Everyone Can Ask Powerful Questions

Excerpted with permission from the 20th Chapter of “When Everyone Leads” by Ed O’Malley and Julia Fabris McBride

It’s tempting to think leadership is a superhero saving the day, a president galvanizing a nation, a captain rallying a team to victory.

That “leader as savior” mythology focuses our attention on whoever is in charge—hoping and expecting them to solve the problem, right the ship, make things better. If we are the ones in charge, the “leader as savior” mindset diverts us from engaging others in problem-solving and drives us towardquick fixes without deep diagnosis of the situation.

Diagnosis is fueled by questions. Good questions generate better interpretations and lead to better interventions. Good questions sometimes raise the heat and sometimes work wonders to lower the heat and keep groups in the productive zone.

Albert Einstein famously said, “If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper questions to ask.”

Asking questions is a leadership skill that is available to anyone. It’s one of the simplest (though not always easy) ways for people without authority to exercise leadership. Take these examples:

  • A young professional, after participating in a three-hour meeting covering dozens of topics, meets with their manager and asks, “Of all the topics we just discussed, what is most critical for our success over the next month? I’m confused about how all this fits together.” That question won’t change the world, but it might help the manager realize people are wondering where to focus.
  • A small business has been losing customers. At a staff meeting an employee asks, “What story might our customers be telling about us and how is it different from the one we tell ourselves?” That question could elicit some pretty important introspection for the struggling business.
  • A math teacher notices no evidence of concern among school staff, despite major challenges such as an increasing percentage of students from impoverished families. At the beginning of a staff meeting the teacher asks, “What would be a good outcome for this meeting and how does it connect to our biggest challenges?” That question might nudge the group to be more purposeful.
  • Two friends who work at the same organization are out to lunch. One shares how frustrated she is with her boss. The other empathizes, but instead of fanning the flames of discontent, asks, “What is your team’s most important challenge right now?” and “Where do you suppose your boss feels stuck?” These questions could shift the friend’s attitude from frustration to curiosity, helping her put the challenge (not the person) at the center of her work.

What Makes a Powerful Question?

Powerful questions invite people to explore multiple perspectives. Questions that illuminate adaptive challenges are not the same as those a lawyer would use to interrogate a witness. These questions aren’t trying to box someone in or prove a point. Instead they are open-ended, provoke reflection, and can seldom be answered with one word. They lead to curiosity and discovery. Think back to how we started this book by encouraging you to pose questions like these: “What are your greatest aspirations?” and “What concerns you the most?”

When you are trying to make progress on a leadership challenge, powerful questions can help you:

  • Create consensus about the leadership challenge.
  • Identify who is most affected by the problem (and thus who needs to be engaged to solve it).
  • Explore perspectives.
  • Understand root causes.
  • Clarify collective purpose.
  • Open minds to alternative approaches.
  • Help others see moments to exercise leadership.
  • Raise the heat in large groups, team meetings, and one-on-one conversations.
  • Expose unspoken barriers, shared values, or big aspirations.

Sequencing Powerful Questions

When exercising leadership on a daunting challenge, there is skill in knowing what kind of questions to ask, and when. In general, you want questions that propel more curiosity and discovery early in conversations or projects. Later you’ll want questions that drive to action, experimentation, and commitment.

In the beginning of a conversation or project, ask questions like these:

  1. What would be a good outcome for this conversation (meeting, process, etc.)?
  2. What’s important to you about this?
  3. What would someone with a very different set of beliefs have to say about this?
  4. What’s our intention here?
  5. What is our deeper purpose?
  6. What is worth our best effort?

In the middle of a conversation or project, ask questions like these:

  1. What do we know so far and what do we still need to learn?
  2. What assumptions do we need to test or challenge?
  3. What’s taking shape?
  4. What are we hearing underneath the variety of opinions being expressed?
  5. What new connections are we making?
  6. What’s missing?
  7. What are we not seeing?
  8. If there was one thing that hasn’t been said yet, what would it be?

In the end of a conversation or project, ask questions like these:

  1. How will we experiment?
  2. What’s possible here and how committed are we?
  3. What will progress look like?
  4. How can we support each other in taking next steps?
  5. What unique contribution can we each make?
  6. As we move forward, what challenges might come our way?
  7. How will we meet those challenges?
  8. What will it mean to stick to purpose?

It’s Not Always Easy to Ask a Powerful Question

Asking powerful questions is a leadership move that is available to any of us, no matter our position in an organization or community. But that doesn’t mean it’s always easy. Things (including ourselves) can get in the way.

