Alisa Cohn: Why happy isn't the leader's job, results are

1. 0:00 – 4:48

   Alisa’s background

   1. LRLenny Rachitsky0:00

      I want to dive right into talking about your advice on having difficult conversations, or like in performance review season. What do you suggest when someone's being told they're not going to get the promotion?

   2. ACAlisa Cohn0:10

      Hope for the future is so important. I know this is going to be challenging for you to hear. I'm not going to promote you, but I want you to know this: it's really important to me that you're able to succeed in your career here, and so I want to continue to help you find opportunities to build your skills, and to, you know, advance.

   3. LRLenny Rachitsky0:24

      You're big on helping leaders understand that their job is not to make employees happy.

   4. ACAlisa Cohn0:29

      They're trying to, like, be the leader who everyone loves. But what really needs to happen very often is, you know, we need to drive towards results. This employee continuing to not really do a great job at their job, you don't want to push them because you don't want to upset them, you don't want to give them difficult feedback, so you're just going to keep hoping it works out. Ultimately, that leads to the demise of your company.

   5. LRLenny Rachitsky0:50

      You have some cool advice on just how to make meetings more effective, and how to especially end a meeting.

   6. ACAlisa Cohn0:55

      My three questions to end the meeting are...

   7. LRLenny Rachitsky0:56

      (instrumental music) Today my guest is Elissa Cohn. Elissa is an executive coach who has worked with C-suite execs at both startups, like Etsy, Wirecutter, Venmo, and DraftKings, along with Fortune 500 companies like Microsoft, Google, Pfizer, and the New York Times. She was named one of the top 50 coaches in the world by Thinkers 50, and the number one startup coach for the past four years by Global Gurus. What I love about Elissa is that she gives her clients very specific and actionable advice. In our conversation, Elissa shares specific language and phrases that you can use when having a difficult conversation with your reports to make these conversations go much smoother and be less difficult, also three questions you should ask at the end of every meeting to make the most possible forward progress after each meeting, plus why your job as a leader isn't to make people happy and what you should be focused on instead, and a set of questions that she calls the founder prenup that you should talk through with potential founders to make sure that these are the people that you want to be working with for a long, long time. There's also so much more advice. If you're a leader of people or a founder, and especially if you dread hard conversations, this episode is for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Elissa Cohn. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out of the box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by Rippling, a single platform to build and scale your startup on. Rippling handles all the can't get it wrong admin work of payroll and benefits, giving you back hours every week, but it does a lot more than that. Rippling is a game changer for the entire company, with tools for HR, IT, and spend, all built from the ground up and designed to work together seamlessly. Just hired someone? Rippling makes onboarding easy, whether your new hire is sitting next to you or halfway across the world. In just a few clicks, Rippling automatically generates an offer letter, ships a laptop with the necessary apps and permissions, and even delivers a corporate card. An employee needs to update their benefits contribution? When they do it in Rippling, the change automatically syncs to payroll. CTO forgot her laptop in an Uber? Lock it remotely with Rippling. Many startups I've invested in, like Sprig, Ele.me, and ClassDojo use Rippling because it's a force multiplier for lean teams, helping them eliminate major headaches and operate their business more efficiently. For a limited time, Rippling is giving Lenny's listeners three months off. To redeem, visit rippling.com/lenny. That's rippling.com/lenny.

2. 4:48 – 12:48

   Having difficult conversations

   1. LRLenny Rachitsky4:48

      Elissa, thank you so much for being here and welcome to the podcast.

   2. ACAlisa Cohn4:54

      Lenny, it's so great to be here, and thanks for having me.

   3. LRLenny Rachitsky4:57

      I want to dive right into talking about your advice on having difficult conversations. I personally dread difficult conversations. I feel like I practice ahead of these things. I'm like, I'm going to say these things, it's going to go like this, and that never goes as well as I hope. I always say the wrong thing. Feel like this is, uh, very relatable. They're called difficult conversations for a reason. (laughs)

   4. ACAlisa Cohn5:18

      Totally.

   5. LRLenny Rachitsky5:19

      I know you work with a lot of execs on this specifically, and what I love is you've actually come up with a bunch of scripts that help people make these conversations less difficult. So how about we talk through some of these scripts that people can actually start applying?

   6. ACAlisa Cohn5:32

      Let's do that. I love that idea, and also, um, Lenny, as you just said, very relatable and also, like, not, so you're not alone. I, if I could ask you a question, if you're picturing a difficult conversation that you have had, should have, might have, and you're nervous about, it's hard for you, can you, like, summon up what's hard about it? Because it's, like, helpful to clarify. Like, what is hard about it?

   7. LRLenny Rachitsky5:56

      A great question. (laughs) Uh, I just don't want to make people sad and upset and I worry about their reaction, how to deal with that.... and them just getting really upset and mad and just like, "Oh, man. This really made things worse." So I worry about their reaction, I guess.

   8. ACAlisa Cohn6:11

      Okay. About making things worse or about their reaction?

   9. LRLenny Rachitsky6:14

      Their reaction. Just making someone upset and sad. I don't want this -

   10. ACAlisa Cohn6:16

       Making someone upset. Okay, good. And again, you're not alone about that. Just one more question on that.

   11. LRLenny Rachitsky6:21

       Mm-hmm.

   12. ACAlisa Cohn6:21

       What's the problem if they're sad and upset?

   13. LRLenny Rachitsky6:23

       Mm-hmm.

   14. ACAlisa Cohn6:24

       Like what, what does, what does that mean to you?

   15. LRLenny Rachitsky6:26

       Oh, I love this life coaching-

   16. ACAlisa Cohn6:28

       (laughs)

   17. LRLenny Rachitsky6:28

       ... we're doing. Uh, yeah. So, it's like what happens if they get sad and upset?

   18. ACAlisa Cohn6:33

       Yeah.

   19. LRLenny Rachitsky6:34

       I feel like it's s- it's stuff that I'm gonna have to deal with. It's like this drama all of a sudden, this like new fire I have to think about. And, yeah, it's like the additional work it creates and also just... I don't... Yeah. It's a good question. (laughs)

   20. ACAlisa Cohn6:48

       You can think about it some more, right?

   21. LRLenny Rachitsky6:49

       Mm-hmm.

   22. ACAlisa Cohn6:49

       And I'm not gonna put you on the spot right now, but like just to say for all of us, the reason they're difficult, to your point, they're difficult, but we're, we're putting meaning on, on things all the time. Every day, all the time. And I think it's important is, it, it's actually helpful in motivating you to have difficult conversations, but also in helping them go well if you can get to the bottom of what you're putting on top of it, what you're weighting it with. Because I can understand that. Again, you are not alone. I don't wanna make people upset. Totally. And also, you know, I would just say on the other hand, when you're enlightening someone or you're working out a situation with someone and it's difficult, if you ha- if you, uh, don't give them the opportunity to hear what you have to say, if you don't bring this up, then you're never gonna have the opportunity to help them see something differently or help them improve or help you improve the relationship or whatever it is you're trying to do. And so I can understand, it's a natural thing. Like I don't wanna make them upset. No one wants to make anybody upset. But through that upset, on the other side of that can often be a whole new possibility and a whole new, like, revelation and actually a lot of, you know, joy and freedom. And I think that we forget about all the other possibilities that come out of difficult conversations, and we just land on these really uncomfortable parts about like, oh, it's gonna be a lot of extra work or like they're gonna get uncomfortable or even maybe cry. And I think it's just really helpful to tap into what you make it mean and then also what other possibilities it could mean.

   23. LRLenny Rachitsky8:23

       I love that. And it's, it's like one thing to hear that and say that. It's another to actually, like, feel that deeply and feel like I shouldn't be as worried as I am. I think part of it is doing these enough times where you're like, okay, it's actually not so hard. And the other is having some of the support. To make this even more real, what are just like... Let's give some examples of what we say when we say difficult conversations. There's like you're not getting a promotion that you thought you would. We're gonna let you go. What other examples are like common difficult conversations that you run across?

   24. ACAlisa Cohn8:50

       Those are two very common ones. And then, of course, the most common one is just difficult performance feedback. Or, or less, what we say qu- quote unquote constructive (laughs) performance feedback, which we never mean positive. It only is the sort of things that you're not doing well. I think there are two flavors of that. One is you're screwing up, and the other is, uh, developmentally I'd like to see you add something or change something.

   25. LRLenny Rachitsky9:12

       Yes. I... And as you say that, one of the other fears I have is like them just disagreeing and me feeling like maybe I'm not, maybe it's not right, maybe I'm wrong, you know? And feeling shit, maybe I didn't see something and then just looking worse after the whole thing.

