Lenny's PodcastLessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, GC)
EVERY SPOKEN WORD
135 min read · 27,424 words- 0:00 – 7:52
Lauren’s background
- LILauren Ipsen
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing, and I think that should be the case for both candidates and (laughs) , you know, folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well-known commodities in their organizations, and get great references. Oftentimes, I, you know, encourage founders to simply chat with what good looks like and get a really good sense of kind of what benchmark candidate profiles could be. And who knows where that person will be in a year or what have you, but staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.
- LRLenny Rachitsky
(instrumental music) Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. Today my guest is Lauren Ibsen. One of the most important skills for founders and senior product leaders to develop is the ability to hire great people. You won't be able to build the best company or the best product if you can't hire the best people, and Lauren is one of the most experienced and successful people in the world when it comes to hiring product leaders. She's placed over 80 senior product leaders across tech companies and has worked with some of the biggest companies out there. When I asked a bunch of really smart product leaders who their favorite product recruiter was, Lauren's name came up a ton. In our conversation, we get super tactical about what founders need to do to find the best product talent, what product managers should be doing during their career to give themselves the most opportunity, and we also touch on what recruiters themselves often get wrong when trying to attract great talent. This episode is rich with actionable advice for basically everyone, and I'm really excited to bring it to you. With that, I bring you Lauren Ibsen. Who has an opinion on internal tools? Internal tools are something you probably don't think about until you have to, or it probably didn't even occur to you to think about them. But if you work at a big company, you probably have a bunch of one-off custom apps or dashboards that are laser-focused on just one job to be done for one specific team or just one role, and they're always such a huge pain to build and maintain. And that's why I'm such a big fan of Retool and why I think Retool is so popular. Retool allows teams as small as just one person to build a suite of custom internal apps in a fraction of the time that you think it takes. The productivity gains of custom apps is now within reach, not just for large enterprises but for small teams as well. And as you scale your company, Retool scales with you. Snowflake saves about 26 hours a week of manual spreadsheet work with custom internal apps built on Retool. Amazon uses Retool to handle GDPR requests. Thousands of teams at companies like Coinbase, DoorDash, and NBC collaborate around custom-built Retool apps to operate with greater efficiency. Maybe you've thought about using Retool before but just haven't, and I'm here to tell you that now teams of up to five can build unlimited Retool apps for free. Get started today at retool.com/lenny. Today's episode is brought to you by Miro. Creating a product, especially one that your users can't live without, is damn hard, but it's made easier by working closely with your colleagues to capture ideas, get feedback, and being able to iterate quickly. That's where Miro comes in. Miro is an online visual whiteboard that's designed specifically for teams like yours. I actually used Miro to come up with the plan for this very ad. With Miro, you can build out your product strategy by brainstorming with sticky notes, comments, live reactions, voting tools, even a timer to keep your team on track. You can also bring your whole distributed team together around wireframes where anyone can draw their own ideas with the pen tool or put their own images or mockups right into the Miro board. And with one of Miro's ready-made templates, you can go from discovering research to product roadmaps to customer journey flows to final mocks. Want to see how I use Miro? Head on over to my Miro board at miro.com/lenny to see my most popular podcast episodes, my favorite Miro templates. You can also leave feedback on this podcast episode and more. That's M-I-R-o.com/lenny. Lauren, thank you for being here. Welcome to the podcast.
- LILauren Ipsen
Thanks so much. It's great to be here.
- LRLenny Rachitsky
I've been meaning to do an episode on product hiring and recruiting product people for a while, and when I asked a bunch of smart friends, "Who should I have on to talk about this stuff?" your name came up a bunch.
- LILauren Ipsen
Hmm.
- LRLenny Rachitsky
And so I'm really happy that we're finally doing this.
- LILauren Ipsen
Me too, absolutely. I'm grateful that you asked.
- LRLenny Rachitsky
So to help listeners get a sense of just your background and kind of the journey you've been on to get to where you are now, could you just spend maybe just a minute kinda talking through the wonderful things you've done in your career and what you're doing now?
- LILauren Ipsen
Yeah, absolutely. So I started my career in broadcast. I originally thought that I wanted to be on the news and quickly realized I didn't necessarily want to be the face of sadness. (laughs) There's a ton of that happening in the world. So, made a pivot pretty early on and thought, "Where could I use the communication skills that I've been working so hard on and do something that's impactful in a big way, but maybe just with a little bit of a different angle?" And stumbled across executive search. Exec search is not really something that people major in college by any means or think they're going to end up doing. So it was something I found fascinating. I had...... applied to all of these different companies like Twitter and Snap and Pinterest, hadn't heard back from any of them. Was a, a name in the resumes and thought, "Well, how cool would it be if I can work with all of 'em and have an opportunity to play a part from a different lens?" So got into exec search, was really focused early on consumer mobile build-outs, was doing a lot of work with Twitter and Reddit and TaskRabbit and Nextdoor, Postmates, you name it, and that was probably 85% of the work I was doing, and then as, on the agency side, 15% was obscure. You know, autonomous helicopters selling into the Department of Defense and then retail and robotics, and it was all very fascinating. But for me, who has wicked bad ADD, it was amazing to be able to be so stimulated by so many different industries and feel like I couldn't really master this, you know? So long story short, had an awesome career at Diversa Partners, which is a boutique executive search firm, and thought I was going to be there potentially forever. Was tapped by a awesome individual, Abe Shaffey, who was founding a company. I'd been doing a lot of work for them, they were a client of mine at the time. Placed couple great hires and they said, "We're either gonna kick off a head of talent search with you or you can come over and, and join us." So I was the first recruiting hire over there, built out the talent function in its entirety. I definitely think there was a part of me that, you know, I loved the operating experience, learned a ton, worked side-by-side some amazing people, but was really missing working, uh, with founders and lots of them and keeping a pulse on the market. So General Catalyst tapped me most recently and been working here for the past couple months and it's been great thus far, and I'm specializing in our consumer and crypto investments.
- 7:52 – 9:44
Why the best recruiters seem to be migrating to VC funds
- LRLenny Rachitsky
Awesome. The fact that you're at GC now makes me think about another recruiter that I know who's awesome, Austin Bresndan.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
And it's interesting that a lot of the best recruiters seem to be heading to VC funds, and I'm curious-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... why that is happening. Is it, like, a comp thing? Is there other things that are pulling everyone away into funds?
- LILauren Ipsen
It's a great question. It's definitely not a comp thing, I'll say that. I think it could be a stability of life thing. Search is incredibly volatile and have to hustle so hard and as soon as you have three wins, you've got four more things to execute on. And so there's aspects of it that can be tough, especially in a market like right now where you really do have to chase business and you can't be selective about what you take on. So you could be pitching things that maybe you don't necessarily believe in in its entirety or what have you. So I think that's one component. In-house is obviously difficult right now as well for talent leaders. It's really scary to take a bet on one single company right now and know what it's going to look like six months from now. And so I think th- those things combined might be the reason for an influx in folks leaning more towards venture, and I think it's just timeliness.
- LRLenny Rachitsky
Got it. That makes sense. The downside is it's hard for people to find awesome recruiters 'cause they're... Once you're in a fund, you're just gonna help those startups.
- LILauren Ipsen
Correct.
- LRLenny Rachitsky
And so we're gonna talk later about just how do people find awesome recruiters, what do you look for? But there's roughly-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... three things I wanna spend our time chatting through today.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
One is for founders and hiring managers, just how to find the best talent and what they could do to be successful finding the best talent. Two is for product leaders and PMs how to give themselves the most opportunity from the flip side.
