Law firm leaders often spend years “getting ready” for succession planning without ever starting. After working with dozens of managing partners through this transition, I’ve identified three questions that separate those who move forward from those who stay stuck in analysis.
The “Getting Ready” Trap
A managing partner called me recently with a startling realization: “Doug, I’ve been preparing for succession for three years. But I just figured out something—I’m not preparing anymore. I’m procrastinating.”
Most accomplished attorneys are stuck in the same cycle. They’re refining systems, evaluating potential successors, and building detailed transition timelines. Yet they never actually begin the process.
Why? Because they’re waiting for a level of certainty that succession planning—like most important business decisions—simply doesn’t offer.
We’re in the first full work week of September, and this is typically when successful leaders stop planning and start deciding. While others spend the fall “getting ready,” some leaders will build real momentum toward the future they want.
The difference comes down to honest answers to three specific questions.
The Three Questions That Matter
After years of helping law firm leaders navigate succession transitions, I’ve learned that readiness isn’t about perfect preparation. It’s about emotional and strategic positioning that allows you to move forward despite uncertainty.
Question 1: Are you more curious about what’s possible than worried about what could go wrong?
This reveals the critical shift from protection mode to exploration mode. When you spend more mental energy imagining positive outcomes than catastrophizing risks, something fundamental has changed. You’re not trying to talk yourself into succession—you’re trying to talk yourself through it.
Question 2: Do you trust your judgment enough to course-correct if things don’t go as planned?
Perfect succession plans don’t exist, but experienced leaders who’ve successfully navigated thousands of business decisions do. This question helps you recognize that your ability to adapt and adjust doesn’t disappear during succession planning.
Question 3: If you don’t start this process now, where will you be in two years?
This is often the most revealing question because it forces you to analyze the cost of inaction. Most lawyers focus so intensely on the risks of succession planning that they ignore the bigger risk—staying exactly where they are until they’re too burned out to make good decisions.
Moving Beyond Analysis
The conversations you have this fall will shape your next five years. The decisions you make in the next 90 days will determine whether 2026 looks different or disappointingly familiar.
If you’re tired of analyzing your readiness and want honest clarity about where you stand, these three questions provide a framework that cuts through endless preparation and reveals whether you’re positioned to move forward.
The September Reality Check
Many managing partners discover they weren’t waiting to be more ready—they were waiting for permission to want something different. Permission to pursue interests they’ve been delaying, to build a legacy that extends beyond their personal involvement, to create space for whatever draws them next.
That permission isn’t earned through perfect preparation. It’s something you give yourself.
Take the Next Step
For all three questions plus the complete framework for honest self-assessment, read the full analysis in Beyond the Practice Grind: The Three Questions That Reveal Your True Readiness Level
Want to know where you stand right now? Take my Succession Readiness Assessment: https://summitsuccess.typeform.com/successionquiz — I review every response personally and send you insights based on your specific answers.
