like, you know, you're aware of you need to put food on the table, let's say. You're like, "Oh, gosh, if, if I'm clear and narrow, then I'm gonna lose a lot of opportunities." It's, it's, it's actually the opposite. Recruiters love this, by the way. There's... Recruiters love Never Search Alone in general, but they love this because many people show up at a recruiter not having done this work, which means the recruiter has to do that work. And in many cases, they'll just skip over you, especially in a down market. If you haven't done this work to figure out your candidate market fit, you're making life hard on the recruiter and the potential hiring manager. This is about making it easy for them. You don't wanna have to make them think. Do you remember that book from 20 years ago, Don't Make Me Think? It was a great book early on in the web days. [laughs] Uh-
- AGAakash Gupta
Yeah
- PTPhyl Terry
... that's the same thing here. Don't make your hiring manager, your recruiter partners think. Make it crystal clear, "I'm looking for a PM role, and specifically a director of, of product management in a healthcare, health tech company, Series B." Okay? All right. Look, does that... Then people will remember. Your whole network will remember. You turn your network into what we call listening posts 'cause they're gonna remember. And then if anything that sounds like that comes along, they'll think of you, right? And the recruiters, if they're looking for that kind of role, you are gonna just really stand out. And we, we have this story w- uh, on our, um, on our website, th- this A/B test. So we had a chief product officer, Aakash, who went through the Job Search Council methodology and, and candidate market fit approach. But then, you know, sort of, like, let it be broad, right? Didn't get anything, and then, you know, and then he was like, "Okay, I have to, I have to really do this. Okay, this, this feels so counterintuitive." Got very narrow. Boom, got a jobYou know, and in a down market, you need to find ways to stand out. If you've done the homework, if you're clear and you have that candidate market fit, boy, you are gonna fast-track your way to, uh, an offer.
- AGAakash Gupta
I think the point about expansiveness is the one that holds people back the most because they w- they see all these job descriptions popping up on their LinkedIn and they say, "Well, if I narrow down to Series B, the Series C company just opened up." And it's not that saying you're targeted on Series B is all of a sudden gonna disqualify for you from Series C. They also understand that those are similar stages.
- PTPhyl Terry
They know how to do that, right
- AGAakash Gupta
It matters.
- PTPhyl Terry
They're gonna look at you and say, "Oh my gosh, you're a near-perfect fit. You want Series B, you're probably gonna be open to Series C, like it's not that different." Now, if you, if you say Series B, what is true is that, you know, UnitedHealthcare is probably not gonna look at you. But, you know, we have to make those choices. Like are you... Do you really wanna go work for UnitedHealthcare if you wanna be in a Series B startup? Probably not. That, that, that place will drive you totally nuts. Now, if you said to me, "Phil, that's where the jobs are, and I've done my work and people seem incredible for that," okay, then that's your candidate market fit. Let's be clear, right? I'm not, I'm not s- I'm not... This is... We are just giving examples here. But the point is that narrow in on where you are the strongest. That's the other point that's important. You wanna be going... People say to me all the time, "Oh, I'll just go do a bunch of interviews." Well, I cannot tell you how demoralizing it is to do, quote, a bunch of interviews and not get very far. Or even worse, get to the finalist role and get a silver medal. We talk about silver medals all the time. In the Olympics they're great. In the job search they're terrible. They're actually worse than if you don't get an interview because you got close. And so many people will come to us, they're like, "I got three silver medals in a row." Okay, something's going on with your candidate market fit. We have to-
- AGAakash Gupta
That's exactly how I react too. When they tell me like, "Three second ca-" I'm like, well, that means that you're interviewing okay, right? It means that-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... your fit though for the role based on the experiences they perceive you as, and that's probably the other, I think, mental hiccup that people have, and I had too as I shared is, you have to look at your past experiences and understand how the market is gonna read them.
- PTPhyl Terry
That's right. And again, you might have skills that your past experiences don't make clear, but if the market doesn't see that, it's not going to record it, right? So, you know, this is all, like, again, we all contain multitudes. We all likely can do jobs that our resumes and LinkedIn don't suggest we can do. But in a tough market like this, boy, that's... You, you've gotta get narrow and focused, right? Now, if it's a great market, you can be a little bit more, but even there it's important, you know? I mean, uh, people always ask me, is, uh, uh... People come up with all kinds of things, Aakash. They're like, "Oh, this is only for senior people." Junior people tell me that. Or senior people say, "Oh, this is only for junior people." Or, "This is only for great job markets," or, "This is only for bad job markets." [laughs] I have been running this program for 20 years. I've been testing it, testing it, and testing it in up markets, in down markets, during the great financial crisis and the dot-com crash, you know, during the boom in the mid-2010s, during the pandemic, you know, and now. It works. Like, you know, you wouldn't say to someone, imagine you're... Which- what PM would say, "Oh, product market fit only works in this kind of market"? No, I think we all agree that product market fit is basic, gonna be thing that we need to figure out whatever market we're operating in, right? Though that's not a temporary or, or partial principle. And it's the same thing here. Because again, just to make it super simple, you're the product. You're the product.
- 40:39 – 1:31:47
Signals your candidate-market fit is off: no interviews, no inbound, silver medals
- AGAakash Gupta
Yes, 100%. So we talked about that one indicator, you're getting silver medals. If we wanna pull up my article, the other two indicators I had said were you are not getting interviews-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... or you're not getting inbound. Can you talk a little bit about how important-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... those channels are?
- PTPhyl Terry
Well, certainly. I mean, if you're not getting any interviews at all, generally speaking, there's, you know, there's something going on with your candidate market fit. Usually it's gonna be too loose, too broad. You don't seem like a fit. Maybe, and maybe, I don't know, maybe you haven't paid attention to your LinkedIn, or maybe you're simply doing the spray and pray approach where you're just sending it out to 1,000 companies, which is only gonna irritate you and really demoralize you. It, it... The one benefit of spray and pray is it feels like you're doing something. [laughs]
- AGAakash Gupta
Like washing the dishes. You actually have a sense of accomplishment after.
- PTPhyl Terry
Right. I did something. And, and by the way, there's an important adjacent topic here, Aakash, which is if you're, if you have a partner or spouse, it looks to them like you're doing something. Whereas if you start Never Search Alone, and you're kind of thinking about your two-pager, and then you're having listening tour... And by the way, we're talking about a couple weeks of work here. We're not talking about, you know, a 10-month study. This, th- th- this is all about... A- and, and our data shows that people who go through our program actually get jobs faster than the national average, okay? It's going slow at first to go fast later. 'Cause again, like that woman who spun her wheels for a year and then got her candidate market fit, and bam, that's what we see happen. So they're spinning wheels here, they're spraying and praying, or they're not thinking about... They haven't done any work on their candidate market fit. They're sending their stuff out to companies where they have no, uh, credibility or, again, their materials don't reflect that because they haven't, you know, they haven't thought that through. Or they're, they're aiming for jobs that are just really, you know, they're a director of product and they're trying to get that chief product officer or VP of Product role in a down marketWhere it's gonna be tough to compete there, right? Because j- just, just to make it clear, if we're in a down market like we are today mostly, outside of AI anyway, if you're a director of product and you wanna go interview for a VP of Product role, well guess what? Who is your competition? It's chief product officers who are being pushed down to the VP role, right? So who's that company gonna go for? Are they gonna go for someone who's run, you know, who's been at the VP or C-level, or are they gonna go for that untested VP candidate? Not in a down market. It's, it's not going to be typical that they're gonna go for you. Now, there are always exceptions, which is why I say, like I don't wanna tell people exactly what to do. I wanna give them the how to go and figure it out with their network, with their counsel. Like, like 'cause if you came to me and you just spent two years at OpenAI as a director of product, can you get a VP of Product role? Probably, yes, right? Let's be honest, you know. Or you were at Microsoft, you know, uh, in the AI division, you know, in the AI software group or in the cloud AI c- you know, the AI part of the cloud business, whatever.