- LILauren Ipsen
Yup.
- LRLenny Rachitsky
And then third is just for recruiters. What do they often do wrong? How do they miss out on the best product talent? Does that sound good?
- LILauren Ipsen
Yeah. That sounds great.
- LRLenny Rachitsky
Okay, cool. So on the hiring front, just diving in-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... say
- 9:44 – 13:26
Mistakes founders make in searching for their first senior product leader
- LRLenny Rachitsky
you're a founder or someone really early at a company and maybe you've got a couple PMs and you're starting to think about, "We need to hire a really senior product leader, our first senior product leader."
- LILauren Ipsen
Sure.
- LRLenny Rachitsky
What, what do you find is often the biggest mistake that founders make when they're trying to hire their first senior product leader?
- LILauren Ipsen
You know, I think especially for founders that haven't hired for this caliber of talent in the past, it's really easy to be distracted by shiny objects and look at huge names. You wanna find the CPOs of Google and YouTube or what have you, because that seems like it would be such an incredible opportunity for brand recognition. And to an extent it is, but the fact of the matter is oftentimes those individuals are pretty far from the work and have a great team of executors that they've put into place that are actually the ones that are in the weeds. And so I think that's the biggest mistake I see people make, especially on, you know, the hiring front where they have limited resources and maybe they're an early stage company and trying so hard to bring in big names is not always the best way to go about it, because the fact of the matter is they need to go then hire a team. So I think looking for someone that's a little closer to the work, maybe someone that can step up into that type of role and do so in a way where some days they might actually be operating like a PM and then other days they might be able to build from a leadership perspective, like, that's more of the DNA that people should be targeting.
- LRLenny Rachitsky
Do you think the source of the issue with that going wrong, that they no longer can do that work as well 'cause they've been shielded away from the tactical day-to-day? Or is it that they're not as hungry as they used to be and they're just like, "I already... In my YouTube ten year super success, I don't need to prove myself anymore," and they're just not as hungry, or something else?
- LILauren Ipsen
I mean, I'm not gonna sit here and say that all senior leaders aren't hungry. I think that there's some folks that really lean into the work in a different way and miss that, and often go to startups because they crave building. So it's not necessarily that, but I do tend to lean towards folks that have a chip on their shoulder or have something to prove and want to build a name for themselves.All of that to say, there's a reason that a lot of those people got to where they are, and some of the best talent are some of the senior folks, but just maybe not necessarily the best talent for where this company is today, right? It could be great for 10 years down the road, but the past five years of that individual's career could have been far more focused on camaraderie, team building, operational components, performance reviews, and then aspects of product vision, which just might not be the innovative AB testing type of profile that you, you know, you typically look for in these pre-IPO companies.
- LRLenny Rachitsky
Got it. I imagine there are stories that you can share about people you've placed like that, that have not worked out.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
If you can share one, that'd be awesome, but maybe a side question, is the general advice, just don't assume someone that's been successful at a big company with a fancy background is gonna be great? Sometimes they work out, but not always.
- LILauren Ipsen
(laughs) .
- LRLenny Rachitsky
What's that kinda takeaway?
- LILauren Ipsen
Yeah, I'd say, I would say the general advice is who is going to be best for this specific role at this specific time, not necessarily who is the best talent in the world (laughs) or in the market. Those are two very, very different questions to ask and I think, you know, early on in my recruiting career, I was often just trying to recruit these whales of executives to try and prove myself and say like, "I got this person to entertain this opportunity. How sick is that?" But naturally, that's not necessarily the person that actually can move the needle, and so you need to think very specifically. Just because this is the best talent, that doesn't necessarily mean they're the best talent for this role today.
- 13:26 – 16:07
Questions for founders to ask when thinking about who to hire
- LRLenny Rachitsky
So to double down on that, say you are-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... hiring and you know you're gonna start hiring a senior product leader. What is it that you suggest founders nail down and iron out when they're kicking off the hiring process, either on their own or with a recruiter, like in the job description, what else do they have to get right to find the right person?
- LILauren Ipsen
It's a number of things, like product leaders can come in a lot of different flavors, and so I think it's trying to determine where this person should major and minor, where they should spike. Is this someone that's going to really lean into the design efforts? Is it someone that, you know, actually kind of needs to just operate like a very senior PM and continue to build out a team? Is this someone that really should be focused on product vision for the long haul and then thinking more holistically about how to build the rest of the team? There's so many different ways in which you can hire for a product leader, so I think it's trying to work a little bit backwards and think about what is the actual outcome that we're trying to solve for with this hire, or are we just hiring a head of product because we feel like we need to hire a head of product? Like that's so often what I see is, "You know, the board's telling me we need to hire a head of product and, you know, I don't necessarily think that we do, or I'm not exactly sure what we need in this role." And so whenever you're starting a search in that regard, it's kinda doomed (laughs) from inception. So you need to get incredibly granular on the front end around what is this person going to be coming in to do? What's their mandate? And, you know, if we think about someone that's just absolutely hitting it out of the park and crushing it, what does that look like? So I think just trying to be really specific on the front end.
- LRLenny Rachitsky
I love that last piece, just what does success really look like for this person. On the first piece, that's exactly the same advice I give founders when they're looking for a PM is like, "What do you concretely need them to do day-to-day?" Not like, "We need someone to help us with product." And that often-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... helps illuminate, "Okay, I see. We need someone to help us ship more consistently. We need someone to help us hire engineers." Like yeah, just make a list. Like, what are they gonna do for, in the first month or two or three?
- LILauren Ipsen
Yeah. Yeah, absolutely. I think those are the most important things, like the 90-day plan is something that's overused, but so necessary, and that's just the tip of the iceberg. So that component, and then okay, a year from now, what should this person be doing? Two years from now, do we want them to grow up into a CPO role? Do we think about that in a different way? How are we thinking about the product direction today, 12 months from now, 18 months from now, through IPO? Like, I think it's really difficult to think about things that way, and so often you're thinking about the task in front of you and just trying to, to iterate quickly. But like, that is the type of thought process that needs to be happening from the CEOs and founders.
- 16:07 – 18:27
The three main types of PMs
- LRLenny Rachitsky
Are there archetypes of PMs if you just, like, bucket? Like here's the three maybe most common types of product leaders that founders hire 'cause there's, like, an infinite list of skills and things they could do, but just-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... make it even simpler, like here's probably one of these three you're looking for. Do you have something like that in your head?
- LILauren Ipsen
Yeah. There's platform product leaders or folks that are kind of more indexed on the infrastructure components. There's folks that are typically focused on, like, core product or consumer product, if it's on the consumer side of things. And then you'll have folks that are really indexed, and that can include, like, UX individuals, design folks, and then there's also typically specialists, so individuals that are really hyper-focused on growth or monetization or what have you. Those are the three buckets that I would say I see most often.
- LRLenny Rachitsky
Do you feel like founders sometimes pick one of the wrong buckets and that's a common mistake or is it generally it's the wrong bucket, but then maybe it's not the right spikes of skills within that bucket?
