How to have hard conversations

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Fear of conflict keeps many of us silent, but withholding truth creates more distance than speaking up. Let's explore how to get through it all.

Looking for some support? If now is the time to consider coaching (or a CEO peer circle), reach out?here.

“She has run product for the last few years. A lot of her impact has been positive, but I feel like the company has outgrown her skillset. I find myself lying in bed anxious about it. I think we need to change her role and bring in someone else. Or at least find a better way to support her so that she’s not distracted by the amount of management she’s having to do.”

I listened as my client offloaded the concerns she was carrying about her co-founder.

“Have you shared any of this with her?” I asked.

“No,” she replied.

“How would it feel to share this with her?”

That last question—or some version of it—is one I find myself asking daily in coaching sessions.

I average 40 coaching sessions per month. And I would estimate that in 30% of those sessions, one of the outcomes is a client resolving to find the courage to have a conversation they’ve been avoiding.

My clients are some of the brightest, most thoughtful, mature, heart-led people I’ve ever met. Yet, they too often struggle to find the clarity or courage to have conversations that could drive the most significant change in their organizations or lives.

And so do I.

I bet you do too.

Why are certain conversations so tricky? I’ve been thinking about this in my own life these past few weeks. I know there’s a conversation I need to have with someone I love—one that holds the potential to bring meaningful change and alignment to our relationship. And yet, I’ve been deeply resistant to having it.

Why?

I’ve been asking myself that question. And the answer I keep arriving at is the same one I'd wager keeps many of us from having courageous conversations.

I’m afraid that if I share my truth, it will sever or distance the relationship.

And so I kick the can down the road.

I live in a dynamic with this person where I’m not sharing openly what’s really happening for me. Even as I write this, I can feel conviction:

By withholding my truth, I may be sparing the relationship short-term conflict, but I’m also robbing it of long-term alignment.?

I’m also denying the other person the knowledge of what’s going on for me—and the choice to respond as they would like.

Framed differently, I am so attached to my story of how they will respond—and my own fear of conflict or detachment—that I resist opening up honest communication.

I am a professional CEO coach. I think about communication, human dynamics, and challenging emotions for a living. And I still fall into this trap. Regularly.

What about you??

Where in your life are you resisting sharing openly with someone close to you out of fear of their response? Where are you stuck in a story about how they will respond—or how they’ve always responded—and therefore unwilling to treat them like an adult (or partner) and allow them the freedom to choose their response?

Where are you getting in your own way of the partnership you desire?

Defining a courageous conversation

Let’s define a courageous conversation:

A courageous conversation is one where I must overcome my fear or resistance to share a need, request, or hurt to find greater intimacy or alignment with the other.

We tend to resist these conversations out of fear that having them will create more distance in the relationship.

But here’s what I remind myself:

Withholding the conversation often creates more distance than having it ever could.

Preparing for a courageous conversation

So how do we prepare? Here’s what helps me:

1. Get clear on what I want to say

I know this conversation has the potential to go off the rails if I’m not clear. Writing my thoughts down in advance helps. These prompts (based in part on the Nonviolent Communication framework) can help:

• What am I seeing or experiencing?
• How am I feeling about it?
• What need do I have (or we have as a company, family, etc.) that is not being met?
• What request(s) do I have?
• What do I imagine the other person is experiencing in this situation?
• What do I imagine might feel at risk for them as I raise this topic?
• What would help each of us feel more at ease in this conversation?

2. Set the conditions for success

• I choose a setting where we can both feel relaxed and present.
• I consider the best physical experience. For example, walking is often more helpful than sitting face-to-face. Humans process differently while walking, and it can reduce tension.
• I consider having a trusted third party present. My wife and I, for example, meet with a therapist weekly, regardless of what season we’re in. My clients often bring in a coach or mediator for key conversations. Trusted third parties can be pure gold.
• I prepare my mind in advance. I can’t control the other person’s state of mind, but I can take accountability for my own.

And then? I have the conversation.

These conversations are not easy. But they bring us into closer alignment with the people around us. When we avoid them, we rob our key relationships—and ourselves—of what we desire most.

By finding the courage to get clear on what we need and to have these conversations—even when we fear the outcome—we create the opportunity for more trust, clarity, and connection.

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In the case of my client, by finding the clarity and courage to speak openly with her co-founder, they arrived at a new agreement about their roles and responsibilities. The result??More trust, greater alignment, and a stronger leadership team.?It wasn’t easy. Not every moment felt good. But that’s okay.?We are not responsible for managing the emotions of our trusted partners. We are responsible for sharing our truths and managing our own emotional state in the process.

I am committed to heading into my own courageous conversation as well in the coming days. If you are reading this, feel free to drop me a note and ask me if I followed through!

And if I can support you in any way as you step into yours, please reach out. I’m here.

Looking for some support??If you’re navigating leadership challenges and need a space to think out loud, I’d love to help. Learn more about coaching or CEO peer circles here.

Sending a big hug your way from my desk in Los Angeles.

-Matt