Do You Ask Enough Of The Right Questions?

This is the sixth in a series of 12 articles on leadership issues and the characteristics of successful leaders. Join us on a journey to become a more fearless leader. (To start at the beginning of the series, click here.)

Powerful, reflective questions lead to potent and productive answers.

Questions open our world to possibilities, expand our perspectives, and help us understand ourselves and each other with greater clarity. Questions and reflection challenge us to dig deeply into our psyches to uncover what truly matters to us.

People who don’t ask questions remain clueless throughout their lives. –Neil deGrasse Tyson

In the first article on courage, we noted that looking for answers is the opposite of what we should be doing. Imagine how your leadership could thrive if you were looking for the right questions.

The art of questioning is the path to smart decisions. 

We humans spend much of our time on automatic pilot. To offset that, it is essential that we ask questions to make sense of the world and our place in it. It takes fearlessness to truly embrace the power of questions, as they lead to insights that can accelerate change.

  1. How well do I model the desired culture and values of my organization?
  2. Am I focused on the right outcomes?

Questions Build Your Leadership Muscles

How do you continually develop your leadership muscles? You start by tapping into your core strengths, who you are and what you stand for. You ask questions of yourself and others to become self-aware, to support decision making and to build connection.

As a leader, you are responsible for the quality of your communication. You actively build trust and loyalty with team members so you can rely on their support when it is needed. You push yourself and your team to make sure everyone is focused to reach your objectives.

And you ask powerful, open-ended questions that uncover the uncertainty, false perceptions, and unconscious bias that impede high-quality decision making.

Open-ended questions can’t be answered with yes or no. Coming from a mindset of curiosity, you can use these kinds of questions to test your understanding of the another person’s meaning, to probe how they arrived at their views, to be inclusive, and to promote action.

Knowing the answers will help you in school, but knowing how to question will help you in life. –Warren Berger, A More Beautiful Question

Open-ended questions broaden the playing field and encourage others to challenge your views and perspectives.

The right questions create an openness to possibilities and to others’ perspectives.

Your questions can spur your team be more creative and explore alternative actions and ideas.

Try asking of your team members:

  1. If we had endless resources, what would you most want to accomplish?
  2. What obstacles would be in your way, and how would you overcome them?
  3. Do you see something differently that I am missing?

Asking open-ended questions may take time and effort, but doing so builds trusting relationships and provides vital information for sound, collaborative decision making. You may have times when you want to give up lifting the heavy weights, but with determination and open-ended questions, you can pull one more time and rise to the occasion!

Questions Are Disruptive—And a Foundation For Growth

Questions are at the heart of every decision you’ve taken, even if you don’t realize it. Questions generate fresh ideas that identify opportunities for growth and impact your career and personal life. Change begins with questions.

No matter how knowledgeable you are about good leadership, there is always more to be learned.

Asking questions stimulates your curiosity, a key ingredient of learning and development. Coming from a curious mindset expands your understanding and offers the possibilities of continual learning.

Questions help uncover the layers of what is most important to you and your leadership, and will ultimately unlock areas where you need to grow.

  1. Do I consistently follow through on things I say I will do?
  2. Do I listen fully and communicate clearly? Are others comfortable asking me questions?

Questions Are An Opportunity For Self-Awareness

We all have areas where we know we can be better. Questioning what is and is not working in your life begins your personal change process. Asking yourself the difficult questions demands the necessary work of changing to be the best version of yourself.

These kinds of questions often focus on the negative, because we can be our own worst critics! Use these questions to stir the pot, to get you thinking deeply about what runs your life. There are no easy answers.

Reflect on your answers, feel how they resonate. You may feel uncomfortable or may step into long-held realities that have scared you.

  1. What do I dislike about myself? About my life?
  2. What do I need to do/think/be in order to change this attitude/habit/etc.?

We all have dimensions of our lives we don’t like: careers, relationships, our bodies, etc. We all have things that keep us in denial. We may not show our true selves because we fear being exposed and vulnerable. When you bump up against fear, you can question it.

When you examine the stories that you believe define you, try actively questioning their verity and their current relevance.

Questions are an opportunity to open the door to change. They reveal underlying truths that will help shift your thinking. Identifying these areas allows you to create goals and strategies that lead in the direction you truly want to go.

Live the questions now. Perhaps then, someday far into the future, you will gradually, without even noticing it, live your way into the answer.–Rainier Maria Rilke, poet

Discomfort Is The Nature Of Growth

Questions can challenge your assumptions and make you uncomfortable.

I’ve been an explorer and a seeker of truth and knowledge most of my life. I always wanted to understand the deeper questions of our existence and the truth about others. I have not always been self-directed, but I have been motivated to live an independent existence filled with diverse experiences.

For every transition and reinvention in my life (and there have been plenty of them!), I’ve had to face the hard questions about what I needed to do differently, and make the decision to change. This has defined my life in ways that I never could have predicted. Because I persisted in finding the truth of who I am and who I want to be, questioning has made a better me.

Try these five deceptively simple questions to get started:

  1. Who am I when I am at my best? In what circumstances am I most myself?
  2. Am I overly concerned with being liked? What is that about?
  3. What are my superpowers and how do I apply them?
  4. What portion of my time is spent in self-reflection?
  5. In the best possible scenario, who will I be five years from now?

Finally, take a moment to consider why you are asking these key questions.

When you begin finding some answers, the ultimate definitive question to ask: Why does this matter to me?

Genuine Questions Move You Toward Positive Opportunities

  1. How do I feel when my goals and aspirations and my work effort don’t match?
  2. What one thing can I do to change that?
  3. What can I do that will maximize my strengths?
  4. What would I would be willing to put everything on the line for?
  5. What do I most value in my life? Why?

I believe that great opportunities come when you push yourself beyond your comfort level. 

When you encounter an opportunity, take it!

You may not know where your questions or ideas will take you, but that’s part of the adventure to accelerate your leadership success. With a clear vision, a strong sense of values and purpose, and consistent action, the results may surprise you.


Jacqueline Wales is a motivational speaker, coach, and the author of The Fearless Factor @ Work, The Fearless Factor and other books. She believes in the power of fearlessness for creating the career and life you want.

I’d love to hear your comments and am happy to answer your questions!


Scroll to Top