Jack Dorsey: "I hired a CEO coach and learned nothing" — Here's what he did instead #podcast

By Sequoia Capital

Categories: VC, Startup

Summary

Jack Dorsey ditched his CEO coach despite universal advice, discovering that treating every person and problem as a mentor—requiring intentional learning—proved far more valuable than formal coaching relationships.

Key Takeaways

1. Formal mentorship often fails because passive consumption replaces active learning. Shift from asking 'who's my mentor?' to deciding you'll extract lessons from every interaction.
2. CEO coaches can be ineffective even when well-intentioned. The real value comes from taking ownership of your learning through intentional reflection on daily problems.
3. Learning requires active decision-making, not passive advice-seeking. Frame every problem faced as a teaching moment by consciously deciding to extract insights from it.
4. Reverse mentorship opportunities are everywhere—colleagues, problems, encounters—but only yield value when you adopt a learning mindset rather than waiting for structured guidance.

Topics

• CEO coaching effectiveness
• Self-directed learning vs formal mentorship
• Leadership mindset shifts
• Learning agility
• Twitter leadership lessons

Transcript Excerpt

When I first became CEO of Twitter, everyone was telling me I needed a a CEO coach. And I got the CEO coach >> [music] >> and he was a great guy, but like I was learning absolutely nothing. And it just reminded me of >> [music] >> all these times when you put so much emphasis on like who's my mentor? Who am I learning from? Who's my mentor? Who am I learning from? And [music] around that time I just decided I'm going to shift my mindset and every single person I talk with, [music] every single e...