Dalton & Michael: The hard conversations founders don't want to have

And I'll probably make them again. And I'll probably make them again.

And the only thing that I could say is I know the way out. This is Michael Seibel with Dalton Caldwell. At YC, we often have to have challenging conversations with founders when giving them advice. Today, we would like to talk through some of the hard conversations that founders don't want to have.

Dalton, why don't you set this up for us? Well, look. Let's start by trying to define a hard conversation. By definition, if it's a conversation you're looking forward to having, it is not a hard conversation. A hard conversation sucks. Yeah. That's why it's called a hard conversation. You don't wanna have them.

They're bad. Right? Or they don't feel good. They don't feel good. They don't feel good. You're you dread the hard conversations. And so, you know, a hard conversation is when the stakes are high. Like, it could go bad.

It could go off the rails. It could be you're saying something risky or you're making a point. Maybe you're doing something that's impolite or saying something that's impolite. Because, again, think about an easy conversation. Easy conversation is superficial. You used to agree with someone. It's like, hey. You're great.

Way to go. That's an easy conversation. Right? Yes. Hard conversation is not that. A hard conversation is when you're vulnerable. You're putting yourself out there. You're saying something that someone in the conversation is in a is uncomfortable.

You know, it's funny was as you set that up, what's tricky being a startup adviser is that you know it's gonna help someone to have hard conversations with them, but you also know that they're not going to enjoy it. And I think as an as a as a YC partner in the early days, I think I measured my effectiveness based on how much fun founders had talking to me.

And and and only after couple batches that I realized that doesn't really do anything. And then when I started having honest conversations and talking about, like, my actual opinions about their product or about how hard they were working, oof, like, the job changed. Did you experience that? Yeah. I mean,.

if you just agree with someone, it's easy to, you know and you, like, mirror their body language. Like, there's all these techniques you can do to be likable where you're like, oh, wow. Like, you're so smart. Everything you say is correct. Your jokes are funny. You know? You can do this stuff. And the problem is it's not that helpful if it's just not that helpful.

Like and, again, if you think about us as founders or think about friends, think about our friendship with people. The people that you would consider your two true friends in life are the people that can say the things to you that no one else will. Yes. And if you're surrounded by by crowds of people that, for whatever reason, are unable or unwilling to tell you the truth about anything,.

you're you're having a bad time. One, how are you gonna learn? Right? How are you going to learn when you're giving people inputs and their output back to you is dishonest? Because they would just wanna make sure that you feel good. So let's talk about some of the hard conversations that we have, with founders. Let's take an easy one. I'll give you an easy first example.

The founder comes to office hours with us. They have already made a decision. It is obvious they've already made a decision, and they want us to spend an hour validating that they've made the right decision. That's kind of a hard conversation because, like, Dalton, what do like, if we were being 1000% honest, what would we actually just say, like, bluntly?

Well, here's I I think there's two ways to handle this. There's the dishonest way. The easy conversation is to take them at face value and be like, oh, wow. Seems like you've thought about this really well. I I see no errors in your logic.

A genius. With no You did it again. Exactly. Yeah. With, like, without the information to even verify that. Right? Like, with with no actual facts to verify. Like, what.

amazing strategy. I just I this is just a plus work. And then then there's the hard thing. And what I think the hard thing is is not even disagreeing with it. It's to say it's the question behind the question, which is, hey. It seems like you've already made a decision. Cool. Why are we talking about this?

Yes. Why are we here right now? Like Why are we here today? What's the question behind the question? Is it is it that someone else is it that your cofounder disagrees with you and what you're trying to do is bring my opinion into it to prove that you're right? Yes. Is it that someone else disagrees with like like, there's always a real question hiding behind the scenes.

And, man, people it it's always there. When I when I when I bring this up, they're like they're like, yeah. There is. There is. You know, there's a question behind the question. Yes.

By the isn't this such a common theme? Like, I think if you really wanna understand office hours in a nutshell, 60 to 80% of the time, a founder will go into office hours with one question, and we won't even end up talking about that thing. Like, that's not the actual question.

That's not the actual This comes up a lot with, like, people talking about applying to YC. Like, people are always, like, think it's really important. Michael, I have some really important questions I wanna ask you about applying to YC. And he talks to them, and it's just like, should I apply to like like, there's no There's no there there. Yeah. It's a no op. There's nothing.

there is no my revenue monthly or quarterly?

It's like, what like, who like, just Yeah. And so, again, I get where they're coming from and what they what they're really the question behind the question, I think, is I feel insecure, and I want to talk to you, Dalton and Michael, about this so that you give me validation that I should apply. Great. But and so that's the actual question behind the question, not, hey.

I have this really complicated question about the application that's I don't know. Alright. Let's stick with hard ones.

We're talking to an early stage company, and it's becoming obvious that they're not gonna be able to raise the amount of money that they wanna raise. And they're not gonna be able to execute this magical explosion of spending that they wanna execute, that they've convinced themselves is what's required to get product market fit.

