Handling our current dilemmas: using wicked questions

If I had an hour to solve a problem and my life depended on the solution, I would spend the first fifty-five minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes. Albert Einstein

As some of you know I ask a lot of questions. If it’s any consolation it’s not just of other people, I ask myself a lot of questions too. With all the walking I am doing at the moment to shake episodes of Zoom brain, these questions have been coming thick and fast! One of the things I have been thinking about a lot is the paradoxical nature of organisational change and development – how can things change, when we also want things to stay the same?

We touched on wicked problems in an earlier post, and I would suggest we are probably in the depths of the wickedest problem many of us have ever encountered. Wicked questions can be useful in this context because they help surface the contradictions we may be confronted with. They are a useful way of highlighting the tensions that can arise between our goals and our day to day behaviours. You might recognise some of these:

How do we make change happen and still deliver the work that we have to get done?

How do we help people take more responsibility and give them autonomy while keeping everything consistent and making sure we all head in the same direction?

I think the value of working with wicked questions is that they encourage us to take a ‘both/and’ approach, rather than the more usual ‘either/or’ view that can cause overt conflict or drive the tension below the surface (because people don’t want to be in conflict) with the likelihood it will pop up again when you least need it. Certainly, one of the tensions we are all holding at the moment is how to plan for the long term at the same time as managing the very immediate uncertainties.

Examples of some of my own wicked questions include:

How do I support as many people and organisations as possible and grow my work at the same time as retaining my flexibility as a sole trader?’

How do I build positive relationships at the same time as asking people to confront some difficult truths?

Identifying wicked problems can help:

  • Surface messy reality rather than the sanitised version of life we sometimes tell ourselves
  • Avoid wild swings in approach
  • Evaluate decisions in terms of whether you are addressing both sides of the question
  • Promote innovation and discovery

Thinking in terms of wicked questions is relatively straightforward. Firstly, the important thing is to frame the question and recognise the dilemma it contains, as I have done above.

Then you can use a simple structure to explore it further:

  • What? What do you notice, what facts or observations do you have to consider?
  • So what? What is important about what you notice, are there particular patterns or issues? What conclusions can you draw at this point? How are you interpreting what you have noticed?
  • What now? What action might you take based on the conclusions you have surfaced? Do they make sense in the light of your conclusions?

Holding the two elements of a wicked question can be daunting, particularly when it comes to next steps. One approach to the ‘what now’ element is to keep it small, something I advocate in my Small Change® programmes, or what Gareth Morgan refers to as 15%. It is suggested that most of us have 15% control over our area of work. The remaining 85% is governed by our wider context, including structure, systems, events and culture.

Your Small Change, or 15%, is the first step you can take without additional resources or needing permission from someone else. It keeps your next steps manageable and helps people get comfortable with working on the basis of resolutions rather than solutions. If you are working with a group it can also be helpful to use the 1-2-4-all approach (developed by Henri Lipmanowicz and Keith McCandless).

  1. One minute of silent self-reflection
  2. Two minutes to generate ideas in pairs from your self-reflection
  3. Four minutes in groups of four to share work from your pairs and notice your similarities and differences
  4. Five minutes all together to share ideas and insights – what is the one important idea that stands out?

Repeat cycle as necessary.

As we move towards a gradual re-opening of the sector surfacing and handling the dilemmas you face through wicked questions might help as you manage the ongoing complexities.