Organisation Development Consultant

Follow the Questions: 5 tips for strengthening your questioning muscles

[5-minute read]

Follow the questions – they will lead you into the future.

For most people, facts and certainties are more comfortable than questions. We want answers, clear direction, a way through the tangled jungle of our lives, and the grey areas of our organisations.

But certainties don’t take us to new places. Questions do.

Questions that matter

I don’t mean, “What time is it?” or, “Does my bum look big in this?”

(Though that second one could offer insights into your relationship, or your self-image. ?)

I’m talking about the kind of questions that start a personal journey:

  • Who am I becoming? 
  • What matters most in my life? What do I love? 
  • If I do (or don’t do) X, what will change in my life and the lives of others? 
  • What would it take for me to be happy and feel free? 

Or begin an organisational one:

  • What have I done to contribute to the problems I complain about?
  • What is the crossroads we are facing?
  • How valuable a project do I plan for this to be?
  • How much risk am I/we willing to take?
  • To what extent are we invested in the well-being of the whole?
  • What are the stories about this organisation that I hear myself telling most often?
  • What is the ‘no’ that I keep postponing?
  • What have I said ‘yes’ to that I no longer really mean?
  • What am I grateful for, but have never acknowledged? 

The second list above was slightly adapted from Peter Block’s work, Community: The Structure of Belonging. (Click on the link for a summary of his ideas, including all the questions from which this shortened list comes. They – and the principles used to formulate them – are very powerful.)

Of course, these are just examples: the trick is to find the questions that are alive for you.


Questions and beginnings

Questions open up processes. They lead us to new possibilities, new insights, new ways of seeing ourselves, each other, and the situations we find ourselves in. As facilitators, leaders, and human beings, they are among our most valuable tools for exploring the world, learning about ourselves, and moving towards decisions that are right for us, for our teams and for our organisations.

A skill and an orientation

Many of us were educated in ways that discouraged us from asking critical questions. “It’s the answer that matters!” we were told. But where does that leave us, when the ‘right’ answer is elusive, or multiple, or simply hasn’t been found yet?

Questioning and exploration should be at the heart of the education process, but they often aren’t. And left unused, our ‘questioning muscles’ atrophy. But never fear: they can be developed with only a little practice, and hardly any heavy lifting at all!

5 tips
1. Find YOUR questions

Sit quietly for a while and reflect. Mull over your role at work, your organisation, a challenging relationship … whatever feels important right now.

Allow the questions you have about this area of your life to surface and write them down immediately. Don’t worry about formulating them perfectly. There’s only one rule: they must be questions, not statements, descriptions, complaints, observations, etc.

After doing this for a while, pause and look back at what you’ve written. Formulate at least one (and not more than three) questions that speak to the heart of whatever is unresolved in this area of your life.

Write them down in your journal, on a post-it, or make a note on your phone; somewhere you’ll happen across them occasionally.

Just surfacing these questions starts something moving. Your mind will work on them in the background, even if you do nothing more than this.

Certainties don’t take human beings or organisations to new places. Questions do.

2. Live with them for a while

Don’t rush towards an answer – let your questions percolate, like good coffee. A quote from Rilke springs to mind:

“Be patient toward all that is unsolved in your heart and try to love the questions themselves … Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

3. Journal about them

If you don’t have any kind of regular reflective practice, journalling is a good place to start.

It doesn’t have to be daily, but some regularity is useful. For many, setting aside 30 minutes, or an hour, on a Sunday evening works well.

Use the time to reflect on the week that was, the week to come, and the questions you’re living with at the moment. Over time, you will see real movement in yourself, and in your responses to the people, situations or issues in question.

4. Share them and work with them

Discussing significant questions with friends and colleagues can deepen our conversations and our relationships. Leaders who share the questions they are grappling give others permission to do the same. (No one has all the answers after all.)

On a very practical note, questions are a more creative and energising way of structuring a meeting than a tired list of agenda items. Why not try framing your next meeting agenda in terms of the questions you want to work on with your team?

(Of course, if you’re a facilitator, questions are your bread-and-butter, your stock-in-trade. And the opportunities for practice are endless… Facilitated processes are driven by the questions you frame, and you’ll get immediate feedback on whether or not they’re doing the job.)

5. Keep practising

Make questions part of your day-t0-day practice – in managing people and processes, in learning together and in supporting your team’s development.

Questions can – and will – change your life, your practice and your organisation, if you take them seriously and follow where they lead.

If you’d like to share some of the BIG questions confronting you at the moment – or ask me a question – please do so via social media (Facebook / Twitter / LinkedIn) or feel free to write to me privately

Wishing you a great week!


About these resources

These articles are for people who work with and in organisations of any kind – as leaders, managers, formal or informal change agents. If you are trying to work more consciously and effectively with change in your organisation, I hope you’ll find some ideas here that make your work (and your life) a bit easier, and your organisation a more effective, creative and positive place to be.

If you would like to engage around these ideas, ask a question or discuss the possibility of working together, please drop me a line.