The Leadership Skill No One Taught You: Uncomfortable Conversations 

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We dread them, we dodge them, and when we do have them, we often fumble through. But addressing uncomfortable topics helps us all grow. 

Whether it’s giving hard feedback to a colleague, setting boundaries with a client, or confronting a family issue, the hardest conversations are often the most important ones. We avoid them because they’re uncomfortable, but that’s not a good enough reason to avoid important topics.  

I facilitated a discussion for NABIP Power Hour on this very thing, and it was a great conversation with a lot of input and discussion. We kicked off the session with a short Simon Sinek video clip, where he explains that uncomfortable conversations are learned skills. And the only way to improve is to do them. 

Simon points out that our instinct is to avoid discomfort. But when we do, we choose temporary peace over meaningful progress. Our fear prevents us from stepping up and being leaders, whether at work or in our personal lives. 

Try this at home 

This is a meaningful topic that you can use for a team discussion. Pose this question to the group to get started:  

👉 Share the topic of a potentially uncomfortable conversation you or someone you know may need to have.  

Collect your responses, discuss the following ideas to help prepare, and then revisit the list of topics. After the discussion, ask if people feel they can confidently put a plan together to address the discomfort ahead of them. 

When it’s time to speak up 

As much as we may not want to have the conversation, avoiding it doesn’t make the issue go away. It just gives it permission to keep growing quietly in the background. And that silence sends a message, although probably not one you intend.  

Unspoken issues don’t stay that way forever. They often show up later, messier, and louder. 

Knowing when to speak up and when to keep quiet is part art and part intuition.  

Do some reflection 

Harvard Business Review’s guide to difficult conversations suggests you reflect on whether the conversation is in service of a shared goal, such as performance, trust, or clarity. If it is, that’s your green light to step into the potentially messy waters. 

I also like to take a gut check to help decide if a tough conversation is worth having. Ask yourself: Do I mean it? Can I defend it? Am I saying it with care for the other person? 

If the answer is yes to all three, it might be time to speak up. But be honest with yourself: Does this truth need to be told? Are you ready for potential fallout? There may be damage that cannot be undone. And sometimes, timing and delivery matter more than content. 

What makes it so hard? 

Uncomfortable conversations trigger something primal. The fear of confrontation activates our stress response: fast heartbeat, dry mouth, flushed face. It’s our brain trying to protect us from perceived danger. 

But we can retrain our brains. By shifting the narrative from “I’m about to ruin everything” to “I’m about to offer something helpful,” we can reduce the fear response. If you’ve done your check and know that you’re not delivering a personal attack, reframe it as offering a kind truth. 

A well-delivered hard truth can be a turning point for you, the recipient, or your relationship. 

I don’t recommend going into a difficult conversation by “winging it.” It’s too easy for it to go sideways. Role-playing is a great way to feel prepared to speak and to prepare for a variety of responses from your listener. Having a game plan helps you stay calm and grounded.  

Be the domino 

Discomfort often comes from the filter we bring to the moment. If you truly feel you’re bringing them a useful conversation to help improve something, that’s a gift.  

• Start with heart: Lead with your intention. “I’m bringing this up because I care about our relationship/work/client success.” 

• Name the discomfort: Say it out loud. “This is hard for me to say.” That vulnerability builds trust. 

• Stick to the facts: Avoid assumptions. Share what you’ve observed, not what you’ve guessed. 

• Own your perspective: Use “I” statements. “I feel…” instead of “You always…” 

The hardest part is going first, being the first one to start, but when you do it with respect, courage, and care, you show others it can be done with kindness. 

Also, revisit your intent: 

• Am I okay being uncomfortable if it means being honest? 

• What am I tolerating to avoid a difficult conversation? 

• What kind of culture am I building with my team, my clients, and myself by staying silent? 

There’s power in speaking the truth, even when you’re uncomfortable saying it.

Be the domino. Say the thing. Lead the way.