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The Top 7 Questions for Coaching Leaders to Ask

Coaching has become a fundamental skill for leaders who aim to enhance their team’s performance through personal development and empowerment. Supervisors, managers, and entrepreneurs alike can benefit from honing their coaching techniques, especially when it comes to asking the right questions.  Let’s explore seven impactful questions that coaching leaders can utilize to stimulate insightful responses, encourage reflection, and foster development in the people they lead.

The importance of asking questions as a leader cannot be overstated. It’s about harnessing the power of inquiry to inspire critical thinking and enable others to arrive at their own solutions. But asking just any question won’t do. Specificity in questioning is key. Asking the right question at the right time is the key. Strategic questioning has the potential to unlock potential and ignite creativity in others that you lead.

Check out seven of my favorite questions that coaching leaders should include in their toolbox:

  1. What do you hope to see happen?

This question is super helpful for both the leader and the person being coached. Leaders get a peek into their team members’ dreams or what drives them, or even just the end goal for solving a problem.  This helps to set the stage for personalized development plans and personalized solutions. For the person answering, it’s a chance to share their goals and aspirations, taking charge of their growth path, and adding focus to conversations that involve trying to solve a problem. 

  1. How did that make you feel?

Tapping into emotions can reveal a lot. This question is like opening a window to what’s going on inside. It’s about understanding the impact of actions, not just on outcomes but on feelings too. It’s sort of like saying, “Hey, I see you and how this whole thing is affecting you.” It helps break down barriers and makes conversations more genuine. Plus, it’s a great way for both leaders and team members to connect on a human level which can make a long term difference. 

  1. What is the main issue?

This question helps to cut to the heart of the matter.  The right tone is important when asking this questions. The leader who asks must be sincere in their inquiry. This helps the person who is answering the question to narrow their focus so that viable solutions can be discovered. 

  1. How might other people see this?

This is a great question to help the person answering to consider the perspective of other people.  This is a stimulating question to raise the emotional intelligence of the person answering as they become more aware of others.  Instead of trying to convince a person to be empathetic, use this question to guide them on that journey. 

  1. What have you tried already?

This will help the answerer reflect on past attempts and solutions in a reflective manner. It helps them to avoid past mistakes and to consider how to capitalize on past successes.  If anything, it will remind the listener to be proactive to consider solutions for any problems before bringing it to you.   

  1. What is working best? What is not working?

This is a perfect question to initiate real time feedback from those you lead. It helps to not just look at what has been attempted but to evaluate the impact and effectiveness of the solutions that have been attempted.  Even asking about what is not working is helpful because it helps the listener to consider possible blind spots or areas of ineffectiveness that they may have ignored before. 

  1. What do you think will make the greatest difference?

This is one of my favorite questions. This is a question for gaining focus and developing priorities.  When the listener is faced with many options or many solutions, the ability to prioritize is critical. This question pushes the one who answers, to consider not just all of the answers but the best answer for the moment  Once this question is answered you can move forward with confidence that you have the right priorities. 

Remember, it’s always easy to give someone the direct answer. This will certainly get the job done but it will have to continue to be repeated each time. A leader who is able to coach the people that they lead through asking strategic questions helps to develop their team to be able to think critically and to solve problems on their own over the course of time.