- AGAakash Gupta
Yep, 100%.
- PTPhyl Terry
Yeah. So it's being realistic. You know, and people are like, "Oh, but that's my dream job." I say, "Well, look, if you want that dream job, then you might need to take a two-step strategy." So I tell the story in the book about Robert. Okay, so Robert, Robert was working at a traditional media company, but he was running the streaming business, okay? He was an EVP. He had 200 people. He had a huge product team, design team, engineers, you know, he ran this great organization. And he realized, however, that the company and the part of the industry that he was in, uh, you know, was dying, you know? And so he wanted to go work for a pure play streamer. Guess what? He goes and does his work on candidate-market fit. He discovers he doesn't have a lot of credibility. He can't... He certainly can't move into a C-level role at a pure play streamer. He- his candidate-market fit at one of those companies was gonna be more like an IC, Aakash, if you can believe this. This is a true story. And, uh, you know, so he, he, he was like, "Oh, wow." But I said, "Listen, it's a two-step strategy. You go in there with your background. You do a great job, which you will, in that IC, you know, manager role, whatever. A few years later, guess what? You, you are like, you have a killer candidate-market fit. You've run large teams. You've got great stories to talk about that, and you were on the cutting edge of the streaming business. Now, you know, you can get whatever, you know, whatever you want. You, you... There's a lot of opportunity." That is really difficult to do emotionally, to kind of like come to terms with that. Now, he... There's another option. He could have either stayed where he was, but he, he feared that that was, he, you know, that, that didn't have a great future. Or he could go work for some other media brand, maybe a tier two or tier three brand, maybe was a little bit stronger than the one he had but, but not great. And, and I see people do this, and guess what? They get into their 40s or 50s and then they have no candidate-market fit. Like, they have spent their whole career in a dying part of the industry or something that's slowing down, and then suddenly they can't get any jobs, even an IC role. They're like, they are stuck, and they're virtually unemployable, right? So I am really... You know, so this guy, he was good. He, he, he was in the collaborative game councils and we talked a lot about this and, and he, he took initiative. And so, and he bit the bullet. He took that lower role. Very hard to do emotionally. Go from running, uh, you're an EVP running a big team, right? Not only are you making more money, but there's so much social proof and respect, and you've got the first class ticket on the airplane and, you know, you've got the black car picking you up at work, you know, to now you're in a cubicle land again, right? [laughs] And it was, it was obviously a drop in pay, although he got, he got stock that ended up really outweighing that. But, uh, but he did it. You know, huge respect to that courageous move, and it's totally transformed him. And some of his friends who stayed back, I mean, they're, they're in tough... I just saw one of them last week. They, oh, they're in a tough position now. I feel for them. And it... Look, no matter who you are, even in that position you can figure something out if you're willing to get practical and realistic and accept the situation. It's not personal to you. It's the market's changed. There's gonna be something, but it's gonna take that work.
- AGAakash Gupta
Amazing story. So you have some really cool tips about how you actually build these networking connections. How do you actually get in touch with the right recruiters, right companies-
- PTPhyl Terry
Yeah
- AGAakash Gupta
... right people at the right companies?
- PTPhyl Terry
Yeah. So there's two, th- there's two moments in the Never Search Alone process where I talk about this, right? First is, and when you do that listening tour. And one of the secrets of the listening tour is that there's actually t- at least two things going on. Certainly the first is you wanna get their feedback on you. How do they see you? What's the market? What's your... How do they see your candidate market fit? But you're also... I talk a lot about this, Aakash. My life is kind of predicated n- on this idea of asking for help. If you learn to ask for help well, and I'll define that in a moment, there's a very counterintuitive thing that happens that people do not believe until they've done it, which is that when you ask someone for help well, first of all, they feel honored. Most people don't realize this until they realize when someone asks them for help well, they feel honored. So put the hat, you know, on the other head, if you will, or put the different hat on, and they feel honored. But more than that, they are more invested in your success. They wanna see you. So when you're out there in the listening tour, you're getting feedback, you're getting insights, but you're also building your village of support. You're-... activating your network, right? So that when it comes time where you've clarified that candidate market fit, you go back to them and say, "Okay, Aakash, this is what I'm looking for. I'm looking for that director product in a Series B health tech startup. You're now gonna be a listening post for me." 'Cause you wanna... You're like, you f- you wanna see Phyl succeed. It's totally counterintuitive. People think, "Oh, if I, I can't bother Aakash. If I bother Aakash, then, you know, he's gonna, you know, I, I... He's too busy." Again, I'm gonna talk about how you do it well so that you raise the odds that Aakash says yes. But, but if you do that, it really turns them on. And then when you get to the actual networking part, so you've got these listening posts, then you also go back to them and say, you know, "Hey, who else, who else can I talk to?" Now, each step along the way I want you to, I want you to send
them a newsletter. I want you to create your own little job search newsletter. And people, I can't... This, this is one of my recommendations most people don't follow, Aakash, I'm sorry to say. I wish they would. But I say send out a note once a month to everyone you talk to and your listening tour, everyone who's rooting for you. Give them an update, even if the update is, "I don't have an update."
- AGAakash Gupta
[laughs]
- PTPhyl Terry
Nothing new has changed. I've been trying. I'm working. This is... I'm thinking. I'm sw- I, you know, I'm close to my candidate market fit, or I just did... You know, give them an update. Here's the thing. There's something called the availability heuristic, right? That's... I hate that term. It is, it's, it's, it's academic, and nobody can remember it. My preferred term is the out of sight, out of mind heuristic, which is to say at any given time you can only keep a few people top of mind. I want you to keep your network, you know, I want you to help them keep you top of mind for them, right? So you gotta send them those updates. You gotta be in touch. This... You know, but do it well, okay? Ask for help well. A- Okay, so what does asking for help well mean? It means a couple of things. One is it means do your homework, right? So we talked about this. Work on the Nook and two-pager. Really think about this. Take this seriously. If you do that, you're gonna... This, that's really important. What people don't like, the thing you really want to avoid, is the rip-off ask for help. That's where you do no homework, and you're like... Uh, you, uh... My, my favorite example of this, Aakash, so some people know the name Marissa Mayer. She was, uh, early on at Google and a real leader at Google and then went on to be the CEO at Yahoo. Very prominent. She was a co-founder of my collaborative GAIN product councils with me back in the day, and terrific human being. So [laughs] back in the day, I would get these emails, like, from people I did not know. Oh, oh, Phyl, uh, would you please introduce me to Marissa Mayer? Uh, I have this software product that I know Google would love. I don't know you from Adam, right? And what? I'm gonna... What? What, what planet are you living on? What... Why are you wasting your own time, not to mention mine? Now, I do say in the book, and it's fi- I, it's still the case that I ha- I can... Maybe two people have done this in my whole life, but here's, here's an alternative way to do that. If you don't know me and you think you actually have something for Marissa, you might, if you said, "Phyl, you know, I've thought a lot about this. I've done some research. We're working on this thing. I'd love... I think it's possibly a fit for Google. I may be wrong. Here's the thing I think that works. Would you be willing to spend 10 minutes with me to give me some feedback?" Now, I might not do a phone call with you, but I will respond to that email, and I would actually give you some very clear feedback. Like, y- y- you know, this is not even close to what Google's thinking about these days. Or holy moly, actually, this is something that I know is on Marissa's mind. Let me ask her permission first, and this is the next key tip, Aakash. Huh. I really wish people would do this. Do not send me cold introductions. First of all, I have a rule, and it is 100% true, okay? If you send me a cold introduction, it is a person I do not wanna speak to. [laughs] Now, if, Aakash, let's say you, there was someone that you thought I would wanna speak to, and, and actually you wanted to ask me a favor. May- maybe it's even someone maybe I don't wanna speak to, but you'd like to ask me for a favor. You know, we got to know each other. You brought me onto your podcast. Would I be willing to talk to someone? If you reached out to me and said, "Phyl, I need a favor from you, or I'd like to ask a favor if you're open to it. If not, but here's this person, and boy, it would mean the wo- My niece is looking for her first job. You know, would you be willing to speak to her?" Whatever. "As a favor to me." I'm gonna say yes to that 'cause first of all, you're being honest, you know, and you're, you're asking me for a favor. I'm gonna say that. But if you just send me a cold email, "Phyl, I want you to meet blah, blah, blah," and I know the two of you are gonna really hit it off. Have you had this, Aakash? I know you've had this, right?
