Speaking of Leadership – 5 Questions that Clarify

When I pause to observe my day I notice that almost every interaction with my team either presents or invites a question.

Am I right?

Everything we do in leadership is formed around questions and our effectiveness is determined by the methods we use to reach the answers.


All loaded with questions.

And yet our first temptation is to tell rather than ask.

It’s very easy to drift into telling. Frankly, it feels easier. Why spend the energy when we can just state the answer as we see it and be done? Give in to this temptation enough times and it quickly becomes a bad habit.

Telling isn’t always the wrong choice but it should not be our default.

The temptation to tell comes from the old paradigm that leaders must know, (or at least pretend to know), the answers. Or from the fear that this person or group might not come up with what we think is the right answer.

“If you want something done right you have to do it yourself”.

Then there is the constant pressure to keep things moving. In the moment, it seems more productive to tell someone what to do rather than spend time working through a series of questions or investing in dialogue.

Don’t listen to these stories. They rarely lead to a happy ending.

Want better outcomes? Ask better questions.

Some leaders play at questions, feigning curiosity but never going below the surface. That’s just manipulation. A useless game that still ends with telling. Eventually, people figure out that the answers don’t really matter, get discouraged and stop playing.

Better questions expand the story.

They challenge our minds and nudge us out of our comfort zone. Sometimes they push the limits of our creativity and candor, taking the plot in a new direction, inviting us to play a different role. 

Better questions expose the layers.

They don’t lend to yes or no responses. They generate more and better questions. They might even confuse before they clarify. That’s why we use the metaphor of wrestling. Good questions involve us in a struggle.

Better questions challenge the leader, not just the team.

Tackling tough questions and the answers they generate is important to our growth as leaders. We can’t stay in the shallow end of the pool forever. Eventually, we must learn how to swim.

Better questions require mindfulness.

To ask better questions we must be aware of the opportunities and focused on learning not just doing. We need the mind of a teacher whose desire for her or his students is that they learn to think, not just recite.

Here’s a better question starter kit:

  • Do we understand the problem?
    Oh, the countless hours spent treating the symptoms. Yes, this is fundamental but so often this question never gets answered.
  • What outcome do we want?
    Funny how often we start solving without defining success. The desired outcome will inspire the right questions.
  • What else is possible?
    Invite different points of view. Cut through the easy answers and obvious solutions. This is one of my favorites.
  • How do you see this?
    Seeing invites perspective and creativity. It suggests a different type of inquiry than “what do you think?”.
  • What did you learn?
    “What went wrong”, leads to deflecting instead of reflecting. You should also ask this question when the outcome is a success.

Bonus question:

  • Why not now?
    The right question can open the door to action. There will always be reasons to wait, let’s focus on reasons to start.

Most of us have experienced working for or with someone who asked great questions. Questions that helped us learn and grow. Maybe it was an inspiring teacher during our school years or a mentor or friend we met later in our journey.

You are invited to share your stories and the questions you’ve found valuable in the comment section below. This is your opportunity to pay it forward.

Questions are powerful. You never know how a single question might alter the direction of an organization or a life.


  1. Dear Scott,

    Can we really afford to not follow our passion and purpose before we leave this planet earth? Life is really too short. Do it NOW! Act now!

    Thank you Scott for your inspirations everyday!


  2. I was almost 40 when I met the mentor who forever changed my life. She not only taught me the value of listening but also modeled it and, therefore, taught me to be a better listener. Her questions, after thoroughly listening to the person, was “what do you really want” or “what are you really asking?” Funny how simple these questions are, yet how relevant they are in most situations and how much they reveal. Very often, we do not initially ask for what we really want or say what we really mean. If you catch that and ask the obvious question, you reveal that you really are listening and that you really want to help.


    1. I love that questions, “what do you really want?”. Very powerful to ask oneself, especially in the midst of a difficult conversation or conflict. Thanks so much for sharing


  3. A great article Scott. I am addicted to the asking questions approach and often say that one can lead by asking questions…. From Darrel in Johannesburg SA.


    1. Great point Darrel – one might say that the person asking the right questions is really the leader. Thanks for stopping by and sharing your thoughts.


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