- LILauren Ipsen
Well, it's, it's kind of twofold. I think sometimes people just bring in a head of product to do everything. (laughs)
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
So that's probably not the best way to go about things. Like, I think that ends up being a unicorn, which you hear often in the search world, and it becomes really difficult to hone in on what good looks like. And so, you know, I think, again, it just comes back to, like, having a clear org chart on the front end and determining, are we hiring someone specifically to build out our walled garden ads approach or are we hiring someone to run product marketing or are we hiring someone to help from a product perspective to build a better core user experience? Like, those are all very, very, very different roles, and if you bring in one person to try and do it all, the fact of the matter is they're going to have to bring in some key lieutenants to help them. So is that something you wanna do or are you more focused on bringing in someone imminently to help on the ad side of things? And then we can find that head of product to help them out down the road. Like, that's kind of the way in which I would architect it and think about it is, what's most imminent?... and what do you actually need to hire for today, as opposed to just hiring for the sake of hiring and bringing in that leader.
- LRLenny Rachitsky
And part of the discussion there is maybe they grow up into this head of product long-term, maybe not. Maybe we just need someone to ship the ads platform, right?
- LILauren Ipsen
Mm-hmm. That's exactly right, yeah.
- 18:27 – 21:50
What do job titles mean, and why are they more susceptible to change in a startup environment?
- LRLenny Rachitsky
You mentioned this title of head of product. There's also-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... VP of product, CPO. There's all these titles, and I feel like people sometimes use them interchangeably, don't know which one to use when they're putting out a job description. Do you have any kinda heuristic rule of thumb of just here's how to think about when to use each of these titles? Or is it not even a big deal for, say, a founder hiring their first senior product leader?
- LILauren Ipsen
It's a great question, and it definitely leads to confusion across the board, because I'll have candidates come to me, and they'll say, "I'm only looking for a CPO role," when I'm working with a startup where, maybe on the venture side of things, we've actually advised that startup to not hire C-level executives at this point. And so that naturally could eliminate a candidate that could be amazing (laughs) for the role. Um, similarly, people could feel that way if, you know, it's a VP of product role, but that, in their mind, is the most senior product leader within the organization running everything from end to end, who they intend to be the CPO down the road, but are not in a position where they're ready to hire C-level execs. So it's tough, and it really depends on the organization and the way in which they're thinking about org charts and leveling. A lot of startups at this point are almost allergic to C titles or VP titles or are just more title-agnostic than I've seen in the past. So you see a lot more of these head ofs, and that is sector leaders up until probably C+ or D stage, and then you get to D and E, and you'll see more of the VP, director, CPO type. And I think that is, like, the way that people should be thinking about it is if I'm joining a company very, very early days and it's called head of engineering, that, that is intended to be the most senior engineering leader within the organization. The fact of the matter, though, is there's good reason sometimes why they're not throwing out that C title, and could this person be layered down the road? Potentially, because maybe the talent they need right now is different than, just as we had spoken to earlier, is different than the talent that they might need from a massive CPO in two and a half years. And so I think that rubs people the wrong way, because they want a bit of a promise that things are going to, if they join at this stage, that they'll be in it for the long haul and be that chief product officer that takes a company through an IPO. But companies are so dynamic, and things change so quickly. So, you know, I guess a long-winded way of me saying, like, there's, there's different breadth and depth to each role. But I think for the most part, unless it's a very siloed company with multiple different VPs, if you're coming into a company and they say, "This is the head of product, the VP of product, or the CPO," that all means the same thing dependent on the stage, for the most part.
- LRLenny Rachitsky
And the other takeaway there, which is awesome, is if you're an early-stage startup, probably just start with head of product. Keep it simple.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
Don't overpromise. Everyone understands.
- LILauren Ipsen
Yeah. 'Cause the last thing you want to do is have to demote someone, (laughs) but you know, once you get to a place of having C-level executives, like, that's not going to do any good, but maybe you start as a head of product, and then as the company continues to grow, you lean into the growth side of things more, and so you, you become that head of growth or an SVP of growth. Like, things iterate and change, but you just never know, and you can't predict the outcome of a company on the front end, so.
- LRLenny Rachitsky
A lot of
- 21:50 – 23:14
What should product leaders do ahead of hiring senior product leaders?
- LRLenny Rachitsky
people listening to this probably aren't hiring senior product leaders right now, but plan-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... to and will in the future, and so I wanted to ask, what should founders do when they know they will hire a head of product, say, in the next year-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... that could set them up for success down the road? What should they be doing ahead of time?
- LILauren Ipsen
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing, and I think that should be the case for both candidates and, (laughs) you know, folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well-known commodities in their organizations, and get great references. Oftentimes, I, you know, encourage founders to simply chat with what good looks like and get a really good sense of kind of what benchmark candidate profiles could be, and who knows where that person will be in a year or what have you? But staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.
- LRLenny Rachitsky
That sounds awesome, and it makes sense.
- 23:14 – 27:37
How to network with great talent
- LRLenny Rachitsky
How do you, as a founder, do some of that? Do you just kind of ask folks, like, "Hey, who are some of the best product leaders you know? I just want to chat with them. I'm not hiring, just want to kind of meet people who are awesome." Is that the behavior you suggest, or is there something else you can do?
- LILauren Ipsen
That's a great way to go about it, and by simply saying, "No agenda." (laughs) "I'm not trying to hire you tomorrow. I just want to know great people." And to be totally honest, people feel flattered by that, typically. Most of the time, if you've been referred to someone and heard nothing but great things about them and you really don't have an agenda other than wanting to pick their brain, people are like, "Huh. Well, this is different from the day-to-day. This is, like, fulfilling." And people want to pour their knowledge especially into companies that they believe in. So I think more often than not, you'll find that not just product leaders, but executives across the board are actually really inclined to do so and want to help out, because it's a little bit different from the day-to-day monotony of their work life.
- LRLenny Rachitsky
So the advice is keep track of companies who are killing it, who-... you might be able to kind of poach from in the future and keep a list and keep warm contact with folks that are awesome.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
It reminds me of a founder that, or basically all founders who are really good at hiring and how far ahead they plant seeds and how they just kind of play the long game with the best people they meet, and they just kinda keep the conversation going until they finally convince them to join, like, a year or two later. Is that, z- you find-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... that the same thing?
- LILauren Ipsen
One million percent. Yeah, when I was on the executive recruiting side of things at Diversa, the VP of engineering candidate that we ultimately landed, it was a seven-month game of courtship. And, "Let's bring him in to help out from an advising capacity. Let's ask him how he would think about structuring this org. Let's talk to him about the best talent that he would recommend that we're spending time with." No question that's invasive, but more so just collaborative and exciting. And you'll find that the founder and that leader will build a different level of rapport and trust by not going through a formal interview process and having it feel transactional. And then with that, magic can happen (laughs) and you can, you can land some incredible people.
- LRLenny Rachitsky
This all sounds like a lot of work and a lot of time. Do you have-
- LILauren Ipsen
(laughs) Yeah.
- LRLenny Rachitsky
... guidance on how long it should take to find, like for a sta- early stage startup, say Series A or B, to, like, find someone awesome and/or how much time founders should spend a week, just best practice, on hiring for someone like this?
