Persuasive communication

How Complete Is Your Questioning Toolkit?

Have you ever known a leader or manager who was an expert questioner? It seems like some people have the rare and valuable skill of being able to ask the right question at the right time. You go to them to approve a proposal and they get right to the heart of the matter. Or, you need advice about a situation and they ask you questions that get you to see things from a different perspective and find your own solution.

These people seem to have a natural knack, but nobody is born fully equipped to ask the right questions for every situation. It’s a skill that only looks effortless because it has been developed over years of experience, practice, and maybe even formal training. As you go through your business and personal life, you may pick up the skill by trial and error, learning which questions seem to get the best results, or you may develop the critical thinking skills that allow you to spot the weaknesses in a proposal, or you may evolve standard algorithms/checklists for specific situations, over time you accumulate a toolkit of effective questions.

You need a complete toolkit because you face a variety of tasks, and the types of questions that work very well for one task may be exactly the wrong ones you need in another. For example, the questions that find flaws in a proposal may be helpful if you’re a CFO deciding how to allocate resources, but they will get you thrown out the door if you’re a salesperson.

Fortunately, a lot of smart people have developed excellent questioning protocols and have written about them, which allows everyone to cut the time and pain needed to develop and practice the skills.

A complete questioning toolkit addresses the major tasks that a leader has. Here are some:

Decision-making and problem-solving questions are used to make sure you’re getting the best thinking out of your people, so that you can make the best possible decisions. I’m biased because I teach it, but the best set of questions I have come across for this are Vervago’s Precision Questions, which comprises seven categories of questions, arranged under these general questions:

  • Do we talk about this now?
  • What do you mean?
  • What are you assuming?
  • How do you know?
  • What caused it?
  • What are the effects and consequences?
  • What should we do?

Persuasive questions are used to get people to talk themselves into the direction or solution you want by making it their idea. Whether it’s motivational interviewing used by psychologists, or some variant of SPIN questioning, the basic aim is to bring out gaps between what is and what could be and guide the answerer in the right direction:


  • What are you doing today and/or what would you like to be doing?
  • What needs to change to improve the situation or to  achieve your goals?
  • What happens if you don’t?
  • What do you need to do next?

Coaching questions are used to develop your people. They’re similar to persuasive questions, in that they are meant to steer the conversation toward change talk, preferably making it the answerer’s idea so that they are more likely to fully commit to it. The principal difference is that the initial questions are used to test the perception of the person being coached to assess whether they know their current behavior needs to be changed. There are many different effective models, such as the GROW model:

  • Goals: Where do you want to be?
  • Reality: How far away are you from your goal?
  • Obstacles/options: What obstacles are in your way and what options can you think of to remove them?
  • Way forward: What specific action steps will you take?

Columbo questions are not a formal questioning process, but I’ve learned from being on the receiving end that they can be the most effective general questioning technique of all. Inspired by the famous TV detective, they are merely the application of intense curiosity and almost naïve simplicity:

I’m not sure I get it, could you please explain it again?

How does that work?

Probes are different from these other questions in that they are more reactive, following the thread of the conversation, and because they are useful for all purposes. Here are three simple types that you can use to squeeze the juice out of just about any conversation:

  • Clarify: Can you explain what you mean? Can you give me an example?
  • Dig: Can you give me more detail about that?
  • Extend: What else?

This is not meant to be a complete list of all type of questions for all occasions, but if you can master these you will be one of the people who come to mind when others are asked who is the best questioner they know.

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