   26. ACAlisa Cohn9:26

       Mm-hmm. Yeah. And, and so then I think what's also really helpful to l- you know, p- and part of the process, we can talk about this for sure, is getting into a difficult conversation is number one, tapping into what's uncomfortable for, for you about it. And then number two, also getting your mindset right. So, to say the obvious, are you doing this to hurt someone's feelings? No. Never (laughs) . Right?

   27. LRLenny Rachitsky9:49

       The opposite.

   28. ACAlisa Cohn9:50

       That's not what anyone... That's no reason anyone's doing it. Sometimes people are giving the performance feedback or, you know, talking about something that's been bothering them in order to express themselves and vent. And actually, that is very helpful to identify for yourself, that's why I'm doing it, and then maybe not do it then until you can transform your reasoning. But at the end of the day, the hope is as a manager, the reason that you're giving someone this so-called constructive feedback is 'cause you're helping them get better. You need them to change their behavior. They'll never get promoted if they keep doing that. They'll never be successful if they keep doing that. And so, you know, it's your job as a leader and as a manager to help them out of that, you know, problem and help them do something different.

   29. LRLenny Rachitsky10:33

       The best story I've heard to make that really real for me, I think it was Kim Scott when she came on the podcast, she told this story of, I think it was Bob, where everyone just knew he was terrible and it was like everyone's just like knew he was not good and eventually the boss had a conversation with him like eight months into it and told him like, "It's not gonna work out. You're just doing a bad job." And he's like, "Why didn't anyone tell me? I didn't realize that. Like, if you told me, I would have changed." And everyone assumed he knew. And so, I think, to your point, this is to help the person. It's not, it's not to hurt them.

   30. ACAlisa Cohn11:05

       Yeah. 100%. One of my clients, um, he was running a division and one of his people was, you know, not doing it right, not doing it right, you know, not getting the, the right kind of data, the, not having to do the right kind of analysis, whatever it was. Um, we were talking about it and I said, "Well, how come you haven't had the feedback with her?" And he said, "You know, she's just gonna cry. She's just gonna cry. You know, she's older, whatever, she's just gonna cry. It's gonna be too uncomfortable, whatever." So we worked, we talked and talked and talked. I gave him a script. We really worked it out, and he agreed that he would go in and have that conversation with her, which he did. And he reported back to me and he was shaken. She cried. Of course she did. She cried. That's what he knew she was gonna do. And so she was upset and she went home early and the whole thing. The next day she came in and she said, "Thank you so much for telling me that. I wish someone had told me that 15 years ago. I think I could've had a different career." And I think that is so r- meaningful for all leaders and people who are responsible for other people to understand that y- you know, you're uncomfortable when they start crying, of course, or they have this, you know, they have this difficult reaction or whatever. But honestly, the only way you're going to be able to help someone like grow in their career and become the best person they can be is by a- by leaning into these tough conversations.
3. 12:48 – 20:20

   Scripts for performance feedback

   1. LRLenny Rachitsky12:48

      contexts. So, let's talk through some of these approaches and scripts you've come up with. What do you think would be a good one to start with?

   2. ACAlisa Cohn12:55

      Well, we can start with performance feedback, and we can just sort of take a typical example. So first of all, once you've done your work to get your mindset right, to kinda know what you're doing it, and then you just really wanna h- really be able to, be able to wrap your mouth around the words. So what that looks like is, you know, practicing, and the script could be, "You know, Matilda, I wanna chat with you about the way you're interacting with your peers. So, what I'm hearing from them is that you're missing deadlines on a regular basis and not letting them know you're missing the deadlines, and that also, you're not like c- fully keeping your team up to speed, and so they're kinda confused wandering around. Now, we both know that the most important way you can be successful here and also achieve your goals is to make sure that you are working with your peers in a way that's consistent and that they can count on you and you can count on them. So I wanted to let you know about this. I wanna certainly think, you know, hear what you have to say. But the most important thing is that we leave this discussion knowing how you're going to make sure that you're keeping your peers in the loop and also your team in the loop."

   3. LRLenny Rachitsky13:55

      Yeah. There's so many elements there that are really interesting. Just like focusing on what I'm hearing versus like just coming from you or something you've done wrong. Like, it's here's what people are, here's what I'm hearing from multiple sources. I think that helps people, okay, it's not just you and just like, "Uh, my manager hates me." It's like-

   4. ACAlisa Cohn14:14

      Right.

   5. LRLenny Rachitsky14:14

      ... okay, other people are saying this. And then I love this phrase of we both know where it's like, it's not just me telling you this. It's like you also know this. Like I, I know you're smart and you also know that this is, something is wrong here. And then this like goal of here's what we need to leave. You're like very clear call to action almost (laughs) . Of action item. Like leave this meeting with, let's just be aligned on this thing.

   6. ACAlisa Cohn14:36

      Yeah. Thanks for calling those out. I hope, you know and again my, what I'm trying to convey in my tone is also, you know what? It's Tuesday. We gotta have this conversation. I'm sure we're gonna end, I'm sure it's gonna end well. I'm not mad. I'm, like the whole point about my manager hates me, right? I'm not yelling at you. The more even-keeled and even matter of fact you can be about something that's kind of just run-of-the-mill, you know, feedback, the better. And I think it's just also, I, what I didn't say before and I think it's also important is that as you are recognizing that one of your jobs is to give us feedback is that you have to build a relationship with people so they can hear you through the lens of oh, Alyssa wants to help me. Not, oh, Alyssa hates me. It's always a problem. (laughs)

   7. LRLenny Rachitsky15:19

      Mm. Well how did you start that phrase again? 'Cause the starting is always the hardest part for me. Like how do you kick off the conversation? What was the couple sentences used?

   8. ACAlisa Cohn15:28

      I wanted to have a conversation with you about some things I've been, you know, hearing from your peers about the way you all are interacting together.

   9. LRLenny Rachitsky15:35

      Awesome. So it's not, so there's an element of don't make it feel like a huge deal, just like, let's just have, I wanna have this conversation with you about something and it's just like, let's have this conversation and here's what we want-

   10. ACAlisa Cohn15:44

       Yes.

   11. LRLenny Rachitsky15:44

       ... to leave this conversation with.

   12. ACAlisa Cohn15:46

       Yes. And I can't stress enough that it's actually really helpful to also have spent some time with Matilda or whoever, you know, saying, "Great job on the way that project landed."

   13. LRLenny Rachitsky15:58

       Mm-hmm.

   14. ACAlisa Cohn15:58

       Or, "Hey, launches, when they happen on time and they're smooth, sometimes we don't notice anything. I want you to notice we didn't notice anything. That's fantastic. You did a good job in that launch." Or whatever it is. Because then, you know, when you've had the conversation with them to give them positive feedback and point about, point out what's working, that builds the relationship so that you have the lens of oh yeah, when, when something's working they tell me. When something's not working, they tell me too. That's like how you build trust as well.

   15. LRLenny Rachitsky16:23

       (laughs) They won't wanna be criticizing them every... We need to have another conversation about what we're hearing about problems yet. Uh.

   16. ACAlisa Cohn16:28

       Yeah.

   17. LRLenny Rachitsky16:29

       Obviously if you say it the same way every single time, they're gonna feel like this is weird. Do you recommend it's like this kind of Mad Libs approach? Or is it like make it your own as much as you can? Like what are kind of the key... Or is it like here's actually how you wanna say it every time?

   18. ACAlisa Cohn16:42

       In my book and when I work with my clients, I give specific scripts and what I will regularly say when I'm working with my clients is, "Okay, so this is how I would do it." And then (laughs) you know, land it for them. But they have to make it their own. You always, you always have to make it your own, and I don't think it's a problem if doing it the same way every time. It's not like people are gonna notice, because you're talking about different topics, you know, theoretically. If you have a formula that can work for you, that's gonna motivate you to do it, that is what's important. And what's important is that it's neutral, not, you know, loading on or not, not, not venting on someone, and not unloading on someone.

   19. LRLenny Rachitsky17:19

       I love that we started with this one 'cause it feels like the most common one of just like your p- employee is underperforming and you wanna make sure they understand and adjust. What if you're not hearing something from a bunch of people? What if it's just like your perception of their writing? Like you need to work on your writing skills, or you aren't, you're coming in late. Uh, is there another b- way to phrase it where it's not I'm hearing it from other people?

   20. ACAlisa Cohn17:43

       Oh, absolutely. I, absolutely. So, I'll s- talk about writing. Um, I think it would be something like, okay, Matilda, part of your job is to be able to create these documents and I appreciate that you do them on time. What I've observed is that they can often be not as structured as I'd like them to be, and they also lack a conclusion. So what I'd love you to do is look at these three or four examples of some folks who are doing them really well and see if you can model your writing on theirs. If you need to take additional classes or if you need help in any way, let me know, but ultimately, I wanna get your writing to the level where everybody is appreciating what you bring to the table because the level of your writing really reflects the level of your thinking.

