Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

23:37Actually, any of you are a different point of view. I would like to hear it. Let's talk about it. But we can't keep going on like this where I don't feel like I'm counting 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 in to having these conversations. Because on the other side of that is a much better, stronger connection.

24:09And especially if you do them well. Yes. Following this advice. And it's OK. So again, if somebody's feeling defensive, can you again say how you start that? If you notice that, and then I'll highlight the two elements again of that. The way to pause is to actually say, let's just pause for a second because I'm feeling the energy has changed and I can see that you're getting a little bit heated by what I'm saying. I want you to know that I have no intention of upsetting you. I just want to be able to talk to you about the things that are going to help you in your career. Awesome. And I love, again, just a reminder of here's why this is important to you.

24:50Like here is the benefits to you and why this will help you and then it's like, okay, 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 I mean I can talk all all day

25:07Well, 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 going to get the promotion they expected or wanted? That can be, of course, that's challenging. So again, getting your mindset right, recognizing their disappoint, they're going to be disappointed, recognizing how you felt the time that you, 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.

25:38So sometimes people think they should get a promotion because they were here for a year or whatever. Sometimes people think they should get a promotion because of the only internal candidate issues qualified for this, or they might have a sense of themselves, you know, succeed 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 going to be challenging for you to hear. I know you were hoping to get that promotion. But I want to let you know that we are going to actually be looking for an external candidate.

26:08I want to give you a few thoughts about why. First of all, in discussing this with my peers, I'm realizing that 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 we've identified is really important. So for those reasons, we're going to bring someone from the outside, not going to 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 is going to help you build those skills So fuel elements there that stood out to me one is just being very upfront and not bearing the lead Telling them very early.

27:01Here'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. Yes, that hope for the future is so important. And I think sometimes we're so, it's such an awash 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, if they're a good employee, hopefully they have hope for the future.

27:36I love that. Is there anything else to that script do you think is really highlighting or do you think I touched on the key elements? I think you touched on the key elements. Okay. And again, the way you started is like, I have some bad news for you or I have some disappointing news for you. Yes. Because it's just getting through. You're just getting through it. Yeah. By the way, the other piece on that might be, if it's appropriate, let's, I'd love you to adjust this information and then let's talk about it again next week, you know, to sort of see what you've come up with, 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 in the workplace people you know they're getting going through all their feelings all their emotions disappointments are gonna go home and tell their spouse You know didn't get their promotion or whatever.

28:21It's gonna look 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 resilient in the face of setbacks and ultimately do extra work. 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. 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.

29:02Thoughts on responding to that sort of feedback. I guess that's the defensiveness stuff. Yeah, that's the defensiveness stuff. Again, I hope you've done your homework to identify that actually that person doesn't have those skills. If there is a back, so like for example, what I do have those skills 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 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.

29:35And 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 around here. And 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 going to help the entire company. So that's an example of a discussion that you could have. You know, I do have the skills.

30:07That's kind of interesting. Let's, you know, like I'd love to hear what you see as those skills. And it's not a problem to have the conversation right there and then. But if there's like a, yes, I do know I don't. Yes, I do know I know you don't. That pushback is never productive. And so that's where you want to call you again, take a pause and say, listen, I totally hear you. 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 the decision that I've made.

30:39I love the when they come back to you and like, but here's XYZ 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 there another script that you think might be helpful to talk through that is a common hard conversation people have? Well, the hardest conversation is firing someone. Someone that's good into it. I know it's a leg I'm willing to get into it.

31:13I just want to say two things about that. First of all, when you're firing someone, the hope is that you, 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 essential because the truth is you want to create a culture where people are not surprised by being fired. That's not even true for this one person you're dealing with. That's true for the entire company. So just going to get into the mindset of recognizing that if you shied away from this conversations, kind of like you're the problem here, and you kind of have some ketchup to do.

