The Seven Sins of Questioning admin March 9, 2020

The Seven Sins of Questioning

The Industrial Age Obey the Clock play pushes to get the team moving forward. Since we’ve separated the deciders (blueworkers) from the doers (redworkers), the deciders need to convince, cajole, bribe, shame, or threaten the doers to DO the work they had little or no part in choosing and sounds like “I’ll tell you what you need be doing.” The verb to best describe this is “coerce.”


Deciders COERCED the doers.

We don’t use that word today because it’s ugly, instead we replace it with other words like motivate or inspire.

Leaders MOTIVATE people.


What we need now is Collaboration. Collaborating is only really collaborating if the boss ISN’T using influence, power, rank, talking first, talking more, or talking louder to bring people around to their way of thinking. If they are, it’s not collaborating, it’s coercion.

One way to Collaborate, Not Coerce: Be Curious, Not Compelling.

When we encounter people who see things differently, who think differently, our best next action is to learn what see, know what they think. Going one step further, leaders need to be aware of how others feel. We want to connect with others and that means caring for them and wanting whats best for them. By asking questions that uncover the someone else’s thinking we also listen, giving undivided attention. When this is done successfully, the other person walks away feeling heard and you walk away with more insight.


Being curious about what some else thinks is the foundation of asking good questions.

Stephen R. Covey, author of The Seven Habits of Highly Effective People, considered this concept of “curiosity first” so important he titled
his fifth habit “Seek First to Understand, Then to Be Understood.”

In working with clients we’ve observed many meetings. Intently listening, watching for reactions, and gauging the level of participation with in teams to help us and them better understand how the language we use affects our work. Listening to the language of the boss, how they addressed concerns and questions, what questions they asked and especially HOW they asked them.

Here’s an example of a marketing meeting we observed about a holiday party being thrown for partners of “the business.”

I walked into a room with a long table and ten people sitting along the sides and the director of marketing is sitting at the head of the table–casually leaned back staring up at the ceiling with a pondering expression. The team lead greets me and announces I will be observing the meeting today and for everyone to “just act as they normally would.” The ten team members sit with their notebooks, example flyers, and s laptops ready for action. The team lead -sitting closest to the boss- starts reading her notes about the time of events, possible booths, and vendors who want to attend. In the middle of her talking, the boss–still gazing at the ceiling– asks “What did we do last year for this?” With a pause, the team leads’ eyes darted around the table looking for help from a teammate.

No one else spoke up.

The team sat very still, avoiding eye contact, directing their attention to the notes and papers in front of them.  With a long “Weeeeeellllll…” she began to talk about last year’s event. No more than 10 seconds later the boss interrupts again–this time turning and directly speaking to the the team lead. “How did it go last year?” Sounding a bit confused, the women said “Good. I think it went good.” She looked around at her team members, some of who were gently nodding in agreement. Then the boss says “I need to know what went well last year. That’ll help me decide what to do this year. I mean, how good was last year? Do we really want XYZ here again? And I know everyone liked the doggie snow cone booth but was it worth it? How much did that cost anyway? What budget did you put together for vendor expenses? Did you send me that?”  Just as abruptly as the boss started talking, he stopped and stared at her intently as if she could answer each question now that he had finished.

The silence that followed was alarming. As an observer I was extremely uncomfortable and could feel the tension in the room. The women looked embarrassed and flustered. She shuffled through her papers a few times and then asked a team member how much the doggie snow cone booth cost last year.

Rest of the meeting was very similar. The team was trying to discuss the plan for the event and the boss would question stack. The feeling I had when the meeting ended was that the only thing the team and the director knew for sure was that they were having an event in months. There was no excitement. No one left saying, “This event is going to be awesome!” Instead people shuffled out of there with raised eyebrows and polite half smiles.

I talked to the team lead after and she was curious about what I thought of the meeting. Delicately, I asked what she felt when her boss asked her so many questions at once. “Exhausted,” she said.

Question stacking is one of the seven sins of questioning. Before this meeting I had not witnessed question stacking, but I know I will never forget the way it affected the team. By the second or third question everyone had turned off and tuned out.

Instead of question stacking, ask one question and then stop. One and done. This takes practice because you have to think of the question before you start talking, and then resist the urge to step in after two seconds.


In our new book Leadership is Language, we talk about the other six sins of questioning and give you the words to say instead. Download the Seven Sins of Questioning handout, as an easy reference.

To learn more, watch this Nudge – Leadership Nudge® 299 – 7 Sins of Questioning