What stops people from asking the most audacious and important questions is often a fear of seeming stupid.
But one of the best business lessons I ever received came from a mentor I had during my banking career.
He said to me “If you cannot explain an investment in the language that a 7-year-old child would understand, you shouldn’t be investing in it.” He was right.
The collapse of Lehman Brothers was a consequence of nobody wanting to stick their hand up and say: “I don’t get how this works…” There is audacity in simplicity, particularly in contexts where complexity has been thought of as a badge of honour. In reality, of course, such complexity has sometimes become a smokescreen for unsound and unethical processes, an Emperor’s New Clothes parable for our time.  

In my previous post, I talked about brave spaces. One of the defining characteristics of a brave space is that it is a forum where team members have the confidence to ask ‘stupid’ questions without becoming overwhelmed by fear of judgement, or concern about jeopardising their position by questioning the status quo. 
“Stupid” questions, the kind of questions that might seem obvious or taboo, are going to become more necessary than ever in an age where technology is fundamentally changing the nature of reality at exponential pace, with workplaces, politics and even the way we conduct our relationships all being redefined and augmented by AI.

Innovations such as Chat GPT mean that the ‘answers’ as it were are there instantaneously (albeit with an evolving level of accuracy, sophistication and relevance). In their recent thought-provoking talk, The A.I Dilemma, Tristan Harris and Aza Raskin of The Center of Humane Technology, made a powerful case for the need to create forums for discussion, where big questions can be asked about the kind of future world we want to build. The same is true at an organisational level, where asking questions about corporate culture, strategy and systems are essential, but where fear of rocking the boat is rife.

From a senior leader’s point of view, team members who dare to ask questions may cause discomfort, but also demonstrate curiosity and independent thinking, exactly the kind of human traits that will be most valuable to employers in the AI age. As UCL School of Management Associate Professor Sunny Lee and her co-author Dr Thomas Chamorro-Premuzic write in a recent Fast Co article, “The AI age has amplified the (already high) value of curiosity in the realm of human virtues, redefining the meaning of expertise. What matters today is not experts knowing the answers to all questions but that they are asking the right questions, not retrieving information but critically evaluating and vetting, not collecting insights but making smart decisions based on them.” So, how can leaders encourage curiosity and do what they can to ensure that team members at all stages of their careers feel able to speak up?

State it overtly: No question is a stupid question. It might sound obvious, but by declaring your desire to welcome any and all questions, you create an intention for open dialogue.

Model curiosity by asking questions yourself, by asking questions and pose questions the group might address. Choose audacious questions that relate to the big challenges and forthcoming decisions facing your organisation. Participating in these discussions improves inclusion and accountability of the whole team.

Pause before you respond in a defensive or dismissive way. If a question has been posed that makes you feel a bit rattled or irritated, ask yourself what’s going on. Could it be that the question has touched on a pain point, or highlighted a blindspot or problem that has been ignored until now? Difficult questions sometimes trigger a panic response, and can make people in positions of power feel as if they have to come up with a solution or response on the spot, but you don’t.

If you want to encourage honesty, think about group size. People are more likely to feel comfortable opening themselves up to feelings of vulnerability in front of a smaller group. Create opportunities for this with break out groups as part of away-days or team meetings to encourage more introverted members of your team to speak up.

I encourage my clients to keep asking questions. And make audacious requests. Recently a client of mine, let’s call her Tania, asked a ‘stupid’ question in the Board Room. She was even told so crossly by her boss after the meeting. Tania swallowed hard and said thank you for the feedback. Yet, she was not discouraged. After all, I teach my clients that courage and curiosity are critical skills. At the following Board meeting, Tania made a bold deal proposal and asked some ‘brilliant’ questions. Her courage and curiosity (I call it audacity) landed her one of the best deals the team has ever done.

And at our Audacious Leaders Retreat last month, we played with many ‘stupidly’ audacious questions. Why not? Is still one of my most favourite ones….

What is the most stupid question that you don’t yet dare to ask?