20 Questions Good Leaders Should Ask

Guest Post by Gary A. Cohen

Earn Your Paycheck By Listening First, Talking Later

Are you a leader? You are if you have others who report to you at work.

Contrary to age-old beliefs that leaders need to have all the answers, to be a truly great leader and get the most from your team, you should listen more and ask great questions.

Asked in the right way, open-ended questions allow leaders to showcase their critical thinking skills while processing complex situations. Asking the right questions at the right time also gets others involved and brings diverse perspectives to the conversation. As leaders listen, they learn more about the people who report to them and the subject at hand.

Leaders also convey their all-important values when they cut through and filter out ancillary information that can be a distraction, and get right to the core of the matter. This is how challenges are best confronted and solved. Here are 20 powerful questions that work well in almost any situation.

Conversation Starters

When a new opportunity or threat emerges, people close to the situation sometimes miss the obvious. Some basic questions work great to help people step back and reframe the problem.

  1. What created this situation?
  2. What assumptions have you made about it?
  3. What are the key ramifications of your actions?
  4. What more do we need to know before we pivot or take alternative action?
  5. What current resources would help address this situation?
  6. What makes this situation so challenging?
  7. What would you like to see happen?
  8. How would you recommend doing it?

Confidence Boosters

Leaders are most productive and successful when they focus on the positive rather than dwell on the negative. If a subordinate brings a problem to a leader, in addition to asking the questions above, the leader can ask questions that drive positive thinking.

  1. How can you turn this challenge into an opportunity?
  2. How can I help you bring a successful resolution and positive outcome?
  3. What can we learn from this so we can avoid a situation like this in the future?
  4. How can we turn this setback into a victory?
  5. How can we think outside the box or pivot on our approach?

Team Builders

Leaders should always take the opportunity to reinforce teamwork in addressing situations. They can ask several questions to encourage collaborative thinking.

  1. How can we collaborate with other team members to come up with a more comprehensive solution to this challenge?
  2. In what ways can we work cross-functionally to leverage complimentary skillsets and achieve a better result?
  3. Who in the organization can you speak with who has expertise in this area?

Performance Reviewers

It is critical that leaders hold their teams accountable so expectations can be met or exceeded. Addressing accountability through questions is viewed much less as an attack or assault than direct statements about performance deficits.

  1. How would you assess your success in meeting your objectives on this project?
  2. What can you do to accelerate your progress so we can meet our targets?
  3. What impact will failure to meet your objectives have on our organizational (or departmental) plan for the current period?
  4. What can you do differently to achieve a better result?

Asking questions encourages leadership by example.
You should be a mentor to those on your team, and if you are garnering their respect as a leader, they will be more likely to adopt much of what they have seen in you as they begin to lead others. They will also begin to ask probing and powerful questions.

The bottom line is that asking well-thought-out questions demonstrates knowledge, mastery and leadership through collaboration. Asking questions also enhances the ability of members on your team to think more critically and learn how to be better problem-solvers.

The same approach can work equally well in your personal life. Great communicators make better leaders in any environment.

Gary A. Cohen


Gary A. Cohen is an award-winning educator, teaching International Business and Global Trade Management to MBAs and Executive MBAs at the University of Maryland – Robert H. Smith School of Business.  You can connect with Gary on LinkedIn




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