31:43The second thing is that before you fire someone, I think it's helpful to have the conversation before the fire in conversation because you know something you said Lenny is like, oh, but maybe I'm rock, you know, maybe I'm not sure and that leads into maybe I haven't been clear with this person. So you want it because 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, well, maybe, which means no, Which means no, you've not been crystal clear or you don't proceed even crystal clear So the way to make sure that your crystal clear is by having the conversation before it comes to that and what that looks like is Listen until that 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 misdeadlines 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 you're operating on your own without coordinating with them.

32:50And 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 going to have to find a way to part ways because 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 That is very crystal clear. Yes crystal clear. Yeah Okay, so yeah, that was a great. So it starts with being upfront. This is a difficult conversation Just to set expectation.

33:31They're like oh shit and then I get it seems like you come back to again multiple times this happened like observing here's happening. It's happened multiple times. They keep hearing multiple from multiple people. He used to be a problem. 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. Yes. Yeah. And I love that you also give them a little like there's always that 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 bottle blah blah.

34:03but still this is a big problem and it's like communicating how critical this is. Yeah, and it's a deal breaker. It's a deal breaker, right? Like if you have so many talents, but if you can't do these two things, then it's a deal breaker for all of us. And I think it's important to really sort of see that both. Sometimes people think, well, but I'm so talented. But your talents are not going to make up for these two deal breakers. Yeah. And I feel like, I know we were going to talk about like the firing conversation, but I think that this is even more important than that because hopefully this addresses the problem.

34:33me don't need to fire them, which is more valuable. Yes. 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. Yeah. So basically the script is like we're getting, I have a, there's going to be a difficult conversation. I've seen multiple times this thing and we talked multiple times and it's still not as fixed. And here's what I just want to be very clear about. Is there also script you have for just actually doing the firing or is that less scriptable. Well, the script for doing the firing is again, please everybody, talk to your HR professional, talk to your lawyer.

35:11Okay, I'm not a lawyer. So you have to like make sure that you're all buttoned up on what you're going to 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 knew you didn't make these changes. You haven't made these changes and we're going to you know, Sarah from HR or whatever, and we're gonna talk through 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. It feels very reasonable to me. Is there anything else along these lines?

35:47I think what I wanna say is that the conversations you have to 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 manager I was doing in a training program, she said, I don't like like getting positive feedback.

36:30I don't 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 where 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, 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 doing that.

37:03That's really working for you. If you do that often enough, you do get in the half. First of all, it's positive, obviously. You become in the habit of getting better positive feedback, which is extremely motivating people at work. It helps them see their progress because that person I just mentioned, she's like, really keep her head above water. 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. Then one day, if you have to give her these difficult messages, you've already laid the reservoir of goodwill.

37:37I love giving positive feedback. It's obviously so much easier, but to your point, you have to really think about how to do it well. It's not that easy if you do it well, which is a really good point. When it was in these scripts, trying to get really good positive feedback and have great conversations. That's interesting. There's less demand for that. How do I have better great conversations or compliments? Right. Right, too. No, man. Today's episode is brought to you by LiveBlox, the platform that turns your product into a place that users want to be. With ready -made collaborative features, you can supercharge your product with experiences that only top -tier companies have been able to perfect until now.

38:16Think AI co -pilots, like notion, multiplayer, like Figma, comments, and notifications, like linear, and even collaborative editing like Google Docs. And all of that with minimal configuration or maintenance required. Companies from all kinds of industries and stages count on live blocks to drive engagement and grow in their products. Join them today and give your users an experience that turns them into daily active users. sign up for a free account today at liveblocks .io slash Lenny. I want to go in a little bit of a tangent, something that it kind of touches on all the things we've been talking about, which is your big on helping leaders understand that their job is not to make employees happy.

39:01What is your job instead? 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? For a while, I work with a lot of founders, and so don't forget that the entry level position for founder is leader. And they 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.

39:36For the all the reasons we talked about why you don't upset people, nobody wants to upset people. And so there's this idea of, you know, we're trying to now be 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 going to job as towards results or 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 want to push them because you don't want to upset them You don't want to give them difficult feedback.

