Karin’s Leadership Articles

Your team has questions they’re afraid to ask. They’ve got limited information, but they figure if you wanted to tell them you would.

They worry that raising the issue will look like insubordination, or somehow make them look less in your eyes. Maybe you can share, maybe you can’t. But that doesn’t make the questions go away.

If you want to build trust and connection, anticipate the questions on their mind and start the conversation. I’ve been asking around for input into one simple question “What question would you most like to ask your leadership (but are afraid to). And this question is at the heart of my Asking For a Friend Vlog.  Here are the top 10. Please add yours.

10 Questions Your Teams Afraid to Ask

  1. Why are we doing it this way?
  2. How’s our company really doing?
  3. Why didn’t you ask us?
  4. Why is _____________ not dealt with?
  5. If I speak up, will it hurt my brand?
  6. Do you think I’m ready for a promotion?
  7. Why is there so much turnover?
  8. How can we get past this feeling of constant crises?
  9. Is this really as urgent as you’re making it out to be?
  10.  ________________________ (what’s your #10?)

Conversation Starters

If you want your team to ask more of their scary questions, here are a few ways you can start the conversation.

  • If I were you, I might be wondering…
  • The last time something like this happened I had a lot of questions such as __________
  • I just read this blog post about questions your team’s afraid to ask, and it made me wonder, what questions do you have that I might be able to answer 😉

Ignoring the tough questions doesn’t make them go away. In fact, your team is likely asking the questions, to themselves and to one another. Tackling the tough conversations head on will go a long way in building trust and respect on your team.

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Karin Hurt

Karin Hurt helps human-centered leaders resolve workplace ambiguity and chaos, so that they can drive innovation, productivity and revenue without burning out employees. She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. She’s the award-winning author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Winning Well: A Manager’s Guide to Getting Results-Without Losing Your Soul and a hosts the popular Asking For a Friend Vlog on LinkedIn. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. Karin and her husband and business partner, David Dye, are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.


  1. Steve Borek

    Leader, why aren’t you doing what you said you would do?

    • Karin Hurt

      Steve, That’s a great one.

  2. Jon Mertz


    Great questions to ask that many may be afraid to ask. One to add is “What more should I be doing to be a stronger leader, and what will you do to guide me?” Asking this question takes guts, and it takes guts to answer it honestly. Both need to engage and have honest conversations to strengthen leadership skills of both.


    • Karin Hurt

      Jon, Great add. That could lead to such an important exchange.

  3. Terri Klass

    Outstanding questions Karin and certainly worth asking! I would add: Would you mentor me to grow in this organization? or Would you be an advocate for me in finding opportunities that fit my talents and strengths? I think people need to feel they can turn to their leaders for real help and navigation. Millennials in particular might ask these questions.

    Thanks Karin for sharing some really important concerns when working on a team.

    • Karin Hurt

      Terri, I so agree. So often people are afraid to ask for help, when actually people would be delighted to support them.

  4. Alli Polin

    Great list and conversation starters, Karin! I’ll also add, “Can I have an opportunity to lead something?” I know many people that think that if they do great work and stay heads down their manager/boss/leader will notice and ask them to lead a special project. However, many of those special projects often go to the people who are willing to ask (and do great work too!)

    • Karin Hurt

      Alli, That’s a great one. The best way to learn leadership is by leading. Leaders love it when their team takes initiative. Just ask.

  5. LaRae Quy

    I love those conversation starters, Karin!

    I’ve used those very same questions to get folks started talking…it always helps to start a conversation with something like, “I had something similar happen to me” or “this is what I’d be wondering.” It allows the leader to share part of themselves, and people can relate…

    Thanks for the great post!

    • Karin Hurt

      LaRae, Thanks so much. Ahh yes, creating connection opens the conversation.

  6. Zic Info

    Thanks for sharing, this is amazing information keep it work.

    • Karin Hurt

      Thank you!

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