The Deer on the Runway: A Hard Truth About Succession Planning

When my father died suddenly, I inherited the CEO seat of our family business overnight.

No vision. No plan. No runway.

I was forty years old, and I genuinely believed that leadership was a title — something you earned, with perks attached. What I learned about succession planning, in the hardest season of my life, is that leadership is a responsibility you steward for the people who depend on you. And when no one prepares for the handoff, the cost lands on everyone at once.

That company didn't survive.

We moved from the home we had built and the city we had lived in all our lives. 

The life we had made changed, because the succession conversation never happened in time.

I've spent the last eleven years helping founders of $5 million to $30 million companies avoid the version of that story I had to live. And here's the pattern I see, again and again, in owners who are otherwise sharp, disciplined, and successful:

The risk that takes them down is almost never the one they're watching.

The thing you can't see from your own seat

Years ago, before this work, I was a flight instructor. I had a student on short final — moments from touching down — when I told him to go around. Abort the landing. Climb back up and try again.

He was frustrated. From his seat, everything looked fine. What he couldn't see, at his angle, in that moment, was the deer standing on the runway.

I could see it because I wasn't flying the plane. That was the whole value of the second person in the cockpit: not to take the controls, but to see the thing the pilot structurally could not, and to say so in time.

That is exactly what happens with succession.

The gaps are real, but they're invisible from where you sit. You're too close, too busy, too central to the daily operation to see what would happen if you suddenly weren't there. So the gaps stay hidden — until a deadline, a health scare, an acquisition offer, or a sudden loss forces them into the open.

And by then, the time to fix them is gone.

Most owners aren't avoiding succession. They just can't see it clearly.

I want to be fair to the founders I work with, because I was one of them. When succession gets postponed, it's rarely because the owner doesn't care. It's because the whole topic feels foggy and far off, and there's always something more urgent on today's list.

But "my successor will be ready when the time comes" is one of the most expensive sentences in business. 

Ready how? 

Ready by when? 

Ready according to whom? 

Readiness isn't a feeling you have about someone. It's specific and measurable: Can they make sound decisions without you in an ambiguous situation? Do your key clients already trust them? Can they handle a crisis you're not there to manage? Do they even want the seat?

Those are answerable questions. Most owners simply never sit down and answer them.

A better way to see it

Here's the reframe that changes everything for the owners who get it: succession is not an event you execute someday. It's a strength you build starting now.

Every leader you develop, every decision you teach someone else to make, every client relationship you transfer — that isn't preparing to leave. It's making your business more valuable, more durable, and frankly more enjoyable to run today.

The founders who understand this stop waiting for a transition timeline to force their hand. They build continuity while things are calm, on their own terms, rather than in a crisis on someone else's.

But you can't build what you can't see. The first step is simply knowing, honestly, where you stand.

See your own runway

That's why I built the Succession Readiness Audit — and why I give it away free. It's a confidential, twenty-minute self-assessment across the five areas that actually determine whether a business survives a leadership transition: your leadership pipeline, your successor's readiness, how knowledge gets transferred, whether your culture outlasts you, and how dependent the business still is on you personally.

It won't flatter you. There are no right answers — only the truth of where you are today. And most owners find that one or two areas score lower than they expected. That's not a problem. That's the point. That's the deer on the runway, spotted while you still have the altitude to do something about it.

I'd rather you find the gaps this way than the way I did.

If you're a business owner who knows this conversation is coming and hasn't had it yet, the audit is where it begins. Reach out, and I'll get it to you.

The climb is hard. But the view is worth it — and the worst time to discover you're not ready is when you no longer have a choice.

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David McGlennen is an executive coach, leadership facilitator, and fractional executive who helps owners of small to mid-sized companies build leaders and prepare for what they can't yet see. To request the free Succession Readiness Audit, get in touch.