10 Questions Every Leader Should Ask Themselves

We all agree that leadership reflection is a powerful tool for growth. But in practice, most leaders struggle with it. They sit down, and their mind is either blank or it is a chaotic mess of to-do lists. The problem is not a lack of time; it is a lack of structure. The engine of reflection is not time; it is the quality of your questions. The right question can cut through the noise, challenge your assumptions, and be the catalyst for profound self-awareness. These questions are the same tools a professional coach uses. They are coaching prompts you can use on yourself to unlock your own potential. If you want to grow as a leader, stop looking for answers and start asking better questions. Here are 10 questions every leader should ask themselves regularly.

1. What is the one thing I am avoiding?

This is a powerful prompt for uncovering your biggest barriers. Often, the one thing we are procrastinating on is the most important thing we need to do. It might be a difficult conversation with a team member, a decision on a failing project, or a strategic choice you are afraid to make. This question forces you to confront the “strategic friction” that is holding you and your team back. Answering this honestly is the first step to getting unstuck.

2. Am I being a bottleneck or an accelerator?

This is a critical coaching prompts for self-awareness around micromanagement. As a leader, it is easy to believe you are “adding value” or “ensuring quality” when in fact, you are simply a bottleneck. Ask yourself: Is my team waiting for my approval on most things? Do I empower them to make decisions without me? If you are the bottleneck, you are capping your team’s growth and your own.

3. Whose voice am I not hearing?

In any meeting or on any team, there are dominant voices and quiet ones. It is easy to mistake silence for agreement. This question forces you to think about inclusion. The quietest person in the room often has the most well-thought-out perspective because they have been listening. Are you actively creating space for that voice? The answer often holds the key to an idea or a problem you are missing.

4. How did my actions and emotions impact my team this week?

This is a core leadership reflection question for building emotional intelligence. Your mood as a leader is contagious. If you were stressed, rushed, and irritable, you created a stressed, rushed, and irritable team. If you were calm, focused, and optimistic, you created that environment. This question forces you to take responsibility for your “emotional wake” and to become more intentional about the culture you create.

5. What is one assumption I hold that might be completely wrong?

This question is a direct assault on a fixed mindset. We all operate on a set of assumptions about our customers, our competitors, our team, and our business. “Our customers will never pay for that.” “This employee is not ‘high-potential’.” This coaching prompts forces you to challenge those beliefs, which is the only way to find new opportunities and see the potential you have been overlooking.

6. What did I do this week that only I could do?

This is the ultimate delegation and prioritization question. Go through your calendar. How much of your time was spent on work that a member of your team could have done (and probably grown from)? Leaders should be spending their time on the few, high-leverage activities that *only* they can do: setting the vision, coaching key talent, and managing high-stakes relationships. This question is a brutal but effective audit of your time.

7. If I were my successor, what is the first thing I would change?

This is a brilliant self-awareness hack. It mentally removes your ego and personal attachments from the equation. It allows you to look at your team, your processes, and your strategy with a fresh, objective set of eyes. The answer to this question is almost always the thing you need to change *right now*.

8. What part of my job gives me energy, and what part drains it?

This is a personal leadership reflection question that is key to long-term sustainability and performance. If you are spending 80% of your time on tasks that drain you, burnout is inevitable. You cannot eliminate all draining tasks, but you can work to redesign your role. How can you delegate more of what drains you to someone who might find it energizing? How can you proactively schedule more of the work that puts you in a state of “flow”?

9. How did I help someone on my team grow this week?

This question shifts your mindset from “manager” to “coach.” If your answer is “I’m not sure,” you are failing at one of your most important jobs. Did you delegate a challenging new task? Did you give specific, constructive feedback? Did you ask a great question in a 1-on-1? This prompt forces you to be an *intentional* developer of talent.

10. What am I most grateful for this week?

This is not a “soft” question. It is a powerful neurological tool. Practicing gratitude is a proven antidote to the “negativity bias” that consumes most leaders (who are trained to find problems). It reduces stress, builds resilience, and shifts your perspective. A leader who practices gratitude is more optimistic and approachable, which directly impacts team morale and performance.

How to Use These Coaching Prompts

Do not try to answer all 10 at once. Pick one. Write it on a sticky note and put it on your monitor for the week. Use it as a journaling prompt at the end of the day. Bring it to your 1-on-1 with your own manager or coach. The goal of these coaching prompts is not to find a “right” answer. The goal is to trigger the act of leadership reflection itself. The quality of your leadership will be a direct reflection of the quality of questions you are willing to ask.