The Questioning Leader

Lead people with statements and they will follow. Lead people with questions and they too will lead. ~Dr. Brett Hulett

Asking > Telling

I do not like being told what to do. Telling me what to do immediately raises my hackles and puts me in defensive mode. Had I enlisted in the military instead of going to university, I probably would have spent a good portion of my time either on KP duty or in the brig.

I once had a manager tell me I was difficult to mentor. Part of that dynamic was based on the manager’s approach to mentoring. The technique used was to tell me what I should have done or should do. If questions entered the conversation, they were designed solely to get me to see things from a preordained perspective rather than come to a collaborated solution we both could own. Even when mentored with questions I will push back and challenge. But, in the end, I will buy into the solution.

Part of the challenge in the dynamic is my intense dislike of being told what to do. This dislike is most likely genetic. Family stories say the first 5 words I learned to say were all “No!” or some variation thereof. One of my peers commented that I need more autonomy than the average person. Telling me directly infringes on this need to be autonomous.

Statements generate resistance while questions generate conversations. Conversations are important in that both sides have the opportunity to express their thoughts, to be heard. In healthy conversations, both sides are understood. Not necessarily agreed with but heard. Being understood leads to a person feeling valued. Someone feeling valued is more likely to be open to new ideas. In the dynamic with my boss, I never felt valued resulting in me being labeled as ‘difficult to mentor.’

What could my manager have done differently? For starters, lead me with questions instead of statements.

My Leadership Methodology

Knowing my intense dislike of being dictated to, I, when acting in a Leader or Coach or Mentor role, make it a point to rarely tell anyone what to do. It has become my defacto leadership methodology. I did my best to practice this with my children. Today, they all have the skills necessary to make adult level decisions.

The exceptions to this rule are when there are issues of personal safety or compliance to a governing body. If someone can get seriously hurt because of a decision, I will jump in and ensure safety is in place. My children were required to wear helmets while the road their bicycles.

How then do I lead?

I lead with questions. When discussing options or tactics with someone, I ask them open-ended questions designed to ensure they are required to think the answers through.

These conversations are rarely short. I once had a subordinate come to me with an issue. I knew an answer by the time she finished explaining the situation. The conversation could have been over and done in five minutes. I say could have but, in actuality, it turned into a two-hour conversation ending with her coming to the same answer I would have provided in those first five minutes.

“What a waste of time!” you might say.

“Wrong!”, I say.

Those two hours were an investment in her personal growth. As her Manager, it was my responsibility to ensure she remained a viable employee. Viability goes hand in hand with employee growth. An employee that is not growing is losing ground and runs the risk of becoming obsolete. Just giving the answer would be neglecting my duty as a leader.

By working through the conversation with me asking many questions, we explored multiple ways to handle the problem and the consequences of the various options. Some of the solutions were dead end rabbit holes while others were workable possibilities that, if not the best choice for the current situation, could be utilized, depending upon the nuances, of a similar problem.

Now, if a situation arises, she has the tools to analyze and come to a workable solution. Plus, by coming to the answer of her own accord, she owned the solution. When someone owns a solution, they will put in the extra effort to make it work because no one wants to see their ideas fall flat. This method ensured she could not come back to me later and say, “I did what you told me to do but it didn’t work.”

While working in India, I coached around 34 people. I also mentored another 6. (I define mentoring as coaching on steroids.) My coaching sessions were typically monthly, 1:1 conversations with occasional, informal side conversations during the month. The people I mentored were those identified as taking the group into the future after I returned to the US following my 24 month assignment. For the people in the mentoring pool, 1:1 meetings ranged from every two weeks to three times per week.

One of the mentees used to ask point blank, “Dave, what should I do?” I almost always responded with, “What do you think you should do?” or “what options do you see?” We would then spend time discussing scenarios.

We engaged in many deep conversations. Some extended outside the office under the watchful eye of Jameson Irish Whiskey. The plan of attack always came from and was owned by the mentee. A number of times, the plan was not one with which I agreed. Still, I backed the person’s decision. Sometimes, I was right and the solution did not pan out. Other times, I was wrong and the solution worked better than anything I could have dreamed up. The beauty is that we both learned and grew in this process.


Leading with questions requires the leader to lose their ego. Ego wants to provide the answer to demonstrate their power. Real power is in questions that stimulate others to think for themselves.

Leading with questions helps a person think and own the answers. They live with the consequences of their decisions. Consequences are required for a person to grow.

Leading with questions help both parties see problems from unexpected vantage points. These unexpected vantage points help develop unique solutions which are independent of preconceived notions, biases, deeply rooted assumptions.

Leading with questions is an art. It is not a techinque learned by reading rather by practicing the art on a regular basis. Questions are one of the many tools a leader must master to become a true artist.

Leading with questions develops leaders while leading with answers creates dependency upon the leader. Ultimately, it is the leaders responsibility to develop leaders not to generate more followers.


My challenge to you: replace answers with questions in your leadership and free your people to grow.

Author: David A Olson

I often find my mind wandering to various subjects, subjects that make me stop and think. The blog, Musings of a Middle Aged Man, is a catalog of those thoughts I muse upon as I search for significance in life. I am the father of 3 children and the grandfather to 2. I spend my days working for a medium sized multinational corporation where I am an Agile Coach. I view myself as a Servant Leader, have a passion for leadership, particularly, in helping people develop their individual leadership skills and abilities. In October 2012, I went to India on business. After a week of being there, I still had not talked to or texted my 7-year-old grandson. He asked his mom, "Is Papa dead? He hasn't texted me all week." To facilitate communication now that he and I no longer live together, I started a blog for us to communicate. It's titled, "Correspondence Between Luke and His Papi". In April 2013, I moved to Pune, India on an 18-month delegation. It's an adventure that was 1.5 years in the making...The experience is captured on my blog, "The Adventures of an American Living Abroad" My two latest blogs are "The Learning Leader", a topic I have been studying since 1990, and "Lipstick on a Pig", a foray into the fashion sense of this middle aged man.

One thought on “The Questioning Leader”

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.