October 9, 2018

Harnessing Your Superpower(-ful Questions)

Alison Hovind

What’s more powerful than the perfect answer? A well constructed and delivered question. Questions can empower employees, guide conversations, and help discover hidden issues.  There’s at least one thing in common between top consultants, coaches, and leaders; they have powerful questions in their toolbox and they know how to use them.

According to a Harvard Business Review Survey, 71% of Senior Managers said “meetings are unproductive and inefficient”, 64% said “meetings come at the expense of deep thinking”, and 62% said “meetings miss the opportunity to bring the team closer together.” Let’s look at how we at The Wilshire Group construct and deliver powerful questions to avoid this trap.


  • Simple: As with most things, questions are best kept simple.  They should not be led with a story, be strung together, or be confusing.  Asking a short and simple question that is to the point will often lead to a more powerful answer.
    • Example, “What is the action plan?” is much better than, “So you said that you reviewed XYZ, and think there’s problems with ABC, do you have an action plan to address them and what are your next steps? The other department said they had a similar issue, do you know about that? Is that incorporated in…?”
  • Open-ended: When we are trying to engage, dig deeper, or help guide others to their own insights, we should keep our questions open-ended.  These are the kind that cause a pause, a brief moment of thought, and can’t be answered with a single word. Get the other person talking, sometimes insights require verbal momentum.
    • Example, “What about the new project excites you?” is much more powerful than “Are you enjoying the new project?”
  • What or how, not why:  When in doubt start your questions with what or how.  These two words usually lead to better answers without triggering defensiveness.
    • Example, asking “What may have contributed to the issue?” or “How could the issue have been prevented?” carries a much different tone than asking, “Why did the issue happen?” This creates a safe space for the individual to open up, explore answers, and speak truthfully.

Some examples of powerfully constructed questions:

What do you think is best?

What is the challenge?

How do you suppose you can find out more about it?

What do you plan to do about it?

What was the lesson?

How can I help?


  • Invite clarity, action, and discovery: Questions should be in service to the individual and/or issue. Because questions are powerful it is easy to use them inappropriately such as leading, interrogating, or demonstrating knowledge. This can break trust and rapport, or even cause embarrassment and should be avoided. Powerful questions should aim to bring out the brilliance of another.
  • Follow the energy or tonality: People are rarely aware of, or communicate, the root truth right off the bat.  Situations and issues are often complicated and interconnected. It usually requires that we ask a series of questions to get to the bottom of something. One method is to follow the speaker’s energy or vocal tonality.  Large dips or spikes in either usually indicate something else is there (most likely unconscious to the speaker) and may be a place to dig deeper. This requires what some refer to as level 2 and 3 listening skills, which we will cover in a later post.

How can you use powerful questions to increase your effectiveness? The best organizational leaders not only guide and hold others accountable, but also help them reach their highest potential.  They aren’t always the expert in the room, however they are excellent at asking powerful questions. In doing so, they have the potential to transform an individual, a meeting, or an entire organization.

We at The Wilshire Group utilize these strategies to increase meeting effectiveness and overall project outcomes, and offer this as thought leadership for your organization.  Let us know if we can be of any assistance, we’d love to hear from you.

Alison Hovind

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