The Hard Conversations Founders Don't Want to Have

**Michael Seibel** (0:00)
I think so much about being a YC partner is exactly that. I've made all these mistakes before.

**Dalton Caldwell** (0:07)
And I'll probably make them again.

**Michael Seibel** (0:10)
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?

**Dalton Caldwell** (0:39)
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.
That's why it's called a hard conversation. You don't want to have them. They're bad, right?

**Michael Seibel** (1:00)
Or they don't feel good. They don't feel good.

**Dalton Caldwell** (1:03)
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 just agree with someone. It's like, hey, you're great.

**Michael Seibel** (1:29)
Way to go.

**Dalton Caldwell** (1:30)
That's an easy conversation, right?

**Michael Seibel** (1:31)
Yes.

**Dalton Caldwell** (1:32)
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 uncomfortable.

**Michael Seibel** (1:47)
You know, it's funny was, as you set that up, what's tricky being a startup advisor is that you know it's going to help someone to have hard conversations with them, but you also know that they're not going to enjoy it. And I think 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 only after a couple of batches that I realized that doesn't really do anything.
And then when I started having honest conversations and talking about my actual opinions about their product or about how hard they were working, the job changed. Did you experience that?

**Dalton Caldwell** (2:35)
Yeah. I mean, if you just agree with someone, it's easy to, you know, and you like mirror their body language. 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, think about us as founders, or think about friends, think about friendships with people, the people that you would consider your true friends in life are the people that can say the things to you that no one else will.

**Michael Seibel** (3:17)
Yes.

**Dalton Caldwell** (3:17)
And if you're surrounded by crowds of people that, for whatever reason, are unable or unwilling to tell you the truth about anything, you're having a bad time.

**Michael Seibel** (3:29)
Well, and how are you going to 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 want to 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 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, if we were being 1000% honest, what would we actually just say bluntly?

**Dalton Caldwell** (4:19)
Well, 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 see no errors in your logic.
You're a genius. You did it again.

**Michael Seibel** (4:37)
Exactly.
Without the information to even verify that, right? Like with no actual facts to verify.

**Dalton Caldwell** (4:45)
What an amazing strategy.
This is just A plus work. And 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.