The best leaders ask the best questions; it is as simple as that and as complex as that. They ask themselves these questions first and develop the skill of asking better questions to others.
Socrates’s quote that “the unexamined life is not worth living” is an important starting point to argue that a life lived without self-awareness and critical reflection is devoid of the purpose that makes us truly human.
In my work with senior managers, CEOs and executives and with my work with 2U in Cape Town I noticed one important distinction between “average” managers and those who seem to drive superior performance and aspire to “lead”.
They do two things differently: they have developed a reflective practice which leads in turn to them asking better questions of themselves and others.
How do they do this and how can you?
One critical question emerges that moves you from a manager to a leader. But first, what do I mean by “leadership”?
Leadership is focused on asking what adaptations are necessary for this organisation or team to thrive; it can start as an individual quest but needs to become a community activity to thrive. Leadership is community activism.
In traditional leadership, the leader is often seen as the expert who has all the answers. In adaptive leadership, the leader is a facilitator who guides and supports others in their own learning and development.
Most questions I observe in the C-suites of firms are deeply disappointing. They seem more focused on the ego of the authority figure asking questions to demonstrate and underline their own insecure power foundation. To make others look inadequate to counter their own frailty.
How do you spend your time? On the dancefloor of the firm, managing day-to-day (or even micromanaging), or on the balcony, working on the bigger picture — trends, strategy, values?
Conduct a mini experiment: note the last 20 questions you have been asked over the last few days. What does it tell you about the culture you live and work in? What is the best question you have asked today?
The best leaders ask the best questions, and this can be taught and learnt in equal measure. By encouraging a culture of better questions, better attempts at answers will emerge, and those being asked will create a positive cycle of feeling valued and involved.
How can I ask better questions?
The key is to build a practice of reflection. Let me ask you a question in the first person: how do I reflect?
Experiment and set the timer of your phone to 10 minutes to write out longhand (yes, neuroscience says this helps) your answers to this question.
Now let’s evaluate your words. Have you answered a different question, that is, “Where do I reflect?” For example, outdoors, running, cycling, in the shower?
Or perhaps you did answer the question, “How do I reflect?” Some examples include writing a journal, discussing a specific issue with a confidant, writing a gratitude list each day, or through structured (or unstructured) meditation.
Building a reflective practice will ground you in a way that releases a new sense of agency and possibility. It will develop better and better observation skills and prepare you for greater generation of multiple interpretations for the one constant question we should always be asking ourselves at our workplace: what’s going on here? What’s really going on?
By building a reflective practice, you prepare yourself even in a microsecond of frustration to pause in the midst of action, and, as a result, you will be more helpful not only to yourself but also to your team.
In the words of Warren Bennis: “Experiences aren’t truly yours until you think about them, reflect on them, and finally understand them.”
So what is the key question to ask yourself as a leader and then others?
Simply, how do you spend your time? On the dancefloor of the firm, managing day-to-day (or even micromanaging), or on the balcony, working on the bigger picture — trends, strategy, values?
Take a check over the last six months — were you on the dancefloor or on the balcony? Of course you need to do both, but you will never really lead if you don’t do balcony work.
Is moving from working “on” the organisation rather than “in” it the true work of leadership? Are you asking this question of yourself?
- Mostyn is the author of Why Great Leaders Ask Great Questions. He is an associate fellow at Saïd Business School, University of Oxford













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