Firing people is the kindest thing you can do.

Barrett Brooks spent years as COO of ConvertKit, scaling the company past $30M before becoming an executive coach to founders and leaders. He joins hosts Adam Jay and Dale Zwizinski for a conversation about the uncomfortable side of people-first culture.

They get into what most leaders get wrong about kindness, accountability, and the gap between what a company says it values and what it actually rewards.

We discuss:

• Why a "people-first" culture can quietly protect your worst performers
• The real reason firing conversations get avoided, and why that's not kindness
• How to close the gap between stated values and lived behavior
• Building comp plans for intrinsically motivated, creative salespeople
• A simple exercise to learn what actually drives the people on your team

Chapters:
(00:00) Treating coaching like an athlete's craft
(01:29) Talent as a Culture Multiplier
(02:18) The hidden cost of an overly people-first culture
(05:00) "We should have fired more people"
(06:17) Setting boundaries like you would with a toddler
(09:14) The 1% of managers willing to have the hard conversation
(11:28) Where values collided with P&L at Kit
(14:50) What actually builds a winning culture
(18:46) Rebuilding a team after burnout
(25:56) The unsolved psychology of comp plans
(31:55) Monday Morning Move: closing the culture-phrase gap
(38:40) The Craft & Commerce speaker equity story
(41:48) Uncensored Questions

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