She didn’t leave for more money.
She left because you’ve been “thinking about retirement” for three years but won’t commit to a timeline.
The Story Nobody Tells You
I had coffee last week with a former operations director who’d just resigned from a company she’d been with for 12 years. Brilliant at her job. Knew the business inside and out. The owner had told me separately that she was “essential to any succession plan.”
So why did she leave?
“I couldn’t take the uncertainty anymore,” she told me. “Every six months he’d mention retirement. Strategy meetings became pointless because we didn’t know if there’d even BE a company in two years. What if he just winds it up, what if he just keeps going for the next 10 years, with the odd carrot of “retirement” dangled in front of us? It’s hard to stay engaged when you don’t know if you have a future.”
Uncertainty Is Toxic to Talent
Here’s what most business owners don’t realise: whilst you’re wrestling with the big questions—when to retire, whether to sell, if your children want the business—your management team is wrestling with their own questions:
- Will there be a business to lead in five years?
- Am I wasting my time building something that might be sold or shut down?
- Could I be part of the succession plan, or should I be looking elsewhere?
- If new owners come in, will they want their own team?
Your silence isn’t neutral. It’s a decision that drives your best people away.
And here’s the cruel irony: the longer you wait to have these conversations, the less valuable your business becomes. Because when your key people leave due to uncertainty, you’re left trying to sell a business that’s suddenly far more dependent on you than it was before. You’ve done all the hard work building a strong team, then you go an undo it all yourself with your silence and uncertainty.
The good managers leave first. They have options. The mediocre ones stay because they have to. And your business valuation drops accordingly.
What You Should Do Instead
You don’t need to have all the answers. But you do need to start the conversation.
Be honest about where you are in the process. “I’m 62 and thinking seriously about what the next 5-7 years look like” is infinitely better than years of vague hints of retirement followed by periods of silence.
Ask your key people what they want. Your operations director might want to buy you out. Your financial controller might want to stay on with new owners. Your sales manager might be ready to retire too. You won’t know unless you ask.
Give them a realistic timeline. Even if it’s “I’m exploring options over the next 18 months and will make a decision by the end of next year,” that’s something they can work with. It shows respect for their careers and futures and demonstrates your trust in them.
Consider them in your options. Management buyouts, employee ownership trusts, earn-out arrangements—there are structures that can keep your best people invested (literally and figuratively) in the business’s future.
Bring them into the process where appropriate. If you’re speaking with advisers or potential buyers, your senior team should know. They’ll find out anyway, better they hear it from you. There might be some NDA concerns, but buyers will tend to be reassured that your management team is invested in the future, can be trusted and isn’t just being kept in the dark.
The Real Cost of Silence
The business owners who successfully navigate succession don’t do it alone. They do it with the team that helped them build something worth passing on.
But that only works if the team knows there’s something to stay for.
Your best employee didn’t leave because someone offered them £10,000 more. They left because after three years of uncertainty, someone else offered them clarity.
Don’t let your reluctance to start the conversation cost you the people who make your business valuable in the first place.
