10 Assessment Questions Leaders Must Ask


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 you to stew on, but first let's think about why asking questions is so important.

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.

John Maxwell would add his hearty "Amen" to De Pree. Maxwell says, “The better the questions, the more gold you will mine from your thinking." So here are ten questions you can ask to get to the gold.

10 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. Am I approachable? How am I creating an environment where people will tell me what I need to hear, but maybe don't want to hear?

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? Ho-Hum? Are we avoiding risk?

8. Hiring: 

Are we 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 responsibility to help individuals reach their potential. Have I checked lately to see that this opportunity exists and that people know I care about it?

Think about it . . .

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


Key Resources

Two books that are helping me ask better questions are:

  1. Leadership Jazz: The Essential Elements Of A Great Leader by Max De Pree. Max De Pree distills the essence of lifetime of leadership in an attempt to identify key aspects of leadership.
  2. Thinking For A Change by John Maxwell. Maxwell examines eleven thinking skills that successful people need.

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.