The Hard Conversations Founders Don't Want to Have

Dalton defines a hard conversation as one with high stakes that makes someone uncomfortable. Michael says he initially measured his value as an advisor by how much founders enjoyed talking with him, then learned to share candid views about their products and effort. Dalton argues that trusted friends and advisors are willing to say what others avoid.

Dalton describes founders who arrive at office hours having already decided and seem to want validation. He and Michael suggest asking what is really driving the meeting, such as a disagreement with a co-founder or insecurity about applying to YC. They say many office-hours conversations end up focused on a different issue than the one the founder first raised.

When a startup may not raise enough to fund its planned spending, Michael recommends preparing for the difficult outcome while staying optimistic. Dalton compares this to carrying a parachute in case it is needed. For requests to spend hours on a deep dive, they suggest identifying the underlying concern, talking to customers when customer knowledge is missing, and arriving with an agenda.

Dalton says co-founders need to practice disagreeing without saying things that permanently damage their relationship. Michael adds that people handle conflict differently, so a founder may need to give a colleague time to process rather than pushing for an immediate discussion. For employees, he recommends being open to the possibility that someone is a poor fit and sharing company realities, including short runway, so good employees can respond with useful ideas.

Michael and Dalton say they do not always handle hard conversations well, but they try to ask whether they are deceiving themselves and what question sits beneath the initial one. Michael closes by describing the YC partner role as helping founders through mistakes he has made before and knowing a way forward.