   21. LRLenny Rachitsky18:27

       Mm-hmm. Wow. I like that. (laughs) Uh, I would wanna-I want to... I'd wanna follow your advice when I... if I got that. So, the way you started that is what I've observed, which is, uh, which also is not like here's what I think, or here's what you just need to do. It's more like here's what I've noticed, here's what I've seen, here's what I've observed about what you're doing. And then it, it reminds me of, um, what is it? Uh, non-violent communication. That whole framework of just, like, focus on what you see. Not like what is wrong with them, not what they've done, yeah. I guess, is there anything that you wanna say just, like, the importance of focusing on what you've heard from people or what you observed versus maybe what people often do instead?

   22. ACAlisa Cohn19:05

       Yeah. I think... I mean, you just really said it, and I think it's such an important point. Observable facts. You know, the idea that this is not a judgment. This is not... Uh, as, sort of as less judge-y as possible is also very helpful. It makes it neutral. It's observable facts, and it's also sort of based on expectations, right? So, the writing is at a cert-... We expect it to be at a certain level, and it's not that way. And here are the reasons it's not, the specific reasons it's not. The way you interact with your peers, it's important to meet a certain standard, and here's why. Because when we all work together, we're gonna be able to execute, and when we don't, unfortunately we won't be able to. So, you staying in sync with them is important. And the observation is that they don't feel fully in sync with you. And so every time we talk about this, it doesn't become this, "Oh, I don't know, I just feel..." By the way, some things you have to give feedback on and they are kind of a feeling. And those are diff- more difficult. But you... So many things, if you do the work to really think about what is the observable data? What's my... I always ask my clients, "What's my evidence that this is happening?" And you have to spend some time thinking about it. But it's really worth it, because it makes the feedback e- easier for you to give and easier for them to hear.

4. 20:20 – 25:07

   How to respond when someone is defensive or upset

   1. ACAlisa Cohn20:20

   2. LRLenny Rachitsky20:20

      Is there anything else along the lines of this specific type of feedback that is worth sharing before we move on to a different type of, uh, feedback?

   3. ACAlisa Cohn20:29

      Well, I think just that the, the reason... One of the many reasons that people have gotten comfortable, uh, giving feedback is that somebody might get defensive or they might start crying, as we talked about. And so, I have a script also which is if someone gets defensive. Which is, you know, it's like, "I'm giving you this feedback and you're getting defensive." And I say, "Well, let's pause for a second. First of all, I want you to know that I'm telling you this actually just to make you better. Because I know how important your career is to you. I know how important the success is to you, and it's important to me too as your leader. The second thing is my observation is that you're getting a little bit emotional. I wanna know if we can continue having this conversation now, or if we need to kind of pause it. At the end of the day, we really have to have this conversation and I really wanna see you make changes, but I understand you might need a few moments to digest it." The importance of that for you is not even what you say, but that you have prepared and you are prepared for if someone has that kind of reaction. And that you don't have to yourself react to it. You know, "No, I'm not doing that. No, no, no, no." Whatever. And you can say, "Yes, you are!" Right? And now we're in a fight, and that is not cool for anybody. It's certainly not cool for you as a leader. So, it gives you the opportunity to recognize that you have another tool in your toolkit rather than just react.

   4. LRLenny Rachitsky21:48

      So, if, if you find yourself feeling defensive or they're just not hearing and just fighting back. The tool is just pause. Let's just pause for a moment. A- and it feels like there's kind of two parts to what you just shared. One is, uh, remind them why this is im- why this is important to them and why you're talking about this. And then, two is if there's just, like, emotions kind of taking over, give them a chance to, like, let's just pause and maybe come back to this, because maybe you're not in the right state yet, right now, to, to listen.

   5. ACAlisa Cohn22:19

      Yeah, exactly.

   6. LRLenny Rachitsky22:20

      Sometimes people get upset when you mention, like, you're getting emotional or... I don't know. Is that a thing that you deal with of just like, "How dare you say I'm feeling emotional?" (laughs)

   7. ACAlisa Cohn22:29

      (laughs) Right. I'm not emotional. Why are you talking about emotional?

   8. LRLenny Rachitsky22:31

      Yeah.

   9. ACAlisa Cohn22:31

      Right, exactly. Um, yes. Of course. That when someone's crying, they're obviously getting emotional. When they're defensive, it's possible that you might want to use a different word. Like, "I can see that this is really upsetting you." Or, "This is really triggering you." Or, "I can see that, like, the temperature, uh, between us has just changed." You could say something like that. I do think, also, it's helpful to know your people. Because sometimes you're, you could realize that, like, actually they can deal with that. But then sometimes you have to really find the delicate words that you need to use to pause the conversation.

   10. LRLenny Rachitsky23:05

       Yeah. And it's... And I find as... To your point, it's helpful to you too as the person giving it. And I feel like sometimes you may be feeling like I should just pull back and, like, maybe I'm wrong. Maybe, maybe they're right. Maybe I should stop. And instead, this gives you a chance to know, um, actually, I can't. I can't pull... Like, I need to stay strong about what I believe. 'Cause I... You know, you put so much thought and effort into this already. It's unlikely you're just like, "Oh, totally wrong about what you're saying."

   11. ACAlisa Cohn23:30

       Yeah. Exactly. There's something going on. There's something going on. And then also, the whole point about it being a conversation is that actually it's a conversation. Actually, Lenny, if you have a different point of view, I would like to hear it.

   12. LRLenny Rachitsky23:40

       Mm-hmm.

   13. ACAlisa Cohn23:40

       Let's talk about it. But we can't keep going on like this where I don't feel like I can count on you for, you know, for whatever it is that we're talking about. So, we need to have this conversation and recreate a set of expectations between ourselves. Ultimately, that kind of conversation has the potential to really build a relationship and build trust. And that's another reason I encourage everybody to get over their discomfort and to lean into having these conversations. 'Cause on the other side of that is a much better, stronger connection.

   14. LRLenny Rachitsky24:09

       And especially if you do them well. (laughs)

   15. ACAlisa Cohn24:11

       Yes.

   16. LRLenny Rachitsky24:12

       Following this advice. Uh, and so, okay. So again, with the... If somebody's feeling defensive, can you again say how you start that? If you notice that. And then I'll... And then I'll highlight the two elements again of the...

   17. ACAlisa Cohn24:25

       The... So the, the, the way to, to, to pause is to actually say, "Let's just pause for a second, 'cause I'm feeling the energy has changed. And I can see that you're getting a little bit heated by what I'm saying. And I want you to know that I have no intention of upsetting you. I just wanna be able to talk to you about the things that are gonna help you in your career."

   18. LRLenny Rachitsky24:45

       Awesome. And, uh, and I love, again, just a reminder of here's why, uh, this is important to you. Like here's the benefit to you and why this will help you. And then it's like, okay, let- let's just maybe take a pause and come back to this conversation if you're feeling like this isn't the best time. Awesome. Anything else along that line before we go to another type of-

   19. ACAlisa Cohn25:02

       I mean, I could talk-

   20. LRLenny Rachitsky25:03

       ... hard conversation?

   21. ACAlisa Cohn25:03

       ... all, all day about (laughs)

   22. NANarrator25:05

       (laughs)

   23. ACAlisa Cohn25:05

       ... this, of course, but I'm happy to move on.

5. 25:07 – 31:00

   Scripts for handling promotion disappointments

   1. ACAlisa Cohn25:07

      (laughs)

   2. LRLenny Rachitsky25:08

      Well, let's pick another topic. I know you have kind of five buckets and types of conversation. Maybe the promotion one that feels like, I think we're like in performance review season, feels like these are happening a bunch. What do you suggest when someone's being told they're not gonna get the promotion they expected or wanted?