- LILauren Ipsen
I mean, I think if you're going to search, um, so if you're looking for this individual, it's really so case-to-case. Like there's searches that I've been in that I call three people, I know they're amazing for this. I tell the founder and CEO, "These are the three people you should chat with. Hire one of them." And it's that easy. There's others where it's a lot of trying to figure out what the person's actually looking for, if there's, you know, some, some, uh, they hit it off from an emotional standpoint. There's so many different things that come with it. I would say from a timing perspective, like, it's not a hard number. It's more of just put yourself in the room with great people. If you have a tremendous amount of respect for someone, continue to harvest that relationship and ask what good looks like. Find excuses to continue to touch base with people that are important in your network. If you remembered that they mentioned that they were going to some event and you think that you might wanna hire them down the road, in a non-creepy way, show up to that event. (laughs) Like, these are, these are things that I'm constantly doing and I think that founders can do a better job of. But just make yourself known and relevant, and then when you reach out and timing is right, it won't feel so, so obscure or so s- so transactional.
- LRLenny Rachitsky
That reminds me of this time at Airbnb where we had these meetups for engineers every month or so-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... where it was like a tech, oh, it was a tech talk. And then all the engineers get a target engineer that is coming to event, like get-
- LILauren Ipsen
(laughs)
- LRLenny Rachitsky
... they get their profile and their picture and their job is to make sure they have a great time and try to convince them to join someday. (laughs)
- LILauren Ipsen
Oh my God. But it's so real. It's similar to college trips where you're trying to get recruited for a sport and they, you have to ensure that you're, yeah, just continuing to give people the best experience possible and staying top of mind for people.
- LRLenny Rachitsky
Yeah, but it could seem creepy. (laughs) They have no idea. There's just-
- LILauren Ipsen
But that is- (laughs)
- LRLenny Rachitsky
... some signs now. But it works. It worked great. It was a great tactic. (laughs)
- LILauren Ipsen
That's awesome. (laughs)
- 27:37 – 29:02
Why the timetable for recruiting is variable
- LILauren Ipsen
- LRLenny Rachitsky
Um, I wanna come back to a question that I asked, but I feel like you'll have an actual more concrete answer to the specific piece of just what's your guidance per week how much time you should be spending on hiring broadly, and specifically, like, heads of product if that's any different. Do you have any just, like, advice? 'Cause I imagine it's always spend more time than you think. It's gonna take a lot of time.
- LILauren Ipsen
Yeah. It's definitely spend more time than you think. If you are in an actual search, then you should devote all of your time to it. (laughs) I know that sucks to hear, but, like, you should be really carving out concrete time. The thing that's tough though is you could spend, I guess what I was trying to say is you could spend one hour on something or you could spend 10 hours on it, but it's more so around are you doing things to be impactful during that period of time? Like, are you actually doing things that are going to move the needle? Are you just blindly reaching out to people on LinkedIn? Because that's not going to be the way in which you're going to find the best of the best. Some of the greatest talent, uh, th- they're not even on LinkedIn. And so I think it's building a really strong network in advance, and then once you actually get to a place where you need to hire that person, like, calling all of those amazing people that you've built relationships with and saying, "Now tell me who your favorite person is and who the best person you've ever worked with is. And could you put me on a thread with them?" Like, how are you going to differentiate yourself from the rest of the market? So it's less, in my mind, like a quantitative number of hours and more of how are you doing things differently than the rest of the market?
- 29:02 – 30:27
How to be productive with your time by tapping your network
- LILauren Ipsen
- LRLenny Rachitsky
I wanna pull on this thread. Okay, so spending one hour versus 10 hours, and your point about how you could spend one hour and get as much done maybe in those 10 hours. What sorts of behaviors and actions should folks take to make use of, say, that one hour in hiring? Like, how do you not waste your time?
- LILauren Ipsen
I mean, I would say I've got probably five of my all-time favorite product leaders in the world that I tap whenever I'm kicking off a search. And they know that whenever life (laughs) brings them to an opportunity where they are going to start looking or want to lean into board opportunities, that I'm going to set them up and shout their name from the rooftops. So oftentimes, they're willing to point me in the right direction of great people, make those introductions, what have you. And I'm going to know simply because of how great they are that they would never put me in touch with someone that wasn't equally as qualified. So that, I think, because the quality is there, so I'm not just blindly guessing on quantity, spending a ton of time on LinkedIn and then having to call unknown entities and ask for back channel references when they also might not even feel comfortable sharing the dirt. (laughs) You know? So it comes back to rapport and people that you have around you that you know you can trust and tap into and ensuring that you're spending the time in the right areas.
- LRLenny Rachitsky
Got it. Yeah, so tapping your network makes a lot of sense.If you don't have that yet, I guess,
- 30:27 – 33:17
Why recruiting via LinkedIn might not be the best use of your time
- LRLenny Rachitsky
is it worth spending time on LinkedIn, just cold messaging people as a founder? And any tips there for just cold outreach that you think worked for a founder doing it versus you who are a professional at it?
- LILauren Ipsen
I do think it is worth that time. If you see someone that looks amazing, hell yeah, reach out to them. (laughs) Spend time with them. Why not? And oftentimes, again, people are excited to see, "Oh, this CEO and founder wants to pick my brain. Doesn't look like they're coming at me to try and recruit me, but rather just to have an open-ended conversation." For sure. And they can sense, you can definitely sense that type of interaction and feel comfortable with it, whereas sometimes the walls immediately go up when someone senses that they're trying to get poached. And so, you know, it's, it's I think something that's worth them doing for sure. It's just if you are going to look for a key executive and are on a time crunch, I don't necessarily think the best use of your time is blindly reaching out to executives when you don't necessarily have the expertise in knowing which companies were thriving during that period of time, which organizations were great and which were a little bit weaker within companies. Like all of those things are just the inner workings of the recruiting atmosphere in technology, and I think like tapping people, if you don't have the network, talk to a great recruiter or, or just spend some time kinda doing some research on who's great. You can ask investors or board members in your companies as to who you should be targeting. So there's always gotta be one or two people that can at least point you to another three or four.
- LRLenny Rachitsky
That reminds me of a tactic Gokul shared on this podcast about one of his best tricks is you think of, if you're hiring salespeople, instead of looking for who are just the best salespeople, you look for the company that is known for being really good at sales and then you go-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... find people there and try to poach their lieutenant types, not like maybe necessarily their head of sales. Do you think that's a good move?
- LILauren Ipsen
Yes and no.
- LRLenny Rachitsky
Oh.
- LILauren Ipsen
I th- Yes and no, because I think if the organization is incredibly good at sales, then the majority of the folks are probably amazing. But you always have weak links.
- LRLenny Rachitsky
Mm.
- LILauren Ipsen
And just because someone has a brand on their resume at the right time, I think oftentimes CEOs and founders will do this thing where they kinda over-generalize. "Well, you know, Amazon's Prime team at this time was amazing," or something like that. (laughs) It's like, they definitely could have been, but just as any other company, there's going to be people that are breakout, top 1% type individuals, and then other individuals that get to ride the wave and reap the benefits of being at the right place at the right time. And I think that's a good starting place, but then also spending time getting a little bit deeper on who the best people are within that organization. But yeah, we always start with market mapping, so determining who the best companies are within a specific area, and then I just encourage everyone to take that a layer deeper.
- 33:17 – 37:30
Lauren’s favorite placement of all time
- LILauren Ipsen
- LRLenny Rachitsky
Got it. It just comes back to your previous piece of advice. Don't assume someone that has an awesome logo is gonna be great, but sometimes they are.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
There's a question I should have asked you at the beginning that I'm gonna ask now. How many folks have you placed? How many companies have you worked with? And then also, is there a story of just like your favorite person that you've placed/company you helped hire that comes to mind?
