Tom was stuck.
For two years, he’d been thinking about succession.
He knew he needed to start the conversation with his top associate. He knew time was passing. He knew waiting made it harder.
But he couldn’t start.
Not because he didn’t know what to do.
Because he didn’t know what to do PERFECTLY.
The Perfectionism Trap
Here’s what Tom told me:
“I can’t have the succession conversation until I know the answers. What’s the timeline? What’s the buy-in structure? What percentage of equity? How do we transition clients? What if I change my mind later? I don’t want to waste their time with half-baked ideas. I want to be thorough. I want to get it right before I bring it up.”
That all sounds reasonable, right?
Strategic. Thoughtful. Protective.
But here’s what it actually is:
Perfectionism masquerading as professionalism.
So Tom kept waiting.
Planning in his head. Running scenarios. Trying to figure out the perfect answer.
But here’s the thing about perfectionism:
It doesn’t help you build a better plan. It keeps you from starting.
And while he was waiting to have the perfect plan, his top associate was watching.
And wondering.
And starting to look around.
What Your Team Actually Needs
One day, after two years of paralysis, he finally took an imperfect first step.
He didn’t have the timeline figured out. He didn’t have the buy-in structure. He didn’t have the transition plan.
He just asked one question:
“I’m thinking about what succession could look like. I don’t have it figured out yet. But I’m curious – what does your ideal career path look like over the next 5 years?”
That’s it. One imperfect question.
Here’s what he expected the associate to say:
“Well, what’s the timeline? What’s the equity split? What’s the transition plan? I need details before I can answer.”
Here’s what the associate actually said:
“Honestly, I’m just relieved you’re thinking about it. I’ve been wondering if there was a future here or if I needed to start looking elsewhere. The fact that you don’t have all the answers yet – that’s actually better. Because it means we can figure it out together instead of you presenting me with a finished plan I have no input on.”
Tom sat there, stunned.
He’d spent two years trying to build the perfect plan so he could present it with confidence.
But his associate didn’t want the perfect plan.
His associate wanted to know it was REAL.
That something was actually happening.
That there WAS a future worth waiting for.
What Perfectionism Sounds Like
Here’s the thing about perfectionism:
It doesn’t announce itself.
You don’t think: “I’m a perfectionist and that’s why I’m stuck.”
You think:
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“I’m just being thorough.”
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“I want to make sure I get it right before I bring it up.”
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“I don’t want to waste their time with half-baked ideas.”
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“I need to have all the information before I make a decision.”
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“I’m protecting them from uncertainty.”
These all sound reasonable. Strategic. Thoughtful.
But they’re all perfectionism.
Disguised as:
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Thoroughness (”I’m being responsible”)
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Professionalism (”I want to get it right”)
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Respect (”I don’t want to waste their time”)
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Protection (”I don’t want to create false expectations”)
And because it SOUNDS like good leadership, you don’t question it.
You just keep waiting. And waiting. And waiting.
Until two years have passed.
The Two-Purpose First Step
Here’s what that imperfect first step did:
For Him:
It broke the paralysis.
He’d been stuck in his head for two years. One question got him unstuck.
It generated information he couldn’t get from planning.
He learned what his associate actually wanted. It wasn’t what he’d assumed.
His associate wanted to stay local (he’d been planning for someone who wanted to grow). His associate wanted work-life balance (he’d been planning for someone who wanted to scale).
One question taught him that his perfect plan would have been the WRONG plan.
It showed him what the second step should be.
He didn’t know what step two was until he took step one.
Now he did: “Let’s talk about what work-life balance looks like in a partnership structure.”
For His Associate:
It showed this was real, not just talk.
The associate had been hearing “someday I’ll figure out succession” for years.
One conversation changed that from “someday” to “we’re working on this.”
It built trust through action, not announcement.
The managing partner didn’t say “I have a plan.”
He said “I’m figuring this out. Want to help me?”
That authenticity created more trust than certainty would have.
It signaled there’s a future here worth waiting for.
The associate wasn’t asking for a perfect roadmap.
He was asking for evidence that there WAS a roadmap being built.
One imperfect conversation provided that evidence.
What Perfectionism Actually Does
Here’s what I’ve noticed with a lot of managing partners:
You think: “I can’t start the succession conversation until I have answers.”
But perfectionism doesn’t help you plan better. It just gives you permission to keep delaying.
It keeps you stuck.
While you’re waiting to figure out the perfect plan, time is passing.
Your top performer is getting older. Your energy is decreasing. Your options are narrowing.
Perfectionism feels like you’re being strategic. But you’re actually just delaying.
It’s creating distance with your team.
Your team sees you NOT talking about succession.
They don’t know you’re planning in your head.
They just know: no conversation is happening.
And in that silence, they’re drawing conclusions.
“There is no plan. I need to start looking elsewhere.”
It’s making you inauthentic.
Your team doesn’t need you to be perfect.
They need you to be real.
When you show up with uncertainty and say “I’m working on this, I don’t have all the answers yet” – that’s MORE trustworthy than showing up with a finished plan they had no input on.
Because they know life doesn’t work that way.