- AGAakash Gupta
All the time, yeah.
- PTPhyl Terry
Have you ever gotten a clo- a cold intro that you wanted?
- AGAakash Gupta
I somehow just try to act like I haven't seen them. [laughs]
- PTPhyl Terry
Yeah, you just ignore it, right?
- AGAakash Gupta
Yeah.
- PTPhyl Terry
Now, the... Look
- AGAakash Gupta
So sad.
- PTPhyl Terry
If Marty Cagan and I have known each other for, uh, 25 years. We're, we're very good friends. If Marty sends me a cold intro, I'll respond to that, right? That's the poi- If someone who's a very close friend of yours does this, generally speaking, they're also not gonna do it for someone that you don't wanna talk to 'cause they know you well, right? So there's one or two exceptions. But that is it. I mean, like... And, and by the way, I will, I still will always ask Marty his permission even though he said, "Phyl, you don't need to ask me." But it's just, it's just how I roll, right? I just wanna make sure that person wants to, wants to get that introduction. And, and by the way, I won't ask them permission if it's something I know they're not interested in, right? Uh, unless it's just-Marty, my nephew, would you please talk to them? [laughs] You know, like that kind of thing. And it's a favor to me, you know. So permission-based introductions, Aakash, so important. And, you know, when... I actually give people templates for this. So when you're networking, and let's say, okay, so I'm talking to you, Aakash. Let's say you work at OpenAI, right? And, um, I'm just gonna make this up. I'm an engineer, you're a PM, and I wanna talk to somebody in engineering there. And I ask you, "Will you do that?" And you say to me, uh, "Sure. Here's this person's name. Go ahead and email them." Well, that's okay, but what I want you to do is say, "Aakash, would, would you mind actually asking them permission, uh, to introduce us? Would that- would you be up for that?" And if you are, here, I'm gonna even give you the template to make your life easy. Here's my, my attempt in your voice to ask this other person permission to introduce them to me, okay? Make it easy. Make it easy for everybody. Not everybody's gonna agree to that, and some people are gonna say, "No, I, I don't have time for that. Here's the email." But if there's someone you have a good relationship with, they generally do that, right? I was on the phone just with someone yesterday. I run a, um, a high school business literacy program. Uh, this is a fun thing which we may get a chance to talk about at some point. By the way, I'm, I'm going to eventually open it for adults, 'cause p- every PM should go through it, right? Every, uh, PM need to know basic stuff about, about business and finance and balance sheets and P&Ls and stuff like that, and how, how the stock market operates. It's just good, basic stuff, right? Not every PM has that in, uh, has that fundamental knowledge. Anyway, the point is, I was talking to, um, someone prominent in the, in the ed tech world, and, uh, they were gonna introduce me to someone else, and they're like, "I'll just give you their email," and I did. I said, "Listen, i- if it's, if you're open to it, would you, would you ask her permission first and then introduce?" And he was like, "Oh, that's a better idea. Yeah, I'll do that," right? Now, he might've said no. Fine enough. "Yeah, give me the email and I'll reach out to her and say I don't, you know, you know, Phyl suggested I reach out. I don't know if you're open to talking." And that's it. Just always be really, like, just, "Are you open to talking? You know, i- if you're too busy, no worries. Thank you. I..." You know, like that kind of tone. It really matters, right? It's a, you're a real person. By the way, all of us, how much spam do you get every day from all of these companies, all their software products they're trying to sell you something f- you know, most of the times it's, like, totally irrelevant, but even if it's relevant, it's like I'm not gonna respond to these. I don't know why these people do it. Uh, somehow enough people must respond. I don't know. So to speak as a real human being with courtesy, you know, with an understanding for how busy folks are, and, you know, and nonetheless representing yourself as a smart, proud person who wants their assistan- and help and deserves that. Is that, is it, are, are those the kinds of tips you were, you were thinking about, Aakash?
- AGAakash Gupta
Yeah, exactly, and I think that what people are trying to do and what they're sending me messages about is, "Can I talk to you for 15 minutes?" But they completely missed, like, all of the elements of getting a warm introduction to me, having a reason to talk to me, having potentially some value to even offer because they did their homework. I think all of those elements that you mentioned, that's what makes an effective networking strategy. And because we're narrowing people's aperture, right? They al- they always wanna be expansive, but we're saying be narrowed. They get scared, like, "What do I do next?" But these are the steps you take next. You get warm introductions, you get permission-based ones.
- PTPhyl Terry
And do the homework. Like, if you're asking for a warm introduction to, you know, someone who's a VP of Product at Airbnb, please know something about the challenges and the product challenges that Airbnb has. Go listen to that person on a podcast. Go see th- you know, whatever, if they give a talk or just... You know, like, come in there. Like, and it's funny. I, like, early on when the, when the book came out, uh, one of my old friends but n- not... Someone we hadn't been in touch with for a long time, not really friends, but contacts, whatever, was like, "Oh, Phyl, I've, I've got a friend." Uh, they cold introed me to someone, like, "Oh, they're looking for a job. I was wondering if you'd get on the phone with them." Like, I just wrote the book, right? No, I'm not gonna get on the phone [laughs] with you. What, what are you thinking about here exactly? A- and I said, "Listen, I..." I, what I actually said, just out of respect, was, like, "I'd be, I'd be happy to talk, but it's not gonna be useful for you or me to talk right now. Get on the Job Search Council. You know, read the book. Do a listening tour. When it comes to the point where you've got a candidate market fit, if you want help, uh, you know, give me a call." You know, like, go do some homework, right? And, and then actually we can have a fruitful conversation. 'Cause that's the other thing. What am I gonna say to somebody, you know? Let, l- l- let's get on the phone, tell them about how to look for a job. Like, [laughs] what? I wr- I fucking wrote a book. It took me 10 years. I went through 400 drafts. I tested it. By the way, y- your, your listeners should know I dogfooded the heck out of this thing, right? Like, I, we went through 400, I went through 400 drafts of this book. I was testing and testing and testing and testing it. I had people not just reading it, but using it, forming job search councils, going through the mannequin two-pager, the candidate market fit. What did... So if, if any point you're reading the book and you're like, "Oh, how does Phyl know I have that question," right, when I was reading that paragraph? Well, it's a simple answer: because somebody told me they had that question when they were reading that book. You know, or they struggled with that point and that I had to get more clear at that. I really... You know. So, um, be aware of who people are, you know? And i- it's not, we're, we're not talking rocket science here. You don't have to study them for years. I'm just saying, you know, do a little bit of homework. Yeah. And, and I, I c- I, I can tell you that, um, I s- even a- even after I talk about this publicly and wrote it in the book, I still don't get people approaching me that way, Aakash.
- AGAakash Gupta
It's very rare. So it stands out, and if you do it, you tend to get a pretty high response rate. Not 100%, but you will get a greater than 30 to 40% response rate. So if you're doing it to three to four people, you will get conversation.
- PTPhyl Terry
And that's important to point out, by the way. This is, this is not 100%. I'm so glad you're saying that. Part... And, and we all hate networking, right? I, I do, too, by the way, but that's why you want that support group, and you wanna be smart about it. And when someone doesn't reply, it has nothing to do with you. You know? How many emails do you have in your inbox, Aakash?