- LILauren Ipsen
Yeah. So both great questions. I've placed probably 85 executives over the course of my career.
- LRLenny Rachitsky
Wow.
- LILauren Ipsen
And lots of entry-level employees when I was in-house, and also some great key leaders. Yeah, probably 85 searches that I've opened and closed. So that's been incredibly fulfilling work. It's also fun too on the exec side of things because you hire the VP of engineering at Postmates and you see firsthand the product change, you know? You, you watch those types of things happen before your eyes, which is, it's fulfilling stuff. It's really cool.
- LRLenny Rachitsky
And delivery gets there faster too.
- LILauren Ipsen
Yeah. Yeah, exactly.
- LRLenny Rachitsky
(laughs)
- LILauren Ipsen
So that's really fun. Favorite placement of all time has got to be the VP of engineering that I placed at IRL, which is, to be completely honest, a big reason that I joined that company. Alex Strand is his name, and he is just the most incredible, atypical, high emotional intelligent engineering leader, still super technical but has managed teams in the hundreds, built out Amazon Prime Day, then went on to, to build the core messaging platform at Snapchat. Called him and he was like, "Why would I ever leave? There's a ton of financial incentive and a team that I've built that all loves me," and we got him to ultimately make a move in two weeks, which is just kind of unheard of, although it ended up being like a seven-month push for a start date, but that was a big reason why I went and joined IRL was to work side by side him and help build out his team and learn to get more deep on the technical side of things. Because oftentimes on the executive level, as mentioned before, can be sometimes more of that people management type role, and so he just felt like this unique hybrid of an individual and yeah, I've... You know, you close searches and you, you cross your fingers and hope for the best and feel very good about it, but he was one where I just, I had all the confidence in the world that I could not have done better, (laughs) you know? I just felt so, so great about that. So that was a good one.
- LRLenny Rachitsky
I don't know how much more confidence you can instill in a candidate joining a company than the recruiter also then joining the company.
- LILauren Ipsen
Yeah. (laughs) That's, I did say that to him. I, you know? I kept saying, "And if I were to go in-house, I swear this is probably the company I would do it for," and then about four weeks after he signed, I texted him and I said, "Well, you'll never guess." (laughs)
- LRLenny Rachitsky
Wow.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
Amazing. What a stamp of confidence.
- LILauren Ipsen
Yeah, and a full circle life moment. I sent him a box of cookies, he sent it back and said, "Your turn."
- LRLenny Rachitsky
And is he still there at IRL? Awesome.
- LILauren Ipsen
Yes, he is. He's great.
- LRLenny Rachitsky
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- 37:30 – 40:16
The importance of diversifying your experience
- LRLenny Rachitsky
I wanna shift a little bit to kind of flip to the product person's perspective and talk about, how do you be successful as a product leader in finding new opportunities and giving yourself opportunities in this space? And so, maybe a first question is just, generally, what should product leaders and PMs focus on to give themselves the most opportunity in their career?
- LILauren Ipsen
I think breadth is incredibly important. It's so critical, especially if someone has an end goal of wanting to step into a product leadership role to have been able to have touched lots of different components, as opposed to specializing in one specific thing. So I would say that's very important to be able to, to make sure that you're maximizing opportunities for yourself down the road. And then as mentioned before, just always keeping a pulse on the market, regardless of how happy you are in your current company, regardless of what the project is that you're so incredibly excited about that isn't going to conclude until Q1 of next year. It's just so important that you always know the companies that are doing great things and keep those windows open for people, because, you know, you never, you never know what the next 12 months hold and you want to be in a position where you're never running out the door looking for what's next, but rather, you know, being able to be super selective about the things that you have in front of you. And that comes with time and network building and relationship building over years, honestly.
- LRLenny Rachitsky
And when you say breadth, are you saying things like work on the platform team for a bit, work on the user-facing team, maybe the internal tools team? Like, different types of product or, or something else?
- LILauren Ipsen
Mm-hmm. Exactly that, yeah. I think there's people that probably want to just be a specialist in, in growth or want to get super deep on ads. And if that's the case, then by all means do so. And I think there's something to be said about that as well because those types of skillsets will be needed, but if you're looking to diversify your skillset, continue to grow from a career trajectory perspective and think about potentially being in a head of product type role, I think it's really important that you touch all aspects of that.
- LRLenny Rachitsky
I'm really happy to hear that 'cause that's exactly the advice I give new PMs, that a variety of experience is one of the most powerful things you can do, because you'll, you also just become a better PM 'cause you can see how different types of products are built and how different types of teams operate, and it just makes you better.
- LILauren Ipsen
Yes. Variety of experience, I think taking a bet on doing something more entrepreneurial, starting something, and then also joining things that are a little bit later and more established to get best practices. Like, there's... I, I think diversifying your skillset within an organization but also diversifying the work in which you're doing and the companies that you're spending time with is awesome.
- LRLenny Rachitsky
Yeah. So on
- 40:16 – 43:23
The art and science of staying long enough to have a meaningful impact
- LRLenny Rachitsky
that, something I'm always weary of is folks jumping around between all the fancy companies to get a bunch of logos on their resume. "Oh, I worked at Snap and Facebook and Netflix." And I feel like you're just, like, building your resume and then your life flies by and you forget that you should enjoy the things you're doing and work on things that are fulfilling and optimize for not a great resume.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
And curious your thoughts on just how often you think you should move from company to company. One, to optimize for opportunities in the future or just, like, generally, do you recommend people try to move around or go deeper at their company? Like, there's a bunch of questions there-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... but take it wherever you want to go.
- LILauren Ipsen
Yeah, yeah. Okay, sounds good. I think it's an interesting one because logo collecting is never something that you, you know, wanna be known for. And the first thing you're taught, like entry level recruiting 101 is recognize patterns of candidates that jump from place to place and don't give opportunities a full chance. So you're spot on. Like, that is definitely not something you wanna be known for if you're a prospect. There's also something to be said about staying somewhere too long, though, and I will say that I think sometimes you find people that are almost loyal to a fault and companies have tanked and all executives have left and the writing's on the wall and they're holding onto the fact that they were hired by a really good guy or gal (laughs) and they want to make it work because they, they care about the human being. And I think sometimes in your career, you do have to be a little bit more selfish and think about what's going to be best for you in the long haul. And so maybe that is still keeping your head down and working hard while also being thoughtful about other things that are, that are out there and not saying hard nos to, to opportunities that knock on your door. So it's kind of, it's, it's one where I would say it's an art and a science because you have to be thoughtful about taking on new things and knowing when it's worth taking a, a bet on yourself, but also you can't run as soon as things get hard (laughs) because that, that is recognized. And if there's a riff or an internal dispute or a new leader brought in and that is so quick as to make you run for the fences, that's not something that people look for because startup world is hard. Tech is hard. Look at the crypto world right now. Like, things are incredibly volatile and difficult and you want to be able to bring people in that are gonna...... hang with you through the highs and lows. We're always looking to see w- where people moved the needle, especially on the product side, where their fingerprints were, what they can actually point to that they did and, you know, are proud of during their time there. And so if all that they can say that they did was onboarded, (laughs) and moved on, then doesn't matter where you were, but it's not going to be something that I can at least stand on to, to cheer you on. (laughs)
- LRLenny Rachitsky
I really like that. A lot of
- 43:23 – 47:57
The importance of creating real impact as a leader
- LRLenny Rachitsky
this comes down to what impact have you made-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... and I was gonna touch on that. And your point is one kind of heuristic for how long to stay at a place at the minimum is, like, have some meaningful impact you can point to that you led. That sound right?