   3. ACAlisa Cohn25:23

      That, that can be... Of course, that's challenging. So again, getting your mindset right, recognizing they're disappointed, they're gonna be disappointed. Recognizing how you felt the time that y- when you didn't get a promotion or whatever. And so kind of coming to it with some compassion, and also you have to get your reasoning right. So sometimes people think they should get a promotion 'cause they were here for a year or whatever. Sometimes people think they should get a promotion because they're the only internal candidate who's qualified for this, or they might have a sense of themselves, you know, ex- succeeding or achieving that is, you know, more inflated maybe than you see them. So you know, trying to think about where they're coming from. And then the conversation is just, "Matilda, I know this is gonna be challenging for you to hear. I know you were hoping to get that promotion, but I wanna let you know that we are gonna actually be looking for an external candidate. I want to give you a few thoughts about why. First of all, in discussing this with, you know, my peers, I'm realizing that we're needing, we need someone who has done this role multiple times in the past and has that experience. Number two, I think it's really important that they have an expertise in a specific realm that, you know, we've identified is really important. So for those reasons, we're gonna bring someone in from the outside, not gonna promote you, but I want you to know this. Number one, it's really important to me that you're able to succeed in your career here. And so I want to continue to help you find opportunities to build your skills and to, you know, advance. And then number two, when we bring this person in, I'm committed to finding someone who's a great people leader, who's gonna help you build those skills."

   4. LRLenny Rachitsky26:54

      So a few elements there that stood out to me. One is just being very upfront and not burying the lead. Telling them very early, "Here's what I've decided," and like as you said it, I could see my heart sinking immediately when I feel that. So at least that's like over, and then it's here's why, and that starts to help you feel like, okay, I get it. Like I understand at least how you thought about this. And then there's the hope for the future you're painting of here's how I can get there eventually.

   5. ACAlisa Cohn27:21

      Yes. That hope for the future is so important, and, um, I think sometimes we're so, such in a rush to kind of deliver the bad news that we forget there's a human being over there who needs hope for the future, and hopefully if they're a good per- if they're a good employee, hopefully they have hope for the future.

   6. LRLenny Rachitsky27:36

      I love that. Is there anything else to that script that you think is worth highlighting or do you think I touched on the key elements?

   7. ACAlisa Cohn27:41

      I think you touched on the key elements.

   8. LRLenny Rachitsky27:42

      Okay. And again, the way you started is like, "I have some bad news for you," or, "I have some disappointing news for you."

   9. ACAlisa Cohn27:48

      Yes. 'Cause it's just the truth right?

   10. LRLenny Rachitsky27:49

       Just get right into it.

   11. ACAlisa Cohn27:50

       Yeah, just get right into it. Yeah. By the way, the other piece on that might be, if it's appropriate, let's, "I'd love you to digest this information, and then let's talk about it again next week, you know, to sort of see what you've come up with or see how you feel about it." Because you know, you want to send... This is not the script, this is for me to you. You want to send the I care about you message, because that's the other thing. It r- in the workplace, people, you know, uh, they're go- going through all their feelings, all their emotions, disappointments. They're gonna go home and tell their spouse, you know, didn't get the promotion or whatever. It's gonna loom large, it's gonna be demoralizing. When you as a leader signal a lot, I care about you, I care about your feelings, I care that you're disappointed, I care about your career, you are always going to be able to help people stay re- you know, resilient in the face of setbacks and ultimately do, you know, do extra work, like, like do the right work for you and be engaged in your company because you've spent the time and energy making sure they know that even when things are not going their way, they have an ally in you.

   12. LRLenny Rachitsky28:56

       What do you do if they just disagree, if they're just like, "But I do have those skills and I don't think this is fair"? Thoughts on responding to that sort of feedback. I guess that's the defensiveness stuff.

   13. ACAlisa Cohn29:06

       Yeah, that's the defensiveness stuff. And you know, again, I hope you've done your homework (laughs) to identify that actually that person doesn't have those skills, and if there is a back... So like for example, but I do have those skills, or s- or sometimes people, I think more, even more often, they don't respond to what you just said. They will instead explain to you that they've been here for a year, or (laughs) they're like, or, or like they're the only internal candidate, or their peer got promoted, right? They'll sort of explain to you things which are not part of your decision-making process, and then it's helpful for you to say something like, "Yeah, listen, Matilda, I really understand that you were thinking that after a year you'd get promoted a- around here, and you know, in the past, I do think because of the stage of our company, probably people have been promoted at that period. That's not the place we're at right now. As we scale, we really need to think about not just what we need for today and tomorrow, but for the future, and that's why I want these specialized skills in here. I think it's gonna help the entire company." So that's an example of a discussion that you could have. You know, "I do have the skills." "That's kind of interesting. Let's (laughs) you know, like I'd love to hear what you see as those skills," and it's not a problem to have that conversation right there and then, but if there's like a, "Yes, I do. No, I don't. Yes, I do. No, I, no, you don't," that pushback is never productive, and so that's where you want to probably again take a pause and say, "Listen, I totally hear you. You're, you and I have a different point of view about this. I'm not sure if it's productive to continue discussing right now. Let's talk about it again in a week, but I also want you to know this is a deci- decision that I've made."

   14. LRLenny Rachitsky30:39

       I love the, when they come back to you and like, "But here's X, Y, Z," and you're like, "That's not what I was saying necessarily," I love that you basically mirror back, "I hear what, like I understand you believe... I understand you've been here for a year. I understand you're the only internal candidate." Like, making them feel very heard. That's a really powerful mechanic there. That is a good tool.Is

6. 31:00 – 35:44

   Scripts for handling terminations

   1. LRLenny Rachitsky31:00

      there another script that you think might be helpful to talk through that is a common hard conversation people have?

   2. ACAlisa Cohn31:05

      Well, the hardest conversation is firing someone. So- (laughs)

   3. LRLenny Rachitsky31:09

      (laughs) Let's do it. Let's get into it.

   4. ACAlisa Cohn31:10

      I know. So let... I'm willing to, to get into it. I just want to say two things about that. First of all, when you're firing someone, the hope is that you've... It's not a surprise to them. You've had multiple conversations with them that they're not living up to your expectations. It's, it's essential because the truth is, you want to create a culture where people are not surprised by being fired. Beca... And that's not even true for this one person you're dealing with. That's true for the entire company. So just kind of getting in the mindset of recognizing that if you shied away from these conversations, kind of like you are the problem here and you kind of have some catch-up to do. The second thing is that before you fire someone, I think it's helpful to have the conversation before the firing conversation because, you know, something you said, Lenny, is like, "Oh, but maybe I'm wrong, (laughs) you know, maybe I'm not sure." And that bleeds into, "Maybe I haven't been clear with this person." So you want to... 'Cause then regularly with my clients I'll say, "Okay, have you been crystal clear about what you need from this person?" And what they always do is the hand motion. Like, "Well, sort of," (laughs) or, "Well, s- maybe," which means no, which means, "No, you've not been crystal clear," or you don't perceive you've been crystal clear. So, the way to make sure that you're crystal clear is by having the conversation before it comes to that. And what that looks like is, "Listen, Matilda, we have to have a difficult conversation right now. I've talked to you multiple times about coordinating with your peers and not having them surprised about missed deadlines, and I've talked to you multiple times about keeping your team in the loop on different things. After six months of these conversations, I want you to know that the peers continue to feel like th- you're operating on your own without coordinating with them, and I continue to hear from your team that they're not fully on the same page. I need you to know that this is very important. I need you to fix this within the next 30 days. Otherwise, I'm sorry to say, we're gonna have to find way, a way to part ways, 'cause I can't keep this going with you. I know you have it in you to change. I value all you bring to the table, but if you don't fix these things, we're not gonna have a future together."

   5. LRLenny Rachitsky33:19

      That is very crystal clear.

   6. ACAlisa Cohn33:20

      Yes. Crystal-

   7. LRLenny Rachitsky33:21

      (laughs)

   8. ACAlisa Cohn33:21

      ... clear.

   9. LRLenny Rachitsky33:22

      Yeah. Okay. So-

   10. ACAlisa Cohn33:24

       What do you think of that?

   11. LRLenny Rachitsky33:25

       Yeah. That was great. So it starts with, uh, being upfront. "This is a difficult conversation." Just to set expectations. They're like, "Oh, shit." And then like, uh, it, it seems like you come back to again, multiple times this happened, like observing, "Here's it's happening, it's happened multiple times, I keep hearing multiple from multiple people, continues to be a problem." Uh, and so it's just like, "I need you to know," and you're just like very clear, "Here's what will happen if this doesn't change."

   12. ACAlisa Cohn33:52

       Yes.

   13. LRLenny Rachitsky33:52

       Yeah. And I love that you also give them a little... Like, there's always that, uh, hope for who they are and how you see them as... They're not, like, worthless. It's just like, "You are great at a lot of things. You have these skills, you're great at blah, blah, blah. But still, this is a big problem." And it... And y- and it's like communicating how critical this is.

   14. ACAlisa Cohn34:08

       Yeah.

   15. LRLenny Rachitsky34:08

       Being very clear about that.

   16. ACAlisa Cohn34:08

       And it's a deal breaker. It's a deal breaker.

   17. LRLenny Rachitsky34:10

       Yeah.

