The Three Questions That Reveal Your True Readiness Level
A managing partner called me on Tuesday morning.
"Doug, I've been preparing for succession for three years. Systems, training, financial planning—the whole thing. But I just realized something: I'm not preparing anymore. I'm procrastinating."
He paused. "How do I know if I'm actually ready, or if I'm just scared?"
That conversation stuck with me because it's the question I hear most often. And it reveals something important: most lawyers have been using "readiness" as sophisticated avoidance.
We demand more certainty from succession planning than we've ever demanded from hiring key staff, expanding practice areas, or making major investments. We've set an impossible standard and then wondered why we never meet it.
But some leaders break through this cycle. They stop waiting for perfect readiness and start acting on the readiness they already have.
What separates them? Three questions they're willing to answer honestly.
Question 1: Are you more curious about what's possible than worried about what could go wrong?
This is the emotional inflection point most leaders miss.
It's not about eliminating worry—legitimate concerns about succession planning exist and should be addressed. It's about what gets more of your mental energy.
One client described it perfectly: "I used to lie awake thinking about all the ways succession could fail. Now I lie awake thinking about what I could do with my time if I wasn't managing every decision."
That's the shift. From protection mode to exploration mode.
When you catch yourself spending more time 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.
Leaders in exploration mode ask different questions:
"What would need to be true for this to work well?"
"How could I structure this to minimize risks while maximizing opportunity?"
"What would I do with the freedom this creates?"
Leaders stuck in protection mode ask:
"What if my successor makes bad decisions?"
"What if clients leave?"
"What if the firm's value crashes?"
Both sets of questions are valid. But only one moves you forward.
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 made thousands of good decisions under pressure? They exist.
The question isn't whether your succession plan will unfold exactly as designed. It won't. The question is whether you trust yourself to guide and adjust the plan as reality unfolds.
A managing partner recently told me, "I realized I was demanding more certainty from succession planning than I'd ever demanded from any other business decision. When we expanded into litigation, I didn't know exactly how it would work out. When we hired our first associate, I didn't have guarantees. Why would I suddenly lose my ability to adapt?"
That confidence—not in the plan, but in your ability to steward the plan—is what separates leaders who move forward from those who stay stuck in analysis.
Think about the biggest decisions you've made in your practice. How many came with guarantees? How many unfolded exactly as you initially envisioned?
Yet you navigated them successfully. You adjusted when assumptions proved wrong. You course-corrected when circumstances changed. You figured it out as you went.
That capability 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 the question that surprises every leader I've asked. And it's often the most revealing.
Because most lawyers spend so much time analyzing whether they're ready to start succession planning, they forget to analyze the cost of not starting.
Where will you be in 24 months if you continue operating exactly as you are today?
How will you feel about carrying the same weight, managing the same daily decisions, being pulled into the same fires?
What opportunities will you have missed while waiting for perfect readiness?
One client put it starkly: "I realized I was so focused on the risks of succession that I ignored the bigger risk—staying exactly where I am until I'm too burned out to make good decisions about anything."
The cost of inaction compounds. Your energy doesn't increase with time. Your patience for managing every detail doesn't improve. Your enthusiasm for the grind doesn't grow.
Meanwhile, your potential successors are gaining experience elsewhere. Your systems are becoming more dependent on your personal involvement. Your options are narrowing.
The September Reality Check
We're in the first full work week of September. In four months, 2025 will be over.
This is the time of year when successful leaders stop planning and start deciding. When they choose momentum over perfection.
While others spend the fall "getting ready," you could be building the foundation for the future you actually want.
But first, you need honest answers to those three questions.
Where Do You Stand?
Here's what I want you to consider:
If you answered "yes" to curiosity over worry, "yes" to trusting your judgment, and you don't like where continuing the status quo leads, you're more ready than you think.
Not ready in the sense of having perfect plans. Ready in the sense of being positioned to start creating them.
The readiness you're waiting for isn't tactical. It's emotional. And it might already be there.
Taking the Next Step
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 to know where you actually stand, I've got something for you.
P.S. Want to know where you actually stand? Take my Succession Readiness Assessment: Succession Readiness 2025 — I review every response personally and send you insights based on your specific answers.