The ability to deepen understanding, unlock insight, and encourage independent thinking by asking thoughtful, well-timed questions. It involves using curiosity to surface assumptions, challenge fixed ideas, and guide individuals or teams toward greater clarity, learning, and action, while fostering openness, engagement, and shared ownership of outcomes.
“I probably give fewer answers and I ask a lot more questions….It’s almost possible now for me to go through a day and do nothing but ask questions.” – Jensen Huang (cofounder & CEO of Nvidia)
Why asking good questions matters
Asking good questions matters because it is one of the most effective ways for leaders to deepen thinking, strengthen decision quality, and create shared ownership of outcomes. In a fast changing environment, thoughtful inquiry helps teams surface assumptions, clarify problems, and explore options that may otherwise go unnoticed. Leaders who use questions skilfully improve collaboration, accelerate learning, and enable their organisations to make better informed choices that stand up under pressure.
Without strong questioning, teams rely too heavily on assumptions, narrow perspectives, or the loudest voices in the room. This limits adaptability and increases the risk of poor decisions that could have been avoided with deeper inquiry. When leaders ask good questions, they build resilience by encouraging reflection, challenge, and independent thinking. This fosters confidence, improves followership, and strengthens leadership credibility and impact.
“Questions are the engines of intellect.” — Isaac Asimov
What good and bad looks like for asking good questions
| What bad looks like | What good looks like |
|---|---|
| Asks rapid, surface level questions that simply confirm what is already known. Moves on quickly and misses chances to explore assumptions or uncover gaps. | Uses clear, well timed questions to deepen understanding and broaden perspective. Slows the conversation just enough to reveal what matters and strengthen the quality of thought and decisions. |
| Jumps in with answers or advice before others have finished explaining their view. Dominates the discussion and reduces the team’s ownership of the issue. | Holds back from offering immediate solutions and creates room for others to think aloud. Uses inquiry to help people frame problems clearly and generate their own insights. |
| Frames questions in ways that feel leading or judgmental. People become cautious and hesitate to share concerns or alternative ideas. | Poses open, respectful questions that encourage honesty and wider participation. Creates a climate where people feel able to raise doubts, challenge ideas, and speak freely. |
| Sticks to familiar question types and repeatedly asks for updates or explanations. Misses opportunities to stretch thinking or spark new options. | Draws on a wide repertoire of question types to explore facts, possibilities, meaning, and concerns. Adjusts approach to match the situation and needs of the group. |
| Speaks quickly to avoid silence and inadvertently shuts down reflection. Treats pauses as uncomfortable rather than productive. | Allows space for people to reflect before responding. Uses silence as a deliberate tool that helps others reach deeper insight and contribute more considered answers. |
| Avoids asking challenging questions because they fear it may create tension. Leaves unspoken issues untouched and slows progress on difficult topics. | Uses constructive challenge to surface risks, hidden assumptions, and unresolved concerns. Keeps the tone respectful while helping the team face the real issues shaping decisions. |
| Directs most questions to confident or vocal contributors. Overlooks quieter team members and narrows the range of input. | Ensures questions reach the full team and invites contributions from those who hold different or less visible perspectives. Values the diversity of thought this brings. |
| Treats questioning as a task to complete rather than a habit that improves thinking. Rarely reviews the impact of their questions or adapts their style. | Reflects on which questions created the most value and adjusts their approach over time. Treats inquiry as a continuous leadership discipline that sharpens judgement and performance. |
“Successful people ask better questions, and as a result, they get better answers.” — Tony Robbins
Barriers to asking good questions
Pressure to have the answer: Leaders often feel expected to speak with authority. This can discourage asking open-ended questions, especially in front of peers or senior stakeholders.
Time urgency: In fast-moving environments, inquiry is easily sacrificed for speed. Leaders may jump to conclusions instead of pausing to explore the issue fully.
Fear of appearing unsure: Asking questions can feel like exposing a gap in knowledge. Some leaders avoid this vulnerability, especially when they feel they need to project confidence.
Consensus culture: In teams that prioritise harmony, challenging assumptions or posing dissenting questions can feel risky. This can lead to silence instead of inquiry.
Comfort with the familiar: Habitual ways of thinking can narrow perspective. Leaders who rely on well-worn approaches may overlook opportunities for fresh or generative questions.
Unspoken norms: In some cultures, questioning may be viewed as disruptive or disrespectful. This discourages honest curiosity and makes people hesitate to speak up.
Expertise bias: Deep knowledge can reduce openness to new lines of inquiry. When leaders assume they already understand the issue, they may stop exploring too soon.
Low psychological safety: In some teams, people worry their questions will be judged as naïve, off-topic, or unhelpful. Without trust, honest questioning rarely happens.
Valuing answers over inquiry: Many organisations reward decisiveness and solution-finding, not exploration. This creates a culture where asking thoughtful questions is undervalued.
Narrow questioning habits: Some leaders default to a limited set of question types. Without practice or tools, they miss opportunities to stretch thinking across different dimensions.
“Judge a man by his questions rather than by his answers.” — Voltaire
Enablers of asking good questions
Model curiosity: Demonstrate the value of asking questions by doing it yourself. When leaders ask thoughtful, open-ended questions, they give permission for others to do the same. This sets a tone of inquiry and shared learning across the team.
