Please Stop Pimping

Questioning Skills

Questioning Skills

By Starla

September 28, 2022

 Minute Read

10 Mistakes Leaders Make When Asking Questions

Questioning is an often overlooked but uniquely powerful tool for unlocking communication and collaboration. It spurs the exchange of ideas while strengthening rapport and trust among team members. Unfortunately, not enough leaders have been trained in the communication art of questioning, and throughout my years as an executive coach, I've noticed ten mistakes that leaders often make when trying to lead with questions. Here they are in no particular order.


Asking Questions Designed as Traps, Tests, Gotchas, or Assaults

In most cases, this results from the leader's motives deteriorating into unnecessary agendas like winning, punishing, demonstrating intellectual superiority, teaching a lesson, calling attention to mistakes or deficits, etc. The leader asks a question not from a place of genuine curiosity but with the intent to use the respondent's answer to carry out one or more of these agendas. This destroys trust and diminishes a team's willingness to engage further in conversation.


Asking Leading or Loaded Questions Designed to Bias or Manipulate

These questions are designed to elicit the leader's desired response and often sound something like, "Would you agree that..." or "Don't you think it was a bad idea to..." 


Asking Too Many Questions At Once

I'm guilty of making this mistake, especially when I've already prepared my follow-up questions. I ask my initial question and then quickly ramble off my follow-up questions for the various ways the respondent may answer. In my mind, what I believe I'm doing, is giving them a heads-up on what's coming next. But what is really happening is that I'm creating confusion with too many questions that cover multiple issues.


Asking Questions That Are Impossible to Answer

For example: "Why doesn't anyone tell me anything?"

(Writing this post made me realize I need to capture these questions better when I hear leaders ask them. Please help me out here. Are there Impossible To Answer questions others have asked you? If so, drop them in the comment section of this post. I would to hear them.) 


Answering A Question After Asking It

This is an indicator that the leader is more interested in hearing themselves talk rather than listening to and understanding your answer. When leaders do this, they are simply using their question to create an opportunity to keep talking and demonstrate their knowledge or intellect.


Giving Up After Asking A Question Only Once

When a response is not forthcoming, the best questioners don't give up. Instead, they (1) rephrase their question with clarifying comments to elucidate the intent of the original question or (2) break the question down into more manageable parts.


Not Allowing For Uninterrupted Silence

This type of dialogue isn't supposed to be fast-paced. Moments of silence are to be expected, and the most effective leaders use them to their advantage. Pausing to think between an answer and the next question creates the space needed to absorb and process the response before building on it and asking thoughtful follow-up questions.


Not Listening and/or Repeatedly Interrupting Before Others Finish Responding

These are telltale signs that other motives are at play and working against the leader's interest in your response.


Using an Aggressive or Condescending Tone of Voice and/or Responding with Facial Expressions & Body Language that Alienate & Erode Psychological Safety

Grimacing, audibles like huffing or sighing, and physically turning away from the responder are telltale signs that the leader has transitioned from seeking to understand to evaluating and judging what was shared.



Pimping is the act of asking a series of difficult questions to demonstrate and establish respect for your superior knowledge and intellect. These questions are asked in rapid succession and are unlikely to be answered correctly. Pimping rarely achieves what the leader thinks they're achieving. Instead, it leaves their team feeling demoralized and less engaged, and the only person that is impressed is the leader themselves. If you're a pimper, please stop pimping.

Pulling It All Together

To become a remarkable leader who challenges the thinking of others, empowers growth, and helps others find their own solutions and problem-solve effectively, do your best to minimize these mistakes as much as possible. No one is perfect, and we will all likely make them from time to time. But with focused practice, you CAN do this because effective questioning is a skill that can be learned and honed over time. Give it a try and let me know how it goes.

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