- LILauren Ipsen
Yeah. Exactly. And have that meaningful impact be something that others can speak to.
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
You know? I think that's huge. If you built something within the organization that you're proud of but no one knows about it, then that's more difficult to have as your stamp of approval for what you are able to accomplish there. But if you did something that cross-functional leaders were speaking to, that your team all sings the praises of, then that is something that you can put a feather in the cap and say, "Okay, I, I left this place better than I found it and that's the reason that I've decided to move forward."
- LRLenny Rachitsky
And I imagine part of that is reference checks. People are gonna check to see if you actually were successful.
- LILauren Ipsen
All the time.
- LRLenny Rachitsky
Yeah.
- LILauren Ipsen
Yep. Whether you are exploratory, opportunistic, not looking at all, people are constantly calling each other and the world of tech is so, so, so small, and no matter how fired up you were leaving a company, (laughs) or what went sideways, it is so critical that you try to leave the place better than you found it and do so as seamlessly as possible because you want people to have nothing but positive to say, and oftentimes that... The thing that I always find too is if I call 10 people that were a part of the same organization as someone during a given period of time and they can't speak to anything they did, in that case, it's no news is not necessarily good news. You wanna have an impact. You want, you wanna be able to say, you know, "I did X, Y, and Z. I'm super proud of this and the reason I moved on is because, you know, I, I did what I came in to accomplish."
- LRLenny Rachitsky
It's a little bit innately tricky for product leaders, I imagine you run into this, that sometimes-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... you have to upset people as a product leader to get stuff done that needs to get done and maybe-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... they disagree and then later it's like, "Okay, I see what you did." Is that true? Do you deal with that or is it generally like, oh, yeah, yeah. The great people everyone knows, like, 100% of people will say they're awesome?
- LILauren Ipsen
It's a really good question. I think there's a way to navigate conflict without rubbing people the wrong way so that they'll, you know, say negative things. There's a way to be an impactful product leader and disagree and make change and maybe your engineering leader and design leader and marketing leader completely disagree with the direction in which you're going, but because you have all of the data to support it and because you've gone about things in a way that feels very fact first and less emotional, it's really difficult for them to then point to why they dislike this person. (laughs)
- LRLenny Rachitsky
Yeah. This is interesting. So say you make those 10 calls-
- LILauren Ipsen
Yeah. (laughs)
- LRLenny Rachitsky
In your experience, the leaders you wanna hire, are you finding 10 out of 10 are generally like, "Yes, this person's amazing, you should hire them"?
- LILauren Ipsen
There's ones that are slam dunks and no one has any negative to say. That's incredibly rare. More often you find some people like to just have something negative to say just to have something negative to say. I also take all of my back channels with a grain of salt. Maybe the person I'm calling to back channel this person with, I also have been back channeled, right? (laughs) So every single thing that hear, you just take, make note of, and then move on and think more holistically about, but I think typically what I would say is the glaring nos are very obvious. People that are polarizing individuals or have done wrong within an organization or made bad calls across the board are, you can get that information typically pretty quick. It's the mixed ones where it's I think that person was decent, those are pretty tough. (laughs) And you need to really find people that worked super closely with them because otherwise it's pretty difficult to say whether or not they were able to make an impact, which again comes back to, like, why right off the bat it's so nice to just have people that you can tap within every organization that's, like, an academy company or a great company and say, "Point me in the direction of the three best people." I don't, I don't wanna have to go through the, the burden of having to try and back channel all of the maybe middle 50% or what have you.
- LRLenny Rachitsky
Yeah. Most people don't have that, which is a reason to hire, work with a recruiter. You come-
- LILauren Ipsen
Yeah. (laughs)
- LRLenny Rachitsky
... built in with all-
- LILauren Ipsen
Totally.
- LRLenny Rachitsky
... with that network.
- LILauren Ipsen
Totally fair, yeah.
- 47:57 – 49:35
Good questions to ask references and how to dig deeper
- LILauren Ipsen
- LRLenny Rachitsky
There's a couple things I wanna touch on that I wasn't planning to touch on, but reference calls. You do a lot of them I imagine and I'm curious, do you have any tips for how to ask questions on a reference call where you actually get useful advice where it's not just, "Yes, I like them. They're great. Hire them."?
- LILauren Ipsen
Especially on references, provided references, I've only had two candidates where provided references have come back negative.
- LRLenny Rachitsky
Hmm. Real bad.
- LILauren Ipsen
Which that's tough. Outside of that, typically references are a standard. It is important to, to dig pretty deep and ask the hard questions.
- LRLenny Rachitsky
What's the hard questions?
- LILauren Ipsen
Yeah. Why would I not hire this person? What are their biggest weaknesses? And then if they give you, like, the typical, "Oh, they work too hard," it's like, "No." (laughs)
- LRLenny Rachitsky
(laughs)
- LILauren Ipsen
"Tell me more. What are their actual weaknesses? What are things that we should be really cognizant of?" You know, would you hire this person again? Would you report to this person? Would you endorse this person if you knew that your name was attached to it? Things like that, I think...... get people thinking. And even if you just sense the slightest pause, that in itself will be enough to-
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
... to kind of make you think twice.
- LRLenny Rachitsky
Oh.
- LILauren Ipsen
Right? So, it's a lot of reading the room and probing harder than you think necessary, which is tough. But back channel references, I think, will always provide a greater source of truth than provided. It's similar to, like, an Instagram Reel as opposed to the photos you're tagged in.
- LRLenny Rachitsky
Yeah. (laughs)
- LILauren Ipsen
(laughs) That's the way I think of it. It's like, this is what you want the world to see or think of you as, and then these are what your peers and your direct reports and the people around you actually say about the work that you did during this time.
- LRLenny Rachitsky
Awesome. Coming
- 49:35 – 53:39
Resume red flags and the importance of honesty
- LRLenny Rachitsky
back to a point you made about recruiter training 101, you learned how to find patterns and red flags-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... in people's resume. What else is a red flag in your resume that you wanna avoid/ there's a rule of thumb of, like, if you're at a place for less than a year, it's a bad. Is that true? How do you feel about that? How do hiring managers generally feel about that?
- LILauren Ipsen
It definitely depends with regards to being at a place less than a year. If that's a recurring theme, of course that's a, that's a big red flag e- even if it's happened two or three times. Three, definitely. If it's happened twice, it's like, "Huh. That feels off." You gotta let people tell their story though and their side of things, and- and again, it comes back to, like, reaching out to different people and understanding if what they're saying is true was actually th- the truth. And so when you have a really good pulse on what's happening in tech and whether there was a rift and the reason that person was let go was actually for in- a- because they weren't prioritizing a certain part of the product or whatever, like, those things, it happens. That's life. Especially right now, right? If we were to X every single person that has a short stint that joined a new company over the course of the past year, like, that wouldn't do anyone any good. You know, another thing I've found that's pretty interesting is that people will often, because they're so afraid of that narrative, they'll often not include on their resume, companies that they didn't stay for a year.