What do you do in those situations? You know, that's a that's a really tough one because you want people to be optimistic as we've spoken about before. And it's hard to you never wanna be short on someone's startup. And so what I would usually say on this one is think about what a great life philosophy it is to set your expectations low and prepare for the worst.

And then if you get surprised, you get surprised on the upside, not the downside. And so the key in this hard hard conversation is not to debate someone that their plan is bad. Keep the optimism. You know? But isn't it better to sort of have a plan for the worst and not be surprised on the downside? And if you're surprised on the upside, fantastic. Right, man? You're winning.

And, again, people don't wanna hear this. This is a hard conversation to have. It's like going up in the airplane. Do you wanna bring the parachute with you or not? Like, I'm not trying to be grim by saying bring a parachute, but wouldn't you wanna bring the parachute? Yeah. If you had the choice. What's the downside of bringing the parachute?

You don't use it? It's fine.

Alright. So here's another one that comes up a lot. Dalton, I'd like to spend two hours really going deep on this problem, but our office hours, don't go that long. How do you how do you deal with me? I wanna do a deep dive?

Yes. This is another one of those question behind the questions. And, again, it can be different things depending on the people. I think sometimes what's going on is you are an idiot, and I don't have confidence you can give me advice unless I spend two hours showing you a slide deck so I can explain everything to you. Sometimes it's it's not really about the meeting.

I just want a lot of FaceTime so we can build the relationship or whatever. On And so this is Yes. Yeah. Okay. That's fine. But you see what I'm saying, man? There's usually when someone asks that, there's something else going on. And, again, my it's usually the first one for me where they think we don't understand.

Again, maybe we don't. I don't know. But, like, they're instead of them directly saying, I am concerned that you do not sufficiently understand our business, And so I wanna make sure you do x y and z. Okay. That's a hard conversation, but then I'm like, okay. I know where you're coming from. Alright. I hear you.

Yes. But some weird, like, can we meet for three hours? Yeah. I'm always like, why? Yes. I wanna know the question behind the question. You know? Yes.

Well and what's so funny is if they just said,.

I don't think you're smart about this particular thing, we would get to the we would get to the meeting. Right?

We would get to the meeting.

Now I think there's a couple others that I see. One is this assumption that we are, like, godlike advisers with complete understandings of every user base and every problem in the world. And, like, they can kind of, like, shortcut talking to users if they just spend enough time talking to us.

And so that one is just like, folks, like, so often in this one, I'm just like, you're having a conversation with me that you should have with your customers. Like, talk to them. Like, I don't use your product. Talk to the people who do. I think the other one, which, I really try to push back on is I'm lazy and I didn't come up with the agenda. I wanna, like, roam my random thoughts.

And over the course of two hours, we will have twenty minutes of productivity. But I don't wanna organize my thoughts, and I want you to accommodate that. And for that one, I'm always just like, that's like you're not training yourself for success here. Like, you expect more from yourself.

Like, if your competitors can get twenty minutes of input, twenty minutes of output, they will do way better than two hours of input, twenty minutes of output. And just you know, that seems to kick people into gear. What's another one that that that you're excited I.

I think we can shift gears to a couple other context for hard conversations. Let's talk about hard conversations, not with us, but with cofounders. And so the the thing I wanna set up here is the classic thing is people become cofounders. Yes. They've never once had a disagreement or hard conversation. It's all been superficial. We're best friends. We work to you know, it's all wonderful.

And then the first time they have a hard conversation, that's.

it. Explosion. Tell tell you've seen this, man. Like, what what's going on here? Like Well, first things first. Right?

This is why we like teams who known each other for at least a little bit and have some kind of work or personal relationship because I always say that, like, when you have some kind of non you know, if you have some kind of base relationship that you might wanna maintain even if this startup doesn't work, you won't say that thing or you'll think really hard before saying that thing that will, like, shatter the relationship.

But when you're like, oh, the only reason why I'm even talking to you is because of this start up, and now I'm convinced that our start up's fucked, which by the way, you'll be convinced your start up's fucked just continuously. That's like a normal feeling. And then you're like, well, fuck it. Man, like, you can't you know, there are things you can't unsay. And, wow.

Sometimes the original sin was like, shouldn't have started the company with this person. But, like, let's say you are doing a company with your cofounder and it's just really frustrating. What's the advice you give to founders on how to kind of process them? I think it's like.

you have to learn how to fight, and maybe fight's the wrong word, how to disagree. It's like you have to learn how to pull your punches and have a disagreement that's a real disagreement and actually release the pressure of the disagreement in a way that doesn't cross the line so that the relationship is irreparably harmed. And it's a skill you have to learn.

And if you don't and if you've never been through a major disagreement with someone or had the skills for both of you to have a fundamental disagreement and talk it through yet not blow the relationship up Yeah.

And, again, this is a skill like any other skill, man. It's a skill. You know, it's funny because the analogy that I'm thinking in my head is that, like, you know, it's a pressure release valve, and you don't wanna just rip it open.

Yeah.

