Few business leaders like to talk openly about planning their exit – until they have to.
Either they’re far too focused on the day-to-day: growing the business, hiring colleagues, fixing problems, delivering work.
Or, discussing an exit can feel unsavoury, like a betrayal of what they’ve built. The idea of leaving the very thing you’ve poured so much time and effort into can be deeply uncomfortable.
Yet exiting is inevitable. Every business has a lifespan, and no founder or owner can be in charge forever. We all hope this will be a planned transition, sale or retirement – rather than something more unexpected. But what’s clear is that how much you plan for that day (or fail to) can be hugely influential.
Businesses that achieve high valuations and continue to thrive after their founders have left are those which have prepared best for that transition, long before it happens.
And what’s interesting is that many of those preparations are also key for owners who want to achieve a healthy work-life balance. Preparing well also gives you more choice about how you ultimately exit.
Over my years as a business and executive coach, I’ve noticed a few patterns of that preparedness, and how it can lay strong foundations, however far in advance of an exit you might be:
1. You start with the right questions
Contrary to what your accountant might tell you, a business exit is about a lot more than the financials.
Naturally, the valuation you can achieve is going to be important, but the best prepared owners start one step before that: with the right questions.
When looking towards an exit, whether that’s in 5, 10 or 25 years’ time, it’s helpful to understand:
- Why do I want to exit?
- What are my non-negotiables to feel that I’m exiting on ‘my terms’?
- What do I want my life to look like next?
- What parts of this business matter, and what parts don’t?
2. You build something that can live without you
Most businesses start out like infant children – completely dependent on their parents.
You’re likely to have found yourself working long hours, covering 42 different jobs, and doing everything that’s required to keep things moving.
Starting and running a business is hard work.
But that also makes for a fragile organisation.
A common pattern I see is an owner who knows how to do everything, and often still does most of it. It might be productive right now (although I’d question that too), but it makes an eventual exit incredibly difficult.
And it’s why business sales so often include the owner staying on for a number of years to make a transition.
Ask yourself this:
“If I stepped away tomorrow, what would happen?”
A thoroughly prepared legacy plan requires delegation, systems that work without constant oversight, clarity of roles, and a culture strong enough to sustain itself.
3. You build your next life too
“I never really thought about what I’d do next.”
It’s what I hear from so many leaders at exit time.
And it’s entirely reasonable when they’ve been so focused on work.
But preparing for an eventual exit isn’t just about preparing the business. It’s also about preparing yourself, and that can be a much trickier task.
For many founders their business becomes their identity. (How about you: Do you have a clear idea of your purpose post-exit? What will your day look like then?)
I’m not saying you need a detailed plan, but at least having started to imagine your next life can make the transition feel a lot less like a loss.
4. You treat exit planning as leadership work, not an accountant’s job
Now I promise I haven’t got anything against accountants, but exit planning all too often ends up being managed by either them or the firm’s lawyer.
Instead, the leader should be running it.
That means it’s up to you to make decisions today that will lay solid groundwork. Asking questions that don’t have neat or easy answers, and being honest with yourself and the people around you.
Some of the most prepared leaders I’ve worked with started planning long before they felt ready to exit – not because they intended to leave soon, but because they understood that the work of preparation was itself shaping a stronger, more resilient business.
And paradoxically, that made them feel more in control, not less.
If your business feels worth stewarding for the long haul – not just for next quarter, but for the next chapter – then preparing for an eventual exit isn’t a luxury. It’s leadership.
And the earlier you start, the more confident you’ll feel when the time finally comes.
Kind Regards,
Chris