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
And, in my personal opinion, that's actually almost more of a red flag because that, that did happen and you don't want to just pretend like that wasn't a dec- decision you made in your life. And usually, you know, if handled with grace, you can speak to the reason that you decided to make a bet, the reason that you went there, and the reason that you moved on in a way that people can typically resonate with. But I've seen executives just put that they've simply been advising for two years or something like that, when in reality, they had two companies that failed. And the fact of the matter is, I have some CFO candidates I'm talking to right now and their past three years have been short stints because they were brought in to take a company through an IPO, and then that changed. Or they were brought in to- to enter into a SPAC and then that became less of the buzz, right? So, like, these things happen and roles change and I think it's just allowing people to tell their story is the most important thing. So I would say, red flag is, for me, you should always be honest about, like, when you started, when you left a company. You know, if I see that someone still has present on their LinkedIn but they've been gone for two years and they kind of are acting like they're still there, that doesn't feel good. You just want people to give you the truth, the straight facts, so that you can support them and tell their story and represent them in a way that makes you feel like you have all the details.
- LRLenny Rachitsky
Got it. So basically, don't lie. That makes sense. (laughs)
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
That reminds me a little bit of people kind of upgrade their titles a little bit-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... because maybe they don't have an official title or they just wanna sound a little important. How do you feel about when people do that on their resumes?
- LILauren Ipsen
Yeah, I don't love that. I also don't love on the resume when people, (laughs) and some people do this and it's okay, but when people say, like, silly, vague names like... They'll say something along the lines of whatever at Reddit, like, as their title.
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
Or master of blank at this and it's like, "Okay, what- what were you actually doing?" (laughs) So-
- LRLenny Rachitsky
But I think- I think they do that to avoid recruiters reaching out to them.
- LILauren Ipsen
Exactly. As their direct target, I'm pissed. (laughs)
- LRLenny Rachitsky
(laughs)
- LILauren Ipsen
So I feel-
- LRLenny Rachitsky
Yeah.
- LILauren Ipsen
... directly attacked in that regard.
- LRLenny Rachitsky
Yep, yep. Yep.
- LILauren Ipsen
(laughs) So that's something that throws me off but that could definitely be a personal thing. And I think overall, like, f- for the most part, people don't have any other things that really just throw me for a loop and the fact of the matter is, resumes we look at less and less, especially at the executive level, and it's a lot more of allowing people to tell their story, meeting in person, talking with their different people that support them and getting kind of more of the big picture around who they are.
- LRLenny Rachitsky
I wanna talk about what recruiters often do wrong and what you've learned there, but before we get there, one last question.
- 53:39 – 57:29
Interview tips for product managers
- LRLenny Rachitsky
Do you have any tips-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... for a product manager in the interviewing process? How to be more successful interviewing.
- LILauren Ipsen
I've had this come up a few times when I've interviewed product folks that they'll speak down on their counterparts or say that, you know, the reason they weren't able to- to meet deadlines or push product in the right way was because of th- the engineering team or because of other components of the business and it wasn't them. And so I think that's never a good way to go about it. So, you know, it seems obvious but it- it- you'd be surprised how not obvious it is. So, you know, thinking about things more holistically, speaking honestly about your strengths and things that you want to continue to grow and improve upon and then being able to tell your story. Like, practice telling your story. So often people don't do that, especially when they're not looking for jobs, and then it's not until their 10th interview that they know how to tell their story and what they did and what they impacted and why they were someone to be missed when they moved on. Those are things that you wanna know how to speak to and unless it's something you've been doing or practicing, it's less natural. That's some advice I think just off the top of the head.
- LRLenny Rachitsky
Awesome. That's really good advice. One thing that makes me think about, I know... I- I wanna get to this last section, but do you think the best product leaders have their kind of story figured out in the future and work backwards from that and have a sense of where they wanna end up or just kind of take it as it goes? 'Cause I'm the latter. I just- I had no plan.
- LILauren Ipsen
Hm.
- LRLenny Rachitsky
I just want to see what- f- follow the path.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... that was presented. Do you think that is generally true for folks that end up being successful? Or do you recommend people think about, "Here's where I wanna be in five years. Here's what I need to do to get there." Do you have any guidance there?
- LILauren Ipsen
I mean, for what it's worth, I'm definitely more with you.
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
I don't know where I wanna be in five years, so it's tough for me to say. I, but I do think that typically someone that has the end goal of being a CEO will put the pieces into place to try and get there. And so it's not a bad idea if you do have an end goal of wanting to run your own thing to inch towards that. So maybe you go from being a product-specific leader to then operating in some type of GM of a business unit capacity and owning a P&L. And then although it's more of a product-oriented role, you're still getting closer and closer to that end goal of COO or CEO. So if it's something like that, then I think that naturally makes sense. I do think people can be enticed by shiny objects, so excited because it's a step up from a title perspective and things like that. And I think that's just so not important in the grand scheme of things. You could be the VP of product or CPO of what? You know? So that's so vague. (laughs) Like if someone just says, "I wanna be a chief product officer. That's the end goal," I always say, "Of what?" (laughs) Like you could be the chief product officer of your household. Is it of a multi-billion dollar consumer brand or... So I guess what I'm trying to say is work backwards from a goal for sure, but don't allow titles or valuation bubbles or other things to derail something that feels good. If you're in a role and you feel like you're making an impact and you're learning and you're growing and are excited about the work you're doing, do not allow a title of some other company to make you feel like what you're doing isn't worthwhile.
- LRLenny Rachitsky
I love that advice. So many people just chase some fancy new role, new title, new logo, and end up getting there and they're like, "Man, this sucks."
- LILauren Ipsen
Exactly. Yeah.
- LRLenny Rachitsky
This reminds me, I did a meditation retreat once, and one of the teachings there was you don't wanna be fixated with achieving a specific thing, but you wanna push your cart in that direction. Just like head in that direction-
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
... and have a s- general sense but not, "I need to be that thing and that's what'll make me happy."
- LILauren Ipsen
Exactly. I think that's exactly right.
- LRLenny Rachitsky
Awesome. Okay. Final topic
- 57:29 – 1:00:57
Common mistakes recruiters make
- LRLenny Rachitsky
is from the recruiter perspective-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... what do you find recruiters do wrong most often or miss when they're trying to attract great product talent to a company?
- LILauren Ipsen
Yeah. So this is one I feel especially passionate about because I do think recruiters have a bit of a reputation, and I think that it's for some good reason. There's naturally people that forget that these are human beings that we're dealing with every single day that have lives, have families, have careers, or ambitions outside of their career. So I think it's essential that you remember that this is another human being on the other end of things and that you should treat them with the same level of respect that you would expect to be treated. This has become even more apparent now that I have gone through some of my own recruiting cycles where I was looking for different jobs and a transactional recruiting call just will rub you so the wrong way and will make you want to put things on your resume, like I just alluded to, that say things like whatever at Reddit or what have you, because you just don't wanna deal with it. And so I think you have to be a human. You have to start with a relationship, find common ground, build rapport, listen to people. Like actually listen and remember what they say. So if someone says, "I never want to do a crypto company," and I just am only shoving crypto companies down their throat, that's just insanely tone-deaf. Or if they say, "I have this vest that I really want to be around for in May of next year," and I just keep hitting them up prior to that, that's just so not receptive to what they just said. Things like that. Make notes if easier 'cause we speak to so many people all day long, so it's definitely not easy to do. But I'll have a note on my calendar that John Kim's vest just happened in March, and then I'll be like, "Oh, okay. Might be a good time for me to, to catch up." I won't say, "Congrats on the recent vest." I'll say, "You wanna grab a coffee? Or do you wanna catch up about this?" Or, "Hey, I saw that you were speaking at this conference. Love what you spoke about with regards to this." You got to find ways to connect with people outside of just shoving them into a job. And so I would say something that I've learned and become very good at is starting with the foundation of relationship building, gaining trust from people, because once you have that, then people will hear you out on jobs, and people will listen to you and actually trust your advice from a career direction and perspective. But that takes time to build that, and it's definitely not going to be built by just chucking things at the wall and seeing what sticks with people and seeing where you can shove them temporarily. In fact, that will make them lose trust. And once you lose trust in a candidate, it's impossible to get it back.
