The Most Dangerous Question a Leader Can Ever Ask

Posted: December 3, 2015 in Uncategorized

November 29, 2015

business future uncertain?“Terry my boy, what do you think?”

There it was, finally, the question I was waiting for from my brilliant but mercurial multi-multi-millionaire boss.

I had been pondering the answer for several weeks. We were working on an important project in the fall of 1990, and there was a problem, one demanding some out-of-the-box thinking.

As the Project Manager, I had many hours of meetings with all the key players involved, and diligently forged a consensus on a proposed course of action – so we could present it to the boss with a united front.

With all that work and discussion completed, my confidence high, and with several of my colleagues around me for support, I took a deep breath, and started to answer his question.

It didn’t take too long to realize that I had just stepped onto a land mine, and it was about to explode.

“My God man, that is the most insane idea I have ever heard – how could you possibly think I would like it?”, he said.

I stammered for a couple of moments, regained my composure, and started to explain myself. For two seconds.

My boss pointed at the person next to me and exclaimed , “Mr. _____, don’t you think that’s the stupidest idea you’ve ever heard??”

“Oh yes sir, it most certainly is”, said the person who a mere 5 minutes earlier was in absolute agreement with me.


My balloon deflated. That confidence was now totally gone. I felt about two inches tall.

Just because somebody asked me “What do you think?”.

It was all downhill from there. After another 5 minutes of butt chewing, I was done. In subsequent meetings I simply clammed up, and just dealt in facts, never offering up any strong opinions about anything.

I became a “Yes Man”.

Eventually (and mercifully) I left that job, but not without learning a very valuable lesson about asking someone’s opinion:

You have to really want to hear the answer, AND with an open mind.

Or else, what SHOULD be one of the best things a leader can ask can easily become a dangerous weapon of destruction.

I know, it’s leadership 101, right? Asking teammates what they think is one of those feelgood tools that implies inclusion, concern, collaboration, openness, and, if really used correctly, humility (i.e. “I don’t know all the answers“).

So for most leaders who have been through any kind of training, or read any kind of leadership books or manuals, it feels like a “slam dunk” win to sit in a meeting and ask that question.

Nothing says “I’m practicing good leadership, see?” more than asking for an opinion. You can literally see that on the faces of some people when they do it.

But here’s the really big catch – you have to really WANT another opinion. You have to have an open mind, even if your views have already hardened.

And you certainly can’t trash it almost immediately, with prejudice. And then force everyone else to trash it too, for good measure.

The real danger is in how YOU respond, or don’t respond. You don’t get the “credit” just for asking the question. If it’s just an excuse to ridicule, or you show no real intention to absorb, comprehend, consider, or even just LISTEN and acknowledge the full opinion, you are way way better off just not asking for it.

Otherwise you will confuse, alienate, and anger your teammates, and deflate their willingness to contribute or go out on a limb in any appreciable way.  All in the name of trying to “act” like a leader and asking for an opinion you didn’t want.

Recognize the dangers here as I have (painfully), and don’t turn what should be one of the best questions you’ll ever ask into the most dangerous question of all. Please.

Lead well!


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