Leadership Coaching Blog | Coach Dan Estby

The Blog

From the Field

Weekly notes for managers stuck in the Vise, teams tired of mistaking motion for progress, and anyone who’s sat through a meeting wondering where the energy in the room just went.

From “Doers” to “Directors”: Evolving Your Leadership for the AI Era

TLDR; In the AI era, leaders must shift from managing “doers” focused on raw output to empowering “directors” who provide strategic judgment and oversight. Success requires redefining psychological safety so teams feel secure challenging AI ,…

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The Enterprise Agility Manifesto: A New North Star

tldr; PMI and the Agile Alliance have released a new Manifesto for Enterprise Agility. This isn’t just another framework for teams; it’s a strategic pivot for the entire organization. If we want to move beyond the…

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The Balancing Act: Protecting Your Team Without Losing the Win

tldr Explore the critical leadership challenge of protecting a team’s psychological health while simultaneously holding them accountable for high-quality delivery. Watch out for the “Nurture Trap,” where over-protection leads to stagnation, and the “Delivery Delusion,” where…

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From Directing to Coaching: The “Guide” Playbook

tldr; Directives are the siren song of efficiency that actually kill curiosity. If you want a team that thinks for themselves, stop giving them the answers. Today we look at how to build psychological safety, lead…

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Is your “directive” style sapping your teams innovation and effectiveness?

tldr; Directiveness feels efficient, but it’s often a “Checklist Trap” that kills curiosity and stalls growth. If you find yourself doing all the talking or approving every minor decision, you aren’t just managing—you’re dismantling your team’s…

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Is your chain of command killing your teams problem solving skills?

 tldr; When managers get involved in resolving differences of perspective or opinion, rather than challenge their teams to work together to solve problems – they engage in a game of professional “telephone” that drains efficiency and…

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The “Vacation Test” Part II: From Hero to Guide

tldr; Awareness is the first step, but action is where the transformation lives. If the “Vacation Test” revealed that you have opportunities to improve, the next step isn’t just to “step back”—it’s to intentionally build the…

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The Checklist Trap: Are You Transforming or Just Transmitting?

tldr; If you are trying to scale your transformation by handing out “quick tips” and checklists, you aren’t changing your culture—you’re just increasing the noise. True transformation requires moving past the assignment of tasks and, instead…

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The “Vacation Test”: Are You Essential… or an Obstacle?

  tldr; It has been suggested that I type… a lot. So, here is the short version! If you stepped away for a month, would your team thrive or dive? We often blame our teams for…

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