- AGAakash Gupta
Yeah.
- 47:48 – 49:50
Networking that works: asking for help well (and avoiding cold-intro mistakes)
- PTPhyl Terry
Yeah. So there's two, th- there's two moments in the Never Search Alone process where I talk about this, right? First is, and when you do that listening tour. And one of the secrets of the listening tour is that there's actually t- at least two things going on. Certainly the first is you wanna get their feedback on you. How do they see you? What's the market? What's your... How do they see your candidate market fit? But you're also... I talk a lot about this, Aakash. My life is kind of predicated n- on this idea of asking for help. If you learn to ask for help well, and I'll define that in a moment, there's a very counterintuitive thing that happens that people do not believe until they've done it, which is that when you ask someone for help well, first of all, they feel honored. Most people don't realize this until they realize when someone asks them for help well, they feel honored. So put the hat, you know, on the other head, if you will, or put the different hat on, and they feel honored. But more than that, they are more invested in your success. They wanna see you. So when you're out there in the listening tour, you're getting feedback, you're getting insights, but you're also building your village of support. You're-... activating your network, right? So that when it comes time where you've clarified that candidate market fit, you go back to them and say, "Okay, Aakash, this is what I'm looking for. I'm looking for that director product in a Series B health tech startup. You're now gonna be a listening post for me." 'Cause you wanna... You're like, you f- you wanna see Phyl succeed. It's totally counterintuitive. People think, "Oh, if I, I can't bother Aakash. If I bother Aakash, then, you know, he's gonna, you know, I, I... He's too busy." Again, I'm gonna talk about how you do it well so that you raise the odds that Aakash says yes. But, but if you do that, it really turns them on. And then when you get to the actual networking part, so you've got these listening posts, then you also go back to them and say, you know, "Hey, who else, who else can I talk to?" Now, each step along the way I want you to, I want you to send
- 49:50 – 1:02:50
Maintain momentum: updates, availability, and structured outreach accountability
- PTPhyl Terry
them a newsletter. I want you to create your own little job search newsletter. And people, I can't... This, this is one of my recommendations most people don't follow, Aakash, I'm sorry to say. I wish they would. But I say send out a note once a month to everyone you talk to and your listening tour, everyone who's rooting for you. Give them an update, even if the update is, "I don't have an update."
- AGAakash Gupta
[laughs]
- PTPhyl Terry
Nothing new has changed. I've been trying. I'm working. This is... I'm thinking. I'm sw- I, you know, I'm close to my candidate market fit, or I just did... You know, give them an update. Here's the thing. There's something called the availability heuristic, right? That's... I hate that term. It is, it's, it's, it's academic, and nobody can remember it. My preferred term is the out of sight, out of mind heuristic, which is to say at any given time you can only keep a few people top of mind. I want you to keep your network, you know, I want you to help them keep you top of mind for them, right? So you gotta send them those updates. You gotta be in touch. This... You know, but do it well, okay? Ask for help well. A- Okay, so what does asking for help well mean? It means a couple of things. One is it means do your homework, right? So we talked about this. Work on the Nook and two-pager. Really think about this. Take this seriously. If you do that, you're gonna... This, that's really important. What people don't like, the thing you really want to avoid, is the rip-off ask for help. That's where you do no homework, and you're like... Uh, you, uh... My, my favorite example of this, Aakash, so some people know the name Marissa Mayer. She was, uh, early on at Google and a real leader at Google and then went on to be the CEO at Yahoo. Very prominent. She was a co-founder of my collaborative GAIN product councils with me back in the day, and terrific human being. So [laughs] back in the day, I would get these emails, like, from people I did not know. Oh, oh, Phyl, uh, would you please introduce me to Marissa Mayer? Uh, I have this software product that I know Google would love. I don't know you from Adam, right? And what? I'm gonna... What? What, what planet are you living on? What... Why are you wasting your own time, not to mention mine? Now, I do say in the book, and it's fi- I, it's still the case that I ha- I can... Maybe two people have done this in my whole life, but here's, here's an alternative way to do that. If you don't know me and you think you actually have something for Marissa, you might, if you said, "Phyl, you know, I've thought a lot about this. I've done some research. We're working on this thing. I'd love... I think it's possibly a fit for Google. I may be wrong. Here's the thing I think that works. Would you be willing to spend 10 minutes with me to give me some feedback?" Now, I might not do a phone call with you, but I will respond to that email, and I would actually give you some very clear feedback. Like, y- y- you know, this is not even close to what Google's thinking about these days. Or holy moly, actually, this is something that I know is on Marissa's mind. Let me ask her permission first, and this is the next key tip, Aakash. Huh. I really wish people would do this. Do not send me cold introductions. First of all, I have a rule, and it is 100% true, okay? If you send me a cold introduction, it is a person I do not wanna speak to. [laughs] Now, if, Aakash, let's say you, there was someone that you thought I would wanna speak to, and, and actually you wanted to ask me a favor. May- maybe it's even someone maybe I don't wanna speak to, but you'd like to ask me for a favor. You know, we got to know each other. You brought me onto your podcast. Would I be willing to talk to someone? If you reached out to me and said, "Phyl, I need a favor from you, or I'd like to ask a favor if you're open to it. If not, but here's this person, and boy, it would mean the wo- My niece is looking for her first job. You know, would you be willing to speak to her?" Whatever. "As a favor to me." I'm gonna say yes to that 'cause first of all, you're being honest, you know, and you're, you're asking me for a favor. I'm gonna say that. But if you just send me a cold email, "Phyl, I want you to meet blah, blah, blah," and I know the two of you are gonna really hit it off. Have you had this, Aakash? I know you've had this, right?
- AGAakash Gupta
All the time, yeah.
- PTPhyl Terry
Have you ever gotten a clo- a cold intro that you wanted?
- AGAakash Gupta
I somehow just try to act like I haven't seen them. [laughs]
- PTPhyl Terry
Yeah, you just ignore it, right?
- AGAakash Gupta
Yeah.
- PTPhyl Terry
Now, the... Look
- AGAakash Gupta
So sad.
