The Art of Questioning: Coaching’s Superpower
In this article, we’ll explore how effective questioning creates insight, the traps that coaches can fall into, and how to use questioning with confidence, whether you’re an executive coach, a team leader, or someone building a coaching culture within your organisation.
Questions may be described as the precision tools in the coach’s toolbox. When used well, they help people think more clearly, view situations from new perspectives, and deepen their self-awareness. But there’s more to questioning than simply being curious or asking whatever comes to mind. Questioning is a tool that unlocks insight, deepens awareness, and ultimately leads to real change.
It’s easy to assume that good questions come naturally, or that curiosity is enough. But in coaching, the quality of the question shapes the quality of the answer. Too many managers (and even trained coaches) slip into advice-giving or solution-sharing, when what’s really needed is a well-placed pause and a powerful question.
A well-placed question can create a moment of pause – a chance for someone to hear their own thinking in a new way. It can provoke reflection, deepen awareness, and illuminate a path forward. In contrast, poorly timed or poorly framed questions can confuse, intimidate, or shut down thinking altogether. The difference lies in intention and technique.
Coaching is, at heart, a thinking partnership – one that hinges not on having the right answers, but on asking the right questions. Yet, despite its power, questioning remains underused, particularly among time-pressured leaders, who may default to telling, advising, or problem-solving.
What makes a great question?
A good coaching question is:
- Open-ended: beginning with ‘what’, ‘how’, or ‘where’, rather than ‘why’ or anything that leads to a yes/no answer.
- Succinct: a great question is often fewer than ten words.
- Free of judgement: even subtle implication can close someone down.
- Focused on the coachee’s thinking: not the coach’s ideas or advice.
Some of the most powerful questions are deceptively simple:
- What does success look like?
- What’s really going on for you?
- What’s the most important thing to focus on right now?
- And what else?
These questions aren’t formulaic prompts. They are genuine invitations for self-discovery. Often, the silence that follows a good question is where the work gets done.
Even experienced coaches and managers can fall into subtle traps. Among the most common are:
- Leading questions: These suggest an answer, even if unintentionally. For example, asking, “How can you be more confident?” presumes that confidence is the issue. A cleaner alternative might be, “What’s happening for you in those moments?” or simply repeating the coachee’s words back.
- Judgemental ‘why’ questions: While not inherently wrong, ‘why’ questions can sound accusatory and put people on the defensive—e.g., “Why did you do that?” Better to use, “What led you to that decision?” or “What were you hoping would happen?”
- Multiple questions: Asking several questions at once can overwhelm and confuse. It’s usually a sign the coach is thinking aloud. Instead, ask one question. Pause. Wait.
- Needing a quick solution: One of the most subtle yet damaging pitfalls is when a coach feels a need for the coachee to find an answer. This places unspoken pressure on both parties and can close down exploratory thinking. The coach’s job is to hold the process, not rush the content. Coaches must remain neutral, staying in their own territory (the process), rather than crossing into the coachee’s (the content).
A good check for the coach or manager to ask here is, am I asking this question because I am interested or because it is useful? - Talking too soon: Coaches often feel compelled to fill silences, but silence is where thinking deepens. If unsure, simply ask, “Would you like a moment to think, or shall I ask another question?”
A good check for the coach or manager to ask here is, am I asking this question because I am interested or because it is useful?When (and how) to offer advice or insights
While the gold standard in coaching is to ask rather than tell, there are appropriate times to offer insights, suggestions, or even advice, particularly when you bring relevant expertise or experience.
However, timing and permission are key. A good approach is to ask, “Would you be open to an observation?” or “May I share a thought?” This respects the coachee’s autonomy and keeps the conversation collaborative, rather than directive.
Suggestions should be framed as options, not prescriptions. For instance, “One thing that’s worked for others is xxx – how might that land with you?” This invites consideration rather than compliance.
Coaching versus directing: the leadership balance
Managers often struggle with the balance between being a coach and being a leader. In high-pressure situations, decisiveness is necessary. There are times when a manager needs to give direction, not ask questions. The key is clarity.
When coaching, the leader supports the other’s thinking. When directing, they take ownership of the decision. What matters is not staying in one mode, but switching appropriately, and making that switch transparent. Phrases like, “Let me take off my coaching hat for a moment…” can help signal the change. It helps to explain clearly why it is necessary for the leader to make the decision in this instance.
Ultimately, what makes a question ‘coaching’ is not the wording, but the mindset: respect, a belief in the coachee’s capacity to think for themselves, and 100% focus on the coachee’s agenda.
Why it matters now
In fast-moving environments, there’s pressure to be efficient, to provide answers, and to lead from the front. But leadership today demands the kind of thinking partnership that coaching provides: a place where people can hear themselves think, in the presence of someone who knows how to listen, and how to ask the right question at the right time.
Go deeper with my book “Performance Coaching” or train with us individually or inhouse at www.coachingcultureatwork.com.
About the author
International speaker, journalist and author, Carol Wilson, is Managing Director of Culture at Work and a Fellow of the Institute of Leadership & Management, the Professional Speaking Association and the Association for Coaching, where she is also a member of the Global Advisory Panel. A cross-cultural expert, she designs and delivers programmes to facilitate change management and create coaching cultures for corporate and public sector organisations worldwide. She has won awards for coaching and writing. She is the author of ‘Performance Coaching: A Complete Guide to Best Practice Coaching and Training’, now in its third edition and featuring Forewords by Sir Richard Branson and Sir John Whitmore, and ‘The Work and Life of David Grove: Clean Language and Emergent Knowledge’. She has contributed to six other books and published over 70 articles including a monthly column in Training Journal.
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