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 summaryAllison Dunn has spent thirty years coaching entrepreneurs and executives — over a thousand of them — and has just written her first book. But this conversation is about so much more than a business framework.Allison's premise: the most capable, most driven leaders eventually become the very bottleneck holding their organizations back. Not because they're failing — because they're succeeding in exactly the way that made them successful in the first place. They keep having the answers. And in doing so, they unintentionally teach everyone around them to stop thinking.Laurie and Allison dig into the five strategic thinking methods in Think First — and why the book reads less like a typical business book and more like a practical manual you'll actually use. But the conversation goes much deeper than the framework. Allison opens up about writing the book in the wake of losing her husband Mark and, shortly after, her mother — and what that loss taught her about legacy, about outgrowing an old version of herself, and about finally clarifying what actually matters now.This one is for anyone leading a team, a family, a household, or just their own life — and tired of being the only one solving every problem.What we cover in this episodeAllison's origin story: getting into a New England prep school at 16, being told no by her parents, and the single question her future father-in-law asked that changed the trajectory of her lifeThe unlikely, full-circle story of how Allison ended up relaunching Deliberate Directions, the same company originally founded by her late husband's fatherWhy Allison wrote Think First now, and the personal loss that made the timing undeniableThe core premise: why becoming "the answer person" is the most common — and most dangerous — habit of successful leadersMethod One: Clarify What Matters — why most of us are achieving goals without ever stepping back to ask if they're still the right goalsThe difference between addition and multiplication, and why most leaders (and most of us, in life) keep adding instead of finding leverageThe Post-it note on Allison's computer: "Is this urgent or is this important?"  and how that single question changes daily decision-makingWhy having all the answers is, in Allison's words, "the worst thing you could possibly have" as a leaderA generational shift in how leaders approach balance, autonomy, and contribution ...and what Gen X is learning from the generation coming up behind themThe identity piece: why letting go of "I have to have all the answers" is so difficult, and what it actually requiresAllison's reflection on outgrowing the version of herself who had a five-year plan with Mark, and what it looks like to rebuild clarity after profound lossWhat Mark would say about Think First being out in the worldQuotable moments"Could you give it the possibility that you could earn the tuition without your parents?" — the question that changed Allison's life at 16"Having all the answers is the worst thing you could possibly have" as a leader."Is this adding or is this multiplying?""I've outgrown the old version of myself.""Too many people hold onto the version of themselves that someone else expected them to be... as things change, letting those old versions go and getting back on track to clarify what matters.""It's not my job" — on no longer carrying the weight of what other people think."It's about the journey. And when you have the time, take it."Resources + links mentioned→ Think First: Stop Being the Bottleneck. Start Building Thinkers by Allison Dunn → Deliberate Directions → The Deliberate Leaders Podcast — hosted by Allison Dunn, listen on Apple Podcasts or Spotify → Connect with Allison on LinkedIn and on InstagramConnect with the School of Midlife → Apply for the BEST LIFE Mastermind → Book a 15-minute call with LaurieIf this episode resonated, the most meaningful thing you can do is share it with someone who needs to hear it. And if you haven't already, please subscribe, leave a five-star review, and know that Laurie reads every single one.📩 JOIN MY MAILING LISThttps://www.schoolofmidlife.com/newsletter👉 CONNECT WITH LAURIE:📩  Email Laurie 💻 WebsiteOn InstagramOn LinkedInWork with Laurie