- PTPhyl Terry
If Marty Cagan and I have known each other for, uh, 25 years. We're, we're very good friends. If Marty sends me a cold intro, I'll respond to that, right? That's the poi- If someone who's a very close friend of yours does this, generally speaking, they're also not gonna do it for someone that you don't wanna talk to 'cause they know you well, right? So there's one or two exceptions. But that is it. I mean, like... And, and by the way, I will, I still will always ask Marty his permission even though he said, "Phyl, you don't need to ask me." But it's just, it's just how I roll, right? I just wanna make sure that person wants to, wants to get that introduction. And, and by the way, I won't ask them permission if it's something I know they're not interested in, right? Uh, unless it's just-Marty, my nephew, would you please talk to them? [laughs] You know, like that kind of thing. And it's a favor to me, you know. So permission-based introductions, Aakash, so important. And, you know, when... I actually give people templates for this. So when you're networking, and let's say, okay, so I'm talking to you, Aakash. Let's say you work at OpenAI, right? And, um, I'm just gonna make this up. I'm an engineer, you're a PM, and I wanna talk to somebody in engineering there. And I ask you, "Will you do that?" And you say to me, uh, "Sure. Here's this person's name. Go ahead and email them." Well, that's okay, but what I want you to do is say, "Aakash, would, would you mind actually asking them permission, uh, to introduce us? Would that- would you be up for that?" And if you are, here, I'm gonna even give you the template to make your life easy. Here's my, my attempt in your voice to ask this other person permission to introduce them to me, okay? Make it easy. Make it easy for everybody. Not everybody's gonna agree to that, and some people are gonna say, "No, I, I don't have time for that. Here's the email." But if there's someone you have a good relationship with, they generally do that, right? I was on the phone just with someone yesterday. I run a, um, a high school business literacy program. Uh, this is a fun thing which we may get a chance to talk about at some point. By the way, I'm, I'm going to eventually open it for adults, 'cause p- every PM should go through it, right? Every, uh, PM need to know basic stuff about, about business and finance and balance sheets and P&Ls and stuff like that, and how, how the stock market operates. It's just good, basic stuff, right? Not every PM has that in, uh, has that fundamental knowledge. Anyway, the point is, I was talking to, um, someone prominent in the, in the ed tech world, and, uh, they were gonna introduce me to someone else, and they're like, "I'll just give you their email," and I did. I said, "Listen, i- if it's, if you're open to it, would you, would you ask her permission first and then introduce?" And he was like, "Oh, that's a better idea. Yeah, I'll do that," right? Now, he might've said no. Fine enough. "Yeah, give me the email and I'll reach out to her and say I don't, you know, you know, Phyl suggested I reach out. I don't know if you're open to talking." And that's it. Just always be really, like, just, "Are you open to talking? You know, i- if you're too busy, no worries. Thank you. I..." You know, like that kind of tone. It really matters, right? It's a, you're a real person. By the way, all of us, how much spam do you get every day from all of these companies, all their software products they're trying to sell you something f- you know, most of the times it's, like, totally irrelevant, but even if it's relevant, it's like I'm not gonna respond to these. I don't know why these people do it. Uh, somehow enough people must respond. I don't know. So to speak as a real human being with courtesy, you know, with an understanding for how busy folks are, and, you know, and nonetheless representing yourself as a smart, proud person who wants their assistan- and help and deserves that. Is that, is it, are, are those the kinds of tips you were, you were thinking about, Aakash?
- AGAakash Gupta
Yeah, exactly, and I think that what people are trying to do and what they're sending me messages about is, "Can I talk to you for 15 minutes?" But they completely missed, like, all of the elements of getting a warm introduction to me, having a reason to talk to me, having potentially some value to even offer because they did their homework. I think all of those elements that you mentioned, that's what makes an effective networking strategy. And because we're narrowing people's aperture, right? They al- they always wanna be expansive, but we're saying be narrowed. They get scared, like, "What do I do next?" But these are the steps you take next. You get warm introductions, you get permission-based ones.
- PTPhyl Terry
And do the homework. Like, if you're asking for a warm introduction to, you know, someone who's a VP of Product at Airbnb, please know something about the challenges and the product challenges that Airbnb has. Go listen to that person on a podcast. Go see th- you know, whatever, if they give a talk or just... You know, like, come in there. Like, and it's funny. I, like, early on when the, when the book came out, uh, one of my old friends but n- not... Someone we hadn't been in touch with for a long time, not really friends, but contacts, whatever, was like, "Oh, Phyl, I've, I've got a friend." Uh, they cold introed me to someone, like, "Oh, they're looking for a job. I was wondering if you'd get on the phone with them." Like, I just wrote the book, right? No, I'm not gonna get on the phone [laughs] with you. What, what are you thinking about here exactly? A- and I said, "Listen, I..." I, what I actually said, just out of respect, was, like, "I'd be, I'd be happy to talk, but it's not gonna be useful for you or me to talk right now. Get on the Job Search Council. You know, read the book. Do a listening tour. When it comes to the point where you've got a candidate market fit, if you want help, uh, you know, give me a call." You know, like, go do some homework, right? And, and then actually we can have a fruitful conversation. 'Cause that's the other thing. What am I gonna say to somebody, you know? Let, l- l- let's get on the phone, tell them about how to look for a job. Like, [laughs] what? I wr- I fucking wrote a book. It took me 10 years. I went through 400 drafts. I tested it. By the way, y- your, your listeners should know I dogfooded the heck out of this thing, right? Like, I, we went through 400, I went through 400 drafts of this book. I was testing and testing and testing and testing it. I had people not just reading it, but using it, forming job search councils, going through the mannequin two-pager, the candidate market fit. What did... So if, if any point you're reading the book and you're like, "Oh, how does Phyl know I have that question," right, when I was reading that paragraph? Well, it's a simple answer: because somebody told me they had that question when they were reading that book. You know, or they struggled with that point and that I had to get more clear at that. I really... You know. So, um, be aware of who people are, you know? And i- it's not, we're, we're not talking rocket science here. You don't have to study them for years. I'm just saying, you know, do a little bit of homework. Yeah. And, and I, I c- I, I can tell you that, um, I s- even a- even after I talk about this publicly and wrote it in the book, I still don't get people approaching me that way, Aakash.
- AGAakash Gupta
It's very rare. So it stands out, and if you do it, you tend to get a pretty high response rate. Not 100%, but you will get a greater than 30 to 40% response rate. So if you're doing it to three to four people, you will get conversation.
- PTPhyl Terry
And that's important to point out, by the way. This is, this is not 100%. I'm so glad you're saying that. Part... And, and we all hate networking, right? I, I do, too, by the way, but that's why you want that support group, and you wanna be smart about it. And when someone doesn't reply, it has nothing to do with you. You know? How many emails do you have in your inbox, Aakash?
- AGAakash Gupta
Yeah.
- PTPhyl Terry
I mean, I can... I, I used to... We were, back in the day, we were the sort of founders of the whole inbox zero concept. You know, we're talking 25 years ago. [laughs] It's been a long time since I could keep a zero inbox. It just, it just doesn't... I can't do it, you know? Um, so if someone doesn't respond, even they may not have even seen your email, you know? Or they might have seen it briefly, but they were in the middle of launching a product or doing whatever they were doing. Um, and so that's why you, you know... And so we have w- we, we have tools, uh, in the book for your council to keep each other accountable on the number of outreaches you're doing, the number of meetings, the number of attempts of outreaches. Like, and you... It's, it... Once you've got your candidate market fit set, and you've got your LinkedIn profile synced up with that, then it is a numbers game, right? The pro- You don't wanna do the numbers game, though, until you have an a- until you have an idea of what you're doing. You're gonna spin your wheels, like I've seen happen, especially in a market like this. And if it's a better market, you might just wind up with suboptimal offers.
- 1:02:50 – 1:11:31
Interviewing + negotiating to win-win: Job Mission with OKRs
- AGAakash Gupta
Yeah. You don't wanna go cast a net in the middle of the ocean where there are no fish. You wanna go spearfishing near the coral reef. So we've got you spearfishing near the coral reef. You even catch a fish, right? I think I love your perspective on how to negotiate because it's not just about the money, is it?
- PTPhyl Terry
Yeah. No, it's not. And so we have this program for, i- if you don't mind, how to both interview and negotiate, right? So it's sort of a combo. And I will tell you, Aakash, that it is, you know, gee, I can't say it's more powerful than candidate market fit because, boy, is that a strong concept, right? Uh, by the way, funny story on candidate market fit. So I was struggling for years. You wouldn't... It seems so obvious now. I struggled for years to figure out what to call that, and literally the morning I was sending my final draft to Marty to review and consider writing a forward, I woke up at 5:00 AM, and it was like it just, like, appeared in front of me, like candidate market fit. I'm like, "Oh, my God, that is what I've been talking about." You know? It's like crazy that it took that long. Um, I love that concept obviously. But this next one, what I call, uh, playing to win-win, and we, and we use a tool called Job Mission with OKRs. Your audience knows about OKRs, but this is so good. And here's the thing, Aakash. We keep data on this, right? When someone gets a job, we, you know, we, they do an exit survey with us, and we ask them a number of things. But we start with, like, okay, what, w- w- what did you do? And in particular, did you do a job mission with OKRs? And I'm gonna say more about what that is in a moment for the audience. And I will tell you, since day one, and so I'm now looking for a volunteer evangelist whose only job will be within the Never Search Alone community to promote the adoption of this tool 'cause it's so good. It's, it's, it has never gotten above 50% of the people who go through Never Search Alone. I'm not talking about the general public. I'm talking about the people who, you know, get a job search council, do the Milk and Two Vager, do the listening tour, do the candidate market fit, right? And then they start doing interviews, and they don't do this. So I really want your audience to hear this. Please, please, please adopt this. It's so tested, and so... It performs so well. So the concept is this. I want you to help lead the entire conversation. I want you to help build the relationship with the hiring manager. I want you to have a little bit of courage, and this is part of the challenge 'cause it does take a little bit of courage, okay? And now at first, you're not gonna... The, the client's not gonna know anything necessarily except that you show up really well. So what I want... The first step is this. When you start interviewing, I want you to privately, on your own, you're not showing anyone else except your council, I want you to privately start drafting a job description, but I call it a job mission with OKRs. So many companies have terrible job descriptions, Aakash, and they don't have clear OKRs or accountabilities in them. They're general. It's not even clear they know what product management is half the time, right? [laughs]
- AGAakash Gupta
Never clear.
