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a big mistake leaders make when answering questions

A Big Mistake Leaders Make When Answering Questions

by | Nov 11, 2019 | By David Dye, Winning Well |

The wind shifted, the mainsail swung over the boat, and the deck leaned until I found myself staring at water where the horizon used to be. It looked like we were all going to get wet – but I was actually about to receive a leadership lesson in answering questions.

The skipper called out instructions: “David trim the jib … more tension!”

I grabbed the winch handle and began to crank clockwise, hoping to feel tension.


The line moved, but I wasn’t sure if it was enough.

I cranked it the other direction, looked back at Patrick, our skipper, and asked, “Which way should I turn it?”

Patrick’s next words were a powerful leadership moment – but he didn’t answer my question.

At least, not the one I had put into words.

What’s the Real Question?

You might wonder what I was doing controlling tension on the sail when I wasn’t sure how to do it. Hadn’t I been trained?

The answer is yes, but …

I had the privilege of sailing in the San Diego Harbor with several of my colleagues, including our skipper, Patrick Maurer.

Before we left shore Patrick oriented us to the sailboat, explained the vocabulary, gave us instructions and ran us through the roles we could play.  I sat next to the winch that managed tension on the front sail (the jib).

Before we left the dock, he was very clear about how everything operated … especially the winch.

He’d even spelled out the answer to the question I would ask later as the boat leaned precariously: you could turn the winch in either direction.

So I “knew” I could turn it either way–what was it I really wanted to know?

With the boat leaning and seven other passengers counting on me to tighten that line, what I really wanted to know is the same thing your team members often want to know when you’re answering questions:

  • “Am I doing this right?”
  • “Am I going to be okay?”
  • “What do you really want from me?”

Answering Questions

When your team comes to you and asks, “What should I do?” they’re often asking something much deeper. The big mistake leaders make when answering questions is that they answer the immediate question without looking at what’s beneath it.

That’s a mistake because the deeper question reveals an opportunity for your team members to grow. Answer that deeper question and you will build confidence in your people, grow their skills, and free up more of your time.

But if you only answer the question they ask, you can undermine their confidence, keep them dependent on you, and find yourself answering questions all day long with no time for your own work.

Don’t give the answer they want and neglect the answer they need.

If you’re like many leaders, when a team member asks a question for which you know they’ve received training, it can be frustrating.

You might think, “They know this! Why are they wasting my time?”

I would invite you to look a little deeper. In a very short time, you can give them what they need and grow a stronger, more productive team member.

How to Answer the Right Question

When I looked back over my shoulder and asked, “Which way should I turn it?” Patrick calmly, but firmly, answered back, “You can turn it either direction. One way is easier, one way is faster.”

Notice something?

He didn’t answer the question I asked …

I wanted something straightforward: right or left … just tell me!

But he didn’t. Instead, he used a leadership coaching technique called “reducing ambiguity.”

He gave me information that I could use to make my own decision.

(Given that we were tipping over and I was looking down at the water, I chose the ‘faster but harder’ option.)

His words answered my underlying question: “What do you want me to do?” while also giving me the ability to make that decision for myself next time.

From now on, Patrick could spend his time on other aspects of running the sailboat.

And there was something else …

Besides the words he spoke, there was the way he spoke them. Calm. Firm.

His tone answered my other underlying questions: Am I going to be okay? Am I doing this right?

His tone said, “Yes.”

What does your tone say to your team?

Your Turn

When you’re answering questions, spend enough time to figure out what they really need. How do you make sure your team gets answers to their real questions?

You might also like:

9 Questions to Help Your Team Solve Problems on Their Own

The Best Way to Help Employees Have More Confidence

Photos by Craig Price

Want more human-centered leaders in the workplace? Share this today!

Want more human-centered leaders in the workplace? Share this today!


  1. Bhupinder Gogia

    An excellent technique….I shall try experimenting it.

    • David Dye

      Thank you Bhupinder,
      Glad to hear you will try it. Let us know your results.

  2. Billy Ruct

    I was left confused by this article, until I spent 30 minutes researching sailboat jib trimming. Most hand cranked winches (not sailboat winches) tighten and loosen based on the direction the crank is turned. Apparently the winches for the jib (one on each side of the boat) only move one direction to tighten. The internal gearing makes it tighten fast or slow based on the direction the crank is turned. The article is great once this is understood. Kind regards!

    • David Dye

      Thanks for the added information Billy! Glad it was helpful with that addition.



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David Dye helps human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results.  He’s the President of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. He’s the award-winning authors of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and and Powerful Phrases for Dealing with Workplace Conflict, and hosts the popular Leadership without Losing Your Soul podcast. David is a former executive and elected official. David and his wife and business partner, Karin Hurt, are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

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