   18. ACAlisa Cohn34:10

       Right? Like if you, you can't... You have so many talents, but if you can't do these two things, then it's a deal breaker for all of us.

   19. LRLenny Rachitsky34:16

       Yeah.

   20. ACAlisa Cohn34:16

       And I think it's important to really sort of see that both... Sometimes people think, "Well, but I'm so talented." Yeah. But your talents are not gonna make up for these two deal breakers.

   21. LRLenny Rachitsky34:25

       Yeah. Uh, and I feel like I, I know we were gonna talk about like the firing conversation, but I think this is even more important than that. 'cause hopefully this addresses the problem and you don't need to fire them, which is more valuable.

   22. ACAlisa Cohn34:36

       Yes. (laughs) Yeah. Hopefully. But even if you do, it's actually easier because you've, you've already had the conversation, right? They're not surprised. It's clear. We've had the discussion.

   23. LRLenny Rachitsky34:46

       Yeah. So basically the script is like, "We're getting... I have a... This is gonna be a difficult conversation. I've seen multiple times this thing and we've talked multiple times and it's still not iss- fixed. And here's what I just want to be very clear about." Is there also a script you have for just actually doing the firing? Or is that less scriptable?

   24. ACAlisa Cohn35:05

       Uh, well, the script for doing the firing is again, please everybody talk to your HR professional. Talk to your lawyer. (laughs) Okay. I'm not a lawyer, (laughs) right?

   25. LRLenny Rachitsky35:13

       Yeah.

   26. ACAlisa Cohn35:13

       So you have to like make sure that you're all buttoned up on what you're gonna do. But the conversation is actually very simple, which is just, "You know, Matilda, we talked about this multiple times. The last time we had this conversation, I told you I needed you to make these changes. You haven't made these changes. And we're gonna, we're gonna part ways. So I have here, you know, Sarah from HR or whatever, and we're gonna talk through the logistics of that. I'm happy to have a longer conversation with you, but I want you to know we've made the decision to terminate you."

   27. LRLenny Rachitsky35:42

       Feels very reasonable to me.

7. 35:44 – 38:49

   The importance of positive feedback

   1. LRLenny Rachitsky35:45

      (laughs) Is there anything else along these lines?

   2. ACAlisa Cohn35:47

      I think what I want to say is that the conversations you need to have to work... Have at work are not just difficult conversations. What I call them is sort of delicate conversations because what I think people also shy away from is just simple praise, specific praise. And I think it's really important to get in the habit of pointing out what your people are doing well as carefully as you need to prepare for pointing out what they need to improve. And sometimes leaders feel like, "Yeah, it's all working, it's all working. I don't have to tell you or if I do tell you, it's kind of like, 'Good job.'" Right? One time a leader or a, uh, a manager I was, I was doing a training program, she said, "I don't like getting positive feedback. I only like getting negative feedback." And I said, "How come?" And she said, "Oh, you know, positive feedback is just like, 'Oh, good job.' Negative feedback, you can learn something from, you get something from it." So the positive feedback should have the same standard, which is, "I saw the way you run that, ran that launch. It was fantastic. All these different benefits came from it. You're so organized. You know, keep, keep doing that." Or, "The way you're keeping your peers in the loop, considering you've only been here three months, is extraordinary. I've never seen someone so communicative. It's fantastic. Keep, keep doing that. That's really working for you."If you do that often enough, you do get in the ha- first of all, it's positive, obviously. You become in the habit of getting better at positive feedback, which is extremely motivating to people at work. It helps them see their progress, because that person I just mentioned, she's like barely keeping her head above water and, you know, she's having trouble fitting in or whatever. But you come around and point out the things that are working, again, it's very morale boosting, she knows where she stands, and then one day, if you have to give her these difficult, you know, messages, you've already sort of laid the reservoir of goodwill.

   3. LRLenny Rachitsky37:37

      I love giving positive feedback. It's so much, it's- it's obviously so much easier, but to your point, it's like you have to really think about how to do it well, it's not just like a, it's not that easy, if you do it well. Which is a really good point. And we almost need scripts for how to give really good positive feedback and have great conversations. (laughs)

   4. ACAlisa Cohn37:52

      Yeah.

   5. LRLenny Rachitsky37:53

      That's interesting, there's less demand for that. How do I have better great conversations around complimenting people?

   6. ACAlisa Cohn37:58

      Right. Right, true.

   7. LRLenny Rachitsky37:59

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8. 38:49 – 44:55

   Understanding your job as a leader

   1. LRLenny Rachitsky38:49

      I want to go on a little bit of a tangent. Something that, it's kind of touches on all the things we've been talking about, which is you're big on helping leaders understand that their job is not to make employees happy. What is, what is your job instead? Why- why do people think this is their job to make their employees happy, and what should they be thinking instead as their job as a leader?

   2. ACAlisa Cohn39:08

      First of all, I work with a lot of founders. And so don't forget that the entry level position for founder is leader. And they haven't, they've often not had a lot of other experiences being a leader or a manager. And so they're just doing the best they can. It makes sense, right? And they kind of get all this information from other people and their HR leader, you know, wants to have a happy, engaged, you know, workforce, and they don't want to upset people for all the reasons we talked about why you don't want to upset people. Nobody wants to upset people. And so th- there's this idea of, you know, we're trying to now be the- the- they're trying to now be the leader who everyone loves and makes people happy. So they would often bend over backwards to make people happy, to keep people, you know, their morale up. But what really needs to happen very often is, you know, we need to drive towards results. And the way this system is working is not gonna drive us towards results. Or, you know, this employee, you know, continuing to not really do a great job at their job and not like really pushing themselves and you don't wanna push them 'cause you don't wanna upset them, you don't want to give them difficult feedback, so you're just gonna keep hoping it works out. Ultimately, that leads to the demise of your company. I mean, ultimately, right? If you're a startup. If you're not in a startup and you're a lar- large company, it still is very subpar performance, obviously, and you're dancing around hoping and praying they're gonna get there, and they don't really know there's a problem. And so I think it's very misguided for leaders to have this notion that their most important role is to keep people happy, is to create like this, you know, high engagement workforce. High engagement workforce is great. I think what that comes from is winning culture, which means we're set up for success, we got the structure for success, we have the culture for success, everyone understands their role, they know the impact of their role. So doing like the work to figure out and help them figure out the impact of their role, and that when they work together and achieve these milestones, they win. And then we celebrate the wins, and then we do it all over again. And when you create that kind of a workforce, I think it's much more dynamic, even though sometimes in doing that, you have to redirect people and ruffle their feathers.

   3. LRLenny Rachitsky41:26

      Essentially, the way I think about it is like, you think making people happy is not having hard conversations, not pushing them, when really, it's almost working backwards from if we win and are killing it, people will be happy. And what does it take to do that?

   4. ACAlisa Cohn41:41

      100%. And then the right people are gonna want to join your team.

   5. LRLenny Rachitsky41:45

      Mm-hmm.

   6. ACAlisa Cohn41:45

      People who like to win and like to get results.

   7. LRLenny Rachitsky41:48

      Is there like a story, an example of a founder you worked with or does- that comes to mind of this kind of where they thought this was their approach and then they shifted? Or is there kind of a pattern you see often?

   8. ACAlisa Cohn41:56

      Uh, one company comes to mind, one leader I worked with. Sometimes I think to myself, like if I'm writing a book, the book would start with, it all started with the avocado toast. (laughs) Because, you know, like he wants to do right by his workforce, and so, you know, they have avocado toast at 10:00 P- 10:00 AM, like tea time kind of a thing, and it became this great ritual where people would kind of like hang out together, and that was great. And then that turned into, you know, other like longer periods of just hanging out together. Again, these are good things, and that turned into, you know, evening socials, and everybody was enjoying spending time together, but they continued to be not fully clear on what they were actually supposed to do, and there began to be kind of a cliquey, gossipy culture of like who's in and who's out. And that would take up a lot of the socialization time discussions. So rather than talk about expectations about the work and about results, you know, and again, the results were not showing, so like it wasn't a lot to celebrate, they started a- a culture committee. So they had a culture committee to talk about how we can make people happier around here.And you can imagine, there's now layers and layers of things where we're trying to focus on, you know, engagement, and we're trying to focus on the employees having a great experience, and the leader I'm working with is completely sincere and actually wanted to have a great workplace. But the, I think the misguidedness was that, you know, he hadn't done a great job setting expectations. He had not done a great job of, quote unquote, "codifying their culture." 'Cause culture is not just avocado toast and working together and having socials. Culture is, you know, things like, we go the extra mile. Or culture is, you know, we make sure ... Or it could be, we measure twice and cut once. You know, those are kinds of things that are really about the way we get work done around here. And certainly, a focus on results is, you know, like, a- are we following the process to then get the revenue and to then build a profitable company? Or are we just kinda hanging out together? So, he had to come to terms with his own discomfort of addressing this with employees, and his own discomfort in being like a corporate drone of like, oh, expectations (laughs) and like, you know, w- in the workplace and how we do things. And, you know, it turned out, that's the whole thing with coaching and w- with working with people, is that you kind of see what their underlying assumptions and beliefs are, and there's a reason everyone does what they do- the way they do. So there's a reason he's doing what he's doing. We had to come to terms with that, and then he had to really courageously make some changes about the way he was operating. And ultimately, they had to part ways with one or two really toxic people who were kind of creating this gossipy culture and making people feel not included, and not focused on results. And then when they all got on the same page, they were able to gain a lot more traction.

