Quick Links to Some Tools and Techniques

This page provides a brief introduction to a whole series of questioning tools and questioning techniques. Many just 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.

One of 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 Amazon.co.uk). Whilst I could certainly have used it 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!

Which question brings more thoughts to mind:

  • How might Elon Musk succeed in making X the ‘everything app’?
  • How might Elon Musk fail in making X the ‘everything app’?

In this scenario, the second question has infinitely more answers. There are simply a lot more ways in which X could fail than succeed. Those negative answers can then be reversed to generate positive actions.

Similarly, by asking “How might we make this worse?” rather than “How might we make this better?” we will gain insights we may not have otherwise. Also, the list of ideas we draw up will be the opposite of what we might do.

The questioning technique plays into many people’s natural ability to see more problems than solutions and, by specifically asking people to criticise, offers a safe space in which to do so. This might be particularly important in environments in which team members find it difficult to challenge dominant figures or ideas.

> See how it works!

Exploring Conditions and Prerequisites: What Would Have to Be True?

This is a powerful framing technique that urges us to think critically and imaginatively about the world. It allows us to step outside ourselves, step into other people’s shoes, and even transport ourselves to different times and places. The exact question can take different forms depending on the emphasis:

  • What must be true for my neighbour for her to vote Republican? Democrat?
  • What would have to be true for this project to be a success?

Let’s imagine we are working at NASA on the Apollo program. Our objective is to send humans to the Moon and bring them back safely. We therefore start at the end and ask:

What would have to be true for us to land astronauts on the Moon and return them safely to Earth?

This question asks us to stand at the destination and look at what has been accomplished. The technique involves assuming something makes sense, is true or has already happened and trying to understand what the people in question saw or knew to make it happen. It encourages exploration and fosters a problem-solving mindset.

> See how it works!

Brain Writing

This technique is a pure brainstorming idea that is designed to get around the social or hierarchical pressures that normally exist within groups.

The idea is very simple:

  • Define what it is the group needs to think about.
  • Get everyone to write down their own ideas including challenging how the “problem” or “issue” is being framed. For example, it may be an opportunity rather than a problem, a feature rather than a bug.
  • Collect the ideas and rewrite them slightly to ensure they are largely anonymous.
  • Share the ideas with the group in a form that allows each person to honestly consider them without outside influences.
  • Have everyone rate the ideas independently without knowing who has had which idea.
  • Then take the most promising crowdsourced ideas and start discussing them.

It is important that each step is done in such a way that the author of the idea remains anonymous, and that each person gets to rate the ideas without having any inkling as to other people’s opinions.