21 Powerful Questions Leaders Should Ask

Guest Post by Caren Merrick

Asking questions is one of the simplest and most powerful ways to advance your leadership skills and connect with your team. Questions challenge assumptions and encourage us to reach beyond what we think we already know. Good questions lead to innovative products and solutions.

Questions build trust. As children, we ask questions easily and often. When I was about seven, my mom (a working mother with four children), found a resource to answer my constant questions. It was a wonderful book simply called The Curiosity Book.

It was a treasure of my childhood, replete with hundreds of questions, like, “Where do marshmallows come from?” My older sister and I spent hours reading it together.

While curiosity doesn’t appear to diminish as we get older, as adults, we are more cautious about asking questions. Perhaps we become fearful of looking stupid. Or, because we’re moving so fast to meet multiple deadlines, maybe we don’t stop to discuss our curiosity. This occurs even though surveys show that two of the top skills companies want from senior and emerging leaders are good listening and analytic skills. It’s hard to possess these highly valued skills unless you are good at asking questions.

Whether you lead as a member of a board, a seasoned executive, a middle manager, or a new professional, your questions can set you apart as a leader. Good leaders ask a lot of questions because it shows that they value curiosity, that no one is expected to know everything, and that all are welcome to seek.

For an insightful review of the power of questions, read Leigh Buchanan’s interview of business journalist Warren Berger, who wrote A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. Berger is the author and creator of an amazing blog on questions and innovation I just discovered, called A More Beautiful Question.

And, if you’re really concerned about the direction of a project or initiative, asking questions can be more effective (even more subversive) than making statements. Questions are vital when something isn’t working. For example, if you have a specific process that you and your team already know is broken, Alexandra Levit offers excellent Process Improvement Questions You Should Ask.

I’ve found that there are many questions you can ask to gain clarity and cohesion. I’ve also discovered that you can ask these questions with a generosity of spirit, showing appreciation of and respect for the value of the person you are questioning.

Below are 21 helpful questions that I’ve used as an entrepreneur, executive, and board member. Some are those I’ve borrowed from others and some are those I’ve developed myself; I continue to seek new and better ways to ask questions and listen.

Read to the end for a few of the least asked, yet most powerful questions.

For more ideas to advance your leadership skills, including steps to take to join a corporate board, please sign up for my weekly updates.

1. Did you (or we, or they) arrive at this decision or result by logic, intuition, or both? What’s the evidence to support the decision?

2. What problem are we solving for our customers? What’s in it for them? How are we adding value?

3. Where is the leverage of this idea or direction? How does it intersect with our other objectives?

4. How do we measure this? In real terms, how do we quantify the effort and outcome?

5. What will it cost in terms of time? What about in human and financial resources?

6. Could we achieve this better with a partner? Who is (or are) the ideal partner(s)?

7. What’s the risk if we don’t do this?

8. What’s the risk if we fail? What is the worst thing that can happen?

9. Are we close enough to our customers? Who on our team is close to our customer, and what can they tell us? Can we collaborate?

10. What is your most pressing issue?

11. What is your/our ideal outcome? What are the specific results we want to achieve?

12. When? How do we get there? Who is going with us? What is our next step?

13. Can you or I explain this product, service, or direction to my mother? (This was a favorite we used in the early days of AOL, when the idea of connecting with people, businesses, and customers online was so new!)

14. How can we test this idea before committing more resources to it?

15. Do the managers of the team believe more in the team’s potential than the team does?

16. Are there stupid rules we need to kill? Assumptions that sounded right, but are not being proven through our experiences?

17. Have our competitors tried this? What can we learn from them?

18. Who needs to be thanked for getting us into this line of inquiry?

19. Who needs to be encouraged/persuaded to invest in this?

20. How can we quantify and communicate the benefits of this approach?

21. If we had unlimited resources, what would be possible here?

Here’s another smart question I recently discovered and plan to use more often: “Are there any questions we have not asked that should have been asked?”

As you ask questions, pause and “Let silence do the heavy lifting,” as Fierce Conversations author Susan Scott advises. Space after a question allows everyone in the room to reflect, participate, and focus. It allows us to gain clarity on causes and solutions.

Your turn: What are some of the best questions you or your team members have asked? Please share below in the comments!

Note from Bob:  You are invited to join me at the Ziglar “Choose to Win” conference in Dallas, Texas – May 2-3.  You will find all the details @ Ziglar.com/conference

Caren Merrick


Caren Merrick is a serial entrepreneur, investor, and board director who advises leaders on how to grow themselves, their teams, and their businesses.
Readers can connect with me at carenmerrick.com and LinkedIn


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