(upbeat music) So improve the quality of your decisions as much as possible. Try to write things down that you're deciding about. Get other people, trusted advisors, particularly people who have different points of view with you are really important. Here's a really important one. You have to give permission. So when we're trying to seek information from other people, we think that permission is implied for them to say whatever to us, but we have to actually offer that permission and they have to be willing to give it to us.

So I'm sure this has happened to you. You like fire someone or you break up with somebody or whatever. And as soon as you do that, you have a whole bunch of friends who say, "Oh, I'm so glad you did that. I thought you should have done that like six months ago." Has that one happened to you?

- That one hasn't 'cause my wife and I started dating, oh gosh, 2004. So it's been a long time since I've had that conversation. I'm sure it has, but boy, has it been a while. - But like, or you fire someone or you quit your job or whatever. - Yeah, for sure.

- And people say, "I bet you might've said it to somebody when they break up. Like, oh, I'm so happy 'cause really, wish you would've done that sooner." So this is like a really common thing that happens. You know, "Oh, I'm so happy you quit your job. Like, you were so miserable every single day.

I knew you should have done that like a long time ago." And your thought when people say that to you is, "Okay, but like, why didn't you tell me?" And the answer is because there wasn't any explicit permission given. So in order to really find out what somebody thinks, you have to give them permission to say what they think.

- Yeah, I saw this so much in venture capital that I would be in meetings with other venture investors and they'd give feedback to founders saying, "Oh, like, I think it's like pretty good, but it's not a good fit." And then after they'd turn to me and be like, "God, that company's horrible.

It's terrible." I was like, "We should have just told him that." - That's right. - And I think everyone feels bad telling them that. And now every time someone asks me for feedback on their startup, I'm like, "How honest do you want me to be? Like, do you want me to tell you to quit?" So I guess if you're on the other side, you can also invite someone to invite you to be more honest and give critical feedback.

- Yeah, so I actually do that with my friends. I'm like, "Are we having a conversation where you want advice or where you're just offloading, like, your emotion?" 'Cause I wanna know, right? Because sometimes they don't really want your advice. So I think that's really important. I mean, I think that's just really important.

I think Ron Conway, who founded SV Angel, is such a good example of doing this really well, like being a very good decision coach to somebody. So he would actually tell the companies what he thought of them. But he would sit down and he'd basically say like, "I think we can admit this isn't working." As opposed to, "Eh, it seems pretty good.

Just keep going." He'd be like, "Look, it's not working." And invariably the founders would push back on him and say, "No, but I know we can turn it around." So it wasn't so much disagreement that it wasn't working, 'cause I think everybody knows when things aren't working very well, but it was always, "No, but we can turn it around." So he was trying to coach them into letting go, right?

And founders are gritty by nature. Of course they don't wanna let go. So when they said, "No, but I think I can turn it around," his tactic was not to disagree with them, which I think would have just caused a rift, but to say, "Okay, tell me exactly what turning it around looks like." So like, let's think about the next two months, right?

So you're saying you're gonna turn this around. What exactly does that look like? And try to figure out what those benchmarks are. Now he would sit down and do that with the founder so that the founder now owned that sort of along with Ron Conway. And this is a really good trick for decision-making is that often your decision-making is at its worst when you're trying to make the decision right then, like when you're actually facing the decision down.

And this is something that really improves decision quality is to think in advance. As much as possible, do advanced planning on your decisions. It's much more efficient. It creates much better decisions. So that's essentially what he's doing in this moment. He's saying, "Let's think about two months ago, two months from now, rather.

So we're gonna think about two months from now or three months from now, the end of the next quarter. Let's think about what this is gonna look like when you've turned it around." And then basically just set a set of benchmarks. And then in three months, you can sit down with them and say, "But you haven't hit them." And we agreed that that's what it looked like.

And that actually makes those decisions a lot cleaner. And you can do that with your personal decisions as well, right? Like if you ever, we're all in these situations like you have a relationship where it's not, it's just not going well, but you feel like you can turn it around.

You feel like you have so much time invested and you do love the person, but you're like unhappy, but you know, you can make it change. There's kind of two things to do is not, don't face the decision down right then, figure out, but what does change look like?

So at that moment, say, "How long am I willing to tolerate the status quo, the way that the relationship is right now or worse? What do I need to do, do I think, in order to turn this around?" And then however long that is that you're willing to tolerate the status quo, figure out at the end of that time period, say it's six months, what does change look like?

What will it look like when things have actually turned around here? You can do this for a job, right? A job that you're miserable in. What do I need to do? What will it look like that it's actually turned around? What will have changed? And the reason that you need to do that is because when you're actually facing down the decision, that's when you're most likely to be rationalizing things away.

That's when your forecasts are gonna be really inaccurate. That's when the things that you want to be true of the world are going to influence your actions the most. It's when everything kind of goes to crap. And the way that I try to sort of put it to people to get them to understand this is that you can say all you want that you don't wanna eat sugar, but when there's a cupcake right in front of you, it's really hard to say no.

And that's true, not just of like cupcakes or pizza or whatever that are sitting right in front of you. It's also true like when you're facing a breakup or you're facing having to fire an employee, which isn't fun, or you're facing wanting to quit your job, right? Or break up with a friend or whatever.

These things are very hard to do because it's that moment where we're worried about all the time we've put into something, whether it's that moment where you go from in a state of failing to having failed. Because as long as you keep going, you might turn it around and not have to actually sort of put that failure on the books.

You know, like if you buy a stock and you bought it at 50 and it goes to 30, as long as you hold, you could get back to 50. - Yeah, but selling now is kind of accepting that. - It's accepting that, and that's really hard for us. So that's why we want to think about both.

How do we ask for permission for people to tell us the truth? How do we explicitly ask people if they want the truth? Right, so we need to have both of those things going on. And then how do we also figure out how the person can receive the truth?

And that's true whether we're coaching somebody else or we're thinking about how we can do this for ourselves. And one of the best ways for us to receive the truth is for us to think about the truth is something in the future.