40:20So you're just going to keep hoping it works out Ultimately that leads to the demise of your company. I mean ultimately right as you're a startup If you're not in a startup and you're a large company It still is very subpar performance, obviously, and you're dancing around hoping and praying they're going to 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 -engage at workforce. High -engage at workforce is great. I think what that comes from is winning culture, which means we're set up for success.

41:00We 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. Essentially, the way I think about it is like, like you think making people happy is not having hard conversations, not pushing them.

41:33When 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? 100%. And then the right people are going to want to join your team, people who like to win and like to get results. Is there like a story, an example of a founder you worked with or does it come 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? One company comes to mind when 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.

42:08Because you know like he wants to do right by his work force and so you know they have avocado toast at 10 p at 10 a .m. like tea time kind of a thing. 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 continue to be not fully clear on what they're actually supposed to do and And there began to be kind of a clicky gossipy culture of like who's in and who's out.

42:50And 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 culture committee. So they had a culture committee to talk about how we can make people happier around here. And you can imagine that 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. It actually want to have a great workplace.

43:24But 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. Because culture is not just avocado toast and working together and having socials. Culture is things like we go the extra mile. Or culture is, we make sure, or it could be, we measure twice and cut once. Those are kinds of things that are really about the way we get work done around here. And certainly a focus on results is, are we following the process to then get the revenue and to then build a profitable company? Or are we just kind of hanging out together?

44:07So 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 and like, you know, in the workplace and how we do things. And you know, it turned out that's the whole thing with coaching and with working with people is that you kind of see what they're underlying assumptions and beliefs are. And there's a reason everyone does what 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.

44:41And 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 in the same page, they were able to gain a lot more traction. I feel like a lot of leaders and founders can relate to this. I have 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 make a business that works. Always remind me, Charles Sandberg came to a talk at Airbnb once and people are asking, like, what do you do with all this?

45:17We're just like constantly in chaos. Things are always re -organ, 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 is 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 shouldn't be happy. This is the challenge you're running into. I love that. It's so true. 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.

45:50Here's what I thought leadership was going to be. It had to be a great leader. And here's what it really is. Is there anything more there that you find is like commonly what they're wrong about or what they miss and what they have to realize? Yeah, and I think as we grow as leaders, we all have to realize our own blind spots and the difference between what we thought and what actual, what it's actually going on. So, I worked with a founder who, what she wanted to be was a visionary leader, which is fantastic. I love that. And she was 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 achieve milestones and course, correct when they got off course.

46:36And she'd be very frustrated when all those things happened. Right, 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, 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 by the COO or somebody else who could be the person who would be 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 see that, and she did not adjust her style.

47:11And so, there's a lot of 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 There was nothing malicious about it. It's just that she didn't see the situation for what it was and then adjust Reminds me we had a coach on the podcast Joe Hudson and he had this Fraze 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 if you hate a Yeah structure like I actually is reminds me Joe Gabby at Airbnb It was very anti -process at the beginning of Airbnb's like we're not gonna have a process.

47:52I hate process We're gonna run that's a big company stuff and then it just chaos constantly and then eventually it's like okay We need to have us we need to have some process to how we build things And so it's interesting a lot of people have to realize the thing they think was bad is actually I see why people do it this way Yeah, totally. Actually, I'd like to say something about that because so many founders are kind of mavericks and they come into a situation and or they start at this company and they want to do things their own way. And that's fantastic. Otherwise, they wouldn't be a founder.

48:25That's actually fantastic. And so many of the founders I've worked with want to reinvent leadership, right? They want to have it with no process. They want to have no hierarchy. They want to have autonomy whatever it is and my feeling is like God bless you should absolutely try to do that 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 Okay, ours 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 structure a group of people and get them organized so that they can win are kind of well -trod.

49:13And I would say that it's helpful to get through that stage quickly so that you don't have to constantly reinvent the wheels of leadership. Such important context. Like obviously, one of the most successful founders come up with, I 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. I want to get into a couple more tactical things that you often work on with founders. One is running meetings.

49:46Meetings come up a lot on spot cast. People hate them. People love them. They're summer great. Summer bad. Most are bad. 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. Yeah, I'm one of the people that loves meetings. Or I should say I don't love meetings. I love the potential for meetings. 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.

