Asking the Right Questions

Shifting the mindset

When a leader steps back and asks the right questions, something shifts. Suddenly, the team isn’t just following orders; they’re thinking critically, collaborating, and developing their own solutions. They begin to own their work.

This simple strategy fosters a culture of autonomy, growth, and creativity. It may feel awkward at first with long silences or confused glances. However, once it clicks, the team starts solving problems independently.

The Shift from "I Have the Answer" to "What Do You Think?"

Traditional leadership often positions the leader as the all-knowing authority figure, with all the answers. In this model, the leader directs, and the team executes. This directive style has long been the foundation of hierarchical organisations, with its roots in military and industrial models. The approach is clear-cut: the leader makes decisions, and the team follows through.

While this style of leadership may seem rigid, it can be highly effective in certain circumstances. For example, when swift decision-making is critical, such as in a crisis or during an emergency, having one clear line of direction is essential. In situations where there is no room for ambiguity, such as in high-stakes environments like healthcare, military operations, or situations requiring compliance with strict regulations, traditional leadership ensures that everyone is aligned and moving toward the same goal. It removes uncertainty, maintains order, and minimizes the risk of miscommunication or delay.

However, this approach has limitations. It often stifles innovation and creativity because it discourages team members from thinking critically or taking initiative. By positioning the leader as the sole decision-maker, it can create a culture where individuals feel they are merely following orders rather than contributing ideas or solutions. Over time, this can lead to disengagement, as team members may feel disempowered or undervalued.

Unlocking Confidence and Ownership

Asking the right questions builds confidence and ownership. When team members are invited to contribute ideas and explore different perspectives, they feel more responsible for the results. Fostering an environment where people feel valued, not as executors of someone else’s vision, but as active contributors to it.

Ownership drives accountability. When individuals are part of the problem-solving process, they invest more in the solution’s success. The team dynamic shifts from one based on compliance to one built on collaboration, where every member plays an integral role in driving progress.

Creating a Growth Mindset

By encouraging team members to explore solutions through questioning, we show that mistakes are a natural part of growth. Challenges aren’t roadblocks; they’re opportunities to improve. Questions like “What did we learn from this?” or “How can we apply this lesson moving forward?” create an environment where mistakes are seen as stepping stones, not setbacks.

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The Right Questions Aren’t Just Any Questions

Open-Ended Questions

Open-ended questions encourage team members to think creatively and share their ideas. They invite exploration rather than narrow the conversation down to a simple "yes" or "no." These types of questions encourage dialogue and help uncover insights that wouldn't come to light with more directive questions.

  • “What else could we try to overcome this challenge?”
  • “What are the possible outcomes if we took this approach?”
  • “What’s another way we can look at this problem?”
  • “What might we be missing in our current plan?”

By asking these questions, we’re allowing space for fresh perspectives and multiple solutions, ensuring that the team is thinking expansively.

Challenging (But Not Overwhelming) Questions

Great leaders ask questions that challenge their team to think critically but don’t overwhelm them with complexity. These questions should push team members to stretch their thinking, helping them to break free from habitual thinking patterns.

  • “What’s the biggest challenge you see here, and how can we solve it together?”
  • “What assumptions are we making about this situation, and are they valid?”
  • “How would we approach this problem if we had unlimited resources?”
  • “What would our ideal outcome look like, and what’s stopping us from getting there?”

These types of questions invite the team to confront problems head-on and make them actively engaged in generating solutions rather than just responding to a given direction.

Future-Focused Questions

We should aim to direct the team’s attention toward the future, rather than dwelling too much on past mistakes or failed attempts. Forward-thinking questions help maintain momentum, fostering a growth mindset that encourages learning and continuous improvement.

  • “How do we take what we’ve learned from this situation and apply it moving forward?”
  • “What steps can we take now to ensure this doesn’t happen again?”
  • “How can we use this experience to improve our approach next time?”
  • “What do we need to do differently in the future to reach our next milestone?”

These questions turn the focus away from blame and instead create a culture of improvement, pushing the team to apply lessons learned for better outcomes.

Supportive, Not Directive Questions

As leaders, our role is not to dictate every move but to empower our teams. Supportive questions show that you trust the team’s abilities, helping them feel that their input is valued. This approach builds a collaborative environment where everyone contributes to the success of the project.

  • “What do you need from me to succeed in this project?”
  • “How can I help you feel more confident in this next step?”
  • “What resources do you think we need to move this forward?”
  • “Is there any additional support you require to reach your goal?”

Reflection and Learning-Oriented Questions

After completing a task or encountering a challenge, reflective questions can help team members assess what went well and what can be improved. These questions allow the team to internalise lessons and continuously develop their skills.

  • “What worked well in this approach, and why?”
  • “What would we do differently if we were to tackle this again?”
  • “What did we learn from this experience that can apply to other projects?”
  • “How did this challenge change our understanding of the issue?”

Inclusive Questions to Build Team Cohesion

Sometimes, the best way to get people thinking is to bring everyone into the conversation. Inclusive questions ensure that each team member feels heard and valued, strengthening collaboration and trust among the group.

  • “How do we ensure everyone’s perspective is heard on this issue?”
  • “What are the different viewpoints we need to consider in this decision?”
  • “How can we incorporate input from all members of the team to improve our strategy?”
  • “What would you add to this discussion that could change our approach?”

Inclusive questions help foster a sense of belonging and ensure that diverse opinions are heard, making it more likely that the team will come together to find innovative solutions.

Empathy-Focused Questions

Empathy plays a key role in effective leadership. Questions that focus on understanding the team’s needs, challenges, or motivations can strengthen connections and support a healthy team culture.

  • “How are you feeling about the progress we’ve made so far?”
  • “What obstacles do you feel are preventing you from reaching your full potential?”
  • “Is there anything that’s causing stress or uncertainty that we should address as a team?”
  • “How can we improve the working environment to make things easier for you?”

These questions create an emotional connection with the team, demonstrating that you care about their well-being and are actively working to create a supportive atmosphere.

A Culture of Autonomy: How It Feels When It Clicks

At first, building a culture of autonomy can feel like watching a car stall in first gear. There’s hesitation, confusion, and uncertainty as the team adjusts to new expectations. But once it clicks, the transformation is striking. Suddenly, our team is taking ownership, thinking critically, and solving problems like seasoned professionals. The energy in the room shifts. People are no longer just executing tasks, they’re driving the strategy, taking initiative, and actively contributing to the success of the organisation.

When autonomy takes hold, the team members begin to show up differently. They stop waiting for direction and start taking charge. They no longer view problems as barriers to be managed by leadership, they see them as challenges to be solved collaboratively, with each member bringing their unique insights to the table. The shift from compliance to collaboration is palpable. It’s no longer about ‘doing the job’; it’s about improving processes, driving innovation, and contributing to the bigger picture.

Fostering a Culture of Autonomy

Asking the right questions is one of the most powerful tools leaders have to cultivate autonomy. When team members feel trusted to make decisions, they take more initiative. They become more willing to experiment, take risks, and innovate.

Autonomy also increases job satisfaction and retention. Employees who are empowered to solve problems and contribute to decision-making are more engaged in their work. They’re not just fulfilling a role; they’re actively shaping the success of the organisation.

Drawn from lessons learned in the military, and in business, we make leadership principles tangible and relatable through real-world examples, personal anecdotes, and case studies.

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