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courageous conversations

Let’s Talk About It: How to Have the Courageous Conversation You Would Rather Avoid

by | Aug 7, 2023 | By Karin Hurt and David Dye, powerful phrases |

“As a young manager, having not done well at leading, my team approached me and addressed what they saw needed to change. We had a respectful and open conversation about our needs and agreed on what each party needed to change. From there on the collaboration changed completely – not to perfect – but to very good. I am still grateful that they decided to trust me and be open about how they saw the situation!”

Male, 58, Denmark, World Workplace Conflict and Collaboration Survey

The Most Important Courageous Conversation is With Yourself

It can be tempting to avoid a courageous conversation at work. After all, it takes energy to initiate it, and you can’t predict exactly how it will go. That’s why so many people go for the diaper genie and wrap the conversation in so much self-protection that what they’re talking about has very little to do with what they really want to say.

Sure, sometimes it just feels easier to pretend everything’s good, avoid the negativity, keep the conversation light, and wait until you get home to vent to your dog.

And, much is lost when you can’t talk about what needs to be said. We often hear, “I wish I’d said something sooner,” when people finally muster the courage to have the conversation.

5 Questions to Ask Yourself to Start a Courageous Conversation

If you’re looking for the inspiration and tools to have a courageous conversation, here are five good questions to get you started.

1. “What do I want to happen because of what I say?”

This one might seem obvious, but a courageous conversation can be messy. You might want to say all the things. It’s helpful to start with why. When summoning the courage to have the conversation you’d rather avoid, one of the best things you can do is know specifically what you are looking to accomplish.

Get clear on your intention. Consider what you want the other person to think, feel, or do because of your conversation.

2. “Why does what I have to say matter?”

In addition to “what,” another important question is “why.”

Bernard Meltzer hosted a popular radio call-in show called “What’s Your Problem?” He summarized sage advice from many wisdom traditions this way: “Before you speak ask yourself if what you are going to say is true, is kind, is necessary, is helpful. If the answer is no, maybe what you are about to say should be left unsaid.”

That’s a good filter as you consider whether to start a courageous conversation. If what you have to say is true, kind, necessary, and helpful, then it matters.

Connect with that “why.”

3. “What’s preventing me from saying it?”

This is where you get in touch with your own fears and the story you’re telling yourself about what might happen.

Are you concerned about “last times?” Are you worried about the relationship? Understanding what’s holding you back can help form your message for your courageous conversation.

4. “What’s at stake if I stay silent?”

In our Courageous Cultures innovation programs, we’ll often ask participants to talk about one of their most “courageous moments” at work. You know what’s really interesting? In many cases, people tell us, “Well it didn’t feel particularly courageous at the time. It was just something I had to do.”

Those are people who understand the consequences of “safe silence.” Safe silence, isn’t really safe, because it comes at a cost.

Dr. Amy Edmondson,Courageous Conversation the pioneer of psychological safety, often talks about how people are more likely to discount the future benefits of speaking up and overweight their current fear.

When you ask yourself this powerful question, you consider the future and the risks of staying silent.

Martin Sheen shares this poignant Irish tale to emphasize that standing up for what you believe comes at a cost—but that it’s worth it.

A man arrives at the gates of heaven and asks to be let in. St. Peter says, “Of course, just show us your scars.”

The man says, “I have no scars”.

St. Peter replies, “What a pity. Was there nothing worth fighting for?”

When you’re nervous about starting the conversation, consider the long view. Are you the kind of person who cares enough to try?

5. “What’s the worst that can happen here?”

This Powerful Phrase can be strangely empowering. One of our clients, a US Marine veteran is fond of saying. “When I get too stressed about a workplace conflict, I just remember, no one is shooting at me.”

The worst that can happen is usually nowhere near as bad as your imagination suggests.

Powerful Phrases to Invite Others into the Conversation

After connecting with your intention, it’s time to start the conversation. Here are some phrases to begin the conversation with curiosity.

“I’m concerned that we might not be talking about _________. And my hunch is that’s because of _________. Here’s why I think we need to have the conversation anyway. What do you think?”

This technique can help get a courageous conversation started because when you don’t know for sure what’s causing the silence—you might have some hunches. You open with a conversation about the conversation. By providing a possible answer, you make it safer for people to respond.

Here are three variations you can use in different circumstances:

  • “What’s one issue we’re not talking about that would make all the difference in our effectiveness?”
  • “I’m sensing that there’s something important we’re not talking about. Do you feel that way too?”
  • “I care too much about our relationship to not talk about this.”

If you sense your conflict might be due to unspoken fears and misaligned expectations, this next Powerful Phrases cane can use to help everyone know what everyone else feels and thinks. They can lead to incredibly powerful discussions.

“In the next six months, what are you most looking forward to, and what you’re your biggest concerns?”

These questions are powerful when forming a new team, starting a new project, or any new initiative. As people share their answers, the discussion builds connection and an opportunity to solve problems early. It’s amazing how eager people are to share what’s on their hearts and minds. You can easily surface the conversations that need to happen and discuss tangible solutions.

Finding the courage to start an uncomfortable or courageous conversation can be tricky, but when you connect with yourself and invite people into the conversation, you’ll save everyone from future headaches and heartaches.

Workplace Conflict: 12 Powerful Phrases to Turn Conflict to Collaboration

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

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


  1. Eileen Mcdargh

    As always, your clarity and credentials show up through wisdom and words. One thought: in considering whether to have this uncomfortable conversation, I ask three questions: so what? who cares? what different will it make?

    Maybe one day, I can be a fly on the wall and and watch your magic happen.

    • Karin Hurt

      Eileen, Thank you! Love those 3 questions. And yes, I’m hopeful we will find ourselves collaborating in the same room again soon.


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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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