50:15So 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've re -meat, we've re -decided 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, articulate those as deliverables, I promise you you're going to have better meetings. Okay, so what did we decide here?

50:53Who'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 as I put it? Yes, who else needs to know? You know, there's so many executive teams that I've worked within at first They just they go into their room. They have their meeting. They make their decisions and then they leave They don't tell anyone. I made this promise for my team that you guys need to kind of go do or or we decided that a policy of some sort and we forgot to tell everybody. Again, no absolutely no maliciousness, just that they forget or they're too busy.

51:28There's not part of the protocol and the process inside of the company that encourages and really insists that people share important information. So cascading that down. But even the first question, what do 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 do we decide here? and they all write it down, you will get six different answers. You will remember the same meaning. I love that. It's so powerful, but also so helpful to really raise that up to surface that and then to figure out to do about it.

51:58I love that you highlighted that. It's going to say exactly the same thing that you're like, yeah, everyone in their head has the thought of here. Oh, yeah, here's what we decided. It's your point. It's often not the same. So is the advice here? Is this like a template or something you feel at it? of a meeting or is it someone's job to make sure these three things happen? Or how do you operationalize these three questions? I like it that it's someone's job. The person I sort of think of as the meetings are. And typically that's somebody who enjoys follow -up, who enjoys putting lists together and putting things into boxes and whatnot.

52:30And there's usually someone like that on the team. And so then it's kind of exciting for them to be the follower upper. But one way or the other, so you could use a template, I think that actually baking it in is to ritual to the meeting. Because 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. What I'm imagining is say it's the product managers put this dock on the screen in the meeting as the meetings ending and just have it filled out basically and just confirm does this look good to everyone?

53:09Love that. That's a great way to do it. By the way, well, I just would say what's interesting about that is that if we ask people, what do 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's sort of crystal us 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 running short of time.

53:48I worry that somebody might not sit, 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's not what I see. Let's spend some time on that. Well, I actually spend more time on this because 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? Because, you know, like otherwise, it feels like it could just lead to a whole discussion in the last couple of minutes, which I guess could be valuable.

54:22But who do you point the question to? 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 do 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 group of some sort, then you probably want to get a few people just to... I would just even say as a facilitator, two or three people, okay, two people, what do we decide here? And if you think, kind of, get common, great, that's fantastic. Got it. Okay, so if it's a small meeting, you go around the room and everyone just shares you if we decide to hear him, and they could just be like, yep, he's got it, where she's got it.

55:00Awesome. Okay, this is great. So the advice here is next time you have a meeting, especially in exact meeting, just at the end of the meeting, 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? Who needs to do what by when? And then everyone kind of chimes in and you're writing this in this doc. And then what else? Who needs to know about what we decided here? Yeah, Lenny, I love that because also, like, do you have to be the leader of the meeting to do that? But no, you could just be the person in the meeting and just chime in and just start it yourself.

55:33And 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. And this is how you become a leader. Is you just start doing these things and people are like, oh, this is so helpful. She's just on top of it. I feel like 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. Exactly. Exactly. Amazing. Okay. Another topic that I know you spent a lot of time on is something you call the founder pre -know.

56:04And 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 started a company in the past and it's, I don't think people realize how insignificant this decision is in your life. It's basically you are marrying someone in a business context and you're 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?

56:41Well, I just want to reiterate what you just said exactly right. And it turns out that, you know, according to Noam, Noam, Masterstein, 65 % of startups failed 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, with less care than they should. And, you know, bad things can happen because you haven't done the work of getting to know each other before you decide to co -found. Yeah, like it's so easy just to let you have a sort of company with a school idea. Let's just do this.

57:17It's gonna be so awesome. And then you don't realize how much you're committing to and how often things don't work out because of that quick decision. Oftentimes it's like friends, and then it becomes even more challenging because when we're friends, but we're business together. So yeah, let's talk about what you recommend folks talk through as much as we can on this podcast. So I do have kind of an extensive question here, so we just touch on a few things. But 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.

