How to Have Hard Conversations With Founders

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Dalton: A hard conversation is when you're vulnerable. You're saying something that someone in the conversation is uncomfortable. What's tricky being a startup advisor is that it's going to help someone to have hard conversations with them, but they aren't going to enjoy it. "I think I measured my effectiveness based on how much fun founders had talking to me," he says.

Y Combinator group partners Michael Seibel and Dalton Caldwell discuss the importance of having honest and difficult conversations with startup founders. While having hard conversations can be uncomfortable, Michael and Dalton argue that this transparency is essential for founders to grow and ultimately, these experiences help founders have their own hard conversations that they've been avoiding with the people around them.
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