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It’s Not About a Formula – It’s About Intention
One of the greatest myths in leadership interviewing is the belief that there’s a perfect set of questions tucked away somewhere, waiting to be deployed. The reality is far more nuanced. Great questions don’t come from a script – they emerge from a mindset. They are grounded in authenticity, honed through experience, and shaped by genuine curiosity. Like any leadership muscle, it’s developed not through theory alone, but through deliberate and ongoing practice.
A compelling question doesn’t need to be complex. In fact, simplicity is often its greatest strength. When a question is clear and unburdened by jargon, it allows the interviewee space to reflect, think, and respond with clarity. It also signals confidence and control – attributes that define exceptional leadership.
The Power of Listening First
Too often, leaders enter interviews focused on what they need to ask next, rather than what they need to understand now. This tunnel vision not only diminishes the quality of the conversation, it also strips away its potential. Listening deeply, actively, and without agenda allows great questions to surface naturally. It transforms the exchange from a transactional Q&A into a meaningful dialogue.
This is where many leaders falter. They forget that the real power of a question lies not in the asking, but in the listening that follows. Without attentive listening, even the most carefully crafted question becomes redundant. A question, no matter how well phrased, is only as good as the leader’s ability to hear and interpret the response.
Be the Counterpuncher, Not the Script-Reader
Exceptional interviewers know when to deviate from their plan. They understand that great questions often follow great answers. They adapt. They pivot. They respond in the moment. This is where the idea of the “competency counterpuncher” comes into play – someone who uses a candidate’s answer as the springboard for deeper exploration, often uncovering insight that no pre-prepared question ever could.
And while preparation is essential, so is the flexibility to abandon it in favour of something more authentic, more relevant, and more illuminating. This requires courage. It demands presence. And it’s a hallmark of true executive maturity.
Results Matter – But So Does the Funnel
Interview questions that delve into past results are vital – they show what a person has done. But they should be complemented by questions that explore the ‘how’ and the ‘why’ behind those results. Funnel questions – those that start broad and narrow in focus – are particularly useful here. They not only reveal depth of thought and decision-making but also help uncover patterns in behaviour, motivation, and leadership style.
The most insightful executives mix these approaches fluidly. They’re not tied to one structure or another; they know when to probe deeper and when to pull back. They avoid hypotheticals and loaded queries that hint at a “correct” answer. Instead, they focus on real experiences and genuine reflection.
Questions as a Measure of Modern Leadership
There was a time when a leader’s value was measured by what they knew – how many answers they had at their fingertips. But in today’s dynamic business environment, knowledge is no longer the currency of leadership. Curiosity is.
The quality of your questions says more about your leadership than the cleverness of your answers. Are you thinking ahead? Are you engaging your team with empathy and insight? Are you willing to be challenged, to not know, to seek better understanding?
Asking great questions isn’t just about getting to the truth – it’s about modelling a culture of openness, learning, and critical thinking. That’s the kind of leadership today’s organisations need.
Final Thoughts: From Practice to Mastery
So where do great questions come from? Not from a template. Not from a textbook. They come from attention. From authenticity. From a commitment to listen and to lead, not control. They come from executives who understand that interviews are not interrogations – they’re opportunities for discovery.
Ask better. Listen harder. And watch the conversation – and your leadership – transform.
No one becomes a great interviewer overnight. But with intention, reflection, and yes, a lot of practice, your questions will evolve. They will stop being tasks to tick off and start becoming tools of transformation. And when that happens, you won’t need to search for a great question. It will find you.
This article explores themes and concepts from content by John O. Burdett.
John O. Burdett is founder of Orxestra® Inc. He has extensive international experience as a senior executive. As a consultant he has worked in more than 40 countries for organisations that are household names. John has worked on organisation culture for some of the world’s largest organisations. His ongoing partnership with TRANSEARCH International means that his thought leading intellectual property, in any one year, supports talent management in many hundreds of organisations around the world. Get in touch with John O. Burdett »