57:47size, you can find a ton of them online, you can find a list of values and just 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 go together. I might care about excellence and you might care about work -life balance. Wow, let's talk about that because I think it's going to be really important as we go through our start -up journey That we understand both of us like what does work life balance mean and what is excellence mean?

58:25You know because those those two things can at times be at odds with each other It just as a 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 an accident a certain way. You don't know them that well maybe or maybe you've known them as an eighth grader. A 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, I would just say, resolve a lot of problems through where they start.

59:08So signs that your values don't align, it's basically like you're, you keep both can't be true, is almost as well as think about as you talk. It's hard to be like excellent, like focus on excellence, and also not work long hours, which it's possible, but it's hard, those are challenging and worth a conversation. Yeah, worth a conversation, because in fact, 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 going to marry these two values, which might be at odds or might be aligned. But let's talk through what work -life balance means to you and let's talk through what excellence means to me.

59:46And 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, 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, 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 it the biggest assumption about it. And then it caused this conflict that didn't have to happen if they had the conversation in advance.

1:00:25Comes back to where we started of having these conversations is necessary and almost like helps the other person. And because this could, you know, this small issue could become a huge issue over time if you just start assuming and keeps happening and keeps scratching and scratching at you. And letting that person's life escrew it up because you can't do this with you anymore, right? So it's just another reminder of how it's good for the other person for you to engage in a kind of difficult conversation. Yes, very true. Okay, what else? So the values, is there by the way, is there like a values framework you most love the do you can point people to or they're just like a bunch and don't worry too much about which one you go.

1:01:05I mean, the one I use is super simple, which is, you know, on the thing called the internet. 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. God, it's just Google list of values. There's a PDF and just circle the ones that are most and pick like whatever small number don't, you know, half of that. Actually, well, just to give you the process, right? It's helpful to pick like you know 20 for example 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 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 We just more clarity for yourself.

1:01:58Awesome. All right. So values, what else? Yeah. So another one is vision of the company. So 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 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 assuming that you both think the same thing but aren't talking about 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 Ruiz while it's too late, or when it's too late.

1:02:40So an example is that two co -founders I worked with, one of them would say to me, wistfully, they said five or six years into the company. And the company was going well, but it was challenging and they had all their growing pains and like you mentioned about Cheryl, so like all the chaos. And he said to me, gosh, I don't see why we have to grow. I just wish we could actually have fewer employees and I used to love it when I knew everybody's name. And I would just much prefer an environment we didn't have to grow. Well, unfortunately, they were already ventured back. And also, the other co -founder had a very lofty ambition for a very big company.

1:03:19And since they had 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. 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 is shifted for you should probably also have that conversation. Like I don't want to build an IPO venture scale business. I just want to build something chill. So basically a line on what is, how would you phrase that, what does winning look like to you?

1:03:52What is, yeah, what does success look like? What is the vision for the company when it reaches its full potential? Hmm. Okay. Great. What else? 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 want to ask your spouse, you know, someone close to you, how do I handle conflict because you might think, oh I handle conflict with 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 see, until you're ready to bring something up. And it's really uncomfortable in the seething period.

1:04:38So 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 resulted 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 and And they're like, I'm working through it myself.

1:05:15Now you have conflict on over the conflict. And it just turns into a dynamic that's not necessary. 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. 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 this, 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, right?

1:05:51There's like a PDF we can link to. Yes. For sure. Post awesome. Let's do a few more. Another one is how do we decide when we disagree? And that is a very good thing to explore, because there's actually a lot of different ways to decide when you disagree. And they're both they're all good. And if you have it sort of up front, and it's just like an ongoing discussion, but if you have it up front, like when we disagree, because that's definitely going to happen, let's assume that the person who cares the most can win that argument. That would be a great way to do it. It might be the person who's got the best perspective and the most expertise can win that argument.