9. 44:55 – 49:38

   Recognizing your own blind spots

   1. ACAlisa Cohn44:56

   2. LRLenny Rachitsky44:56

      I feel like a lot of leaders and founders can relate to this, of wanting to create a great culture and keep it nice and friendly and everyone's a family, and then things don't quite work out often in those cases, and there's a shift to, okay, we actually need to (laughs) make a business that works. It always reminds me-

   3. ACAlisa Cohn45:12

      Right.

   4. LRLenny Rachitsky45:12

      ...Sheryl Sandberg came to talk at our B2B once, and people are asking like, "What do you do with all this ... We're just like constantly in chaos. Things are always reorging, we're changing, just never ... Like, I'm on different teams every six months. Our goals are shifting. What do you do with all this ... Our culture's changing as we grow." And she's like, "That is a sign of hyper growth and success, and the opposite is even worse, when you are not growing. And you don't want that. And so you should be happy this is the challenge you're running into."

   5. ACAlisa Cohn45:41

      I love that. It's so true.

   6. LRLenny Rachitsky45:42

      So along these lines, you talk about how a lot of founders have to come to terms ... And it's not just founders, it's just like execs and leaders you work with, have to come to terms with, "Here's what I thought leadership was gonna be and how to be a great leader, and here's what it really is." Is there anything more there that you find is like commonly the, the ... what they're wrong about, or what they miss and what they have to realize?

   7. ACAlisa Cohn46:01

      Yeah. And, you know, I think as we grow as leaders, we all have to realize our own, you know, blind spots and kind of the difference between what we thought and what actual, what is actually going on. So, I worked with a founder who, you know, what she, who she wanted to be was a visionary leader. Which is fantastic. I love that. And she was an incredibly visionary person, very inspirational. But what she didn't see is that what her company needed was somebody to structure and hold people accountable, help them create goals, and, you know, achieve milestones, and course correct when they got off cur- off, off-course. And she'd be very frustrated when all those things happened, where people got off course, people didn't have goals, people weren't structured to work together. But what she didn't realize was that was e- that was, in one way or the other, her job to make that happen. Now, maybe she needed to have, and I would talk to her a lot about this, a partner, like a COO or, you know, somebody else who could be the person who would be, you know, sort of managing the internal while she got to be more visionary and inspirational. But ultimately, it was her job to make sure that that was in place, and she didn't sort of see that, and she did not adjust her style. And so like, there's a lotta wheel-spinning that happens from that, even though, by the way, she was an incredibly inspirational person, and an incredibly inspirational leader. And she meant so well, it was not, um ... There was nothing malicious about it. It's just that she didn't see the situation for what it was and then adjust.

   8. LRLenny Rachitsky47:30

      Reminds me, we had a, this, uh, coach on the podcast, Joe Hudson. And he had this phrase that I think a lot of people use, but it just stuck with me, "What you resist, persists." So if you hate confrontation, you're gonna have more, much more confrontation (laughs) than if you hate, yeah, structure. Like actually, this reminds me, Joe Gebbia at Airbnb was very anti-process at the beginning of Airbnb. He's like, "We're not gonna have a process. I hate process. We're gonna run ..." That's the big company stuff, and then it just, it's chaos constantly. (laughs) And then eventually it's like, okay, we need to have a s- we need to have some process to how we build things.

   9. ACAlisa Cohn48:03

      Yeah.

   10. LRLenny Rachitsky48:03

       And so, it's interesting. A lot of people have to realize the thing they think was bad is actually, oh, I see why people do it this way.

   11. ACAlisa Cohn48:10

       Yeah, totally. Actually, I'd like to say something about that-

   12. LRLenny Rachitsky48:12

       Mm-hmm.

   13. ACAlisa Cohn48:12

       ...because so many ... Like, founders are kinda mavericks. And they come into a situation and, or you know, they, they start up this company, and they want to do things their own way. And that's fantastic, otherwise they wouldn't be a founder. That's actually fantastic. And m- so many of the founders I've worked with want to reinvent leadership, right? They wanna have it with no process, they wanna have no hierarchy, they wanna have autonomy, whatever it is. And my feeling is like, God bless, you should absolutely try to do that. (laughs) But at the end of the day, what happens is they kind of invent for themselves the understanding that they need to have process, hierarchy, roles and responsibilities, goals, OKRs, whatever it is. And I think it's helpful sometimes to go through that, that, that fire of thinking we can do it a different way. But ultimately, I think that the ways to, like, structure a group of people and get them organized so they can win, are kind of like well-trod. And I would say that it's helpful to get through that stage quickly, so that you don't have to c- constantly reinvent the wheels of, of leadership.

   14. LRLenny Rachitsky49:19

       Such important context. Like obviously, w-One of the, like the most successful founders come up with, have first principles thinking into how to do stuff. And oftentimes, they find something no one has ever thought about. So it's always this balance of like try a bunch of stuff. A lot of it won't work. Some of it was what will help you win. And I think that's a really good point.

10. 49:38 – 55:57

    Three vital questions to ask in every meeting

    1. LRLenny Rachitsky49:38

       I want to get into a couple more tactical things that you, uh, often work on with founders. One is running meetings. Meetings come up a lot on this podcast. People hate them. People love them. They're some are great, some are bad. Most are bad. Uh, you have some cool advice on just how to make meetings more effective and how to especially end a meeting to help you move forward. Talk about what your advice is there and just generally any advice for better meetings.

    2. ACAlisa Cohn50:01

       Yeah. I'm one of the people that loves meetings. (laughs)

    3. LRLenny Rachitsky50:05

       (laughs)

    4. ACAlisa Cohn50:05

       Or I should say I don't love meetings. I love the potential for meetings. I like we all have smart people in the room. We like have the potential to talk about these great things and make decisions and unfortunately don't go that way. So what happens often, I mean, there's so many downfalls with meetings. But one thing that happens is we keep meeting. Either we make decisions or we don't make decisions, but then we come back to meet again and we don't have any continuity from the last. So then we re- remeet and we re-decide and that is a big problem. So my three questions to end the meeting are, what did we decide here? Who needs to do what by when? And who else needs to know? And if you can capture those, right, art- like articulate those as deliverables, I promise you, you're gonna have better meetings.

    5. LRLenny Rachitsky50:51

       Okay. So it's what did we decide here? Who's gonna do what by when, so basically action items with dates. And then who needs to know about what we decided here? Is that, is that how you put it?

    6. ACAlisa Cohn51:01

       Yes. Who else needs to know? You know, there's so many executive teams that I've worked with and at first they just, they go into their room. They have their meeting. They make their decisions. And then they leave. (laughs) And they don't tell anyone, "I made this promise for my team that you guys need to kind of go do," or, uh, we decided on a policy of some sort and we forgot to tell everybody. And again, no, absolutely no maliciousness. Just that they forget or they're too busy and there's not part of the protocol and the process inside of the company that encourages and, and really insists that people share important information, so cascading that down. But even the first question, what did we decide here? If you really go around the room at the end of a meeting, there's six people in the meeting let's say, and you say to everybody, "What did we decide here?" And they all write it down, you will get six different answers, even if they were in the same meeting. I just, I love that. It's so powerful, but also so helpful to really raise that up to surface that and then to figure out what to do about it.

    7. LRLenny Rachitsky51:58

       I love that you highlighted that. I was gonna say exactly the same thing that like, yeah, you, everyone in their head has the thought of here, oh yeah, here's what we decided and to your point, it's often not the same. (laughs) So is the advice here, is this like a template or something you fill out at the end of a meeting or is it someone's job to make sure these three things happen or how do you op- operationalize these three questions?

