Powerful Question Rolodex: Types of Questions & When To Use Them

coaching leadership Mar 20, 2023
Powerful Question Rolodex

Written by Sebastian Little

I ask a lot of questions as a coach. Here’s a general framework for how I think about them. Interestingly, each question also has a shape. By understanding each question type, we ensure we’re never stuck in a conversation.


What questions expand the conversation. They are often the most simple to use and easy to answer. If you keep them short, they offer a TON of room for possibility. What questions are also GREAT with groups of people. 

Ex. What are you doing? > Lots of possible answers. 


How questions point to process or operations. They invite others to break things down into steps to explain how it happened or how it is going to happen. 

Ex. How do you do that? > I’m hoping to get the step-by-step or play-by-play. 


When questions are temporal in nature - they address time, both past and present. They also widen the conversation. If we’re looking to identify other times that a behavior or mindset might be the same/different, when questions allow us to move through scenarios or moments in time for us to find connections (or not). 

Ex. When has that been successful for you? > Invites curiosity around previous success. 

Ex. By when do you plan to do XYZ thing? > Asks for accountability and a deadline.


Where questions change the context or arena that you’re playing in. Like When questions, they expand the conversation by widening our focus from the current scenario to alternative ones. 

Ex. Where else does XYZ happen for you?

Ex. Outside of this situation, where have you seen this strategy work? 


Why questions get at the root cause. We’re often taught to use these, but be warned, they typically point to analysis of the past. If you’re trying to move forward (on a team, in a relationship, etc.), why questions can get you caught up analyzing some stuff you don’t want to analyze. They can also sound a bit incriminating at times. However, if you want to go deeper and understand, why questions are powerful. Why questions spotlight our core motivations and can offer inspiring insights.

Ex. Why did you do that? 

Ex. Why are you approaching it in that way? 


  • Practice experimenting with different questions. Pick one question type each week and overuse it. Notice the type of responses you get.

  • Set a timer for 60 seconds and create a list of powerful questions. Notice which questions you favor.

  • Before responding, pause and consider which question type would be most valuable to the person and the conversation.

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