Developing the skill of asking high-quality questions derives from being genuinely curious in what the other person is saying.  The more engaged you are in the conversation and the better you leverage active listening, that’s when the high-quality questions will arise.

Why are high-quality questions so powerful? It does the following:

  • Removes ego by not providing our “expertise”
  • Fosters independence
  • Increases problem solving skills
  • Activates learning mode
  • Generates more “ah-ha” moments
  • Better questions lead to better answers and insights
  • Influences a growth mindset
  • Creates opportunities for us to learn

It helps immensely to go into conversations with confidence knowing that high-quality questions will come to mind.  In order to achieve this, preparation is required.  As we know, preparation breeds confidence.

The best leaders that I’ve met and studied have the ability to ask high-quality, open ended questions that reveal the information needed for maximum benefit to the relationship between the team member and the leader.

Let’s look at four areas with high-quality questions to ask in each.


With these three questions that can’t be answered yes or no, you can discover what motivates your team members.

Question 1: “What are the top 3 challenges you face right now? What about your top opportunities?”

Question 2: “What is the biggest improvement you’d like to make in your life right now and what would it be worth to you to make that happen?”

Question 3: “What are you passionate about pursuing (achievement), what makes you feel fulfilled in life (purpose), what would you say are your top 3 core values and on a scale of 1 – 10 how aligned are you with them?”

Understanding what motivates someone can help you tailor your leadership to better resonate, achieving the results you need. 

Future Pacing

Do you know what each of your team members is hoping to accomplish and what they’re striving for?  Getting someone to consider how today integrates into their future is critical for a leader.

Question 1: Imagine the feeling of not having to live paycheck to paycheck, having the financial freedom to buy the clothes you desire, going out to nice restaurants, paying for your parents to go on a vacation, and retiring early.  What would that mean to you? What are the commitments you must make right now to continuously progress towards that ideal life?”

Question 2: “If we were having a discussion 3 years from today, looking back at your experience, both personally and professionally, what has to happen in your life for you to be happy with your progress?”

Question 3: “Step out three months into the future and realize the compounding effect of the improvements you have created starting right now. What do you notice out at this point? What is different? What kinds of results are you creating in your life now?”


It can be uncomfortable to ask about someone’s obstacles because it often points to deficiencies in you, their leader. But it’s important to ask, gaining a clear understanding of the full picture.

Question 1: “What do you need that you don’t currently have to reach this milestone?”

Question 2: “What resources could you tap into to overcome this obstacle? Or is there a way for you to become more resourceful if you don’t have the resources?”

Question 3: “How have you overcome obstacles like this in similar situations in the past?”


As leaders the goal is to make people better by guiding them to self-improvement. That requires questions that can be tough to answer but ultimately inspire reflection and transformation.

Question 1: “When we face great adversity, we are either broken by it, survive it, or it becomes a defining moment. What response would make this a defining moment for you?

Question 2: “What could improve about you that would improve your situation?”

Question 3: “Let’s assume that this situation is custom designed for your inner growth as a leader and a person.  If that’s true, what’s the opportunity here?”

Accepting what you can’t change

If there’s a possibility that a concern or problem doesn’t have a resolution, it can be difficult for some to grapple with. These three questions can help guide team members through.

Question 1: “What would need to improve in your attitude or response for you to function at your best in the midst of this, even if the circumstances don’t get better?”

Question 2: “If you can’t change this, how can you make your peace with it?”

Question 3: “How could this moment become a defining moment for you, where you rise up and engage it out of what you were made to be?”

Final thought

Having a go-to question or set of questions is key to developing your confidence in presenting certain questions in specific situations.

One of my favorites is, “on a scale of one to ten.”

  • On a scale of 1 – 10 how close do you feel you are to your potential?
  • On a scale of 1 – 10 how proud are you of your effort?
  • On a scale of 1 – 10 where is your energy level?

If it’s anything less than a 10, ask them what must happen to make it a 10 and offer to support them on getting there. This is a great way to finish a meeting off when you’re striving to implement real action and accountability between today’s meeting and the next one.

The power of transformation lies in the quality of conversations we have.  By combining active listening with high-quality questions, we are able to help create more impactful transformations.

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