September Reflections: When the Other Person Won't Meet You Halfway

In my last workshop, someone asked me a tough but honest question about when to have a hard conversation:

“What do you do when you’re willing to reach out with empathy, but the other person just isn’t? How do you make progress when they’re being… well, a total jerk?”

This is about deciding when to have a hard conversation and how to prepare with calm and curiosity. Here’s how I think about it:

• Your behavior can influence theirs. When you stay calm, curious, and open, you model the kind of interaction you want to have.

• Even if the conversation feels stuck, asking thoughtful questions can plant a seed that grows later.

• And before you step in, it’s worth asking yourself: Am I ready for this conversation? Sometimes the answer is no, and that’s okay. Boundaries matter.

Conflict doesn’t disappear when the other person is unwilling. But you still have choices: how you prepare, how you show up, and when to step back.

That’s exactly what the Conversation Readiness Quiz is for. It's a quick way to figure out whether a conversation is worth having right now, or whether it’s better to pause and protect your boundaries.

I’ll share more on boundaries in my next workshop with Greatness Calls, Beyond Logic: Making Sense of Conflict, happening October 23.

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If you missed my first session, Managing Important Conversations in 4 Steps, you can now watch the full recording in two parts:

• Part 1: Before breakout session

• Part 2: After breakout session

I’m also developing The Mutual Conflict Map, a focused process that helps you prepare for tough conversations with clarity and confidence. In 90 minutes, we uncover your values and priorities, consider the other person’s perspective, and define desired outcomes, next steps, and conversation prompts. You leave with a personalized one-page map, a clear guide you can rely on to navigate your next conversation, even if the other person isn’t ready to meet you halfway. I'll be sharing more on that soon.

This work connects to a deeper theme I see again and again: what feels like “disrespect” on the surface is often really about dignity. Respect can mean fairness for one person, acknowledgement for another, or safety for a third. Dignity is different. It's inherent, something we all carry, and when it's violated, we react. Respect is how we choose to honor dignity in practice.

I saw this in a workplace mediation where an employee who had been fired felt disrespected because her side of the story went unheard. Once the employer acknowledged her experience and committed to a fairer investigation process going forward, the tension eased and the conversation moved forward.

I wrote more about this in my latest article: What’s the Difference Between Dignity and Respect?

And in just a few weeks, I will be heading to the first Dignity Leadership Summit where I will be diving deeper into ways to continue shining a light on the importance of dignity in our work and lives. I look forward to sharing more reflections after the Dignity Leadership Summit, and I hope you will join me for the workshop on October 23!