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

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

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.

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

They're trying to 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.

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

My three questions to end the meeting are.

Today, my guest is Alyssa Cohn.

Alyssa 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 Thinkers50 and the number one startup coach for the past four years by Global Gurus.

What I love about Alyssa is that she gives her clients very specific and actionable advice.

In our conversation, Alyssa 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 Alyssa Cone.

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

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

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.

I feel like this is very relatable.

They're called difficult conversations for a reason.

Totally. 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?

Let's do that. I love that idea.

And also, Lenny, as you just said, very relatable and also like not so you're not alone.

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, 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?

Great question. 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 it's really made things worse so I worry about the reaction I guess okay about making things worse or about their reaction the reaction just making

someone upset and sad making someone upset okay good and again you're not alone about that just one more question on that what's the problem if they're sad and upset like what what is it what does that mean to you?

I love this live coaching.

Yeah. So it's like what happens if they get sad and upset?

Yeah. I feel like it's it's stuff that I'm going to have to deal with.

It's like this drama.

All of a sudden, it's like new fire to think about.

And yeah, it's like the additional work it creates.

And I'll say just I don't know.

Yeah, it's a good question.

You can think about it some more.

Right. I'm not going to put you on the spot right now.

But like just to say for all 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'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 want to 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 if you don't give them the opportunity to hear what you have to say if you don't bring this up then

you're never going to 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 want to 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 going to be a lot of extra work or like they're going to 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.

I love that. And 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 this support to make this even more real.

What are just like, let's give us 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 going to let you go.

What other examples are like common, difficult conversations that you run across?

Those are two very common ones.

And then of course, the most common one is just difficult performance feedback or, or let's say what we say, quote unquote, constructive performance feedback, which we never made 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 developmentally I'd like to see you add something or change something.

Yes 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.

Yeah and so then I think it's also really helpful to you know and part of the process that we can talk about this for sure is getting into a difficult conversation is number one, tapping into what's uncomfortable for you about it.

And then number two, also getting your own mindset right.

So to say the obvious, are you doing this to hurt someone's feelings?

No, never, right? 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 because 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, as a manager to help them out of that, problem and help them do something different.

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 a 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 going to 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 he 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.

Yeah. A hundred percent.

One of my clients, 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 right kind of data, the not having to do the right kind of analysis, whatever it was.

We were talking about it and I said, well, how come you have another feedback with her?

And And he said, you know, she's just going to cry.

She's just going to cry.

You know, she's older, whatever.

She's just going to cry.

It's going to 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 going to 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 have had a different career.

And I think that is so meaningful for all leaders and people who are responsible for other people to understand that, 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 leaning into these tough conversations.

what I love about the scripts we're going to talk about, which we probably should transition to is like, it's again, one thing to hear them and be like, yes, okay, I need to do this.

I need to get better at difficult conversations.

I need to have that chalk without someone that we should let go.

It's another one. It's like tomorrow is the meeting and you're like, oh my God, I have to have this conversation now.

And so I love that you actually give people a really simple approach to how to lay this stuff out in various different 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?

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 kind of know what you're doing it, and then you just really want to really 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 want to 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 fully keeping your team up to speed.

And so they're kind of confused running 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 want to 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.

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.

OK, it's not just you and just like, oh, my manager hates me.

It's like, 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.

Actually, I don't like leave this meeting with, let's just be aligned on this thing.

Yeah. Thanks for calling those out.

I hope, you know what I'm trying to convey and my tone is also, you know what?

It's Tuesday. We got to have this conversation.

I'm sure we're going to, I'm sure it's going to 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 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 this 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.

How did you start that phrase again?

Because the starting is always the hardest part for me like how do you kick off the conversation?

What was the couple sentences used?

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.

Awesome. So there's an element of don't make it feel like a huge deal.

I want to have this conversation with you about something.

And it's just like, let's have this conversation.

And here's what we want to leave this conversation with.

