231: Leadership Mistakes Destroying Your Succession Plan with Chip Scholz, Scholz and Associates

*"There's a time when an exit is going to be inevitable — there may not be a time certain, but there is a time."* Host Laurie Barkman reunites with Chip Scholz, founder of Scholz and Associates and author of Small Decisions, Big Shifts and the upcoming Handoffs, for a deeply personal and insightful conversation about the hidden leadership mistakes that quietly destroy business succession plans. Chip has spent nearly 30 years coaching executives and family business leaders through some of the most complex transitions in business — and he first met Laurie 13 years ago when she was a CEO candidate in a third-generation family business. Together they explore what great leadership evaluation looks like, why founders hold on too long, how hubris silently collapses delegation and decision-making, and the three stages every leader goes through on the road to retirement. Chip shares what he's learned — and what he's still learning — about the small decisions that ultimately create the biggest shifts.   * * * **Key Insights** 1. **Culture fit is the foundation of every great leadership hire. T**he best organizations are people-oriented and performance-driven — in that order. When performance leads and people follow, bad things happen. Every hire, especially at the CEO level, should be evaluated through three lenses: strengths, motivations, and fit. 2. **Viewing the business as an asset** — not a legacy — is what makes a clean exit possible. Founders who treat their company as an asset can make clear-headed decisions about growth, transition, and sale. Those who treat it purely as a legacy often hold on too long, stall the next generation, and turn what was once a strength into a bottleneck. 3. **Hubris is the silent killer of succession.** When leaders believe they are the only ones who can run the business, delegation collapses, decision-making centralizes, and the organization becomes dependent on one person. Chip has seen companies where no one could spend $100 without CEO approval — and half the leadership team couldn't survive the transition when that CEO finally left. 4. **Retirement has three stages** — and most founders only plan for the first one. Vacation, depression, and meaning and purpose. The honeymoon phase fades fast. Founders who haven't built outside interests, hobbies, or identity beyond the business hit a wall — and without a plan, depression follows. The goal is to reach meaning and purpose before a crisis forces the issue. 5. **Crisis is often the catalyst for transition** — but it doesn't have to be. Whether it's a health scare, a lost client, or a market shift, crises force the introspection that should have happened years earlier. Chip advocates for doing that work proactively — in your 50s or early 60s — before external pressure removes your options. 6. **A hobby isn't a luxury — it's a succession strategy.** Finding something outside the business that gives you purpose, community, and a sense of leadership is one of the most practical things a founder can do to prepare for transition. For Chip, it's woodturning. The point isn't the craft — it's the identity that lives outside the company.   **Chapters:** 00:00  Introduction of Chip Scholz 02:26  Reconnecting After 13 Years — A Personal Story 03:02  Leadership Evaluation: Strengths, Motivations, and Fit 06:37  Family Business Succession: Common Challenges 07:33  Asset vs. Legacy — The Mindset That Changes Everything 12:16  The Third-Generation Company: A Shared Story 14:04  Phantom Stock and Making 100 People Millionaires 16:00  The Five C's Framework for Leadership 17:42  Why Letting Go Is So Emotionally Hard 18:11   Hubris and Delegation: When Founders Won't Step Back 20:14  The $100 Approval Story 21:50  Why "Retirement" Triggers an Allergic Reaction 22:25  The Three Stages of Retirement 23:34  15 Years Preparing for Retirement — A Coaching Story 24:52  The Real Risk of the Depression Phase 26:44  What Does Retirement Really Mean? 29:33  Finding Purpose Outside Work: Woodturning 30:51  Handoffs — The Upcoming Book 35:02 Three Takeaways for Every Business Owner     **Is your business truly ready—and are you?** Take the **Succession Readiness Assessment** to get a clear snapshot of where you stand and what to focus on next. [https://btsherpa.com/succession](https://btsherpa.com/succession "Succession Assessment") **P.S.** Most owners don't realize where they stand until they're already in a transition. Take a few minutes now to understand your readiness—and give yourself more options later.   **Connect with Laurie Barkman:**  Website: [https://lauriebarkman.me](https://lauriebarkman.m "Laurie Barkman website") LinkedIn: [in/lauriebarkman](https://www.linkedin.com/in/lauriebarkman/ "Laurie Barkman linkedIn") YouTube: [@LaurieBarkman\_BTSherpa](https://www.youtube.com/@LaurieBarkman_BTSherpa "YouTube")   **Connect with Chip Scholz:** Website: https://scholzandassociates.com LinkedIn: https://www.linkedin.com/in/chipscholz