They know succession planning is messy and complex and requires iteration.
When you pretend you have it all figured out, they know you’re performing.
When you admit you’re figuring it out, they know you’re authentic.
And authenticity builds trust. Performance doesn’t.
The Pattern I Keep Seeing
Over the past few months, I’ve heard this same story multiple times:
Managing partner paralyzed for YEARS because they don’t have the perfect plan.
Finally takes one imperfect first step.
Learns that their team was RELIEVED to finally start the conversation.
One managing partner waited three years to ask his senior associate if she even wanted to be a partner.
When he finally asked, she said: “I’ve been waiting for you to bring this up. I thought maybe you didn’t see me as partner material.”
He’d been protecting her from an uncertain conversation.
She’d been interpreting his silence as “there’s no future for you here.”
Another managing partner spent 18 months trying to figure out the perfect buy-in structure before talking to his two associates.
When he finally brought them in and said “I don’t have this figured out yet, but here’s what I’m thinking” – they had ideas he’d never considered.
Ideas that made the plan BETTER than what he would have created alone.
He’d been trying to build the perfect plan in isolation.
When he admitted he didn’t have all the answers, his team helped him build a better plan together.
Five Imperfect First Steps
I know what you’re thinking:
“But I can’t just ask them about their career path without having a plan. That would be irresponsible. I’d be wasting their time. I’d be creating false expectations.”
That’s perfectionism talking.
Disguised as professionalism.
Here’s the truth: Your team would rather see you figuring it out imperfectly than waiting for the perfect plan that never comes.
You don’t need to have the succession plan figured out to take a first step.
Here are five imperfect first steps you could take this week:
1. Ask One Question
“What does your ideal career path look like over the next 5 years?”
You’re not committing to anything. You’re gathering information.
You learn: What do they actually want? (Might surprise you.)
2. Include Them in One Client Meeting
Introduce them as someone the client can rely on.
Not as “my associate” – as a colleague.
You learn: Can they handle it? How does the client respond?
3. Share High-Level Financials
Even if it’s just revenue and expenses.
You’re not opening the books completely. You’re creating transparency.
You learn: How do they respond to being trusted with this information?
4. Document One Process
Pick your client intake process. Write down how you actually do it.
It doesn’t need to be perfect. Just get it out of your head.
You learn: What you actually do vs. what you think you do.
5. Have One Honest Conversation
“I’ve been thinking about succession. I don’t have it figured out yet. But I want you to know I’m working on it.”
That’s it. No plan. Just honesty.
You learn: How they respond to authenticity.
None of these steps require you to have the perfect plan.
But each one generates information you can’t get from planning alone.
And each one shows your team: This is real. Something is happening.
What the First Step Teaches You
Here’s the thing about perfectionism:
You think you need to know step two before you take step one.
But the truth is:
You can’t know what step two should be until you take step one.
The managing partner who asked “what’s your ideal career path?” learned his associate wanted work-life balance.
That taught him step two: “Let’s talk about what partnership looks like if we prioritize work-life balance.”
He couldn’t have known that was step two until he took step one.
The managing partner who included his associate in a client meeting learned the client responded really well.
That taught him step two: “Let’s start transitioning this relationship.”
He couldn’t have known that was the right client to start with until he tried it.
The first step doesn’t need to be the right step.
It just needs to teach you what the second step should be.
That’s how you build a succession plan.
Not by figuring it all out in your head first.
By taking imperfect steps. Learning. Adjusting. Taking the next step.
Your Team Doesn’t Need You to Be Perfect
Here’s what I want you to understand:
Your team knows you don’t have all the answers.
They know succession planning is complex and messy and requires iteration.
When you hide behind perfectionism and don’t start the conversation because you’re not ready – they don’t think “Oh, he’s being strategic.”
They think “There’s no plan. I need to start looking elsewhere.”
But when you show up imperfectly and say:
“I’m working on this. I don’t have all the answers yet. But here’s what I’m thinking. What do you think?”
They think: “Oh. This is real. Something is actually happening. And he wants my input.”
That builds trust.
Not because you’re perfect.
Because you’re authentic.
If You’ve Been Waiting for the Perfect Plan
If you’ve been thinking: “I’ll start the succession conversation when I have the answers.”
If you’ve been planning in your head for months or years without taking action.
If you’ve been waiting to be certain before you start.
Here’s what I need you to see:
Your perfectionism isn’t protecting your authority. It’s preventing progress.
Your team doesn’t need you to be perfect.
They need you to be real.
They need to see you taking steps. Imperfect steps. Real steps.
Because that’s what builds trust. Not certainty. Authenticity.
The managing partner I told you about waited two years.
When he finally took one imperfect first step, his associate was relieved.
“I’m just glad we’re finally talking about this.”
Two years of perfectionism.
One imperfect conversation changed everything.
What’s one imperfect first step you could take this week?
—Doug
P.S. I do a small number of strategy conversations each month. No agenda other than figuring out what’s actually going on for you specifically. If it makes sense to keep talking after that, we will. If it doesn’t, you’ll still walk away with clarity you didn’t have going in. Book a strategy conversation here