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

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 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 they want to be criticizing them every we need to have another conversation about what we're hearing about problems yet uh obviously if you say it the same way

every single time they're going to 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 want to say it every time?

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 I land it for them.

But they have to make it their own.

You always have to make it your own.

And I don't think it's a problem of doing it the same way every time.

It's not like people are going to notice because you're talking about different topics, you know, theoretically, if you have a formula that can work for you, that's going to motivate you to do it.

That is what's important.

And what's important is that it's neutral, not, you know, loading on, not venting on someone and not unloading on someone.

I love that we started with this one because it feels like the most common one of just like your employees underperforming and you want to make sure they understand and adjust.

What if you're not hearing something from a bunch of people?

What if it's like your perception of the writing, like you need to work on your writing skills or you aren't, you're coming in late.

Is there another way you phrase it where it's not?

I'm hearing it from other people.

Oh, absolutely. Absolutely.

So I'll talk about writing.

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.

Wow, I like that. I would want to follow your advice if I got that.

So the way you started that is what I've observed, 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 reminds me of, what is it, a nonviolent 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 want to say just like the importance of focusing on what you've heard from people

or what you've observed versus maybe what people often do instead yeah i think i mean you just really said it i think it's such an important point observable facts you know the idea that this is not a judgment this is not as sort of as less judgy 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 certain we expect it to be a certain level and it's not that way and here the reasons it's not the specific reasons it's not the way you interact with your peers it's important to be at a certain standard

and here's why because when we all work together we're going to be able to execute when we don't unfortunately we won't be able to so you stay 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 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 easier for you to give and easier for them to hear.

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 feedback?

Well, I think just that the reason, one of the many reasons that people have gotten comfortable 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 want to know if we can continue having this conversation now or we need to kind of pause it.

At the end of the day, we really have to have this conversation and I really want to 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.

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.

So 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.

And it feels like there's kind of two parts to which you shared.

One is remind them why this is 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 listen.

Yeah, exactly. 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?

I'm not emotional. emotional right exactly um yes of course now 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 could see

that like the temperature 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 be fine to the delicate words that you

need to use to pause the conversation yeah and it's and i find as your 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 i'm actually i can't i can't pull like i need to stay strong about what i believe because i Right.

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.

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.

Let's talk about it.

But we can't keep going on like this where I don't feel I can count on you 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 because on the other side of that is a much better, stronger connection.

And 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.

So 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.

And 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.

Like, here's the benefit 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 could talk all all day about this but I'm

happy to move on 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 going

to get the promotion they expected or wanted that can be of course that's challenging so again getting your mindset right recognizing they're disappointed they're going to be disappointed recognizing how you felt the time that 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 because 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, 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 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.

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 as really important.

So for those reasons, we're going to bring someone in 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 a few elements there that stood out to me, one is just being very upfront and not bearing 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, OK, 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 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 if they're a good employee, hopefully they have hope for the future.

I love that. Is there anything else to that script that you think is really highlighting?

Or do you think I touched on the key elements?

I think you touched on the key elements.

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 get right into it.

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 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, to 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, when the workplace, people, you know, they're going through all their feelings, all their emotions, disappointments are going to go home and tell their spouse, you know, didn't get the promotion or whatever.

It's going to loom large.

It's going to 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.

did. I care about your career.

You are always going to be able to help people stay, 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.

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.

Yeah, that's the defensiveness stuff.

And, you know, again, I hope you've done your homework 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 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.

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 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 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.

That'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.

No, 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 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 decision that I've made.

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 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.

Let's get into it. I know, so I'm willing 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 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 kind of getting in the mindset of recognizing that if you shied away from those conversations, kind of like you're the problem here.

And you kind of have some ketchup 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.

You know, maybe I'm not sure.

And that bleeds into, maybe I haven't been clear with this person.