- PTPhyl Terry
So I want you to write your version, okay? And, and here's the cool thing. By starting to draft it, you're gonna start thinking about that role and that company, and you're gonna realize questions that you need to ask in the interview to get clarity for your job mission with OKRs, which again, you're doing privately so far. You're not telling them anything except you're surfacing great questions. Most people do not bring good questions to the interviews. By the, by virtue of having thought about it a little bit and having some really pointed questions, you are going to stand out array right off the bat, okay? Now, after you've done a couple of interviews, you're gonna start to have a draft. It's not gonna be fully baked, and this is one of the problems that people have. They think it needs to be perfect.Oh, it's just a draft, okay? It's just some initial thinking about the role, about the accountabilities, about the outcomes, about the objectives, et cetera. Okay? So two or three interviews in, I then want you to take that draft, and again, it's not perfect. Say to the hiring manager, and these are very specific words I'm gonna use, okay? So if you're in the audience, I want you to write these words down the way I say them [laughs] . I want you to say, "Hey, I'd love to have a, a quick sidebar with you. I've been thinking about the role, and I wanna make sure I'm understanding it correctly." Okay? So you're, it- you're not going in and telling them how you think it should be. You're actually saying, "Hey, I wanna make sure I understand it correctly," right? So it's... That's important. You're not threatening. You're not saying, "Oh, I know the job better than you," although you might, but you're not presenting it that way, [laughs] okay? You sit down with that hiring manager, and by the way, don't just email it to them and what do you think? No, no. It's gotta be either over Zoom or in a coffee, uh, live, right? I want there to be a conversation. You show this to them, Aakash. Oh my God, it will blow them away. Your imperfect, not fully baked job mission with OKRs, the fact that you did that. So what's going on? There's like five things happening here that I wanna just unpack. Number one, and Aakash, you know this because you have hired people. One of the biggest challenges when you're hiring someone is you wanna know, are they just a good talker or can they get shit done, right? What you are doing is you are showing them that you can get shit done, that you're accountable, that you can make things happen. You take initiative. That's huge, okay? Just that you did that at all. Number two, the fact that you thought about the accountabilities and the objectives, the OKRs, whoa, that's impressive. Number three, you're probably in advance of how they're thinking about it, and that's impressing them too. Like, oh my God. I can't tell you m- how many people have said to me, "Wow." The hiring manager said, "Wow, this is better than the way I was thinking about it." You're... This is... You know, they're like ready to hire you, and that's the point, is that it increases the odds of getting an offer. But one more thing. How many people... Okay, everybody in the audience, I want you to raise their hand, okay? [laughs] How many times did you take job A and it turned out to be job B? How many times did you take a product management role, it turned out it wasn't product management? [laughs] Those were just the words they were using. You know, maybe it was project management, [laughs] you know? Yeah. So- Not quite ... by virtue of doing this, you have a real document where you can have a real conversation about what the job is and what it isn't, and that is so helpful, right? 'Cause if it turns out it's a project management job, well, look, you could... If you need to put food on the table, maybe you decide you're gonna do that. I'm not... I always, I always say that to people. People need to make those decisions. They know what they need to do for themselves and their families. But you at least are eyes wide open about what it is, and you're not gonna get reactive and upset that it wasn't a product management job. The clarity usually mean, oh, okay, so no, not that OKR. It's this one or that or that, and then you both know what it is. It increases the odds of an offer, and then Aakash, here's the cool thing, right? So first of all, none of us knows how to negotiate unless you're like an M&A negotiator. Like, you know, people are like, "Oh, Phyl," like yes, I went to Harvard Business School, but let me tell you, I'm not... I'm like the least ruthless person who went to [laughs] Harvard Business School. I'm not the person that you put in the M&A negotiation, okay? That is not who I am. [laughs] I'm all about collaboration, and that's how this is designed, is collaboration. So when you get that offer, you now have this job mission with OKRs, and guess what? I not only want you to get an offer, I not only want you to get a good offer for a good job that's a fit for you, but I want you to be set up to succeed in that role. That's the most important thing. I don't want you to take a job and then it- you're not set up to succeed. That, that's really demoralizing. This is game changing. This is career changing, Aakash.
- 1:11:31 – 1:24:35
Negotiate for success first (resources, headcount, tech debt)—then compensation
- PTPhyl Terry
If you're set up to succeed in a role, it can change the rest of your career and everything that follows. So what I want you to do when you get that offer is I actually don't want you to negotiate comp first. I want you to negotiate the things that will set you up to succeed to deliver on the OKRs that you have discussed already. Okay? So you're the hiring manager, Aakash, and I know we've agreed that I need to increase conversion rate by 20% or retention rate by 30% or whatever it is, you know, in a SaaS business or in a, a e-commerce business or whatever we're doing, you know. Or we need to... Or it's a qualitative OKR. I need to have this thing launched by X date, whatever. So then I'll say, "Okay, so Aakash, we agreed on these things. Now, you know, I think, I think what we're gonna need to look at here is, um, my sense is we're gonna need to have a training budget. I think this product team isn't really... They, we need to uplevel them, and, you know, we need to get them, uh, you know, subscriptions to Aakash's newsletter, [laughs] and we need to, you know, get them over to a Silicon Valley Product Group workshop or whatever it might be, you know? And, um, oh, what else? You know, I think, uh, I'm gonna... What, what do you need? You know, what do you need? Do you need mentoring? Do you... Are you joining a business in a sector that you don't know?" So when that happens, I'll often say, depending on how senior the person is, you've got to negotiate a mentor, maybe a board member who spends time with you to really, really help you get up to speed beyond sort of the basic stuff. Because if you're gonna be the product lead in an industry that you don't understand, you need to really get up to speed fast, right? What other things? Well, is there technical debt, right? We know what technical debt is in this audience. So, you know, I had two-Chief product officers who were taking CPO, CTO roles. It was, it was crazy. It was literally at the same time both in SaaS companies, okay? One SaaS company had about 10 million in technical debt, and the other had 20 million, okay? The guy who was going for the 20 million saying... I said to both of them, "You've got to negotiate the check for that technical debt as part of your package. Because if you can't erase that technical debt, you're not gonna be able to do anything. You're gonna be dead in the water, right?" We all know that. So the guy who was going for the business with the 20 million in technical debt did that. The CEO agreed. He got a check on day one. The debt was erased six months later. This guy moves fast. He's very good. Six months after that, he was launching new products. Six months after that, so 18 months, he was actually, uh, promoted. He, he retained his chief product officer role, but he was given a GM role, okay? He was now in charge of a division of the company. And then two years into it, he was actually a candidate for the CEO spot, okay? That's what I'm talking about in terms of being set up to succeed. Now, the other guy, and he, he and I were just talking last week. We laugh about this all the time. He's like, "I, I'm, I'm your case study. I know. I know." So 10 million in tech debt. I told him talk to the CEO. He did. The CEO said, "Well, if you come in and really analyze it and make the case and make a good case, then we'll consider it." And this is a guy, by the way, who's done... He had done, like, eight turnarounds over the last 20 years. Like, he really knows how to quickly identi- He knows there's that much technical debt, right? There wasn't much analysis that further needed to be done. And so I said, "Listen, I, you c- you can't, you can't take the job under these conditions. It's..." And in his case, by the way, he, he had, he had, he had financial room to not have to work to, to be choosy. Now, again, sometimes you don't, and I just wanna, I wanna admit that, and you have to make those decisions. But he decided to take the job anyway, okay? I said, "Listen, this, that, uh, uh, uh, you lose your leverage. You lose your leverage." And l- I'm not talking about negotiating against the company. I'm talking about these are in the best interests. What's gonna help you succeed is what's gonna help drive the company. Day one, didn't get that check. Six months in, didn't get the check. 