Leaders: Ask. Don’t Tell.

It is critical for leaders to model the behavior of questioning by making it safe to ask questions in ways that produce results. Reward the asking of questions so questioning becomes a habit.

For decades, I followed the work of Peter Drucker. Then I learned of about his mentee, Frances Hesselbein, former CEO of Girl Scouts of America and then the president and CEO of the Frances Hesselbein Leadership Institute (formerly the Peter F. Drucker Foundation for Nonprofit Management) and its founding president. Hesselbein died in December 2022 at 107. She was a mentor to many people and lived a long life worth remembering.

Years ago, I registered for a Webinar by the Frances Hesselbein Institute just to listen to Hesselbein’s wisdom. During the session, Hesselbein said something I have always remembered. “I pretend I have three invisible tattoos on my shoulders. Ask, don’t tell. To serve is to live. Think first, speak last.” She said those “tattoos” were reminders of what she needs to do as a leader.

The focus of this month’s online issue is training tools and delivery. In my opinion, the best tool and delivery is to remember these “tattoos.” All of them remind us that leadership is a relationship—not a position or title. They also remind us that leadership is not about you as the leader, but about the other person.

The Power of Questions

In this column, I’d like to focus on “Ask, don’t tell”—or the power of questions. To learn more about questions, I read two books: “A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas” and “The Book of Beautiful Questions,” both by Warren Berger. He calls himself a questionologist and writes a column for Psychology Today.

Berger teaches how to use questioning to encourage critical thinking needed for making good decisions. Questions can be used to stimulate imagination and creativity. A powerful way of connecting with others is to ask questions. All of these are important skills needed in workplaces today.

Leaders are not supposed to know all of the answers. When leaders ask questions, they empower employees to come up with solutions and be more engaged in the process. Berger says “our ability to question well is like a muscle.” We have to continually work at strengthening it by practice. “When you change a statement into a question, it tends to become more engaging. It is open-ended and forward-looking, it invites people to think about the question and the possibilities.” But he also outlines the five enemies of questioning:

Fear: Will it look like I don’t know what I am doing?

Knowledge: I know what I am doing, so I don’t need to ask.

Bias: I am certain in what I think, so no need to ask.

Hubris: If I don’t know it already, it can’t be that important.

Time: It takes too much time to ask questions.

Possible Leadership Questions

I was so captivated by the wisdom in Berger’s books that I interviewed him for my monthly podcast called “Becoming a Sage.” I told him that the question I advise my coaching clients to ask is: “How can I support you?” While he liked the question, he told me how to improve it. “What are two ways I could support you?” If the person doesn’t answer immediately, give them time to think about the question and say you will check back in a few days.

Berger shared some of his favorite leadership questions to build relationships:

  • What’s the biggest challenge you’re facing?
  • What are we doing that is getting in your way?
  • What are you working on right now that you’re most excited about?
  • How would you like to see yourself growing in this role?
  • What do you do to keep learning and growing as a person?

Berger has two main questions he believes leaders should ask themselves: Why do I want to be a leader? Why would others want me to lead them? Then compare the answers and see if there is alignment. He reminded me that many leaders aren’t ready for leadership positions or want to be in the leadership position for the wrong reason.

Make It Safe to Ask Questions

In conclusion, Berger told me how critical it is for leaders to model the behavior of questioning by making it safe to ask questions in ways that produce results. Reward the asking of questions so questioning becomes a habit.

I like to ask leaders, “If you had an ‘invisible tattoo’ on your shoulders, what would it be?”

My response has been that my tattoo would be “Honesty with kindness.” Now I would add, “Ask questions.”

The best training tool and delivery method might be shifting from making statements to asking questions. If you want to be a servant leader, think of Frances Hesselbein. “Think first, speak last and ask, don’t tell.”

Jann E. Freed
Jann E. Freed, PhD, is an author, speaker, coach, and leadership development consultant. Her forthcoming book is “Breadcrumb Legacy: How Great Leaders Live a Life Worth Remembering” (Routledge Publishing, 2023). For more information, visit http://www.JannFreed.com