So you want, because 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 perceive even 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 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 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 going to have a future together that is very crystal clear yes crystal clear

yeah okay so yeah that was great so it starts with uh being up front this is a difficult conversation just to set expectations they're like oh shit and then And it seems like you come back to, again, multiple times this happened, like observing here's what's happening.

It's happened multiple times.

I keep hearing multiple from multiple people.

There needs 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 blah blah blah but 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 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 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 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 this is even more important than that because hopefully

this addresses the problem.

You 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 already had the conversation, right?

They're not surprised.

It's clear. We've had the discussion.

Yeah. So basically the script is like, it's going to be a difficult conversation.

I've seen multiple times this thing, and we've talked multiple times and it's still not 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?

Well, the script for doing the firing is again, please everybody talk to your HR professional, talk to your lawyer.

Okay. I'm not a lawyer.

Right. 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 needed you to make these changes.

You haven't made these changes and we're going to, we're going to part ways.

So I have here, you know, Sarah from HR or whatever, and we're going to 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.

It feels very reasonable to me.

Is there anything else along these lines?

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 manager, I was, I was doing in a training program.

She said, I don't like getting positive feedback I 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 or 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 doing that.

That's really working for you.

If you do that often enough, you do get in the habit.

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 really keeping her head above water and 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 messages, you've already sort of laid the reservoir of goodwill.

I love giving positive feedback.

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 that easy if you do it well, which is a really good point.

And we always need scripts for how to give really good positive of feedback and have great conversations.

Yeah. That's interesting.

There's less demand for that.

How do I have better great conversations or complimenting people?

Right, right. No, man.

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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 do people think this is their job to make their employees happy?

And what should they be thinking instead is their job as a leader?

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 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 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 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 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.

I mean, ultimately, right, as you're a startup.

If you're not in a startup in your 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 this high engagement workforce.

High engagement workforce is great.

I think where that comes from is winning culture, which means we're set up for success.

We've 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 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?

A hundred percent. 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 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?

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.

Because, you know, like he wants to do right by his workforce.

And so, you know, they have avocado toast at 10am, 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're actually supposed to do.

And there began to be kind of a clicky, 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 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 want to have a great workplace.

But 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, 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, 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?

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 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 their 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.

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.

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 make a business that works.

It always reminds me, Sheryl Sandberg came to a talk at Airbnb once and people are asking like, what do you do with all this?

We're just like constantly in chaos.

Things are always re -organizing.

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.

too. 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, here's what I thought leadership was going to 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 what they're wrong about or what they miss and what they have to realize?

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 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 and help them create goals and, you know, achieve milestones and course correctly, they got off course.

And 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 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, a COO or somebody else who could be the person who would be managing the internal while she got to be more visionary, 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 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 this 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 going to have much more confrontation.

If you hate structure.

Actually, this reminds me, Joe Gebi at Airbnb was very anti -process.

At the beginning of Airbnb, it's like, we're not going to have a process.

I hate process. We're going to run.

That's the big company stuff.

And then it's chaos constantly.

And then eventually it's like, okay, 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 like founders are kind of 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 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 a 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, OKRs, whatever it is.

And I think it's helpful sometimes to go through 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 constantly reinvent the wheels of leadership such important context

like obviously 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 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.

Meetings come up a lot on this podcast.

People hate them. People love them.

Some are great. Some are bad.

Most are bad. You have some cool advice on just how to make meetings more effective and 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 few people that loves meetings or i should say i don't

love meetings i love the potential for meetings i love 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 -meet, 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, articulate those as deliverables, I promise you, you're going to have better meetings.

Okay. So it's, what did we decide here?

Who's going to do what by when?

So basically action items with dates, and then who needs to know about what we decided here?

Is that how you put it?

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.

They don't tell anyone.

I made this promise for my team that you guys need to kind of go do, or 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 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 or 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're 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.

I love that you highlighted that.

I was going to say exactly the same thing that like, yeah, 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.

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 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 you know putting lists together 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 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.

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 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.

Love 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 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's sort of crystallous 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.