12 months later, didn't get the check. 18 months later, he's looking for a new job, right? And we have to introduce an important concept that is true no matter what career. We all have opportunity costs, Aakash. We have opportunity costs. If we take a job A, that, th- that, the opportunity cost we pay is that we're now taking all the other possible jobs. And if we take job A where we're not set up to succeed, we may pay a really high penalty 'cause we might be pushed back two years in the development of our career. Remember, person A got to that CEO role in two years. Person B is back to the drawing board two years later. We do not have infinite time in our careers. Everything has an opportunity cost to it, even at the more junior levels. Well, people say, "Well, that's all great if you're a senior person, but what if you're a junior college student?" So when I work with college students, Aakash, they're not gonna negotiate technical debt, obviously, and they're not gonna negotiate some big training budget for their team 'cause they're not gonna manage a team. But guess what? They can negotiate their own development path. They can noshi- negotiate what kind of training, mentoring, like, what kinds of... You know, if you're going into a consulting firm, asking, literally asking, "Can I be put on one of the better teams? I wanna be put on some of the top teams." Just asking that. The company's like, "Really? That's cool that you wanna do that. Yeah, we'll make that happen." And, and we had, uh, I had a college student do that, and sh- it was great. It rocketed her career forward. So this is being smart, but it's being collaborative, and it's thinking about the company. Now, if you go and negotiate budget, resources, support... And I mean, and I go through in the book, I have a whole checklist of, of, of the many things you can negotiate, you know? It could be PR, additional PR or marketing resources to make sure you've got enough for the products that you launch. It could be the opportunity to sit on boards of other companies if you want. Whatever it is. Once you've done that, Aakash, first of all, the companies love it. I had this company, the CEO call me. He's like, "Phil, I can't believe it. One of your guys just was a chief product officer, was just negotiating with me for the training budget for the team that they don't even manage yet." That blew me away. That wanted me... That made me want them even more. You know? This is part, this is part of the psychology. And then you talk about compensation. This is a tough market to get more comp, but just this last week, we got more comp for a person because they did this process, and the company was like, "Really, really? Well, okay, okay, fine. We'll pay you more." You know? And I tell people, "Look, comp is not the most important thing in the short run. It's being set up to succeed. Because if you do, then you can command more comp." I want you to make more money. I want you to create generational wealth. It's just, like, how you set yourself up to do that. So is that [laughs] How's that?
- AGAakash Gupta
Yeah, and that's one of those things that I wish your book had come out 10 years earlier because I can talk about a specific role I had where I knew that the... I was coming in at, like, a director-level product person, and I knew that they hadn't hired, like, enough engineers and designers to support a director of product. Like, a director of product, you have to be leading, like, at least 15 to 20 engineers and designers to make enough impact. They didn't have that yet, and they're like, "Oh, you're gonna grow the team." But what I didn't do is I didn't secure that head count. So when it actually came to being in the role, the head count came in much slower than I would've expected, and I'd assumed everybody, you know, was so excited about me they would support what I needed to do to get there, but you lose your leverage.
- PTPhyl Terry
Yeah, and you know, look, if you had brought it up in that interview, in that negotiation, I mean, and said, "Hey, I, you know, we're talking about I'm gonna, I'm gonna be the director of product, so we're, you know, we're talking about 15 head count here, right? Like, we, we understand that. You have the, you have the budget. You know, we're talking, you know, on average, all in with benefits and stuff, probably 150 to 200 a person at least, you know, some a little more or less, whatever it is."And, you know, so what are we ta- we're talking two and a half, $3 million maybe a budget here. Like, do you have that? Is that... Are we on board? Are we on the same page? Oh, uh, no. No, no, no. Well, I was... No, yeah, no. [laughs] Or oh, you're... Yeah, okay. Um, yeah, I think we th- really, yeah. Okay, I think we... Yes, we really wanna make... That's, that's what it takes to do this? Yeah, Akash, I'm, I'm Akash. Yes, that's what it takes to do this. That's, that's what we're talking about here. That's what the market opportunity is, right? That's what we wanna go for? Oh, okay, great. Yep. You know what? We're on for it. Well, you got it. Well, guess what? Day one, bam, you start hiring, right? Instead, in that job, you were now, you spent months negotiating the budget, which they wouldn't do, and this and that, and it, a- and you stalled. And the company paid for it, by the way, right?
- AGAakash Gupta
Yeah, I mean, it just... But then when they came to look at me versus other directors of product who actually had 15 engineers and several designers, they were able to ship so much, and it's like I was able to ship... I had, like, three engineers.
- PTPhyl Terry
[laughs]
- AGAakash Gupta
And so I was able to ship that amount of stuff. [laughs]
- PTPhyl Terry
Yeah, and, and so they didn't, they, they didn't get your full benefit, and they didn't get the benefit of those products that you could've shipped into the market. That's why, again, this is, this is not ruthless stuff here. This is like, "Let's have the conversation about what this is and what, you know, what are we talking about here?" And p- and, and I'm telling you, I spoke... So one of the top guys at Amazon's been a part of the program, and I spoke to him about this recently, you know, and he s- and he confirmed what I knew. He said, you know, "Phil," if... He's hired about 2,000 people in his time. He's like, "Phil, not a single one has ever done something like that. But if someone presented a job mission with OKRs to me during the interviews, I would hire them on the spot." You know? I'd be like, "What? That's amazing." You know, so look, there's a lot of fe- when people get into the interview and negotiating process, there's a lot of fear. They're afraid if they do anything, it'll, it'll hurt their chances. And of course, if you're a jerk or you're arrogant or, you know, whatever, you don't listen, whatever it might be, you'll hurt your chances. But that's not what we're talking about here. This is a collaborative process where we- you will show, not tell, how good you are. You, they will want you more, and you will build that relationship, Akash. So that's... So you now have a relationship, so you start day one. They're... You're already working. You've already been working together, you know? And you, you have each seen how you work together well, and it's not, it's not abstract or generic. You... And by the way, one more thing. I can't t- I, I can't stand how good this is. It really...
- AGAakash Gupta
[laughs]
- PTPhyl Terry
And again, I'm, I'm not touting myself here. I worked with a lot of people to develop this over the years, and this is all free. You know, I'm not selling you anything here. I'm trying to sell you on an idea. Um, very often when you take a job, the hiring manager leaves within a month or two, and then you're totally bereft. Nobody knows sort of what you're doing or what you're talking about. More junior roles are, can tend to be okay, but the more senior you get, that's really problematic.
- AGAakash Gupta
Danger zone.
