This page provides a brief introduction to a whole series of questioning tools and questioning techniques. Many simply change the framing in which questions are posed, pointing to how important it is to explore and understand the assumptions on which questions are built.

I would suggest that no questioning tool or questioning technique is better or more useful than another – they all simply offer us different prompts from which questions can emerge and curiosity flourish.

Where warranted, you will find a link to a further page for a lengthier exploration.

What exactly is a problem? It feels like some form of challenge or impasse we have decided we need to overcome. Whilst there may be a literal problem (my car won’t start), how we frame it conceptionally (my car needs to be fixed, I need another means of transport, this really isn’t my problem, I have other priorities) will condition our next steps.

> Want to rethink your problems?

The first question to ask of any question is “Why am I asking this question?”. This questioning technique walks you through the process of deconstructing questions to become aware of any biases, assumptions or worldviews that might be skewing the question.

> Would you like to ask more transparent questions?

The Socratic Method is a form of question-and-answer dialogue that aims to stimulate critical thinking and uncover underlying beliefs and assumptions. The intention is thus different from a “regular conversation”. I would suggest that its ultimate aim is for the person being questioned to realise that they are not their thoughts and “not to believe everything they think”.

> Want to try some sample questions?

The 5 Whys is a simple yet powerful questioning tool that encourages users to ask “why” repeatedly to identify the root cause of a problem. This technique aims to sidestep surface-level symptoms and delve deeper into the underlying issues behind a problem. Developed by Sakichi Toyoda, the method was first implemented in Toyota’s manufacturing process but is now used widely in business.

> Want to know how to use the 5 Whys?

What Ifs?

The What Ifs technique is an incredibly simple problem-solving tool that does what it says on the tin, namely offering “what if” questions to explore potential solutions or alternatives. It can help break through fixed ways of thinking and stimulate new ideas and possibility, particularly if followed by some How questions.

For example:

  • What if we doubled the price we charge customers? How might this affect sales? How might it affect profits?
  • What if we offered different pricing models? How might this impact cash flow?
  • What if we invested in more sustainable practices? How might this affect our brand image and customer loyalty?

The “What Might We…?” questioning technique is all about open-ended questions. And yet its simple collaborative nature (use of “we) helps encourage creative and innovative ideas.

> Learn more

Step Outside the Story is a technique inspired by narrative therapy and the idea that our lives are shaped by the stories we tell ourselves and others about who we are and what has happened to us. These stories can sometimes be limiting or unhelpful and can prevent us from making positive changes or seeing possibility.

> Learn more

The idea for Question Circles came to me in the course of reflection around ways and means of asking bigger questions. It is intended to create a space for group exploration of a particular issue in the presence of peers. There are no teachers, no experts or indeed answers. The focus is thus on the group and on the process.

> See the full Question Circles process

Questionstorming is a brainstorming technique that focuses on generating as many questions as possible around a particular issue. The idea is to fully scope out an issue through questions rather than seeking immediate answers.

> Learn more about Questionstorming

This exercise comes almost directly from A More Beautiful Question by Warren Berger (link to Whilst I could certainly have used when I co-founded a startup, this exercise is equally applicable to any endeavour that requires full-on commitment. The idea is to cast the process as a mountain climb and ask questions around that.

> See how it works!

In one sentence: Analyse a startup business back and front, top and bottom.

This is the type of process I wish I had when I set up my first startup. We had a great idea, a solid team but there were a host of pitfalls and blind spots that we really weren’t willing to stare down. The 720 is intended to look inside and out, and kickstart the necessary conversations.

> See how it works!

Imagine you are “8“. What might you be questioning?

Embrace the uninhibited curiosity of an 8-year-old to rethink your products, services, strategies or even life. This child-like perspective helps simplify complex ideas, allowing for clearer communication and decision-making. Let go of what you think you know and open yourself up to what you don’t understand.

Don’t shy away from ‘silly questions’ as they often lead to profound insights. Remember, 8-year-olds question without judgment, see connections adults overlook and make fewer (or at least different) assumptions. Their unique perspective can spark innovation and challenge hidden biases, fostering a fresh and creative approach to problem-solving.

Sometimes the most complex challenges can benefit from the simplest and most innocent perspectives. This questioning technique is one of the simplest in theory and yet can be hard to apply in practice until people feel free to give it a go.