I worry that somebody might not weigh in and say, actually, I have a very different point of view of 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.

Let's 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 a 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.

But who do you point this 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 did we decide here?

Now, if you're in a meeting with a large executive team, which I do work with sometimes, sometimes or non -executive team like a group of some sort, then you probably want to get a few people just like I would just even say as a facilitator, two or three people.

Okay, two or three people, what do we decide here?

And if you can 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 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.

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?

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.

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 every time she's in a 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. Amazing. OK, 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 at a company trickle down from the founders having their challenges with each other.

And I started a company in the past and I don't think people realize how significant this decision is in your life.

It's basically you're 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 well i just want to reiterate what you just said 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, with a lot of 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 like, yeah, I'll start a company with a cool idea.

Let's just do oh, it's going to 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.

And oftentimes it's like friends, you know, and then it becomes even more challenging because I want to be 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 questionnaire.

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 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 go together i might care about excellence and you might care about work -life balance wow let's talk about that because i i think it's going to be really important as we

go through 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 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 acts and acts in 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, solve a lot of problems before they start.

So signs that your values don't align, it's basically like you both can't be true, is the way I think about it as you talk.

It's hard to be excellent, focus on excellence, and also not work long hours, which it's possible, but 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.

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 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 if 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 caused this conflict that didn't have to happen if they'd had the conversation in advance.

It comes back to where we started of having these conversations is is is necessary and almost like helps the other person 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 because you're 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 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 that you can point people to, or are there just like a bunch and don't worry too much about which one you go?

I mean, the one I use is super simple, which is 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.

Got it. So you just Google list of values, there's a PDF, you can just circle the ones that are most and pick like whatever small number don't you know half of them actually the 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 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.

Awesome. 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 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 while it's too late, 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 wistfully, 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 Sheryl said, like all the, all the chaos.

And he said to me, gosh, I don't see why we have to grow.

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.

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 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?

What is, yeah, what does success look like?

What does success look like to you?

What's the vision for the company when it reaches its full potential?

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 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 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 let's talk about let's talk about it and they're like i'm working through it myself now you have conflict 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 It's 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 with the questions or 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 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.

It 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.

That's not even a bad thing.

You're smart people.

You have this 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, you know, sort of sulky, difficult conversation.

I 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, you know, to use your word before, it feels like a family.

By the way, that's great.

That's fantastic. I want to have a get it done, results focused culture where we're just like executing the hell out of everything and that we're just focused on winning.

By the way, those two can actually exist together.

But if you're pushing in one direction without the other and your co -founder is 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 client's client 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, you know, lack of sort 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.

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.

But in 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?

Absolutely. I mean, so many examples.

I'm going to give two quick examples.

One is when I first started my coaching practice, I just kind of started.

And 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'd had this conversation with somebody that didn't go very well.

And I just thought, in my mind's eye, I thought, what will become of me?

That was my voice in my head for quite a long time.

What will become of me?

And 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.

and 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 onto the couch and took 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 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 going to turn out to be true.

Wow. Amazing story.

Imagine many people feel those moments and it's empowering to hear that it can all turn out really well, even when you're lying on the floor crying for an hour.

An hour is a long time to cry on the floor.

It is a long time to cry.

It really like I was I thought about it because most people just cry for 10 or 15 minutes.

I was crying for an hour.

I'm positive. Yeah.

Great, great story.

You said yet another story.

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 off sites.

And this was early, early days of my coaching career.

And I was doing this off site 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 uh this like 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 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 offsites after that experience.

I tell you, that was a real low, because 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 going to get what will become for me.

But I turned it into, in my mind's eye, or I should say 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.

What I also love about this is there's this uh this feeling of imposter syndrome is specifically this fear that I do something wrong and 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 Alyssa is terrible forever no 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 Alyssa 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 move to our very exciting lightning round?

The only last thing I want to talk about, just sort of circling back to your role as a leader.

I was one time working with a CEO who was handling the fact that this launch was not going well.