- LRLenny Rachitsky
It's interesting how one of the recurring themes of our chat so far is just play the long game in every way, which takes more time-
- LILauren Ipsen
Yes.
- LRLenny Rachitsky
... and kind of sucks that you have to put in all this time ahead of time before you really need to get something done. But what you keep coming back to is just that's how you end up being successful as a recruiter, as a product leader, as a hiring manager, as a founder.
- LILauren Ipsen
A million percent. Yeah. Yeah. And it's really easy when you've got a quota to hit and you've got, you know, people to provide for and a mortgage to just think about the numbers, but you have to play the long game because people aren't just a commodity. It's, it's so much more.
- 1:00:57 – 1:04:24
Advice for founders looking for a recruiter
- LILauren Ipsen
- LRLenny Rachitsky
And one of the perks of working with a recruiter is they have done that already for you. And so I was gonna ask-
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
... when does it make sense for a founder to engage with a recruiter like yourself, and when should they not?
- LILauren Ipsen
Engaging with recruiters sooner rather than later in a proactive way is always a positive.... Thing. It's just, sometimes companies aren't at the stage where they can necessarily hire a full-time recruiter because of resources and how expensive it is to bring in an exec recruiter. So, you know, having someone that you can bounce things off of in a more informal capacity, bringing in someone like a talent advisor that can help in a, in a consultative way, those types of things, a million percent. Leaning into the venture firms that have backed you, which is a lot of what I'm doing right now, that is definitely areas in which early CEO founders should be leaning into that and trying to get as knowledgeable as possible. And then I would say typically series B feels, you know, series A dependent on, on the check size, and then series B feels like a good time to bring in a couple key big players if the company's well-positioned to do so.
- LRLenny Rachitsky
And bring in, meaning full-time in-house recruiters or a firm?
- LILauren Ipsen
Probably bring in a firm. Yeah. That, that would be my recommendation. I think you can bring in one or two recruiters in the early days, like seed, if it makes sense for the company and they're growing quickly, but it's all kind of case-to-case.
- LRLenny Rachitsky
The fact that you're, you're kind of off the table for most founders now that you're at GC, which is per- ... And is that true? Like, you basically at this point work for General Catalyst founders. Is that correct?
- LILauren Ipsen
I am supporting all of our GC founders in the consumer and crypto portfolio. That being said, I spend all day, every single day networking and chatting with amazing entrepreneurs, people that could be founding a company down the road and need some advice, great people that want to help in an advising capacity, so it is, I would say, 50% networking, 50% actual parachuting into portfolio-
- LRLenny Rachitsky
Mm-hmm. Got it. Okay.
- LILauren Ipsen
... supporting them.
- LRLenny Rachitsky
That's cool. I didn't know that part.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
So outside of that, what do you suggest founders look for when they're looking for a recruiter? And this is second to last question. What are signs that this is a good firm and good recruiter? Just what should you be looking for when you're looking to hire a recruiter, either in-house or a firm?
- LILauren Ipsen
I think it's important t- to provide them with some direction and then see if they can recite it back to you.
- LRLenny Rachitsky
Mm-hmm.
- LILauren Ipsen
You know, tell them the types of things you're looking for and then say, "Did that resonate? 'Cause I'd love to hear from you what you took away from that and what you think we should be looking for." And then kind of off the bat, ask them for a couple candidate ideas. You know, don't give them time to just go call other people. In real time, ask them for some candidate ideas. Where does their brain go? Who are people they would call tomorrow on this? The more that you can get that dynamic relationship formed before you even go to search, the more you can determine whether this is someone you want to calibrate with. So yeah, I think just putting them on the spot a little bit and asking them to sh- show their work rather than just sending over a deck of searches that could have been done by other partners or could have just been done by other people on their team. You want to actually understand who this person is. So that first question is testing their listening skills and their ability to actually hear what you're saying and what you're looking for, and then the second is, "Okay, now how quickly can we get calibrated on what this profile should look like?"
- LRLenny Rachitsky
Awesome. That is great advice. Very tactical. Any final
- 1:04:24 – 1:08:52
Lightning round
- LRLenny Rachitsky
words of wisdom before we get to our very exciting lightning round?
- LILauren Ipsen
This has been awesome, by the way. (laughs) I think more generally the advice is just treat people like human beings, build rapport, play the long game, and gain trust, and that takes time. And so those are the most important things from a recruiting standpoint, is being able to tap people and have them feel like you genuinely have their best interest at heart and that you care about their career and life outside their career. And so I think that's what makes for a really good recruiter.
- LRLenny Rachitsky
Simple advice but often forgotten and easy to overlook.
- LILauren Ipsen
Mm-hmm.
- LRLenny Rachitsky
Awesome. All right.
- LILauren Ipsen
Yeah.
- LRLenny Rachitsky
We've reached our very exciting lightning round. I'm gonna give you six questions. Whatever comes to mind, we'll go through them real fast. Does that sound good?
- LILauren Ipsen
Okay. Yes. Let's do it.
- LRLenny Rachitsky
Let's do it. What are two or three books that you recommend most to other people?
- LILauren Ipsen
The Power of Now and You Are Here.
- LRLenny Rachitsky
Wow. Awesome. What are favorite other podcasts that you listen to other than this one?
- LILauren Ipsen
I mean, there's tech ones, but Your Own Back Yard 'cause I went to Cal Poly, so that one hits a little close to home.
- LRLenny Rachitsky
Wow. Haven't heard of that. Cool. What's a recent movie or TV show that you've watched that you've enjoyed?
- LILauren Ipsen
Top Gun I've watched too many times and-
- LRLenny Rachitsky
The new Top Gun.
- LILauren Ipsen
(laughs) Yeah. And then TV show, oh, it's all trash reality, so I can't, I just can't tell you.
- LRLenny Rachitsky
I get that. I understand.
- LILauren Ipsen
(laughs)
- LRLenny Rachitsky
My wife has that and she can't tell anyone.
- LILauren Ipsen
(laughs)
- LRLenny Rachitsky
Yeah.
- LILauren Ipsen
That's my one secret.
- LRLenny Rachitsky
All right.
- LILauren Ipsen
Yeah. (laughs)
- LRLenny Rachitsky
Okay, great. (laughs) We'll move on, but that's great. What's a, what's a favorite ... Oh, this is interesting. What's a favorite interview question that you like to ask or maybe you've seen someone ask?
- LILauren Ipsen
I love the good strengths and weaknesses question. I think it's really good to see how people self-analyze themselves.
- LRLenny Rachitsky
What do you look for in their answer that's the sign that it's well-answered?
- LILauren Ipsen
Honesty, authenticity. Can read right through a work-too-hard answer or a perfectionist type answer. "What are your weaknesses? Let's talk about it." (laughs)
- LRLenny Rachitsky
For real.
- LILauren Ipsen
So that one I think is always a really good test of character.
Episode duration: 1:08:52
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