Use a range of question types: Don’t just ask “What’s the update?” Incorporate five distinct types of questions to stimulate better thinking: – Investigative questions clarify the current reality (e.g. “What do we know so far?”) – Speculative questions open up new possibilities (e.g. “What if we tried a completely different approach?”) – Productive questions move things forward (e.g. “What should we do next?”) – Interpretive questions make meaning of data and decisions (e.g. “What’s the takeaway here?”) – Subjective questions tap into emotion and hidden concerns (e.g. “What’s not being said?”) Using all five ensures that you explore widely and act wisely.
Start with question-storming: Before jumping to conclusions, take time to generate questions. Question-storming invites everyone to surface uncertainties and ideas. It often reveals assumptions and tensions that wouldn’t emerge through standard brainstorming.
Give space for silence and reflection: Don’t rush to fill the gap after asking a question. Thoughtful answers often need a beat or two. Allowing silence shows respect and encourages deeper contributions.
Recognise good questions: Highlight when someone asks a thoughtful or challenging question. This signals that curiosity and depth are valued, and encourages others to participate more fully.
Provide context before inquiry: When inviting questions, give people a clear sense of the topic, purpose, or decision at hand. Context helps others ask more relevant and effective questions across the five types.
Invite quieter voices to contribute: Some team members hesitate to speak up. Create inclusive ways for everyone to pose questions—through written input, anonymous polls, or structured rounds. Diverse perspectives often surface better questions.
Normalise “I don’t know”: Show that uncertainty is a strength, not a weakness. Phrases like “I don’t have the answer yet, but what do you think?” or “Let’s explore this together” help foster a culture where questions are welcomed.
Include questions in team routines: Build inquiry into how your team operates. Add specific question prompts to meeting agendas, planning templates, and project reviews. Over time, asking better questions becomes part of the team’s identity.
Build questioning skills over time: Help your team grow in their ability to ask purposeful questions. Practice switching between the five types. Use real issues to rehearse asking, and responding to questions, that challenge, clarify, and expand thinking.
Build a question list: Over time, capture the best questions you hear, those that lead to new insights, unlock stuck conversations, or clarify decisions. Organise them by category (e.g. planning, problem-solving, learning reviews) or by the five question types. Consider sharing this mini database of powerful questions, so it becomes a reusable thinking tool that saves time and raises the quality of future discussions.
“The important thing is not to stop questioning. Curiosity has its own reason for existence.” — Albert Einstein
Reflection questions on asking good questions
Who in your world consistently asks powerful, thought-provoking questions? What makes their approach effective, and what can you adopt or adapt from them?
How would you describe your current approach to questioning in conversations and meetings? What types of questions do you tend to ask—and which ones are missing?
What conditions make it harder for you to ask good questions? Is it pressure, time, power dynamics, or something else? What small shifts could help reduce those barriers?
In recent conversations, how often did you ask open-ended questions versus giving your opinion or advice? How might changing that balance improve the quality of thinking and dialogue?
Do you consciously draw from different types of questions—investigative, speculative, productive, interpretive, and subjective? Which ones come naturally to you, and which need more practice?
When someone asks you a difficult or unexpected question, how do you respond? How do you create a culture where questions are welcomed, especially those that challenge your thinking?
What signals do you send about the value of questions in your team? Do people feel safe and encouraged to be curious, or are they primarily rewarded for providing answers?
How do you create time and space for inquiry in your meetings, planning processes, or decision-making routines? What could you build into support deeper questioning?
In what ways have your own best questions helped shift thinking, uncover assumptions, or unlock new solutions? What made them effective?
What practices, tools, or habits could help you become a more intentional and effective questioner?
“The questions that get leaders and teams into trouble are often the ones they fail to ask.” – Arnaud Chevalier
Micro practices for asking good questions
1. Pause before responding: After someone shares information or an idea, pause for a moment before replying. This brief reflection creates space for deeper thought, encourages additional contributions, and allows you to craft questions that uncover assumptions, reveal insight, and guide the team toward more robust understanding.
2. Rotate question types consciously: Deliberately switch between investigative, speculative, productive, interpretive, and subjective questions during discussions. This variety ensures you explore facts, possibilities, meaning, and hidden concerns, helping the team avoid narrow thinking and encouraging richer dialogue that leads to more informed decisions.
3. Invite alternative perspectives: Ask questions that specifically prompt different viewpoints or challenge prevailing assumptions. Target quieter voices or dissenting opinions and use these contributions to expand the team’s awareness, uncover blind spots, and foster a culture where questioning is seen as a valuable and respected practice.
4. Reflect on your questioning impact: After meetings or decision-making sessions, review which questions generated insight or shifted thinking. Note what worked and where engagement lagged. Adjust your future questioning to increase depth and relevance, using these reflections as a personal tool to sharpen your leadership influence.
5. Build questions into routines: Integrate purposeful questions into daily workflows, such as meeting agendas, project reviews, or planning sessions. Encourage the team to consider what is assumed, unexplored, or uncertain. This practice embeds inquiry into everyday work, making thoughtful questioning habitual and elevating the quality of collective problem-solving.
“The wise man doesn’t give the right answers; he poses the right questions.” — Claude Lévi‑Strauss