    8. ACAlisa Cohn52:19

       I like it that it's someone's job, the person that I sort of think of as the meeting czar. And typically that's somebody who enjoys follow-up, who enjoys, you know, putting lists together and, and putting things into boxes and whatnot. And there's usually someone like that on the team. And so then it's kind of exciting for them to be the, the follower-upper. Um, but one way or the other, so you could use a template. I think that actually baking it in as a ritual to the meeting, 'cause the other thing about meetings is that we never have enough time. We go right to the end and we don't leave the five or 10 minutes at the end to make sure that we ask these three questions and make sure that we have an understanding of what the follow-through is on these meetings.

    9. LRLenny Rachitsky52:57

       What I'm imagining is s- say it's the product managers put this doc on the screen in the meeting as the meeting's ending and just have it filled out basically and just confirm, does this look good to everyone?

    10. ACAlisa Cohn53:09

        Love that. That's a great way to do it. By the way, what's, well, I just would say what's interesting about that is that if we, if we ask people what did we decide here, I think there's value in just asking that question in particular because somebody might say, "We decided," I don't know, something. And other people would say, "No, we didn't, but that's actually a good idea. It sort of crystallizes what we did talk about in a more comprehensive way." I think there's value in raising the differences and I think there's value in like stitching those together. So just putting it up on the board is good, especially if you're out of, if you're running short of time. I worry that somebody might not s- might not weigh in and say, "Actually, I have a very different point of view what we decided here." So maybe it's also about building the culture to break in and say, "No, that, that's not what I see. Let's, let's spend some time on that."

    11. LRLenny Rachitsky54:03

        Let's actually spend more time on this 'cause this is really, I think really, this specific detail I think could be really powerful if you do it right. So say you're, say the PM in the meeting. Who do you ask? Do you say to the room what did we decide here or do you look at like the most senior person 'cause you know, like otherwise it feels like it could just lead to a whole discussion the last couple minutes, which I guess could be valuable, but who do you point this question to?

    12. ACAlisa Cohn54:24

        Yeah. So I picture this for like let's say a six-person executive team meeting, which means everyone go around quickly and say, "What did we decide here?" Now, if you're in a meeting with a large executive team, which I do work with sometimes, or non-executive team like a, you know, a group of some sort, then you probably want to get a few people just to like I would just even say as a facilitator, two or three people. "Okay, two, three people, what did we decide here?" And if you can kind of get common, great. That's fantastic.

    13. LRLenny Rachitsky54:52

        Got it. Okay. So if it's a small meeting, you go around the room and everyone just shares here's what we decided here and they could just be like, "Yep, he's got it," or, "She's got it." Awesome. Okay. This is great. Uh, so the advice here is next time you have a meeting, especially an exec meeting, just at the end of the meeting, you, you, the listener of this podcast just ask, "Okay, everyone, let's just make sure we're on the same page. What did you decide here? Uh, who needs to do what by when?" And then everyone kind of chimes in and you're writing this in this doc and then, uh, what else? Well, who needs to know about what we decided here?

    14. ACAlisa Cohn55:22

        Yeah. Lenny, I love that because also like do you have to be the leader of the meeting to do that? No.You could just be the person in the meeting and just chime in and just start it yourself. And if you do that and everyone kind of picks it up, it can become a ritual just by virtue of your own agency. So I love that you just encouraged everyone to do that.

    15. LRLenny Rachitsky55:42

        And this is how you become a leader, is you just start doing these things and people are like, "Oh, Alyssa's so helpful. She's just on top of it. I feel like I could... Every time she's in the meeting, the meetings go better, we get things done." So I think just doing the thing that is useful to everyone is how you move up.

    16. ACAlisa Cohn55:56

        Exactly.

11. 55:57 – 1:08:24

    The founder prenup

    1. ACAlisa Cohn55:57

    2. LRLenny Rachitsky55:57

       Amazing. Okay. Another topic that I know you spend a lot of time on is something you call the founder prenup. And what I love about this is a lot of the problems that a company... trickle down from the founders having their challenges with each other. And I- I- I started a company in the past and it's, I don't think people realize how in- significant this decision is in your life. It's basically you're marrying someone (laughs) in a business context and you're s- stuck with this person for a long time, and you basically came up with a prenup, which is a set of questions of just things you need to talk about to make sure you're aligned before you start this company. Is there any context around this thing before we talk through actually the questions that you recommend people talk through?

    3. ACAlisa Cohn56:41

       Well, I just want to reiterate what you just said. Per- exactly right. And it turns out that, you know, according to Noam, Noam Wasserstein, 65% of startups fail because of conflict with founders or the founding team. So it's really essential to get this right, and I agree that people step into this relationship with a lot of, you know, (laughs) with u- with a lot less care than they should, and i- you know, it... bad things can happen because you haven't done the work of getting to know each other before you decide to co-found.

    4. LRLenny Rachitsky57:12

       Yeah. Like, it's so easy just to like, "Yeah, I'll start a company. We got this cool idea. Let's just do it. It's gonna be so awesome." And then (laughs) you don't realize how much you're committing to and how often things don't work out because of that quick decision. And oftentimes it's like friends, you know, and then it becomes even more challenging 'cause now we wanna be friends, but we're in business together. So yeah, let's talk about what you recommend folks talk through as much as we can on this podcast.

    5. ACAlisa Cohn57:36

       So I do have kind of an extensive questionnaire, so we'll just touch on a few things, but o- one, one thing I think first and foremost is, what are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just, um, pull out your core values and just compare them with each other. Because when you are aligned, it's great, or when you're adjacent, it's also great. Like, I might care a lot about excellence. Lenny, you might care a lot about learning. Fantastic. Those are great values that we can kind of d- go together. I might care about excellence and you might care about work/life balance. Wow, let's talk about that, because I- I- I think it's gonna be really important as we go through our, our startup journey that we understand both of us, like, what does work/life balance mean and what does excellence mean? You know, because those, those two things can, at times, be at odds with each other, just as, as kind of an example. So talking through those core values in advance and updating them regularly even as you go down the path together is so essential, just so you know where the other person's coming from. Because the other problem is someone asks and acts in a certain way. You don't know them that well, maybe, or maybe you've known them as an eighth grader (laughs) , r- a lot o- lot of founders do know each other from, like, you know, their youth and they've matured into different kinds of people. And so, you think they're acting strangely, but actually they're acting in accordance with their values. And so getting a handle on that upfront can solve, uh, I would just say, will solve a lot of problems before they start.

    6. LRLenny Rachitsky59:08

       So signs that your values don't align, it's, it's basically like you're... you ca- both can't be true, is almost is the way I think about as you talk. It's hard to be the, like, excellent, like focus on excellence and also not work long hours. Which, I, it's possible, but it's hard. Those are challenging and, and worth a conversation.

    7. ACAlisa Cohn59:26

       Yeah, worth a conversation, because in fact, a- as you say that, I'm like, "Well, I guess you can do that." Right, you can do that. And so therefore, that's where the conversation has to figure out how you're gonna marry these two values, which might be at odds or might be aligned, but let's talk through what work balance, work/life balance means to you, and let's talk through what excellence means to me, and let's see if we can have a meeting of the minds about it, or at least I know where you stand. One of the founders I worked with, he would, um, you know, text or Slack his co-founder on weekends and the co-founder wouldn't respond, and that was extremely frustrating to the person, you know, to the co-founder I was talking to. And it turned out ef- after they finally addressed it, it really was about wanting to have some downtime and some, you know, quote/unquote balance. Nothing wrong with that, but because they didn't talk about it, both sides made a big assumption about it, and then it, it caused this conflict that didn't have to happen if they'd had the conversation in advance.

    8. LRLenny Rachitsky1:00:25

       Comes back to where we started of having these conversations is, is, is necessary and almost, like, helps the other person, uh, because this could... You know, this, uh, small issue could become a huge issue over time if you just start assuming, and it keeps happening, and it keeps scratching and scratching at you and letting that person's life is screwed up 'cause you're, "Oh, I can't do this with you anymore." Right? So it's just another reminder of the, how it's good for the other person for you to engage in a k- difficult conversation.

    9. ACAlisa Cohn1:00:54

       Yes, very true.

    10. LRLenny Rachitsky1:00:55

        Uh, okay. What else? So values. Is there... By the way, is there, like, a f- values framework you most love that you can point people to? Or they're just, like, a bunch and don't, don't worry too much about which one you go to?

    11. ACAlisa Cohn1:01:05

        I mean, the one I use is super simple, which is, you know, on the thing called the internet, (laughs) there's a lot of lists of values, and I think when you see a list of values, you can pull out the ones that are most meaningful to you, and that's a very simple and helpful and free tool.

    12. LRLenny Rachitsky1:01:19

        Got it. So you just Google list of values, there's a PDF.

    13. ACAlisa Cohn1:01:22

        Yeah.