Like I said, the launch wasn't happening, kick it, put off, put off, put off, put off.

And 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 patience.

So what I want to say to everybody is like, sometimes you need to have patience 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 patience or an issue with process?

I guess, is there a sign that you're like, it's probably a process thing and you're ignoring a glaring problem that everyone will seize.

I think the sign is when if you search your mind, you don't really know how this thing is going to 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.

Those are symptoms that you just need to dive deeper and like just be a little more in touch with what's going on and talk to some folks and look at some data and that might and by the way it might not be a massive process problem it might just be like 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 needs to somehow be just you know surfaced so if you're just expecting if there's just hope this will work out versus like i see a path to this working out it's probably not probably

a problem yeah well said is there anything else that you wanted to share a touch on that you think might be helpful We talked a lot about the co -founder's prenup, which I think people would think like, well, I'm not a co -founder, I don't need that.

I 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 know, 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 larger 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 what'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 let me just let you know when it's done.

And, you know, like 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.

So this kind of what goes into like these read me's people put together.

Here's how you work 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 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 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 things that are really important not just because like

oh you didn't text me when i wanted you to text me being clear what do you know uh is there anything else that you think might be helpful to share before we get to our very exciting lightning round no just that well with that alissa we reached our very exciting lightning round are you ready i can't

wait i'm ready here we go uh first question are there two or three books that you find yourself most recommending to other people so we already talked about uh Kim Scott, the wonderful, amazing Kim Scott, and her book, Radical Candor, is one I recommend a lot to people.

It's fantastic. Working Backwards by, gosh, Colin Bryan and Bill Breyer and Bill something is about sort of the Amazon way of working backwards from the customer.

Super geeky and tactical.

I love it. I slurp it up like Harry Potter.

It's so good. And I definitely recommend to my clients about like Amazon's management science.

And the third is Walt Disney by Neil Gabler, 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.

The first two recommendations we've had on the podcast, Kim Scott and Bill Carr is the other co -author.

He's been on the podcast and people love that episode.

I haven't had Walt Disney on.

I've got to work on that.

Or the writer, Neil Gaiman.

Okay, next question.

Is there a favorite recent movie or TV show you really enjoy?

Yeah, I enjoyed Inside Out too.

I thought it was fantastic.

I can see why you'd love 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 stew 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?

Yes. The Ninja Creamy.

Say 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 is delicious.

And it takes 10 minutes and 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 in 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 your 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 you're

if you don't see where it's all going that's normal that's good wow great one good one i'm gonna i need to do something all these mottos they're so good i need to like carry a poster or something that's a great idea or in your newsletter.

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, exec coach.

If someone was thinking about going down that path, is there like one piece of advice you could share to help them pursue this path, even explore if it's right for them?

If you think you want to become a coach and you immediately want to 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, beneath the surface.

I love how your energy just changed into like coaching mode when you said that.

I love that. That was like such an interesting thing to see.

And that was great advice.

That's easier said than done.

And it's interesting.

You 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.

Alyssa, this was incredible.

Two final questions.

Where can 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.

So feel free to reach out if you want to have a conversation about coaching.

You can find me at alissacone .com.

And actually, I'm going to take some resources and put them at a special link, which is alissacone .com forward slash Lenny.

if you want to download the co -founder prenup.

I also have a personal operating manual and a few other resources I will put there.

AlyssaCohn .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 want to 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.

And 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, and 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.

From startup to grown up, 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.

Thank you so much for listening.

If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.

Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast.

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See you in the next episode.

[Mastering Difficult Conversations and Leadership: Insights from Executive Coach Alyssa Cohn]-[Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)]

📋 Summary

Mastering Difficult Conversations and Leadership

The Art of Difficult Conversations

Redefining Leadership: Results over Happiness

Tactical Meeting Management

The Founder Prenup

Conclusion

🎯Key Sentences

📝Key Phrases

📖 Transcript