Honest conversations are necessary for successful startup advising and maintaining healthy relationships.

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  00:00

  Having honest conversations with founders is essential for successful startup advising.

  • A hard conversation is one where the stakes are high, it's risky, and it's uncomfortable.
  • Having honest conversations with founders about their product and work ethic is key to being an effective startup advisor.
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  02:42

  Founders come to office hours with a hidden agenda, so it's important to be honest and ask the right questions.

  • True friends are those who will tell you the truth, even if it's not what you want to hear.
  • Founders come to office hours with decisions already made, and it can be difficult to have an honest conversation about it.
  • Founders often come to office hours with one question, but the real question is usually hidden.
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  06:02

  Set expectations low and prepare for the worst to avoid surprises when seeking validation from YC.

  • People often ask questions about applying to YC, but the real question behind the question is usually about seeking validation.
  • Set expectations low and prepare for the worst to avoid being surprised on the downside.
  • When faced with a difficult conversation or a deep dive into a problem, consider the potential benefits of taking the time to discuss it.
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  09:01

  People often ask for more face time to build a relationship, but there's usually a deeper concern behind the request.
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  10:12

  Talk to your co-founder and think before speaking to maintain a healthy relationship.

  • Talk to your customers and organize your thoughts to maximize productivity.
  • Having a pre-existing relationship and having had some hard conversations can help co-founders avoid an explosion when they have their first disagreement.
  • Think carefully before saying something that could damage the relationship with your co-founder.
• 🤝
  13:18

  Learning to disagree without damaging relationships requires understanding needs and taking responsibility.

  • Learning how to disagree without damaging the relationship is a skill that must be learned.
  • Conflict resolution requires understanding the other person's needs and taking responsibility to avoid an explosion.
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  15:54

  Have difficult conversations with colleagues to ensure everyone wins, even if the person you hired isn't the right fit.

  • Find the right way to have hard conversations with colleagues to ensure everyone wins.
  • Allow the idea that the person you hired might not be the right fit, even if they seemed good in the interview.
  • Great startup employees want to be in the know, understand the difficulty of the task, and are motivated by the challenge of impacting the company's outcome.
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  18:33

  Showing someone the way out of their own struggle can help them overcome it.

  • Don't put anyone on a pedestal and don't assume the initial questions are complete.
  • Someone who has gone through a similar struggle can help another person out of their own by showing them the way out.