From Our Founder: Five Lessons I’ve Learned About Difficult Conversations

Difficult conversations are everywhere—in our workplaces, our homes, and our communities. Over the years, through facilitating conversations, coaching leaders, and learning from my own missteps, I’ve discovered that the hardest conversations aren’t just about the words we say. They’re about the mindset we bring, the emotions we navigate, and the relationships we want to preserve or repair. 

Here are five lessons I’ve learned about navigating difficult conversations that might help you approach them with more confidence and care:

1. Clarity is a Gift, For You and For Others

One of the biggest traps in difficult conversations is entering them without clarity—about what we want, why it matters, or how we want to show up. Without clarity, conversations can spiral, leaving everyone confused or hurt. 

This is why getting clear on your intention and your desired impact is so important. What’s your ultimate goal in this conversation? Is it to resolve a misunderstanding, repair a relationship, or set a boundary? 

Understand that clarity isn’t just about your goals. It’s also about understanding how the other person might feel or what they might need. When you approach a conversation with clarity for both sides, it becomes less about winning and more about connection. 

2. The Stories We Tell Ourselves Shape How We Show Up

Before any difficult conversation, our brains love to fill in the gaps. “They don’t respect me.” “They’re doing this on purpose.” “This isn’t going to go well.” These stories can trigger our emotions, putting us in a defensive or reactive state before the conversation even begins. 

One of the most powerful tools I’ve found is pausing to ask myself: 

• What story am I telling myself about this situation? 

• What else might be true? 

When we question our assumptions, we open the door to curiosity. And curiosity is a powerful antidote to defensiveness. It allows us to enter conversations with a mindset of discovery rather than judgment. 

3. Avoidance Creates Suffering

Here’s a hard truth: avoiding a difficult conversation doesn’t make the issue go away. It just delays the inevitable, often allowing resentment, confusion, or tension to grow in the meantime. 

Avoidance isn’t just about fear; it’s about protecting ourselves from discomfort. But that discomfort doesn’t disappear—it just shifts into a different kind of pain. One of the most freeing lessons I’ve learned is that stepping into discomfort, while scary, often leads to relief, clarity, and stronger relationships on the other side. 

So, the next time you catch yourself avoiding a conversation, ask yourself: 

• What’s the cost of not addressing this? 

• How might I feel if I approach this with care and curiosity instead? 

4. Repair Is a Skill, Not a One-Time Event

No matter how skilled we become at conversations, mistakes happen. Words come out wrong, assumptions are made, and feelings get hurt. What matters most is what happens next. 

Repairing relationships requires humility and intentionality. It’s about taking responsibility for your impact, not just your intention. A genuine apology—one that acknowledges harm and invites dialogue—can go a long way in rebuilding trust. 

Repair is also about consistency. It’s not a one-and-done effort. Rebuilding trust takes time, especially when harm has been significant. But the willingness to repair, even in small ways, signals that the relationship matters to you. 

5. The Elephant in the Room Gets Bigger When Ignored

We’ve all been in situations where something feels off, but no one addresses it. Maybe it’s an unspoken tension in a team meeting or a lingering disagreement with a friend. Those “elephants” don’t disappear—they just grow, feeding on silence and avoidance. 

The key to addressing the elephant in the room is naming it with care. It might sound like: 

• “I’ve noticed some tension lately, and I want to understand what’s going on.” 

• “I want to circle back to something that’s been on my mind because I value our relationship.” 

When you approach these moments with curiosity and courage, you often find that what felt overwhelming shrinks in size once it’s acknowledged. 

Moving Forward 

Difficult conversations aren’t easy—that’s why they’re called difficult. But they’re also opportunities for growth, connection, and understanding. 

When we approach these moments with clarity, curiosity, and care, we’re not just having conversations. We’re building trust, strengthening relationships, and showing up as the people we hope to be. 

So, my question to you is: 

• What’s one conversation you’ve been avoiding that might bring relief or resolution if you stepped into it? 

Remember, every hard conversation is a chance to practice, to learn, and to grow. You don’t have to get it perfect; you just have to be willing. 

Here’s to showing up—imperfectly but intentionally—for the conversations that matter most.