Picture yourself unreachable for 30 days. No calls, no texts, no “quick question.” If your honest answer is that the company would stall, you’re looking at a structural problem, and structural problems can be fixed.
The dependency you can’t see
Most CEOs would describe themselves as engaged long before they’d call themselves a bottleneck. But the signs are consistent: decisions queue up behind you, key client relationships run only through you, and you quietly backstop roles that someone else technically owns. You re-check the pricing. You fix the report at night. You take the call because the health system asked for you by name.
There’s no grading scale here. The test is yes or no: can the business run without you? Start by writing down all the key decisions only you make and every health system, payer, or partner relationship that runs through you. You can’t hand off what you haven’t mapped.
What buyers do with it
Buyers don’t pay for your calendar. They pay for earnings, and for confidence those earnings continue after you’re no longer the one driving. When diligence shows that key parts of the business run through one person, buyers seldom walk away from a company they like. Instead, they adjust what they’ll pay and how they pay it.
Here’s how it usually plays out. A buyer agrees on a headline number, then learns how much of the business lives in the CEO’s head and relationships. Less of the price arrives at close. More gets tied to a one-to-two-year transition through rollover equity, earnouts, and retention packages for the CEO and the team below them. The purpose is to pay you and your people to do the handoff the buyer would otherwise have to hope happens.
That transition work is coming either way. You can do it beforehand, on your terms, or afterward, on theirs, with real money riding on how well it goes.
Why CEOs wait, and why that’s the wrong call
The reasons are understandable. Losing control is uncomfortable. The bench is thin, and most companies are already running lean, so nobody has the time or budget to hire and develop a second layer. Good talent you can trust, and whose incentives align with the company’s, is hard to find.
The CEOs who sell well do the work anyway. They delegate what they can and train people to support them, not replace them.
The objection I hear most is some version of “I know I’m the issue, but I don’t know who to hire. If I did, I’d have done it already.” My answer is to change how you search. Bring in someone whose job is to find the person: an industry consultant who can look at how your company runs from the outside and bring a network of candidates you may not know exists. That help isn’t free, but a buyer will charge you for the same gap if it’s still there when you sell.
Then there’s the client’s objection: “My relationships are the value.” That’s true, and it’s why each key client relationship needs a second point of contact on your side now. Ask yourself what happens if something takes you out for a few weeks. That’s a business risk today, well before it becomes a deal risk.
Where to start
Map your critical dependencies first, before you decide what to change.
Then hand off two things first: the key decisions only you make that can be written down and delegated, and the day-to-day contact within your key client relationships. Both are fixable well before a process begins, and both surface early in diligence. Fixing them means the questions come with answers already in hand.
Be candid with your advisors. We don’t work inside your company, so we rely on what you tell us. The advice we give is only as good as the picture we’re handed. Diligence will surface every dependency eventually, and it’s far better for us to hear about it from you first. We can’t help with what we can’t see. Once we can, the right team can bring resources and relationships you wouldn’t have thought to look for.
A candid look at where you stand
If you’re not sure how you’d answer the month-away test, that’s a good conversation to have early. We’ll walk through where the company depends on you, what to address first, and who can help. There’s no pitch and no clock running, only an outside view while you still have time to act on it. Reach out when you’re ready to talk it through.
