How to Have a Difficult Conversation

When I ask leaders why they’re not telling people what they need to know, the most consistent response I get is “She or he didn’t ask.”

Quite frankly that’s a cop-out.

Yeah sure–ideally everyone would be ASKING for feedback.

If you’re not asking, start asking now. It may be the only thing standing between you and the truth.

But, if you’re the one not giving feedback, think again before holding back.

Your Team Needs You to Tell Them the Truth

You team needs to hear what you don’t want to say. The difficult conversations are almost always often the most important.

“You’re consistently not getting promoted because….”

“When you start an email that way…”

“If you bathed more…”

“Wearing those Google glasses all day long (including at the elegant dinner party) isn’t helping your brand…”

Confident, humble leaders have difficult conversations because…

  • they care so deeply
  • they want people to grow
  • they know it’s not about them
  • they care more about helping than protecting themselves.

Lessons From The Discomfort Zone

I spoke with Marcia Reynold’s about her new book, The Discomfort Zone:  How Leaders Turn Difficult Conversations into Breakthroughs and asked her for her best advice for leaders having difficult conversations with the people they lead. Here are a few of her tips.

  • Step back and consider, “What does this person really need from me?”
  • Know that your job is not to just develop skills, but develop minds. Ask difficult questions that really make them think.
  • Know that this will be uncomfortable and that there may be an initial negative reaction. That doesn’t mean you aren’t helping, or they won’t be grateful later.
  • If they get emotional, be quiet. Let them experience and breathe through that emotion. Know that’s all part of the process.
  • If you’re trying to help someone get unstuck, ask
    • What’s the worse thing that can happen if you do ____?
    • What’ s the likelihood that could happen?
    • How is that worse than what’s happening now?

She adds, “For true shifts in thinking and behavior to occur, you must be willing to challenge a person’s beliefs, interrupt his patterns, and short-circuit the conviction to his logic even when it feels uncomfortable.  This is a Discomfort Zone conversation.”

Posted in Authenticity & Transparency, Career & Learning and tagged , , .

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. Another component to consider is WHEN to provide feedback or have a difficult conversation. If I just came in from the rain & my coat and pants are soaking wet & my cat was up all night throwing up & I need to call the help desk to fix something on the computer … this might not be the best time to approach me with potentially difficult feedback. Advice I heard during years of partner therapy: ask if this is a good time to talk. “I would talk with you about some feedback I’ve received. Is this a good time to talk?” If not, choose a best time together. Then you’ll have that person at their best.

    • David, Such a very important point. I’ve learned this one the hard way. Thanks for enhancing the list.

    • I agree David. I think these should be private conversations, not public. And when the leaders asks for a good time to talk that day, he or she should says, “There are some things I want to help you with” instead of saying they heard bad things they want to share.

  2. Marcia is a colleague and she’s brilliant. I have her new book coming this week.

    I’ve interviewed her before. Time to get her back on my show.

    Leaders need to be overly curious about their followers. Curiosity leads to a wider avenue and number of possibilities and solutions.

  3. I also know Marcia and she is fabulous. What I like about her book is the fact that she asks us to look at difficult conversations from the perspective of the other person. This is a real addition to the body of conversation literature.

    I have also found that leaders will avoid the difficult conversation because of their fear of the unknown. I like to refer to fear as an acronym for “Fantasized Experience Appearing Real.” Unfortunately we usually allow our thinking to keep us from talking about what matters most. You are absolutely right. We can’t expect things to change if we don’t speak up. Marcia provides some wonderful tools for adding comfort to the “The Discomfort Zone.”

  4. I’m looking forward to reading this book, Karin.

    Difficult conversations require trust if we’re going to push them into the discomfort zone. I’ve known several people with whom I’ve had difficult conversations, and while we may not have liked each other, we could not have moved forward if we hadn’t trusted each other…

    Great article!

    • Larae, So agree. Trust is vital. No one can hear feedback if they’re too busy questioning your motives.

  5. Karin, this was such a perfect posting for me to read this morning. I have been struggling with the concept of courageous leadership recently. The reason being that I’m working on developing a presentation to help teach supervisors and managers to be more courageous in their leadership, yet I sometimes feel like an “imposter” to teach this. I’ve been admonished in the past that shied away from those difficult conversations, or sugar-coated a conversation, so I’m not role model for courage. That said, I appreciate the notion that we are truly helping others by telling them what they need to hear.

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