10 Questions Your Team is Afraid to Ask

10 Questions Your Team Is Afraid to Ask

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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Posted in Authenticity & Transparency, Communication and tagged , , , , , .

Karin Hurt

Karin Hurt, Founder of Let’s Grow Leaders, helps leaders around the world achieve breakthrough results, without losing their soul. A former Verizon Wireless executive, she has over two decades of experience in sales, customer service, and HR. She was named on Inc's list of 100 Great Leadership Speakers and American Management Association's 50 Leaders to Watch. She’s the author of several books: Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates (Harper Collins Summer 2020), Winning Well: A Manager's Guide to Getting Results-Without Losing Your Soul, Overcoming an Imperfect Boss, and Glowstone Peak.


  1. Karin,

    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.


  2. 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.

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

  3. 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!)

    • 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.

  4. 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!

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

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