Ask a room full of business owners if they plan to exit someday, and almost everyone says yes — eventually. Ask them if they’ve actually planned for it, and the room gets quiet.

That gap — between “someday” and an actual plan — is where most owners live. Not because they don’t care, but because exit planning rarely feels urgent until it suddenly is: a health scare, an unsolicited offer, family pressure, or simple exhaustion after years of building something.

The good news is that exit planning isn’t a single event you schedule for your last year in business. It’s a discipline you can start applying today, and it pays off whether you sell in two years or twenty. It starts with an honest look at where you actually stand. Here are seven questions we ask every owner we work with — and the ones you should be asking yourself.

1. Do I know what my business is actually worth today — and what it could be worth?

Most owners have a number in their head. Fewer have a real valuation behind it — one built on defensible financials, industry multiples, and an honest look at what a buyer would actually pay versus what the business could be worth with a few key improvements. That gap between current value and achievable value is often the single biggest lever an owner has, and you can’t pull it if you don’t know it’s there.

2. Could my business run without me for 90 days? Could it transfer smoothly to a new owner?

This is the test that separates a business from a job. If the phone stops ringing for you specifically, if decisions stall without your sign-off, if key relationships live only in your head — that’s not a business a buyer wants, and it’s not one your family could keep running either. Transferability is worth real money, and it takes time to build.

3. Have I calculated my wealth gap — the difference between what I need financially and what I have outside the business?

Many owners have most of their net worth tied up in the company itself. The wealth gap is the distance between what you’ll need to fund the life you want after you leave and what you actually have outside the business today. Until you calculate it, you’re guessing at both your asking price and your timeline.

4. Do I have a plan for my time, energy, and identity after the business?

The financial side of exit planning gets most of the attention, but the personal side is what actually derails transitions. Owners who haven’t thought through what their Monday mornings look like after the sale often struggle more with the transition than with the deal itself — or quietly slow it down because they’re not ready to let go.

5. Is my family aware of and aligned with my transition plans?

An exit plan that lives only in your head creates surprises — for a spouse who assumed retirement meant something different, for children who expected (or didn’t expect) to be involved, for family members who find out about the plan only after it’s already in motion. Alignment doesn’t require full agreement on every detail, but it does require the conversation to actually happen.

6. Do I have a coordinated advisory team, or am I working with disconnected specialists?

Most owners have a CPA, an attorney, maybe a wealth advisor and an insurance agent. What they often don’t have is anyone making sure those specialists are working from the same plan. A CFO who has advised on exits can act as the quarterback — connecting the financial, legal, tax, and personal pieces so they don’t end up working against each other.

7. If something happened to me tomorrow, would my business survive — and would my family be protected?

This is the question owners like least, and the one they need most. Contingency planning isn’t about pessimism — it’s about making sure a health event, an accident, or worse doesn’t turn into a crisis for your employees, your customers, and your family on top of everything else. If you don’t have a documented answer to this one, that’s the place to start.

Where Does That Leave You?

If you read through that list and answered “yes, confidently” to all seven — that’s rare, and worth celebrating. Most owners find at least two or three where the honest answer is “not really” or “I haven’t thought about it.”

That’s not a failure. It’s just where exit planning starts. Whether your exit is five years out or still a distant idea, closing these gaps happens well before any transaction — and it tends to make the business stronger and more valuable along the way, exit or not.

If any of these questions gave you pause, that’s usually the best time to start the conversation.  Contact Kerry George at kerry@crowncfo.com