178. The Worst Thing a Leader Can Do, According to a Coach Who's Worked With 1,000 of Them | Conversation with Allison Dunn
Guest: Allison Dunn, Executive Business Coach, Founder of Deliberate Directions, Host of the Deliberate Leaders Podcast, Author of Think First: Stop Being the Bottleneck. Start Building Thinkers.
Episode summary
Allison Dunn has spent thirty years coaching entrepreneurs and executives — over a thou…
The Loneliness That Grows With Success
The Loneliness That Grows With Success
Success often brings opportunities, influence, and growth. It can also bring something leaders rarely discuss openly: loneliness.
In this episode, Allison explores:
Why leadership often becomes more isolating as organizations scale
How the gap between …
Think First: Better Financial Decisions, Roth Strategies & Long-Term Care Planning (6/27/2026)
Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, invest…
Think First: Better Financial Decisions, Roth Strategies & Long-Term Care Planning (6/27/2026)
Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, invest…
What Peers Actually Give You That Nobody Else Can
What Peers Actually Give You That Nobody Else Can
In this episode, Allison Dunn explores how leaders at high levels can overcome loneliness and information gaps by cultivating the right peer relationships. She emphasizes practical steps to build honest, context-rich connections that foster better …
32 - How Leaders Create a Lasting Impact with Allison Dunn
Allison Dunn is the CEO of Deliberate Directions, and one of the country's most sought-after executive business coaches. Over the past 30 years, Allison has coached more than 1,000 business leaders, helping them shift from reactive management to intentional, strategic leadership.
She is also the a…
The Fire You've Put Out Repeatedly
Recognizing and Overcoming Recency Bias in Leadership
In this episode, Allison Dunn explores the often-overlooked trap of recency bias that can cause even smart leaders to focus on the most recent events rather than underlying issues. She shares personal stories, practical strategies, and question…
When Adding More Makes Everything Worse
When Adding More Makes Everything Worse
Allison Dunn unpacks one of the five thinking traps that makes smart leaders fail: linear thinking. Using a real client example, she shows how adding people, tools, and process fixes can quietly create more complexity, lower profit per employee, and make gro…
The Answer You Already Had
Allison Dunn continues her series on the thinking traps that make smart leaders fail, focusing on validation seeking and why it can look like coachability while quietly eroding judgment. She shares a personal story about nearly buying an unnecessary financial platform and connects it to a larger pa…
The Cost of Not Thinking
The Cost of Not Thinking
“I’ll get to the strategic stuff when things calm down.”
It’s a familiar thought for business owners and leaders. But what if things aren’t calming down because there hasn’t been enough time spent thinking strategically in the first place?
In this episode, Allison Dunn intr…
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