1:06:34It might be, we'll go back and forth when we really disagree, first you win and then I win like that back and forth. There's so many different ways to handle it and if you talk about it up front you'll be much more likely to be able to actually put that into practice when you do disagree because you will definitely disagree there's no way around that and that's not even that thing like your smart people give his dynamic tension in their relationship, you bring different things to the table, you've got different perspectives, disagreeing is normal. Working through it and having a practice and a process of working through it will help it be a good conversation rather than like this sort of silky, difficult conversation.

1:07:11I love it. Maybe one more? Yeah. So another one is what kind of company culture do I think is important? People definitely don't talk about this before they found the company and they assume they're on the same page. So one founder might be, I want to have this great company where everyone loves it and we're all loving together and working hard together and it feels like a free, you know, it's usually where before it feels like a family. By the way, that's great, that's fantastic. I wanna have a get it done, results focus culture where we're just like executing the hell out of everything and that we're just focused on winning.

1:07:51By the way, those two can actually exist together but if you're pushing in one direction without the other and your co -founders pushing the other direction without yours, it really can feel like two different companies and that's, you know, when I go into a situation at one of my clients, clients sites, often. I will hear from the employees. It feels like we have two different companies and two different cultures depending on whose team you're on. And that of course leads to lack of coherent working together and certainly even just lack of different standards and expectations. Awesome. 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.

1:08:32We'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 sound so amazing, everything's always going great, they're killing it. When reality that's not actually how things go. So this ended up being really helpful for people like, oh wow, you don't listen at a really hard time. Sometimes is there a story that you could share?

1:09:04Absolutely. I mean, so many examples. 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 think I had this conversation with somebody It didn't go very well. And I just thought, in my mind's eye, I thought, well, it would probably come of me. That was my voice in my head for quite a long time. What would become of me? And I was living in Boston the time. I got onto the floor, my hardwood floors, in my Brooklyn condo, and I just balled.

1:09:44I'm in the fetal position. I just balled and balled and balled for like an hour. It wasn't like 10 minutes, it was like an hour. And I was so frightened and just upset, like, am I gonna be able to make this work? And it was a while and I got back, I got into the couch into a little stress nap and then I got it 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 literally pick yourself up from the ground and pull yourself forward and when you keep taking action, action, action, when or lose, when or lose, you'll get where you need to go.

1:10:25And that turned out to be true, but in those moments, I was not thinking that was going to turn out to be true. Well, amazing story. Imagine many people feel those moments and it's Empowering to hear that it can all turn out really well. Even when lying in the floor crying for an hour. An hour is a long time to cry in the floor. It is a long time to cry. It really like I was I was I thought about it because most people just cry for 10 or 15 minutes I was crying for an hour and positive Yeah, great great story You said you had another story. Yeah, I'll tell you a second story, which is more focused on actually my work life.

1:11:00So one thing that I do is I do coaching, of course, and I do offsights. 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, that's a failure. 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.

1:11:40So getting aligned with the 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 my mentor on that and I got so great at off sites after that experience. I tell you that was a real look because in the moment, in that moment, I'm not thinking, I'm going to get great at off sites. In that moment, I'm thinking, oh my god, I'm going to get like, what will become for me? 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.

1:12:19And 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 skill to get greater the thing that you're not great at. What I also love about this is there's this feeling of imposter syndrome, specifically, the sphere that I do something wrong and then it'll all crumble and everyone will see I suck and I never I don't know anything and everyone will see it. And I love both these stories are like it doesn't go well and doesn't crumble. It just gives it just you build from there. And no one's like oh, this is terrible forever.

1:12:51No, it's like move on to the next thing and then you use that as fuel to become really good at this thing that didn't go great. Yeah, that's really well said. Amazing. Elizabeth, we covered a lot of stuff. Is there anything that you were hoping to cover or you think might be useful for folks to hear before we moved to our very exciting lightning round. The only last thing I want to talk about just sort of circling back to like your role as a leader. I was one time working with the CEO who was handling the fact that this launch was not going well. Like I said, the launch wasn't happening. I could put up, put off, put off, put off.

