Questioning is a key principle of coaching (something The SLI does a lot of) and is also a useful tool for leaders in the workplace; performance management, difficult conversations, CPD, induction processes and team creativity scenarios all benefit hugely from “the art of asking”. In the words of The Self Leadership Founder, Gemma Perkins:

“As someone involved in training, I am always amazed at the influence a powerful question can have on participants… and the range of questions that can be used to spark a transformational experience. It is important that leaders have a good understanding of why questions are so vital and how they can be utilised to get the best out of people.”

And you might be sat wondering how asking questions could be described as an “art”. The art here really is in developing that instinct, as a leader, for when to switch from telling to asking. Because both have their place; asking powerful, purposeful questions at the right moment is important in supporting development but missing the mark with questioning could lead to teams feeling undermined or not trusted. Using a questioning approach takes skill and practice. Not only in knowing the kinds of questions to use, but also in allowing time for people to think, passing ownership to the individual, knowing when it is appropriate to tell and breaking down questions into manageable parts when needed. This is a skillset that benefits from training to gradually develop and evaluate impact. Are you ready to level up your leadership? Head to the bottom of this article for links to access this support.


There can be a temptation, as a leader, to slip into the mindset that your role is to instruct others, to help them learn or perform. This is especially true in a fast-paced environment where it may feel like it would take too long for people to learn by doing, rather than by doing what they are told. It’s likely that this will lead to telling the person what to do every step of the way, like reading instructions out loud. This will probably produce successful results, and your people will learn how you do things.

An asking approach will release more of your time and energy whilst empowering your people to find their way of doing things. This method is far more effective as it allows people to generate their own process for completing something, which is far more memorable and meaningful than living out someone else’s instructions.

Using questions acts as a prompt to draw from previous knowledge and take ownership of the learning or behaviour. If there comes a point where the person has no idea what to do, then it would become appropriate for you to take on a more instructive role – and then revert back to questions as soon as possible. There’s a great example of a leader making the switch in this video, if you’re more of a visual learner.


  1. Focus on open questions to give your people more space

Open questions allow for more interpretative, explanatory and detailed answers. Generally speaking, open questions are more effective because they allow the person to express their ideas more freely and openly (e.g., How would you do X to achieve Y?) 

  1. Evaluate the scope of your question and “chunk” appropriately

Questions, information and themes can be considered as large chunks or small chunks. People process information at different sizes and so the question will need to fit an appropriately sized chunk. E.g:

Whilst all three talk of these examples are about change, you can see how the scope for each question is different (there are even larger and smaller chunks that could be addressed here, still). As an effective questioner, you will be able to pitch your question at the right level for your audience and be able to ‘chunk up’ or ‘chunk down’ if the original question was not the appropriate size.

  1. Target your question for the kind of answer you need

A well circulated and accepted model for understanding how to target your question for the kind of answer you need is Bloom’s Taxonomy:

Each of these categories is useful in different circumstances and so the questioner has to be aware of the balance of question types they use. Asking “What is a Y?” (knowledge) serves a very different purpose to the question; “What would be the best way to achieve X?” (synthesis).

  1. Be cautious with “why?”

Asking somebody “why?” with regards to their own behaviour can bring about feelings of being judged and automatically lead to a defensive answer. E.g., “Why did you do X first?” May lead to a nervous response of “I thought I was supposed to / that’s what everyone else does / is that not right?”

“Why” may lead people to justify their actions. In contrast, “what” and “how” questions tend to be less intrusive. E.g., “How did you decide to do X first?” This focuses more on the logical process and detaches from personal blame.

Obviously, there is a time and a place for “why” questions: but using these questions that focus on a person’s actions should be avoided, where possible.

  1. Test your skills

The next time you find yourself in a situation where you are tempted to instruct somebody, take pause. Dedicate some time and patience to experiment with the asking approach. Use a series of open questions to help your team members talk through the event themselves. Ask small chunks to start with and then chunk up as they become more confident. Try to vary the types of question you ask so that people focus on a mixture of information, judgements and analytic elements of the task.

The asking approach is great for cementing a learning experience and making it more meaningful to individuals. It also frees up more of your precious time and energy as a leader, as your people take ownership of their performance and processes. The art of asking is a key skill that will level up your experience as a leader.

The Self Leadership Initiative facilitates bespoke training and workshops to support trailblazing leaders like you to become more effective through powerful skills such as the art of asking. You could achieve a far bigger impact in the world with the right support. Book a discovery call today to take the first step.