Dear Business Owner: Start Succession Planning Before You’re Ready to Leave

Dear Business Owner,

Let me guess — you’ve been thinking about stepping back.

Not today. Maybe not even next year. But it’s crossed your mind.

You’re tired of being the one with all the answers. The one everyone turns to when something goes sideways. You’d like a little freedom. Maybe even a break without coming back to a mess.

But every time you imagine stepping away, it gets complicated.

You might think of succession planning as something big corporations do — formal committees, groomed heirs, polished C-suite transitions.

But in the world you live in — the small to mid-sized business world — succession usually looks more like this:

• You’re still making 80% of the high-stakes decisions
• Your name is on the biggest accounts
• You’ve got a great team — but they depend on you more than they should
• You don’t know what happens if you step away for more than a week

So let’s start with the basics.

Succession planning isn’t just about picking your replacement. It’s about making sure your business can survive — and thrive — without you.

That’s what makes it valuable. That’s what makes it sellable. That’s what gives you real options.

For owners of $5M–$30M businesses, succession planning means:

• Building a leadership team that can run the company without your daily involvement
• Creating systems and documentation so the business doesn’t rely on what’s in your head
• Structuring the business — and your personal finances — so you can exit on your terms
• And yes, when you’re ready, identifying and developing someone to take your seat

It’s a process. A long one. And the sooner you start, the more control you’ll have.

Maybe you don’t have a clear successor.

Maybe you’re not sure the business could run without you.

Maybe you don’t even know what it’s worth — or how to get that value out when the time comes.

If that’s you, you’re not alone. I talk to business owners every week who’ve built strong companies — but haven’t done the work to make them stand on their own.

Here’s what I tell them.

Don’t Wait to Start Succession Planning Until You’re Ready to Leave

Succession planning isn’t something you do when you’re ready to walk out the door. It’s something you do when you want to make sure the business — and the people in it — can succeed without you.

It takes time. A lot more than most people think.

Think of Succession Like a Three-Legged Stool

To make a clean handoff (or a profitable sale), you need three things to be ready:

1. You — Financially, emotionally, logistically. Are you prepared to take a step back, and do you know what you want next?
2. Your Successor — Do you have someone in place, or in development, who can truly lead the business? Not just run it, but lead it.
3. The Business — Can it operate without you at the center? Are decisions being made by a leadership team, not just you?

If even one of those legs is weak, the stool tips. I’ve seen it happen. And when it happens fast — when owners wait too long — it costs real money and real relationships.

What’s Really At Stake

Let’s be honest. This isn’t just about process. It’s personal.

You’ve built something. You’ve poured years — maybe decades — into this business. You care about your employees, your customers, your reputation. You don’t want it all to unravel just because you didn’t plan early enough.

And let’s talk money for a minute. The truth is, most owners overestimate what their business is worth and underestimate what it takes to get that money out. Without systems, without successor training, without independence — the value just isn’t there for a buyer.

What You Can Do Now

Here’s what I’d recommend you start — today:

• Write down who your successor could be, and where they still need development.
• Document your most critical business processes. Even a simple checklist is better than nothing.
• Make sure your leadership team is empowered to make decisions without you.
• Get a current valuation — not just a guess.
• Talk to your financial advisor about what it takes for you to step away.

This isn’t about walking out the door tomorrow. It’s about building choices. Maybe you want to sell. Maybe you want to pass it to your kids. Maybe you just want a break.

Succession planning is how you create those options.

Don’t Make This Harder Than It Has to Be

You don’t need to figure this out alone. But you do need to start. The sooner you get clarity — on your successor, your business, your finances — the more leverage you have.

So take the first step. Have the conversation. Sketch out a plan. Bring your team in.

And if you want help thinking it through, I’m here.

Warmly,

Andi