As you start asking powerful questions, remember:

  • You must genuinely want to help others engage in difficult work. If you are most concerned about getting information for yourself, then your questions will be self-serving. You’ll ask things like “When does the meeting start?” “Am I supposed to be there?” and “What do we need to do before we get there?” You might really need to know the answers to those questions, but they are about you, not about others. Leadership is about mobilizing others. Your questions need to serve them. They need to inspire others to think or engage differently around a challenge.
  • Don’t overinflate the risk of interjecting a question. Leadership is always risky, but asking a powerful question is one of the least risky actions you can take. Questions suggest a direction for the discussion and invite people into the productive zone. It might be out of the group norm for someone like you to ask powerful questions, but the risk is likely minimal, especially if you pick the right type of question for the moment. Inflating the risk involved is one of the ways we let ourselves off the hook.
  • Resist “gotcha” questions. Politicians resort too often to gotcha questions. Silly example: “Would you rather vote for my opponent who wants to raise your taxes, take away your puppy and make the sale of chocolate illegal, or for me?” Gotcha questions are designed not to help a group, but to embarrass someone or box someone into a corner. When dealing with heated issues it can be natural to have a strong point of view. Sharing that point of view can be fine. Debating is fine too. But those who exercise leadership find ways to manage themselves, to keep their emotions in check, and to build relationships across divides. Curious, open, and engaging questions help you manage your own emotions and provide a pathway for others to manage theirs. Gotcha questions do the opposite.
  • Avoid “suquestions.” That’s when your question is really a suggestion. If you have a suggestion, make it. But don’t pretend it’s a question. “Have you ever thought about . . .?” and “What would you think of the idea of . . .?” are suggestions disguised as questions. Powerful questions come from a place of curiosity. They are motivated by a desire to help an individual or group access their own creativity and find their way forward.
  • Free yourself from the need to ask the perfect question. A friend of ours was in the midst of a tense and too hot discussion when, not knowing what to do, he glanced at our list of “good in the middle questions.” He raised his voice and lobbed out the first question that caught his eye: “What assumptions do we need to test or challenge?” People took a collective deep breath. The ensuing discussion lowered the heat right before his eyes. There is no perfect question. Almost any open-ended question by our friend in that meeting would have had the same heat-lowering effect.
  • Use silence. When you pose an open-ended question, take care that you don’t rush in to answer it yourself. Give the other person time to reflect. Allow space for a powerful question to land in the heart or gut so it can generate energy for adaptive work.

It’s interesting, isn’t it, how few good questions get asked in organizations. Most of us go days without hearing a genuinely curious question. Keeping a group in the productive zone is everyone’s work. The heat stays hot enough when enough people in a system or organization are prepared to ask questions that matter. Leadership is about seeing and seizing moments. The simplest way to do that can be to notice what question would help propel the group forward right now.

Having lots of people in your organization skilled in asking powerful questions is like deploying an army of executive coaches. Everyone will be asking powerful questions that help peers, direct reports, and even supervisors see and seize more moments to lead. Every time someone asks a good question, they do their part to build a culture where everyone leads.

Making It Real

Dear Ed and Julia,

I’m a volunteer with a food pantry. The founders run everything with the help of just a few volunteers like me. The pantry has done good work to uplift and protect community members during difficult times. But it’s never done much to engage people beyond those founders and their friends. The pantry could have more impact if we had more community support. The answer is partnerships and I’ve worked to connect the pantry to other organizations focused on ending food insecurity. No one has done anything with my ideas and lately I’ve been grappling with whether it is even my place to share them. Thoughts?

—Volunteer Vincente

Dear Vincente,

Try shifting your approach from promoter-of-ideas to asker-of-questions. Get super-curious about what each of the founders wants for the people you serve. Ask questions that invite them to articulate their dreams for how the pantry could have more impact. Don’t wait for meetings or formal opportunities. Ask questions during volunteer shifts and when you see someone around town.

Release yourself from the pressure of making the founders see that partnerships are the way forward. Frame questions that help them reconnect to why they started the pantry in the first place. Ask their opinion about the biggest barriers to eliminating food insecurity in your community. Maybe your questions will lead them to that idea or maybe you’ll inspire a different, but better, approach.

Note from Bob:  Click HERE to order your “When Everyone Leads” book today!


Ed O’Malley & Julia Fabris McBride


President and CEO of the Kansas Health Foundation, Ed O’Malley was founding president and CEO of the Kansas Leadership Center, where over 15,000 people have attended programs from around the world since 2007. A former state legislator and gubernatorial aide, Ed has co-authored three other books including Your Leadership Edge and For the Common Good.

Julia Fabris McBride is chief civic leadership development officer of the Kansas Leadership Center and a certified coach. The programs Julia has developed at KLC have drawn people to Kansas from five continents. She is a co-author of Teaching Leadership and author of Your Leadership Edge: Teacher Companion. Julia splits her time between Wichita and Matfield Green, Kansas.


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