Thought Leader and Influencer Interview with Dean Miles, President, Executive Coach & Advisor, Bridgepoint Coaching & Strategy Group

At a Glance

Dean Miles, President, Executive Coach & Advisor, Bridgepoint Coaching & Strategy Group Focus Areas: Business Continuity, Coaching, Leadership, Mental Health. Thinkers360 In-Depth Profile & Portfolio: Dean Miles Social Media: LinkedIn | X Podcast: The Good Life Conversations Newsletter: The Unlocker Highlighted Content: Your Continuity Plan Is Missing One Thing: The Leadership Team, Who’s in the Room Under Pressure. Thinkers360 Awards & Recognition: Top 50 Global Thought Leaders and Influencers on Business Continuity 2026, Top 50 Global Thought Leaders and Influencers on Coaching 2025, Top 50 Global Thought Leaders and Influencers on Mental Health 2025.

 

Thought Leader and Influencer Interview

Thinkers360 thought leader interviews profile prominent members of the Thinkers360 community who embody the power of ideas in their work. In this edition, we speak with Dean Miles, President, Executive Coach & Advisor, Bridgepoint Coaching & Strategy Group. His work focuses on executive coaching, leadership development, and helping organizations navigate complex leadership challenges and improve performance.

With more than 13,000 hours of one-on-one coaching experience, Dean advises presidents, CEOs, CFOs, and leadership teams across industries, helping them navigate complex challenges, make critical decisions, and lead effectively under pressure. Selected for the 100 Coaches community in 2021, he brings a distinctive perspective shaped by his experience in law enforcement, pharmaceutical sales and training, and executive coaching. In this conversation, he shares insights into his professional journey, his approach to leadership and organizational culture, and his advice for emerging thought leaders.

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Thinkers360: Tell us a bit about your background and areas of expertise.

DM: I came to coaching sideways. In my twenties I ran an undercover narcotics office. Then I spent thirteen years at Pfizer and Merck, first in sales and then training the people who did it. I started Bridgepoint in 2007, and my first real coaching work was in 2008, on drilling rigs. I was coaching rig supervisors, and if one of them made a bad call, it showed up in the injury report before it showed up anywhere else. We cut the recordable incident rate by a third. I tell people that everything I’ve done since is that same moment at a different altitude.

These days I work with presidents, CEOs, CFOs, and their teams. Energy, manufacturing, financial services, healthcare, tech, sport, family businesses. I’ve logged a little over 13,000 hours of one-on-one coaching with 245 leaders, and the organizations they run add up to more than $300 billion in revenue and assets under management. If you want the one-sentence version: I advise leaders when the stakes are high, the situation is complex, and the next move isn’t obvious.

For the credentials people ask about: I’m a Certified Professional Co-Active Coach, certified in Marshall Goldsmith’s Stakeholder Centered Coaching, and I was selected to the 100 Coaches community in 2021 out of more than 18,000 applicants. I was a Fellow of the Institute of Coaching at McLean Hospital and Harvard Medical School from 2016 to 2024. I have an M.A. in Executive Leadership, and I’m finishing a PhD in Organization and Management. The dissertation is on why capable founders scale too early, and what self-regulation has to do with it.

Thinkers360: What are your current responsibilities and what does a typical day look like?

DM: Most days I’ve got two or three coaching sessions, usually with somebody in the middle of a hard quarter. In between I’m building session materials, reading what a client’s stakeholders told me, and writing. Lately that’s been a four-part whitepaper series on leading at the point of pressure, my newsletter on LinkedIn, and the dissertation. A few days a month I’m on site with a leadership team, facilitating. I try to protect the early morning for thinking and the late afternoon for the phone, because that’s when clients call about the thing they didn’t put on the agenda. Those are usually the best calls of the week.

Thinkers360: What’s the favorite part of your current role?

DM: There’s a moment I wait for in every engagement. A leader has been stuck on a problem that keeps coming back, and they’ve been asking “which one do I pick?” Then something shifts and they start asking “how do I hold both?” Most of what lands on a senior leader’s desk for the third time isn’t a problem at all. It’s a tension between two good things. Watching someone see that for the first time has never gotten old for me.

The other favorite is quieter. It’s when a client calls between sessions about something that has nothing to do with what we’re working on. That’s when I know it’s working.

Thinkers360: How do you utilize Thinkers360?

DM: Honestly, as a record and a front door. It’s where I keep the articles, podcasts, keynotes, and media in one place, so somebody considering me doesn’t have to take my word for it. They can go look.

The rankings have opened doors I wouldn’t have thought to knock on. I rank #1 in Business Continuity and Top 10 in Coaching, with Elite Expert status in both, and the business continuity piece surprised me. I’d been making an argument that most continuity plans protect operations and forget the leadership team, and it turned out there was an audience for that I didn’t know existed.

 

             Editor’s Note: See Dean Miles’s profile to work with him directly. 

Thinkers360: How do you like to work with brands who wish to engage you as a thought leader?

Thinkers360: What’s a belief you held early in your career that the work has since changed?

DM: For years I thought culture carriers were the people who embody the values. Then I started paying attention to what they actually do, and it isn’t that. They protect conditions. Over and over, and usually at some cost to themselves. The plant manager who thanks the operator for stopping the job, in front of the crew, even when the stop cost the shift an hour. The executive who says “I disagree, and here’s why” in the meeting, then walks out and backs the final call with her team. A culture carrier is what a conditions protector looks like from downstream. So I don’t ask leaders what culture they want anymore. I ask them what they protect.