1:13:26And his point of view was you need to have patience with it as it goes. And my point of view is because I've talked to a lot of the people around was that there was a massive process problem going on that he was not kind of touching into and really investigating because like the project the product manager wasn't experienced was kind of hiding it because he knew he didn't have the skills was fighting with engineering. It wasn't it just wasn't working. And when the CEO was telling me and we really had a long discussion about this, where I kind of enlightened him about some of the issues that he needed to get involved in fix, he kept thinking, I need to have patients.

1:14:04So what I want to say to everybody is like, sometimes you need to have patients and sometimes you need to look at the process. And I think you as the leader need to have the kind of the wisdom to the difference, but also your finger on the pulse to recognize, is this an issue with patients or an issue with process? I guess is there a sign that you're like it's probably a process thing you're just ignoring a glaring problem Evernal sees I think this sign is when If you search your your mind you don't really know how this thing is gonna come together There's no like plan in your mind you haven't touched in with people or talked to people about what's going on You kind of hear this uncomfortable silence about it But those are symptoms that you just need to dive deeper and just be a little more in touch with what's going on and talk to some folks and look at some data.

1:14:55By the way, it might not be a massive process problem. It might just be one little thing that needs to get unstuck, but you as the leader need to recognize that and figure out a way to make that unstuck. And if there's, of course, a big problem, it used to somehow be just, you know, surfaced. So if you're just expecting, if you're just hoping this will work out versus like ICAPAT that this working on, it's probably not, probably a problem. Yeah, well said. Is there anything else that you wanted to share to touch on that you think might be helpful? We talked a lot about the co -founders prenup, which I think people would think, well, I'm not a co -founder, I don't need that.

1:15:26I just want to invite everyone to also think about a different tool that I have, which is called the personal operating manual. And it helps prompt you to talk about working style together, because you may not be co -founders, of course. But you're working on a team with a bunch of people, and they all have their different working style. So it's kinds of questions like what communication style do you like the best? How do you like to work? You like large like large uninterrupted blocks? Do you like you know sort of meetings here and there? When I'm trying to get a hold of you for something important.

1:15:56What's the best way to do that? What is one of your pet peeves or some of your pet peeves? How can I get a gold star with you? Those kind of you also this is my favorite. What's your delegation style? Do you want me to check in with you regularly, like once a week as I'm working down the path of a project? Or do you want me to just let you know what it's done? And, you know, just tell you at the end that it's been complete. So lots of different ways people assume other people work because it's like your style, but actually it's just your style. So those kinds of conversations can be great for working together and also be a great team activity.

1:16:34So this kind of what goes into these Read Me's people put together, here's how it works with me. I really love the Gold Star concept because I feel like people want to know how do I be super awesome How do I be really successful working for you? And I like that visual of the Gold Star and the pet peeves. I feel like a lot of people will identify that What what are my pet peeves so that people don't do these things because I don't know right? They don't know until you tell them nobody nobody knows what's your what's your operating style until you tell them and the more you can showcase the more Everybody will be able to do it right for you and you'll be able to do it for them and then you'll be able to have better workplace harmony and save your conflict for what things that are really important.

1:17:10Not just because like, oh, you didn't text me when I wanted you to text me. Mm -hmm. Being clear, what do you know? Is there anything else that you think might be helpful to share before we get to very exciting lightning around? No, just that. Well, with that, Alyssa, we reached our very exciting lightning round. I can't wait. I'm ready. Here we go. First question. Are there two or three books that you find yourself most recommending to other people? So we already talked about Kim Scott, the wonderful, amazing Kim Scott, and her book, Radical Candor, is when I recommend a lot to people. It's fantastic.

1:17:43Working backwards by, um, gosh, Colin Bryan and Bill, Bryan and Bill, and Bill something is about sort of the Amazon way of working backwards from the customer. Super geeky and tactical. I love it. I slurped it up like Harry Potter. It's so good. And I definitely regretted to my clients about like Amazon's management science. And the third is Walt Disney by Neil Gableur, because it really shows how Walt Disney sort of it's everything about his youth and how he turned into a very bad entrepreneur and ultimately into a fantastic, inventive entrepreneur. And it shows all the origins of how he invented these different pieces that now make up the Walt Disney company.

