Are You Developing Your Team’s Thinking — or Their Insecurities?

I coached an executive who wanted his team to think more deeply, more critically, and to bring ideas that were examined from different angles before being proposed.

Most of us agree that’s the right move for developing top talent.

But this intention can backfire and produce the exact opposite.

Asking questions like:

What options did you explore?
Which option are you recommending?
Why is that your recommendation?
How do you propose the risks be mitigated?

All valid.

Effective leaders teach their directs to be prepared to answer these questions and think through the nuances.

But here’s the blind spot.

When your questions never seem to stop, drill at every detail, and keep circling:

What else is possible?
What else needs to be considered?
What else needs to be mitigated?

You are not developing skills.

You are developing your team’s insecurities.

The difference is subtle.

And you probably don’t know you are doing it.

But what happens at the end of these discussions is the biggest tell.

When meetings rarely end with a path forward, even an imperfect one, you have not empowered them.

Instead, they leave and spiral in self-doubt.

It is no longer about trying to solve the problem.

It is about trying to solve YOU.

No real direction.
No ownership.
No stake in the ground.

This executive needed to see that the impact he was having was the opposite of what he intended.

At first, he both resisted the feedback and knew it resonated.

He could have dismissed it.

Instead, he chose to experiment.

Together, we built a framework that helped both him and his directs explore, but with guardrails.

Permission to stop when the process kept circling.

Explicit signals when it was time to choose.

Agreement on next steps even when the path wasn’t perfect.

When I interviewed his directs a few months later, they were truly grateful.

Finally, a way to build success instead of constantly missing a target he had inadvertently kept moving.

If you like to ask lots of questions, like I certainly do, make sure there is a destination everyone can reach intact.