Guest Post by José Cruz, Jr.

How often do you sit down and really communicate with each member of your team?

I don’t mean the usual “hello” or “thank you”, but a real and honest conversation filled with the kinds of questions that open the dialogue in meaningful and powerful directions.

A more important question may be: When was the last time you had a powerfully impactful conversation with a member of your staff?

Think about it for a moment and then ask yourself, “what helped make that conversation so meaningful?” Chances are, it was a deep and honest inquiry into a matter of deep importance and value to your team member. Chances are, also, the team member was thankful you had the courage to ask, and gave them permission to answer you.

Getting to the heart of such meaningful inquiry is the purpose of this post, and the greatest tool any leader can bring into a conversation with their team.

The ability to ask great questions is a critically important skill for leaders. Questions determine the answer, and the course of a conversation. The moment a question is asked, the entire course of events can change. A well worded question is truly THAT powerful.

Questions can open up meaningful dialogue, or they can close up responders behind a wall of fear and self-preservation. How we ask questions is nearly as important as the questions themselves, but the best place to begin a conversation about communication between leaders and members of their team is with the questions themselves.

Here are ten with which to start, in no particular order:

1. How are you doing?
2. What do you need to help you succeed?
3. What will get us where we need to go?
4. How can I help?
5. How can I be of better support to you?
6. What do you think about…?
7. Do you have some time?
8. Where do you see yourself in five years?
9. When should we meet again?
10. Who should we invite next time?

There are perhaps many good questions leaders ask of their teammates each and every day. The starter list above could easily be replaced with ten others. These ten, however, represent the ten that have served me well over the last eighteen years as a senior leader. They solicit open conversation, deter quick “yes/no” responses, and maintain meaningful communication channels with the team.

Next steps: make an effort to engage each member of your team over the next few days. As the opportunity presents itself, and it will, begin with one or more of the questions above, and allow the conversation to deepen and grow. I think you’ll be pleased, surprised, and thankful you did.

What questions do you find most helpful when engaging your team? I would be very curious to hear some of your suggestions. Share them below and THANK YOU for doing so.

JoseCruzJrJosé Cruz, Jr. is a leadership consultant, master trainer, and executive coach with two decades of senior leadership experience in American higher education. Follow José on twitter:@JoseCruzJr, email him at, or visit him and the rest of the team at



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2 thoughts on “10 Questions Great Leaders Ask Their Teams”

  1. Pam Smith says:

    Just finished with an employee who was double-minded on an issue (heart vs. procedure) and wanted to know my thoughts. I asked: “What are YOUR thoughts?” which helped her to land on a solution. When I repeated the solution back to her, she nodded and said “Okay….” I have learned that “okay” can mean “I’m settling.” I then asked, “How do you feel about that solution?” which opened up a deeper level of thought. The outcome: the issue will be resolved well with an understanding of the importance of procedure.

    1. Bob Tiede says:

      Great Questions Pam – reflecting Great Wisdom! Thanks for sharing.

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