The Painful Conversation You’d Rather Not Have


After my post last week about a difficult conversation I’d had with a colleague, several people reached out to me to share their own experiences. They told me things like:

  • We have tense dynamics like that in our partner group.
  • I’m struggling to have a hard conversation about performance with an employee.
  • I’ve been there. It’s both a punch in the gut and a gift rolled into one 🙂

The response that really stood out, though, was from the colleague I’d written about. Here’s what he said:

The opening paragraph was particularly meaningful to me. While reading it, I wondered if there may be others, like me, who really want to know what you think about what you experienced. For what it’s worth, I’m perfectly OK standing shoulder-to-shoulder with you in the vulnerability if that helps you say what you need to say. 

So I thought back to the conversation and what that experience was like for me. How did it feel? Well, it sucked.

At one point in the conversation, I was shaking with adrenaline. I wasn’t at all convinced that our relationship would survive. Several times, I wanted to give up and walk away. But, looking back on it, I’d pay that price 10 times over again. Our relationship is both restored and stronger than ever.

Of course, there’s no sugarcoating things. Trust was broken, and more work needs to be done. But now we’re in a safe and connected place to do that work.

Here are four reflections from this and other painful conversations I’ve had:

  1. Culture creates the playing field. My colleague and I both accepted the invitation to have a painful conversation without hesitation. To be sure, neither of us wanted to have it, but we both implicitly knew that this is how we do things in our company.

    Over the years, the organization had celebrated stories of people doing difficult things in relationships. We’d collectively held up our values about the importance of authenticity, generosity, and collaboration. We’d made decisions that reflected the value of people over short-term profit.
  2. Decide why before how. Despite all my thoughts, emotions, and problem-solving in the midst of this recent painful conversation, I centered in on advice my Dad gave me years ago: Focus on what you want in the relationship.

    I knew that I wanted restoration, trust, and the ability to work together. Now, did I also want to be heard, do justice in the situation, and know that he felt bad about it? Of course. But those had to submit to my greater desires.
  3. You don’t wing it in a painful conversation. To guard myself from my own impulses and emotions, I entered the conversation with a plan. I thought about the plan. I discussed the plan with a couple of trusted advisors. And I even wrote the plan on a note in my phone.

    Here’s what my plan was: (1) Follow Dale Carnegie’s sage advice to begin in a friendly way. (2) Talk objectively about what I observed and how it made me feel, which would provoke sharing instead of fighting. (3) Listen and be genuinely curious about his perspective. (4) Accept that more conversations need to happen.
  4. Confidence fuels the doing. In addition to reminding myself why this conversation was important, I also had to get myself right before (and during) the dialogue. I physically relaxed myself through breathing and stretching. And I emotionally relaxed myself by praying and remembering. I remembered who I am and that I’ve had other painful conversations before. This gave me the courage to have the conversation, despite the discomfort.

Distilling those reflections down into four discrete lessons, I’ve realized that, to restore and strengthen a relationship, a painful conversation requires:

  • a sturdy, supportive playing field
  • perspective
  • a plan
  • a belief that you can do it

So there you go, trusted colleague and friend. Thank you for encouraging me to reflect and for standing shoulder-to-shoulder with me in vulnerability.

How about you? What painful conversation do you need to have?

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