Questions, Questions, Questions – Asking Better Leadership Questions

Our headlines are filled with questions. Did he? Did she? Who did what and when? Why? All of these questions consume our attention and build tensions between opposing factions. For what real good? (Ha, another question!)


Questions can be used for good or bad. Well-intended questions can add clarity. A properly structured question uttered in the context of a healthy discussion can help two parties share information and grow together; learning can happen and prosperity emerges. However, questions asked with hidden meaning or mean spirit can only serve to undermine confidence and credibility.

The Leadership Question

For executives, managers, and business owners, the effective use of a proper question is very powerful. Yet using an ill-timed or poorly thought out question only serves to muddy the waters.

I speak with clients all the time who express concerns that their questions cause disruption rather than unity. Managers who like to manage by walking around can’t help but ask questions out on the floor. While the messages are usually very innocent, they can stir quite a controversy without any good framework.

There are business leaders who like to know what’s going on. How else can you do that BUT by asking questions? Then there’s the situation where you just got hired or promoted to fill a big role, but you don’t know what you don’t know, so you start asking questions.

Inevitably the questions do more harm than good. Here are some the usual reactions employees have after your question gets asked:

  • Why did he/she ask that?
  • Is there something I am missing?
  • Are we changing directions?
  • I thought he should know that.

Stump the Chump

Questions can also become “gamey”. Ask too many questions and people start to feel like you are playing stump the chump. You know, the game where the “expert” gets asked a hundred questions to determine whether they really know their stuff or not.

I tell the story of walking the floor one day in my banking days. I managed a large team of loan administrators. One of my senior administrative people stopped me. He said he had some questions. I agreed to weigh in.

He proceeded to test me on the calculations he had done. I answered all the issues then asked him why such questions because there really weren’t any open items to discuss.

He said he was curious if “the Big Dog” knew his stuff. My response? “How do you think I got to be the BIG DOG?”

The Answer

Here’s my advice to executives worried about the questions they ask. I recommend using a technique I call the bookend approach. Open with one bookend. Frame your question with context. Start by explaining where you might be going. Examples are “I need to know more about X.” Or “Remember we talked about ________, please tell me more.”

Then proceed with the question or questions. But close the interaction with another bookend. “Ok this helps me a lot.” or “I didn’t realize how that worked.” Even more important “Good, this is right on target with our vision and direction.”

By using bookends, you open and close the exchange with specific ideas. You eliminate the wondering and wandering that people’s thoughts may do merely by you asking a question out of the clear blue.

The added bonus is you get credit for being an effective communicator.

Try this the next time you are out talking with your team. I promise you will see better reactions.

Originally posted on DougThorpe.com

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