Am I too late to turn this around?

Three weeks after I took my first job leading leaders, the boss who hired me left the company.

I was leading a marketing team at American Express, managing former peers who had been at the company for decades longer than I had. And suddenly, I’d lost my biggest advocate.

There was so much to do I felt like I was shoveling out dirt. For every shovel out, two more shovels of dirt were poured in.

Everything ran through me. And the harder I worked to keep things moving, the more it felt like the team needed me involved in everything.
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What took me longer than it should have was understanding why.

They had learned that checking in with the boss was safer than deciding without one. I wasn’t just buried in work - I was the bottleneck they had been trained to need.

And I’ve seen more and more leaders step into bigger roles - usually replacing someone who has been there for a long time, leading a highly tenured team, and getting stuck because this new team seemingly wants to be micromanaged.

Sometimes there is a real skill gap.

But often, people have learned that taking initiative is riskier than waiting for approval.

Usually I get the phone call about 12-18 months into the role, when the leader is almost at their breaking point. Their boss isn’t happy, their team isn’t happy…and worst of all, they aren’t happy.

One CFO, 14 months into her job, said to me, “Am I too late to turn this around?” I replied, “Nope, I’d say you’re right on time.”

The fix is not working more hours. It’s diagnosing what’s keeping the team dependent on you and changing those conditions around them.

If you recently stepped into a new leadership role or are about to, this is a pattern to watch out for.

And if that is not you right now, it’s still worth one honest question about your own team. How much of what reaches your desk actually needs to? This is a systemic issue that eventually impacts almost every leader.