    14. LRLenny Rachitsky1:01:22

        You can just circle the ones that are most... and pick, like, whatever small number down, you know, half of them.

    15. ACAlisa Cohn1:01:26

        Actually the... Well, just to give you the process, right? It's helpful-

    16. LRLenny Rachitsky1:01:29

        Yeah.

    17. ACAlisa Cohn1:01:29

        ... to pick, like, you know, 20, for example.

    18. LRLenny Rachitsky1:01:31

        Mm-hmm.

    19. ACAlisa Cohn1:01:31

        Great. And then you winnow them down to, let's say, 10, and then you do the difficult work of winnowing them down to three to five that you feel are core to you.And that's a good exercise for everyone to do, actually, like, every year, because things can change. Uh, it also forces you to make the difficult decisions about when it comes down to it, what are the things that really are important to me? The more you know your values, the more you can operate in the world with just more clarity for yourself.

    20. LRLenny Rachitsky1:01:58

        Awesome. All right. So, values. What else?

    21. ACAlisa Cohn1:02:01

        Yeah. So, another one is vision of the company. So, you know, when this company is successful, what does that look like? And what that might look like is, we're in control of our destiny and we, you know, are able to operate this business independently, and we have a lot of freedom. What that might look like is a big venture outcome that we all read about. And if you are both, like, assuming that you both think the same thing but aren't talking about it explicitly, or talking about the trade-offs you need to make inherent in that, then what often happens if you have differences is they come home to roost be- while it's too late, be- or when it's too late. So, an example is the two co-founders I worked with, you know, one of them would say- said to me whistlingly ] This is, like, five or six years into the company, and the company was going well, but it was- it was challenging, and they had all their growing pains. And like- like you mentioned about Cheryl said, like-

    22. LRLenny Rachitsky1:02:54

        (laughs)

    23. ACAlisa Cohn1:02:54

        ... all the- all the chaos. And he said to me, "Gosh, I don't see why we have to grow. I- I just wish we could actually, you know, have fewer employees, and I used to love it when I knew everybody's name. And I would just much prefer an environment where we didn't have to grow." Well, unfortunately, they were already venture-backed, and also, the other co-founder had a very, you know, lofty ambition for a very big company. And since they hadn't talked about that, it was way too late to even have that conversation, and it was a very painful reckoning for both of them to realize they were not on the same page.

    24. LRLenny Rachitsky1:03:30

        (clears throat) Totally see the value of this one. I could totally see how people would have different goals. I imagine it also changes over time, so there's probably an element of if something has shifted for you, you should probably also have that conversation. Like, "I don't want to build a- an IPO venture scale business. I just wanna build something chill." So, basically align on what is... Oh, how would you phrase that? What would- what does winning look like to you?

    25. ACAlisa Cohn1:03:52

        What does... Yeah. What does success look like?

    26. LRLenny Rachitsky1:03:53

        What does success look like to you?

    27. ACAlisa Cohn1:03:54

        Or what's the vision for the com- what's the vision for the company when it reaches its full potential?

    28. LRLenny Rachitsky1:03:57

        Mm. Okay, great. What else?

    29. ACAlisa Cohn1:04:01

        Another one is, it's sort of a two-part question. How do you handle conflict? So, how do you handle conflict, but then you might wanna ask your spouse, you know, someone close to you, "How does... How do I handle conflict?" Because you might think, "Oh, I handle conflict with, like, such an enlightened person. I'm so neutral about it. I'm so great at bringing things up." But the person who's close to you might say, "You seethe (laughs) until you're ready to bring something up, and it's really uncomfortable in the seething period." So, it just gives you a little more self-awareness about how you actually handle conflict, and that's really important because I might be the kind of person who wants to bring up conflict and talk about it immediately. The other person might be a person who totally wants to talk about the conflict but wants to let it settle first, and wants to also, kind of, go through their own thinking process about what's important to them, and might actually feel like they've resolved it themselves without having to have a conversation with you. And if you're like the person who's like, "Let's talk about it, let's talk about it, let's talk about it," and they're like, "I'm working through it myself," now you have conflict on- over the conflict (laughs) . And it just turn- it turns into a dyna- dynamic that's not necessary.

    30. LRLenny Rachitsky1:05:22

        As you go through these questions, it's absurd to imagine people don't do this when they find a co-founder and work through stuff. And I know most- nobody does, really. Like, and, like, the percentage of people that do this sort of work ahead of time is very low. And so, I love that we're helping this percentage go up, but it also reminds me of just how crazy it is people don't have these conversations, and how it explains why so many founder relationships don't work out. So, these are awesome. What else? I know you have a whole list, and we'll link to it, right? There's like a PDF we can link to-
12. 1:08:24 – 1:13:00

    Failure corner

    1. LRLenny Rachitsky1:08:24

       Okay. To kind of start to wrap our conversation, I want to take us to a recurring segment of this podcast that I call Fail Corner. We've talked a lot about failure at this point, and just all the ways people fail. I'm curious if, in your career or life, there's a story that might be helpful for folks to hear when things didn't go great and you failed, and if you learned something from that experience. And the reason this is something I do is, I feel like people listen to this podcast, everyone's like, "Sounds so amazing. Everything's always going great. They're killing it," when reality that's not actually how things go. So these end up being really helpful for people, like, "Oh wow, even Alyssa had a really hard time sometime." Is there a story that you could share?

    2. ACAlisa Cohn1:09:04

       Absolutely. I mean, so many, so many examples. Um, you know, I'm gonna give two quick examples. One is, when I first started my coaching practice, I just kind of started. And so I just did everything I could to get clients, to build a business, to build a practice, to build my brand, all the things. And I was working so hard, and I, I think I'd had this conversation with somebody that didn't go very well. And I just thought, in my mind's eye, I thought, "Well, what will become of me?" That was my voice in my head for quite a long time, "What will become of me?" And I, I was living in Boston at the time. I got onto the floor, my hardwood floors, in my Brookline condo, and I just bawled, in the fetal position, I just bawled and bawled and bawled for like an hour. It wasn't like 10 minutes, it was like an hour. And I was so frightened and just upset, like, "Is this gon- Am I gonna be able to make this work?" And it was a while, and I got back... I got, gone to the couch into a little stress nap, and then I got up from my stress nap, and I just started making more calls and kind of doing more things. And that was definitely like a rock bottom moment for me, and I think what I learned is you have to pick- literally pick yourself up from the ground and pull yourself forward, and when you keep taking action, action, action, win or lose, win or lose, you'll get where you need to go. And that turned out to be true. But in those moments, I was not thinking that was gonna turn out to be true.

    3. LRLenny Rachitsky1:10:32

       Wow. Amazing story. I imagine many people feel those moments, and it's, uh, empowering to hear that it can all turn out really well, even when-

    4. ACAlisa Cohn1:10:41

       Yeah.

    5. LRLenny Rachitsky1:10:41

       ... you're lying on the floor crying for an hour. An hour is a long time to cry on the floor. (laughs)

    6. ACAlisa Cohn1:10:45

       It is a long time to cry. It really... Like, I was, I was... I thought about it, 'cause most people just cry for 10 or 15 minutes. I was crying for an hour. I'm positive. Yeah.

    7. LRLenny Rachitsky1:10:52

       Great, great story. Um, you said you, you had another story.

    8. ACAlisa Cohn1:10:56

       Yeah. I'll tell you a second story, which is more, like, focused on actually my work life. So one thing that I do is I do coaching, of course, and I do offsites. And this was early, early days of my coaching career, and I was doing this offsite. And it wasn't going well, and I was debriefing with my client, like, during the breaks, and at one point she said something like, "I just think we should end this offsite. I just think we should just decide it's over and it's not working." And I felt horrible, obviously, humiliated certainly, and just like, "Ugh, this, like, th- that's a failure. That's, like, that's like, oh, fail." And I know that what I took away from it was that I can improve my skills in every aspect of running an offsite. So, p- getting aligned with a client in advance, making sure that I had the right activities getting us to our goal, being very goal-oriented and focused, and making sure that I had kind of understood the rhythm of what it takes to bring people together. So I took some training on that, I worked with my mentor on that, and I got so great at offsites after that experience. I tell you, that was a real lo- 'Cause in the moment, in that moment, I'm not thinking, "I'm gonna get great at offsites." In that moment, I'm thinking, "Oh my God, I'm gonna get... Like, what will become of me?" (laughs) You know? But I turned it into, in my mind's eye, or I should say, like, I turned it into the ability to build my skills. And I just want to tell everybody, even at your lowest moments, anything that you're learning from that can then be turned into fuel to build your skills to get great at the thing that you're not great at.

Episode duration: 1:23:42