Why So Many Estate Managers Have Short Employment Histories: Are We Asking the Wrong Question?

One of the first things principals and family offices often look at when hiring an Estate Manager is tenure. How long did they stay? Eighteen months? Two years? Three years?

The assumption is often that longer tenure means a better Estate Manager. But what if we're asking the wrong question?

When reviewing a résumé, most people immediately focus on why the Estate Manager left. After years of working with estate leaders, I've come to believe a more important question may be:

What kind of operation were they walking into?

Instead of asking why Estate Managers leave, perhaps we should ask why so many operations struggle to keep them.

Some Estate Managers leave because they're burned out. Some leave because they're offered a better opportunity. But many don't leave at all. They're terminated.

And the reasons why aren't always what people think.

I've seen Estate Managers hired into environments where success was nearly impossible from the start.

They're expected to oversee multiple properties they have never visited, manage staffing shortages, recruit and train new employees, lead construction projects without a construction background, satisfy principal expectations, communicate with the family office, manage budgets, and somehow still find time to think strategically.

All of this with little or no administrative support.

Eventually, performance suffers. Not because they're incapable. Because the operation itself isn't sustainable.

I've also seen the opposite.

An Estate Manager spends several years building systems, hiring the right people, documenting procedures, improving communication, and creating accountability. The operation stabilizes. The principals become more comfortable. The staff becomes more capable. Daily emergencies become less frequent. Things are finally running smoothly.

And then something interesting happens.

Someone begins to question whether the Estate Manager is still needed. After all, everything appears to be under control. Why continue investing in executive-level leadership if the operation seems to be running itself?

What often goes unrecognized is that stability rarely happens by accident. Someone built it. Someone continues to maintain it. Someone is still responsible for keeping the operation aligned, accountable, and moving forward.

Think about an orchestra without a conductor.

A plane without a flight plan.

Or a professional sports team without a coach.

The talent may still be there, but leadership and direction matter.

In both situations, the result is often the same. The Estate Manager leaves. The family starts over. The principal becomes frustrated. And the operation loses valuable knowledge, continuity, and leadership.

The next time you review an Estate Manager's résumé and notice short tenures, don't just ask:

"Why did they leave?"

Ask:

"What kind of operation were they walking into?"

Was long-term success actually possible? Because sustainable operations don't happen by accident. They require leadership. They require structure. And they require a plan. Those are conversations our industry needs to have more often.

Is investing in operational leadership expensive? Absolutely.

But so is the cost of turnover, instability, lost institutional knowledge, and starting over.