I had a conversation this week with a managing partner I’d talked to five years ago.
Five years ago, he reached out. His firm was in crisis.
Associates were leaving. Senior partners were retiring. He had too many files and not enough systems to handle them.
He knew he needed help.
We had a good conversation. He said he was interested.
But then he “wasn’t able to move forward.”
Not “I decided against it.” Not “it wasn’t the right fit.”
“Wasn’t able to.”
Something got in the way. And he went back to grinding.
This week, he came back.
Five Years Later
A lot had changed.
More associates had come and gone. More senior partners had retired.
The firm that had a dozen attorneys when he started? It’s much smaller now.
And his workload? Bigger.
He’s in his late 50s. Working 60-hour weeks. Taking work home on weekends. His assistant flags the vacation blocks he puts on his calendar – the ones he never actually takes.
He’s doing paralegal work himself. Reviewing thousands of pages of medical records. Tracking his own deadlines. Managing his own files.
Not because he wants to. Because he doesn’t have the systems that would let someone else do it.
When I asked what he wanted, he said: “30-35 hour weeks. Staff who own the workflow. Cases that are worth my time. My health back.”
Then he asked: “Should I hire more staff? Or should I just grind it out until I retire?”
The Wrong Question
That’s the question a lot of managing partners in their late 50s are asking right now.
“Should I invest in building something? Or should I just push through for a few more years?”
But here’s the thing:
That’s not really the question.
The question is: Why didn’t I build the systems five years ago that would have made this decision easy?
Five years ago, he knew his firm was dependent on him.
Five years ago, he knew associates were leaving because there was no structure.
Five years ago, he knew senior partners were retiring without succession plans.
Five years ago, he knew something had to change.
But he “wasn’t able to move forward.”
And now it’s five years later.
And he’s asking the same questions. Just with fewer options.
What Five Years of Waiting Cost Him
In those five years, here’s what happened:
More associates came and went.
They didn’t leave because they were unhappy. They left because they couldn’t see a path forward.
No systems. No processes. No clarity about how decisions got made or what partnership might look like.
Just: “Help me with whatever I need help with.”
That’s not a career path. That’s a job assisting someone else’s practice.
So they left.
More senior partners retired.
They’d been talking about succession “someday.” But someday never came.
So they just… stopped working. Took their client relationships with them. Left holes in the firm that nobody was prepared to fill.
The firm got smaller.
Not by design. By default.
People left. New people didn’t stay. The firm that used to have a dozen attorneys slowly shrank.
And the managing partner? He took on more of the work himself.
His stress got worse.
Five years ago, he was working 50-60 hour weeks.
Now? Same. Maybe more.
Five years ago, he was buried in files he couldn’t delegate.
Now? Still buried. Same files. Just older.
Five years ago, he thought: “Once I get through this busy season, I’ll have time to build systems.”
But there’s always another busy season.
The Question He’s Asking Now
“Should I hire staff or just grind until I retire?”
Here’s what he’s really asking:
“Is it too late to build the firm I should have built five years ago?”
And here’s the truth:
It’s not too late.
But it’s harder.
Because now he’s five years older. With less energy. With fewer high-performing associates to develop. With client relationships that are harder to transfer.
The firm he could have built at 52? That’s not the same firm he can build at 57.
Not impossible. But narrower.
Why Hiring Staff Won’t Fix It
Here’s what I told him:
Hiring more staff without building systems first is like hiring someone to bail water out of a boat that’s still taking on water.
It doesn’t fix the problem. It just adds overhead.
Because here’s what happens when you hire a great paralegal or associate without systems:
They ask: “How should I handle this?”
You say: “Let me show you.”
They bring you decisions: “What should I do here?”
You make the decision.
They work on a case. You review it. You fix it. You redo parts of it.
Because there’s no system. No process. No clarity about what “good” looks like or how decisions should be made.
So they learn: Wait for the managing partner to tell me what to do.
And you stay the bottleneck.
Except now you’re paying someone to wait for you.
What Research Shows About Retention in 2026
Here’s what the data says about what actually retains people in 2026:
“Pay still matters – but it’s no longer enough on its own. Workers will only commit to organizations that show a clear commitment to them in return.”
What does that look like?
“Visible career pathways, regular progression conversations and genuine investment in training and development.“
Not bigger paychecks.
Career path clarity.
Your associate wants to know:
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Is there a path forward here?
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What does it take to get there?
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What’s the timeline?
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Will this firm always revolve around the managing partner – or is there room for me to build something?
If you hire someone without answering those questions, they’ll leave in 18 months.
Not because you don’t pay them enough.
Because they can’t see a future.
And in 2026 – when 48% of workers feel more financially stressed than last year, when 30% of young professionals cite career uncertainty as their primary source of anxiety – people aren’t waiting around to find out if there’s a path.
They’re looking for clarity. And if they don’t find it with you, they’ll find it somewhere else.
The Pattern I Keep Seeing
Over the past few months, I’ve talked to several managing partners who all said some version of the same thing:
“We talked years ago. I wasn’t able to move forward. But the problem didn’t go away.”
One is now 62. Solo practitioner. The firm had 10 attorneys when he joined. Now it’s just him.
Another is 58. Three associates came and went in the past four years. Now he’s doing their work himself.
The one I talked to this week is in his late 50s. Senior partners retired. Associates left. Now he’s wondering if he should hire staff or just grind until he can sell.
All of them knew years ago they needed to build systems.
None of them did.
Now they’re years older, working harder, and asking the same questions.
What He Should Have Built Five Years Ago
Five years ago, he should have built:
Systems for client intake and qualification
So he’d stop taking cases that trapped him. So he could delegate the screening process. So his team would know what a “good case” looked like without asking him every time.
Systems for delegation and decision-making
So his associates would know: “Here’s when you make the call. Here’s when you bring it to me. Here’s what good work looks like.”
So they’d stop waiting for him to tell them what to do.
Systems for knowledge transfer
So client relationships weren’t hoarded – they were shared. So associates were in the room for strategy conversations. So they could own the relationship over time.
So when a senior partner retired, the clients didn’t leave with them.
If he’d built those systems five years ago, hiring staff today would be easy.
Because they’d have something to step into. A process to follow. A path forward.
Instead, he’s asking: “Should I add overhead?”
Because without systems, hiring people IS just overhead.
The Brutal Truth
You think you’re protecting the firm by keeping control.
By managing the key relationships yourself. By making the strategic decisions. By not creating expectations before you’re “ready.”
But here’s what you’re actually doing:
You’re showing your future self that you’ll still be doing this in five years.
Because the work you don’t systematize today is the work you’ll be doing yourself five years from now.
The decisions you don’t teach your team to make are the decisions you’ll still be making.
The knowledge you don’t transfer is the knowledge that will leave when you leave.
And every year you wait to build systems, you’re making it harder to build them later.
Not impossible. But harder.
Because you’re older. More tired. With fewer high-performers to develop. With less time to see the return.
If You’ve Been Delaying This
If you’ve been thinking: “I’ll start building systems when things slow down.”
If you’ve been keeping the strategic decisions to yourself because your team “isn’t ready yet.”
If you’ve been protecting client relationships because “I built this firm, these are my clients.”
You’re not protecting anything.
You’re showing your future self what your life will look like in five years.
And it will look exactly like today. Just with less energy.
Five years ago, the managing partner I talked to this week thought he had time.
Now he’s five years older. Working harder. Asking the same questions.
With fewer options.
You think you have time.
How much time did you think you had five years ago?
—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