Why the Obvious CEO Hire Is So Often the Wrong One

What if the same leader, running the same playbook, could fail in one place and win big in another?That's the question at the heart of my conversation with Jim Citrin, who has spent three decades at the top of the executive search world placing and advising CEOs. Jim is also one of my mentors, so we go past the usual hiring talk into what actually decides whether a leader succeeds: fit. We trace the Bill Perez story across Nike and Wrigley, why the surprising hire is so often the right one, and how aspiring leaders break the permission paradox.Why there's no single mold for a great leaderThe Bill Perez A/B test: same playbook, opposite outcomesHow the New York Times hired against the spec and 20x'd its valueThe permission paradox and how to actually break itWhy roughly 80% of CEO appointments are internal promotionsHow leaders get isolated from the truth, and how the best stay groundedHow to tell a good failure from a disqualifying oneConnect with Jason: https://www.linkedin.com/in/jasonbaumgarten/Email the show here: fithappens.fm00:00 Intro00:17 Meet Jim Citrin01:04 Jim's circuitous path to search03:13 A leadership belief Jim flipped on04:42 Founders vs. the curated path to CEO07:48 Bill Perez: the A/B test of fit11:41 Why the surprising hire often fits12:40 How the NYT hired against the spec16:04 Why the CEO job got harder19:05 The permission paradox22:55 The career paradox that started us25:47 Emperor's New Clothes: losing the truth31:02 Six success factors, 25 years later33:17 The resume trick that exposes bias35:49 Good failure vs. bad failure41:20 A question Jim asks himself daily43:18 Speed round: books, advice, flow