Why Great Leaders Ask Questions and Listen With Curiosity
Most people think leadership is about having answers. However, the best leaders I’ve ever worked with — from senior engineers to project managers to CEO’s — all had one thing in common:
They asked better questions than everyone else.
Great questions shape conversations, uncover blind spots, build trust, and create momentum. They defuse tension, reduce confusion, and transform disagreement into progress.
Jefferson Fisher, in his book The Next Conversation highlights this beautifully when he makes the point that we should “never win an argument”. He goes on to say that “winning an argument is a losing game. Winning means that you have lost something far more valuable – their trust, their respect, or the connection.”
Let’s explore how leaders can develop the habit of asking better questions — and why it is so transformative.
1. Questions Shape Culture More Than Answers Do
Teams don’t rise to the level of a leader’s intelligence; they rise to the level of a leader’s curiosity.
When a leader asks, “What am I missing?” or“What’s the real problem we’re trying to solve?” they create a culture where thinking, honesty, and self-awareness matter. You might think a confident leader somehow as all the answers, but the best leaders are always asking questions in order to find out more about the situation. They are always trying to make the best decisions possible, and many times that involves fact-finding and probing those who actually know.
The next time your boss asks you the following, consider it a mark of a good leader:
- “What does success look like for you?”
- “How can I support you better?”
Often we are quick to judge our superiors and think their questions are meant to make us feel good, rather than actually inform their present or future decisions. However, consider that when you do well, your boss does well as a consequence. When you are happy and content, usually so are they!
2. Good Questions Lower Defensiveness
When people sense judgment, their brain shifts into protection mode. They stop listening, stop collaborating, and start defending. This is why great leaders don’t push harder—they ask smarter.
Questions are disarming because they invite participation and show respect. They often slow down heated arguments and turn them into exploration.
Compare these two responses:
Option A:
“Why didn’t you get this done?”
Option B:
“What got in the way of you completing that task?”
Option A looks for blame while option B looks for understanding — which is what most leaders actually want. Good leaders avoid questions that corner someone and make them defensive. Great leaders ask questions that uncover and explore!
3. Questions Build Accountability
Questions are one of the most powerful tools a leader possesses for fostering accountability within a team. Instead of issuing commands or demanding status updates, effective leaders use questions to shift the responsibility for thinking, problem-solving, and action onto the team members themselves. By asking open-ended questions like, “What is the next action you plan to take on this?” or “What resources do you need to complete this task by the deadline?” leaders move away from being the central source of control and toward being a supporting coach. This process naturally requires the team member to articulate a plan, set an internal commitment, and identify potential roadblocks. This verbal articulation transforms a vague intention into a concrete commitment, directly tying the individual to the outcome.
This shift creates a culture where team members feel ownership over their work and its results, which is the foundation of true accountability. When a leader consistently asks, “What’s the real problem we’re trying to solve?” or “How will we measure success here?”, they signal that critical thinking and self-awareness are valued over simply following orders. This practice helps individuals internalize the goals and the standards, making them accountable not just to the leader, but to the project and to their own stated plan. Ultimately, questions act as prompts for self-governance, ensuring that accountability is driven by a deep sense of personal responsibility rather than external pressure.
The next time you are in a conversation with one of your peers or subordinates, try one of the following:
- “What do you see as the next step?”
- “What timeline feels realistic?”
- “Where might this get stuck?”
- “What support do you need from me?”
These questions make the other person a true partner in the solution — not the passive recipient of orders. This not only builds trust, but it creates accountability.
4. Questions Make You a Better Listener
The act of asking a thoughtful question fundamentally transforms the communication dynamic from a monologue into a genuine dialogue between both parties, compelling the questioner to become a better listener. When you formulate a meaningful question—one that probes for deeper understanding, clarifies a statement, or encourages elaboration—you automatically create an expectation for a response. This mental preparation for the answer shifts your focus from what you intend to say next to what the other person is about to say. By opening the space for the other person’s perspective, the questioner adopts a posture of receptivity and curiosity.
This intentional pause and shift in focus is the very definition of active listening; it moves the communication away from the transactional sharing of information and toward the relational building of understanding.
Furthermore, the quality of the questions asked directly reflects the quality of the listening that has already occurred. A follow-up question, such as, “You mentioned the timeline was tight; what part of the process is causing the most pressure?” can only be asked if the questioner truly registered and processed the initial comment about the timeline. These probing questions demonstrate that the listener has not only heard the words but has also internalized the context and implications. This feedback loop is crucial: the act of listening generates better questions, and the asking of those questions deepens the engagement with the speaker’s response. In essence, thoughtful questioning acts as a continuous practice in active listening, improving comprehension, retention, and empathy in every conversation.
Asking better questions forces you to slow down and care about the other person’s perspective. It also detaches you from your own need to be “right”.
5. The Three Types of Leadership Questions
Here’s a simple framework to elevate your questioning habits:
1. Reflective Questions
Help people understand themselves.
- “What’s important about this to you?”
- “Where do you feel unsure?”
- “What part feels most challenging?”
2. Clarifying Questions
Cut through confusion.
- “Can you walk me through your thinking?”
- “What problem are we actually trying to solve?”
- “What assumptions are we making?”
3. Forward-Moving Questions
Keep momentum without pressure.
- “What’s the next visible step?”
- “What would good progress look like this week?”
- “How will we know we’re on the right track?”
These three types of questions create a positive, forward-moving dialogue where both people walk away clearer than when they started.
6. How to Build the Habit (Even If It Feels Awkward)
Here’s a simple way to practice asking better questions:
Step 1: Pause for two seconds before responding.
Interrupt the instinct to react.
Step 2: Ask one clarifying question before giving your view.
One question is enough to change the tone of a meeting or conversation. The answer to it might just change your entire outlook!
Step 3: Replace statements with curiosity.
Instead of “Here’s the problem,” ask:
“What do you think the real issue is?”
Step 4: End every conversation with a forward-moving question.
When you are about to end a meeting or conversation, try:
“What do you think your next step is here?”
This asks for accountability without sounding like you are micromanaging.
Conclusion
Leadership isn’t about knowing everything or having all the answers — it’s about drawing the best out of others. Asking thoughtful, forward-moving questions turns you into a clearer communicator and a more trusted leader. If you are not leading in your role, thoughtful questions make you a better listener, a more strategic thinker, and often a calmer presence
If you want better outcomes, aim for better conversations. And to get better conversations, ask better questions.
It’s a leadership habit that compounds — one question at a time.