But if you don't release any pressure, you also have a It builds up and blows up. Yeah. Either way, it blows up. Either way, it blows up. If you let the pressure just.

build, build, build by only having superficial conversations for years, one day someone will snap. Boom. And on the flip side, if you just, like, leave it open all the time and you fight constantly, that ain't gonna work either. No. It's sort of like the happy medium thing. No. I think the biggest thing that I had to learn.

and and Amy, our former batch director, used to talk about this a lot, is this concept that, like, people will deal with conflict differently. I love to engage and, like, lean in and talk through conflict, But it's just as likely the person that I'm working with wants to avoid conflict or wants to take time to process conflict or doesn't process conflict through conversation.

And, like, I have to look at those cues. I have to understand who I'm talking to and realize that when I have to kinda take a step back, even though I'm unsatisfied because I'm creating more of a problem by, like, continuing to push forward. And I think that this is one of those situations where you can't blame the other person for, like, not acting correctly.

Like, you have to take responsibility, because you can both blame each other into an explosion all day long. Right? Like, that's easy.

So next, what about what about employees? What do you think there? I think it's I think it's the same sort of situation. Again, the dynamic might be a little bit different. But if you're only ever having easy, superficial conversations with people, it's cool until it's not.

And sometimes the best way to work with folks at your company or whether colleagues, employee, whatever we wanna call them, is to find the right way to have some of these hard conversations. And you know what they are. You know? You're probably I'm sure someone watching this is like, yeah. I I can think of a few hard I can think of some things I would say if I weren't afraid of the consequences.

Yes. Know, like, there's a right way and a wrong way to do it. We're not saying go blow people up, but if you're just avoiding hard conversations,.

no one wins. No. And the most importantly, the employee doesn't win. Because, like, the employee probably knows something's wrong. And if you're the boss, they probably expect you to be the one kind of addressing it. You know, one thing that I say about employees a lot and I I wanna limit this to, like, startups and startup employees.

Like, first, like, allow the idea in your head that you might have picked the wrong person, that the person isn't the right fit. Like like, it's like, even if you did your best in interviewing and they're really good and da da da, like, allow in your head the idea that, like, that might not be the right fit. And, like, this person might be able to do 10 x better work somewhere else.

And, like, that would make their life better just as much as make your life better. Like, allow for that because sometimes people feel like they have to solve unsolvable problems. And then the second thing I think about with, like, good start up employees is they want honesty.

Like, they good start up employees kind of understand this is a really hard task and that, like, the likelihood of being successful is really low. And they want to be in the know. They want transparency. They wanna know how the company is doing, and they wanna know how they can do 10 x better to impact the outcome of the company.

That's why you join a startup because you want an early stage job because you wanna impact the outcome of the company. I've been often surprised at, like, sharing bad news. Like, oh, we only have two months of runway. Right? I would think would be demotivating. But for great start up employees, they're like, alright. How the fuck are we gonna fix this? And then you can get juice from them.

You're like, well, alright. I mean, if we're all in the trenches together, maybe we can make something happen. But, like, it's really bad when, like, you know your start ups in the trenches and your, like, employees are, like, clueless. Well, well, I thought everything was going fine. You raised a bunch of money. You never told me anything was wrong. You're, like I.

think that to our credit, you and I say this a lot. If we were doing office hours with ourselves, what would what would we say? And man. I think sometimes we dodge hard conversations. Like Oh, sure. Like, we're not saying to be vulnerable here, we're not saying we always get this right a % of the time.

In fact, I might argue many times the first conversations we have are wrong. I think the only thing that we do well is we continuously ask ourselves, are we lying to ourselves? Or is there, like, what what did you say? What's the deeper question? What's the question behind the question? What's the question behind the question?

I think we are good at asking that, and sometimes we assume that the initial salvo of questions are complete bullshit ourselves. Within.

within YC itself. And I think that's life, man. I guess what I'm trying to say is no one's perfect. Don't put anyone on a pedestal. It doesn't matter who they are. They have their own shit. And that should be freeing and empowering and make you feel optimistic and not bad. Right?

Isn't that the right takeaway here? That's the right takeaway. You know,.

to close out, this reminds me of this, like, scene in the West Wing where one of the characters has a drug problem that's that's pretty bad. Another character is going through PTSD and is really struggling but doesn't want anyone to know. And this character is like a drug addict that, like, cleaned up and so on and so forth and is noticing the first character is struggling.

You know, the way the kind of story goes is that other people who don't understand how much pain the person's in will, like, say, oh, you should go see a psychiatrist or you should go get a prescription. Like, they'll do these superficial things. But this character knows. And so, like, he actually you know, the analogy is, like, he jumps down to the bottom of the well with him.

It's like, I'm at the bottom of the well struggling, and then my friend jumps down with me. And the, you know, the thing that they say at the end is that, like, well, I'm jumping down with you because I've climbed out of this well before and I know the way out. And I think so much about being a YC partner is, like, is is exactly that. Like, I've made all these mistakes before.

I'll probably make them again. Yeah. I'll probably make them again.

And the only thing that I could say is I know the way out. As opposed to like, oh, we play error free ball, which is obvious.

Man. Great chat. Thanks.