Four Questions Every Leader Should Ask Their Team

Guest Post by Ken Gosnell

Originally posted @

Questions are a vital aspect of good leadership. Great leaders ask good questions of their teams, and they are open to being asked the hard questions by those who the leader trusts.

Leaders need to think intentionally about the questions that they want to ask of those they lead. A leader would be wise to have an advanced list of questions they would like to ask team members daily, weekly or in scheduled meetings. In an article for Rework magazine, human resources consultant Leigh Limpic writes, “Your employee will know you are engaged and listening when you ask appropriate, challenging questions. Don’t interrogate. Your questions should help you understand the situation and give you the chance to acknowledge great decisions, actions or results or help them identify where they may need to do more planning.”

The best leaders become masters at asking the right questions at the right time. Each question should be specific to the person with whom the leader is engaging. The questions that the best leaders ask are designed to start a more in-depth conversation that has both meaning and significance.

Four Questions Every Leader Should Ask Their Team

1. What problem are you dealing with that I can help you solve?

Leaders are problem solvers, and one of the best uses of their time is to help their team members solve problems that they are dealing with that are hampering their work. When a leader spends time helping their team solve problems, they help the team member understand how the leader thinks and how the leader makes decisions. These two aspects are critical in making better decisions in the future and to growing a successful organization. The leader who is always available to ask the team how they can help solve problems is a leader who leads with the team, not out in front of the team. This leadership position engenders respect and credibility and challenges the entire team to make decisions as the leader would make decisions.

2. How can I help you give your best to the organization or a current project?

Leaders can remove the problems and the obstacles that often hinder a team member from doing their best work. A leader should be quick to offer assistance to their team by removing barriers that prevent the person from doing their job effectively. When a leader listens to their team and responds by helping a team member give their best to the organization, they become a leader who inspires and motivates. The leader should always be calling out the best of their team. Many people have accomplished great things because someone believed in them enough to challenge them to achieve great things. That is the role of the leader, and so the best leaders ask questions of their teams to help the team member give their best to the organization.

3. What achievement are you proud of that you want me to help you celebrate?

Leaders are at their best when they are celebrating the successes of their team. Too often, leaders do not recognize or even know the best achievements of those who they lead. Successes and breakthroughs that are celebrated are more likely to be repeated. Leaders who hope to lead their organization well will learn the critical achievements of those they lead, and they will highlight and celebrate those successes. Team members are often deeply moved when a leader takes the time to highlight and call out their accomplishments. Many leaders only focus on where team members need to improve. When leaders ask team members about a win or breakthrough to celebrate, it emphasizes that the leader is looking at both what needs to be improved and what successes need to be celebrated. This “both-and” leadership style is balanced leadership and increases the morale of the team.

4. What have you learned that I need to know that could improve the organization?

Innovation and new ideas often come from the best employees doing the work of the organization. A leader should make it a priority to continually ask team members what they are learning as they do their jobs that could help improve the organization. The question is a question of humility, and it inspires the team member to think about the organization as a whole and not just their department or area. The best ideas for an organization can come from aware employees but will only come to light when the leader asks the questions and encourages the team member to share their insights. Leaders should not be afraid to ask their team how to improve the organization. Team members can often become the organization’s best set of eyes that lead to ideas that can propel the organization forward.

In their book The Trusted Advisor, authors and business experts David Maister, Charles Green and Robert Galford share their ideas about the importance of asking questions to influence. “If you want to influence someone, you must find out what influences them, or at least how they are likely to be influenced,” the authors say. “The only easy way to do this is to ask questions, more questions and even more questions.”

Asking questions is an essential aspect of good leadership and a key component to leading a great business. I am often asked by CEOs and leaders what one thing they could do to improve their effectiveness. The answer that I give is simple but challenging. I tell leaders that the one thing they can do to grow as a leader is to ask more and better questions of themselves and those they lead. When a leader asks the right question, and they ask it often enough, they will find the answer that leads to better deliverables and better outcomes for themselves and their organization.


Ken Gosnell


Ken Gosnell is the CEO and Servant Leader of CEO Experience (CXP). His company serves CEOS and leaders by helping them to have great experiences that both transform them and their organizations that enable to go further faster. Ken is the publisher of the CXP CEO Executive Guide that is designed to help leaders learn faster by encouraging to give themselves a monthly learning retreat. His monthly CEO retreats have helped thousands of CEOs and their leadership teams to enhance strategic, operational and people accomplishments. He is a keynote speaker, executive coach, and strategic partner with CEOs and successful business leaders. He is also the author of the book Well Done – Biblical Business Principles to grow a business and a Kingdom Impact due out in early 2020. Connect with Ken on Twitter & LinkedIn


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