Casey Winters: evaluation

Transcript context

…Yeah. I don't know. I'm not that good with Sheets formulas. Shifting course a little bit, you also wrote this really interesting post on founder intuition versus team expertise. There's a lot to it, and I think it's a really interesting topic because it's this classic discussion that startups have. How much should a founder trust their gut, and how much should it be top-down, "Here's what we should be doing" versus the team, bottom-up, figure out what to build? I'd love to spend a little time here. Maybe just to start broadly, what is this? You came up with a framework of how to think about when founder intuition should overrule, say, team expertise, and how that change over time, so maybe just talk about that. Yeah. If founders are lucky/good enough to find product-market fit, they've usually built up all this intuition about their customers, about their product, and their business that are really hard to explain to others and may even be subconscious. When they start to hire people, these people will come in with a lot of excitement, ideas, maybe even really relevant experience, especially senior leaders. I've seen some founders are like, "Cool. I need to let these experts start to own these areas and get out of the geek house. " I think that's actually the opposite of what you want, because none of these people know the business as well as you get it. You actually need to direct them until they show you they've really got it and are making better decisions than you would. This is not a founder example, but I remember when I hired Erika Warren to build out our loyalty program at Grubhub, and she now leads growth at Change.org. After a month or so, she was like, "Dude, you're in all my meetings. I got this." That let me know she was in a different part of the situational leadership framework than I had put her in, so I backed away, and she crushed it from there. Founders will put a lot of new leaders in that delegate bucket too quickly. It's like, "Ah, they got it. They know more than me," when founders actually know the right answer and should just tell them. This can, of course, change like in the case of Erika. If you hire the right people, they do get smarter than you. You can and you should start delegating. Many founders don't notice the signals where their founder intuition has been usurped by team expertise, or maybe it's just ebbed in effectiveness over time. That, of course, makes sense. Founders have all these different things they're dealing with, and your employees can really dive deep in certain areas. I encourage employees to proactively signal both directions, like, "Hey, I need direction from you." Or, "Hey, I got it from here. Trust me on this one." Interesting. You're saying, as a founder, the heuristic should be if you feel confident about a decision, generally, you should be clear, like, "Hey, I think I know what we need to be doing here," and don't just make people feel better, necessarily, by just saying, "Okay. You tell us what you want to do." Then on the flip side, as an employee at the company, if you feel really confident about something, make it clear to the founder like, "I really think this is the right move." Is there anything more you want to add there?…

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