This question arose recently when a client (let’s call her Claire – not her real name) indicated she had made a decision to start studying another career while staying in her role. Because of the time commitments, she would nevertheless need to reduce the scope of the work. Claire is a department head, reports directly to the CEO and also sits on the board. She felt this was in the organisation’s long-term interests but hadn’t yet run it by the CEO.

It felt like Claire had given extensive thought to her decision but not how it would be viewed by and impact on the organisation in the short to medium-term. So, I invited Claire to make it real by imagining all the key stakeholders sitting around the table (the CEO, board members, key clients, key colleagues…). I then asked her to sit in each chair in turn (You have just been appointed CEO, Board Chair….Congratulations!) and ask herself:

  • What am I hearing?
  • What questions do I have?
  • What concerns do I have?
  • What assurances do I want?
  • How might this negatively affect me?
  • How might this negatively affect the organisation?

Not only going around the table but also asking these questions in the first person allowed Claire to literally take different perspectives. She pretty instantly saw just by sitting in the CEO and the Board Chair’s seats that they might have some real concerns. How might she address them? They would also likely want additional details on the potential impact on organisational objectives and service delivery that she didn’t yet have.

In giving herself this space and following this very simple process, Claire gave herself the time to carefully consider how she might present the decision to the other stakeholders. In fact, she ultimately decided she wasn’t ready to make her pitch.

Playing out the conversations thus allows you to make more considered decisions. You clearly won’t consider all the points others might raise but it will make your pitch that bit stronger. Also, ask yourself:

  • How might this stakeholder benefit from this decision? How might I make them an ally?
  • Equally, how might they lose? What exactly might they lose? Are there ways of mitigating this?
  • Who will really benefit from this decision in the short, medium and long-terms?

Questions in the Image:

  • What concerns might stakeholders have?
  • What questions might they have?
  • What assurances might they want?

Want to Read More Around This Topic?

Six Thinking Hats by Edward de Bono (link to This is a classic book on perspective-taking and critical thinking. De Bono presents a simple but effective method for encouraging different ways of thinking within teams or when grappling with complex problems.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day. In fact, the last of the original 20 episodes of the Time Academy Podcast just launched today. It is a somewhat different time management podcast that asks questions of our relationship with time. I am therefore reflecting on what I have learnt in the course of doing it. In truth, I sense that it comes down to the theme of the final episode: Your Priorities Are What You Do. We may say one thing, but it is what we do that matters because that is what gets our time, energy and attention. We are saying No to everything else. So, looking back on your day so far, What were your priorities?

About Tom O’Leary

My mission is to help others think differently – meaning more broadly and deeply – and thereby make better decisions. The key to thinking differently lies in our curiosity.

The more we question, the more possible answers we uncover, and the more we expand what we thought possible. Life has taught me that possibility lies not so much in seeking answers but in learning to ask better questions – the ones that help prioritise what is truly essential.

And yet, in a culture obsessed with efficiency and productivity, the paradox is that much energy and resources are wasted by a bias towards action over contemplation. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages, particularly amongst leaders because of the impact they have on us all. In my vision, leaders aren’t boxed in by traditional thinking or established playbooks. They are curious, open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning.

What Thoughts Would You Like to Share?

I welcome your thoughts, feedback, or personal experiences related to these questions or any insights they may have sparked.