- PTPhyl Terry
You... Right? Y- it... Starting at the director level, you know, you built, you, you, you know, suddenly you don't have a hiring, suddenly you don't have a manager and someone's not looking out for you. You have a temporary person. Every time that's happened, the person has ended up leaving, except when they have that job mission with OKRs, because they can show that new boss or that interim boss, "Here's the role and the OKRs that we discussed and what I'm working on." "Oh, okay. Great. That's what you're working on? That's what you've got? Yep, I'll support that." You know? And off you go. So it's, it's, it's really valuable to not just get the offer but to get that set up to be suc- to be successful, including if you lose the m- hiring manager who you built that relationship with early on, which happens all the time. I had recently a member who moved from the United States to, well, two times, to Sweden and one to Spain, to work with a particular person. Moved their whole family, okay? They get there. Within a week, the guy announces they're leaving. Now they're, like, in a different country and stuck and have no political capital inside that company, no one who's gonna, uh, advocate for them, and, and, you know, and, a- a- and the whole thing just crashes. It, it, it... I've never seen that work well except when I've seen people have this job mission with OKRs. It... Now, there's been a couple of instances where even that didn't, you know, make the difference. There's no guarantee. We're just trying to raise the odds here of success, right? How can you be successful? Um, and in nine times out of 10, I've seen it succeed in that case. It's kind of an insurance contract.
- AGAakash Gupta
Phil Terry, thank you for being so generous with these ideas. I think-
- PTPhyl Terry
Yeah.
- 1:24:35 – 1:31:47
Building a movement: purpose, volunteers, events, and how to join (even as a ‘slow seeker’)
- AGAakash Gupta
How does it feel changing so many people's lives?
- PTPhyl Terry
You know, Akash, if you get a chance like this once in your lifetime, you are profoundly lucky. I am... I can't tell you. So my mother started the first council in 1960. I tell this story in the book. And, uh, and I... And it's sort of in, it's sort of in the blood. It's a family business almost, if you will. And, um, you know, I dedicated the book to her. I talk about her a lot. It, you know, it's one of the reasons everything is free, because it's, uh, it's a way to honor her and the legacy and, and what she taught me and so many others. But I, you know, I just... I can't tell you. I mean, I've done a lot in my career and I, that I'm proud of, but the ability to work with so many volunteers and to create a movement like we're doing, we've had 30,000 people participate in the program. We have 4,000 job search councils today, and we feel like we're very much day one with this.And you know what's so cool? And every dollar from the book goes into the community. It doesn't go to me. I've made that life, it's a permanent commitment. And, and sometimes people say, "Well, why won't you wanna take that money?" Well, this is... I, I'm in the fortun- I'm not a billionaire, but I'm in the fortunate position that I can afford to do that, number one. But number two, it's like, wow, given that I can do that, to b- to be able to do that, you know, you c- uh, the, uh, I- it's just such a privilege. I can't, [laughs] I can't tell you. You know, it, it is, it is so meaningful. And we all, we all wanna have that in our lives, that s- that sense of meaning, that sense of purpose. And we can find it in a lot of ways. People tell me, "Oh, I..." You don't just have to be doing something like this to find it. You could be working in a standard company, but you're creating a great team, a great product team, empowered team, you know, where, where people are growing. There's so much satisfaction in seeing people grow and develop under your wing and, you know, building great products and supporting customers. There's a lot of purpose to be created in the world. But this, this, this has been special, and I feel, I truly feel grateful. Uh, you know, it, it, the team has been, the volunteer team. I just have to name a few people. Emily Teeter start... So basically what happened is wh- when the book came out, I had not anticipated building this whole suite of free services. [laughs] I thought, "Okay, we'll put out the book, and we have the free tools, and people will do this on their own." And then, uh, a good friend of mine, longtime collaborative game member, a guy named Brent Toretsky, who's terrific if you haven't met him. He's worth having on the show. He's now the SVP of Product at Peloton, and a just incredible product guy, okay? Longtime member of my product councils. He said to me, "Phil, I think, I think you might wanna do something to help people find each other." [laughs] Now, he had run a job search council as part of the writing of the book. He'd given me a lot of great feedback on the book. And so, you know, I, I, and, a- and I respect and I listen. So at first, so I, I asked Emily, who's also in one of our product council mem- uh, councils. I, "Would you like to help me out with this?" And she said yes. So we put up a, a, we had a Google sheet, [laughs] you know? And we were almost immediately overwhelmed with that. We're like, "Okay, well now we're gonna have a Google form that goes to a Google sheet. Then we're gonna do a little Google script." Well, now we have, you know, we've, we've, we've got a more robust... But, but even that, like we are, we, we joke sometimes behind the scenes, all the work that the volunteer team does and the matching. We feel like we're in an ER. We can never catch up. There's so much need here. And in the next couple years, we're gonna build a m- a, a, a seriously robust platform, right? Yeah. So we do now have automatic matching, but even that, you know, there's always exceptions and where it's, there's tons of communication and stuff. But Emily Teeter, she has put in 3,000... She's had a full-time job as a product manager, where by the way, she like wins awards at the company for like best employee and amazing product leader, and she's put fi- 3,000 hours into this. Completely free, Aakash. Completely free. There's no way I could've done this without her. And then behind her comes Tamara Adlin, who I, who was one of my original council members when she was at Amazon, and now she runs all the orientations, and she does, she hosts the LinkedIn Live. And then, you know, I could go on down the list. Bagashree Gage is now the team coordinator and do- Like it's a m- we have this robust team. They're all volunteers, Aakash, and they're doing incredible work. Steve Cook, who runs our recruiter network, is a chief product officer. Amazing. So it's amazing to work with them, and it's amazing to, to, to be able to do something. And by the way, you know what's cool? Is we're not government funded, so nobody can cut our budget. [laughs]
- SPSpeaker
[laughs]
- AGAakash Gupta
Doge has not come for Never Search Alone job councils. [laughs]
- PTPhyl Terry
I'm sorry, Doge can't touch us, baby.
- SPSpeaker
[laughs]
- PTPhyl Terry
The, uh, Trump can't pass a tariff or something. I don't know. [laughs] You know, we're gonna, we, we're here. You know? It, it, we're operating in this interesting space. And, uh, for your, for your listeners who li- whe- when is this gonna come out, by the way? Do you know yet?
- AGAakash Gupta
Um, it usually takes about three weeks.
- PTPhyl Terry
Okay. So if people listen to this before April 22nd, I'm throwing a big party in San Francisco, Tuesday, April 22nd. If you are interested, you can go to phyl.org and get a link to that. Um, if you miss that, we're doing things all over the country, and you can certainly go to phyl.org. You, you can, uh, watch videos. You can sign up for a job search council. It's all free. We don't actually... We do require you read the book, because we found that if people didn't read the book, they weren't go- jobs... So we don't actually require that you buy it, though. You can get it from the library, borrow it from a friend. If you do buy it, know that every dime goes into the program, doesn't go to me, and that's permanent. We've made that commitment. I've made that commitment. Um, and we're here for you, and if you wanna come at any time... And by the way, if you're in a job, we didn't talk about that, Aakash. If you're in a job and you're unhappy and you wanna look for a job, you can also join one of our councils. We'll put you with other people in jobs. We call them slow seekers, people who can't do a full-time job search 'cause they have a full-time job. But we'll, we'll match you up with other slow seekers as you start to think about what you wanna do next.
- AGAakash Gupta
I have r- very rarely met someone as generous with their time, their wisdom, their knowledge. Thank you so much.
- PTPhyl Terry
That's wonderful, Aakash. You, uh, I, I, you, you're a wonderful interviewer, and I feel r- really grateful to have been here today, and I really appreciate you letting me share this with your audience. It's cool what you've built.
- AGAakash Gupta
I really hope you guys enjoyed that episode. It would mean a ton to me and the team if you could please subscribe on YouTube, follow on Apple and Spotify podcasts, and leave a rating and review. Those ratings and reviews really help grow the show and help other people discover the show, and they help fund the production so that we can do bigger and better productions. Can't wait to share the next episode with you. Until then, see you later
Episode duration: 1:32:00
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Transcript of episode fnBX7uc14tw
