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Ask Tough Questions

In every strategic planning session I’ve conducted with clients, there comes a time when THE tough question has to be asked.

It’s the one that nobody on the executive team really wants to address.

It’s the one that, without being dealt with, derails all other planning.

It’s THE one.

Then, it happens. The moment of truth.

HOLY COW – he did it. He asked THE question.

The team begins to shift from side-to-side in their chairs. Eye contact is dicey. The person that asked the question is waiting on someone/ anyone to be honest with the answer.


And then, someone steps up and tells the whole truth – not just the part of the truth that has been allowed to hold the company back.

Chances are, the people in the room already knew the answer but were afraid to say it.

Does this situation sound familiar?

As I said in the beginning, I have never experienced a strategic planning session where some version of this story doesn’t happen.

Frankly, it’s the hardest and most satisfying part of the day.

Zeroing in on the issue and coaxing / encouraging the dialog to happen in a productive manner is the hard part. But, once it happens, it’s the breakthrough moment when the team around the table comes together.

You can feel the weight being lifted and the conversations have more meaning. There is a feeling of commitment to the task at hand that was missing.

It feels like we’re all on the same team and the goals begin to align.

These moments are hard.

The answers are usually pretty simple.



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