Questions Every Great Leader Should Ask

Speaking is an essential skill for transformational leaders, but every great leader also needs to be able to listen. I often see leaders who focus more on telling without gathering the proper context, which always begins with asking the right questions. When you engage the people you lead with great questions it builds rapport, allows you to collaborate with them, and provides the necessary context for you to pour into them and provide the right advice, guidance, and encouragement.

Leader standing with colleagues

In working with leaders and helping our clients to develop their leadership culture, we have found the following questions to be especially helpful and effective if you want to be a transformational leader:

  • How are you doing? – Notice that this question is not “How’s it going?” which demands a response of a status report. This question focuses on them and how they are personally doing. It can be a conversation starter and allows you to understand what has been going on in their lives. It also gives them a chance to voice their level of engagement in life and expand on personal activities that they are passionate about or have brought meaning to their life. It facilitates a connection.
  • What are you most proud of over the last few months? – This is a different way to ask “How’s it going?” When you ask this question, it gives them a chance to passionately talk about the work they have been doing and the impact it has had on others including team members, clients and customers, and the community. It also gives you a lens into what they are passionate about, which can be helpful as you assign them to future roles. This question reveals what brings them the most contentment.
  • What opportunities have you leveraged? – This question allows you to gauge their initiative and creativity. Many times when I have asked this of the people I have led, their eyes begin to light up as they talk about new ideas and the process of discovery. The best leaders help others discover possibilities and leverage opportunities. This question facilitates curiosity.
  • What successes have you had? – Great leaders catch people doing the right things and celebrate their successes. Asking this question allows them to articulate the wins and breakthrough moments and gives you insight into their strengths. This question strengthens commitment.
  • What challenges, if any, do you have in front of you? – Some leaders fear asking this question, because there may be a response that requires them to do something. Moreover, these very same leaders don’t want challenges, they want things handled and solved. While it is true that responsibility and authority should be given to others along with the permission to solve challenges, the best leaders ask this question to gather context and stay engaged in the process. They also ask this question to gauge the intuition and discernment of the people they lead. Finally, great leaders ask this question, because they must. It is their opportunity as a leader to invest in and show concern for their team and to collaboratively engage with them. This questions serves as a catalyst for courage.
  • How can I help? – A lot of leaders fail to ask this question, especially after asking the question about challenges, because they know this question demands an answer that will require their time, commitment, and effort. They seem to disappear from the conversation almost in a “Good luck with that one” kind of way. Truly engaged leaders consistently ask this question after gathering the proper context in order to leverage their power and influence to pave and prepare the way for the people they lead to be successful. Asking this question promotes collaboration.

Transformational leaders are purposeful and passionate about engaging with their team. They listen well and ask the appropriate questions in order to provide the right support. As you consider the roles that you play in life and the leadership opportunities and influence that you have, I encourage you to ask these questions. They will help you effectively connect with the people you lead and help you make a positive impact that extends beyond your reach.

Question: What questions have you used to effectively connect with your team? You can leave a comment by clicking here.

Please note: I reserve the right to delete comments that are offensive or off-topic.

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