10 Assessment Questions Every Leader Must Ask

Editor’s Note: The following post was originally published on March 12, 2012 at Link to original post:

Leaders ask questions . . . of themselves, of their organizations, and of others. It is part of what helps them to improve. Of course, this requires time for reflective thinking. Maxwell notes that reflective thinking is like the “crock-pot of the mind.” In this post I share 10 assessment questions for your to stew on.

The Importance of Questions

Max De Pree had a long and distinguished career with Herman Miller, Inc. In Leadership Jazz, he writes,

“The quality of our work as leaders and the quality of our lives depends significantly on the questions we ask and the people about whom we ask the questions.”2 John Maxwell says, “The better the questions, the more gold you will mine from your thinking.”

The Questions Leaders Must Ask

  1. Leadership: Do I have a personal growth plan to improve myself as a leader? Is it written down? To whom have I made myself accountable for it?
  2. Inner Circle: Have I spent enough time with key players? What can I do to help them be more successful? In what areas can I mentor them?
  3. Listening: Have I learned to stop? When I stop, do I stop to talk or to listen?
  4. Approachability: Followers sometimes treat leaders like an emperor. Do I have my clothes on? Do people tell me when I’m naked?
  5. Assessment: Is what I measure today different from what I would measure when I’m seventy? Would the light of mortality affect my measure?
  6. Trust: Has anyone in this place confided in me lately?
  7. Risk: Do I have a nose for stale air? Have things become mechanical? Conservative? Do people here avoid risk like the plague and isolate themselves?
  8. Hiring: Have we stopped hiring people better than we are?
  9. Change: When did I last abandon a program?
  10. Potential: Is the organization succeeding at the expense of individual potential? It is the leader’s special province to guard the chance of individuals to reach their potential. Have I checked lately to see that this opportunity exists and that people know I care about it?

Key Resources

Two books that are helping me ask better questions are:

In his chapter, “What Would Bucky say?” De Pree lists twenty-three questions leaders can ask to assess their work. Maxwell’s questions come from his chapter entitled, “Embrace the Lessons of Reflective Thinking.” Most of the questions in this post come from those two sources. The majority are from De Pree.

The better the questions, the more gold you will mine from them. What questions are you asking yourself as a leader?

About Tommy Kiedis

Tommy Kiedis serves as the Senior Pastor at Spanish River Church (SRC). A local church with a global reach, SRC is active in serving the Boca Raton community and has helped to launch 450 churches in the US and around the world. Tommy is husband to Shannan, the father of six, and proud grandfather of 11. He blogs at and and You can follow him on Twitter at TommyKiedis

Leave a reply