1:18:25The first two recommendations we've had on the podcast Kim Scott and Bill Car is the other partner He's been on the podcast and people love that episode. I haven't had walled Disney on get a work on that Or the writer you'll give the writer. Yeah Good tip. Okay. Next question is their favorite recent movie or TV show you really enjoy? Yeah, I enjoyed inside out too Those fantastic the idea you blow it. I feel like it's for all coaches in the world Totally. Just the idea that like, oh yeah, we're all this complex two of emotions and it's okay. I also love that movie. Next question. Do you have a favorite product you recently discovered that you really love?

1:19:03Yes. The Ninja Creamy. So more. The Ninja Creamy turns anything into ice cream. So you can actually make ice cream good, God bless. But I take my protein shake, which is okay and turn it into ice cream, which which is delicious and it takes 10 minutes and it's very little prep and it's simple to use and it works as expected, which so many things do not. The Ninja Creamy, go get it. That's a first for the Ninja Creamy. And I love the holidays are coming around so this is going to be good for people. Do you have a favorite life motto that you often come back to find useful and work or in life? This quote by Joseph Campbell animates my life, which is if you can see your path all the way through to the end, you are following someone else's path.

1:19:51Your path only becomes clear moment by moment as each foot hits the ground. Wow. That's so good. It's so empowering because it helps you realize your if you don't see where it's all going, that's normal. That's good. Wow. Great one. It won. I'm going to I need to do something all these models. They're so good. I need to like carry to poster or something. That's a great idea. Or or read your news for a sound amount? Or yeah, that's the easy path. Okay, last question. So I'm curious and not to create more competition for you, but I feel like a lot of people think about becoming a coach of some kind, like a product coach, Zach coach, if someone was thinking about going down that path, there's like one piece of advice you could share to help them pursue this path, even explore if it's right for them.

1:20:38If you think you wanna become a coach and you immediately wanna build up your coaching skills, Listen to people more deeply and ask deeper questions. Not just respond to what they just said, but why do you think that? Well, where is that coming from? And you will see if you enjoy that process of really going deeper with people, I think that would be helpful for everyone to do, but certainly if you want to become a coach, I think that's essential to be able to get really behind the surface. I love how your energy just changes like coaching mode when you said that. I love that. That was such an interesting thing to see.

1:21:19And that was great advice. It's easier said than done. And it's interesting it could tell people are so good at that specific skill versus not. And so I love that that's the thing to work on is ask better questions, think deeper about the person and what they're coming from. Alissa, this was incredible. Two final questions. working folks find you if they want to reach out, maybe work with you, what kind of people do you work with in case people are interested in that? And finally, how can listeners be useful to you? Oh, thank you. Well, I work with executives at startups and also at large public companies.

1:21:54So feel free to reach out if you want to have a conversation about coaching. you can find me at illicitcone .com. And actually, I'm gonna take some resources and put them at a special link, which is illicitcone .com forward slash Lenny. If you wanna download the co -founder prenup, I just love it of a personal operating manual and a few other resources I will put there. So illicitcone .com forward slash Lenny. And you can also join my newsletter from there. And I think in terms of helping me, I guess there's two things I wanna say. My life's work genuinely is to make a difference. When I became a coach, it was because the music in my head was to make a difference.

1:22:32And so I hope I've made a difference for all of you today, and I would invite you to try one thing that makes you uncomfortable. This week, like as soon as you hear this, this week, try something that makes you uncomfortable and feel free to let me know on LinkedIn or even send me an email and let me know what you did that made you uncomfortable. So that would be very meaningful to me. And the second thing would be very meaningful to me is if you would go find my podcast called From Startup to Grownup and give it a listen. Maybe give it a rating and review because as you know Lenny, the way people find your podcast is when other people are interested in your podcast.

1:23:09From Startup to Grownup, I love that title. Thank you. Alyssa, thank you so much for being here. This was awesome. Thank you so much for having me, Lenny. It was great. Bye everyone.