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Karin And David’s Leadership Articles

If you want better insights, ask clearer questions.

Particularly during times of uncertainty and change, one of the easiest ways to know what’s really going on is to (1) get clarity about what you don’t know and (2) ask your team some courageous questions.

Courageous questions are specific, vulnerable questions that get right to the root of the matter. Courageous questions help eliminate FOSU (fear of speaking up) and create the psychological safety your employees need to speak up and ask for what they need.

In this article, we share insights to help you prepare better courageous questions to gather the insights you need.

Why Courageous Questions Matter

Laura, an IT vice president, was excited to spend some time with her teams, hold a few skip-level meetings, and see their new system in action.

Her team had been holding user experience calls each week and the feedback had been great! Psyched to gather a few success stories, she couldn’t wait to tell the CEO how the new system was making things easier for the customer service reps and, ultimately, for their customers.

Before her first skip-level meeting, Laura sat down with a rep and asked, “Can you show me your favorite part of the new system?”

The rep attempted to pull up the first screen. But after five minutes they were both still staring at an hourglass and waiting for the page to load. She looked apologetically at Laura and said, “I’m sorry to waste your time. This usually takes a while.”

Laura’s jaw dropped. The vendor had promised the new system would be seven times faster—not slower.

Wait, What?

“Can you show me another page?” Laura asked.

She sat through another slow load time. Laura turned to the rep. “Is it always like this?”

“Oh, yeah. We’re used to it at this point, but the system has some other nice features.”

Laura thanked her and hurried to a quiet conference room where she could call her team. After ten minutes of testing, they realized that the center’s servers didn’t have the capacity to run the new system. Hundreds of reps had been suffering through a ridiculous wait that wasted their and their customers’ time.

What happened?

The user experience calls had asked lots of questions, but not courageous questions.

Week after week, supervisors had sat in on user-experience calls, fully aware of the issue, and hadn’t said a word. No one had ever raised the issue!

After replacing the server and ensuring everything was back on track, Laura went back to the reps on the user experience team and asked why they had never brought this up.

courageous questions incubate great ideasWell, no one ever asked us about the speed. Our boss told us that we needed to be “change agents” and model excitement for the new system—no matter what. Under no circumstances were we to be negative.

So we just smiled, sucked it up, and dealt with it.

Have you ever felt like Laura?

The “no one asked” reply might be frustrating, but it is one of the biggest reasons employees say they withhold ideas.

Before you dive into this reflective article, download our free I.D.E.A. Incubator Guide. This is your free guide to a power-packed team innovation session that will mobilize courage and increase team engagement.

What is a courageous question?

A courageous question differs from a generic “How can we be better?” question in that they’re specific and humble (assume that improvement is possible).  You ask courageous questions to get curious about what’s really going on. Not to respond immediately.

When you ask a courageous question, you:

1. Get specific.

A courageous question focuses on a specific activity, behavior, or outcome.

For example, rather than ask “How can we improve?” ask “What is the number one frustration of our largest customer?”

Or, “For the next two quarters, our most important priority is customer retention. We need every idea we can get to help keep our best customers. What is THE NUMBER ONE REASON you see customers leave? What’s THE GREATEST OBSTACLE to keep our best customers? What’s NUMBER ONE LOW-COST ACTION we can take to improve our customer’s experience?”

2. Be humble.

Next, a courageous question creates powerful vulnerability.

When you ask any of these sample questions, you are implicitly saying “I know I’m not perfect. I know I can improve.” This is a strong message—if you sincerely mean it.

You send the message that you are growing and want to improve. This, in turn, gives your team permission to grow and be in the process themselves. It also makes it safe to share real feedback. When you say, “What is the greatest obstacle?” you acknowledge that there is an obstacle, and you want to hear about it.

Humility is at the heart of the question that Don Yager, Chief Operating Officer of Mural Corporation, consistently asks his frontline team: “What are our policies that suck?” That humble question quickly identifies anything that’s getting in the way of a great customer experience.

3. Process before responding.

Finally, courageous questions require the asker to listen without defensiveness. This is where well-intentioned leaders often get into trouble. They ask a good question, but they weren’t prepared to hear feedback that made them uncomfortable or challenged their pet project. They leap to explain or defend.

Asking for feedback and ignoring it is worse than not asking at all. When you ask a courageous question, allow yourself to take in the feedback. Take notes, thank everyone for taking the time and having the confidence to share their perspective. With many courageous questions, you’ll get conflicting perspectives. That’s okay. Describe the next steps.

If you need to process and then respond, tell them when that will happen.

sample courageous questions

Click to download courageous questions samples, and write your own!

Sample Courageous Questions

You can download our Courageous Cultures tool for FREE here. 

Courageous Questions to Improve The Customer Experience

  • What’s one policy that really annoys our customers?
  • If you could make one change to improve the customer experience, what would that be?
  • When customers call, what’s their number one complaint?
  • What is the most important action we take to delight our customers? How would you recommend we do that more consistently?

Courageous Questions to Improve Productivity

  • What is the biggest roadblock to your productivity right now?
  • When you think of missed opportunities to be more effective or efficient, what’s the problem no one talks about?
  • If we could do one thing differently next time to help this project (or person) succeed, what would that be?
  • What’s one task or project you’re spending time on that you think is not worth the time? Why?
  • Do you have a best practice that really helps you be more efficient and effective in your work? What is it?

Courageous Questions to Improve Culture

  • What is the biggest source of conflict you’re having working with X department? (How might we be contributing to the issue?)
  • We’re working to build a courageous culture where everyone speaks up and shares their ideas. As your leader, what’s one area of my leadership I could work on to make that easier?
  • What’s one reason you choose to work here?  How can we build more of that into our culture?
  • What’s one reason people hold back their ideas here?
  • Can you think of one practical idea that would help our team find more joy and meaning in their work?

And don’t forget to Respond With Regard.

Once you’ve asked your team courageous questions, gather your themes and be sure you respond with regard.

when employees answer courageous questions respond with regard

The first time you ask a courageous question, your team may be skeptical. But when you build a reputation of asking important courageous questions and responding with regard to what you hear, you’ll go a long way in building trust, and innovation on your team.

We would love to hear from you.

Where do you most need a great idea? What is one courageous question that would (or has) encouraged deeper thinking, problem-solving and great ideas?

Ready to rally YOUR team for breakthrough results with Let’s Grow Leaders?

Establish a Courageous Culture of critical thinkers, problem solvers and customer advocates in your organization with live leadership training and a Team Innovation Challenge or Executive Leadership Workshop. These strategic innovation events – in person or virtual – will help shape the culture of your organization, skyrocket employee engagement and clear the path for increased team innovation.

Let’s Grow Leaders programs are highly customized to your organization’s needs, hands-on and interactive. Get ready for leadership development that sticks.

Innovation and Results

Other Articles Related to Courageous Questions:

How to Help Your Team Think Bigger

How to Respond to Employees’ Wacky Ideas

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

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


  1. Diane Kissel

    Love this article!

    • David Dye

      Thanks Diane – glad it is helpful!


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Karin Hurt and David Dye

Karin Hurt and David Dye help human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results. As CEO and President of Let’s Grow Leaders, they are known for practical tools and leadership development programs that stick. Karin and David are the award-winning authors of five books including, Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Powerful Phrases for Dealing with Workplace Conflict. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. David Dye is a former executive and elected official. Karin and David are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

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7 Practical Ways to be a Bit More Daring

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