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3 Steps to Have a Difficult Conversation

Over the past several months, I’ve been writing about the figurative and literal destruction that can be caused at scale, as well as its opposite: zooming in. In Braving the Wilderness, Dr. Brené Brown argues that in order to solve major issues in our society, workplaces, and homes, we need less distance and more intimacy. But in a world where more is more, how do we get intimacy?

One answer is by having difficult conversations. By difficult conversations I don’t mean social media comments, and I don’t mean email exchanges.  I mean voice to voice conversations.

Before you think, “Nope, not for me!” hear me out. I understand that hard conversations can feel intimidating, but I want to clarify a misconception: “difficult” does not mean “confrontational.” In fact, it’s the opposite. When executed well, you’ll likely walk away from a difficult conversation feeling neutralized, if not better, than you did walking in.

So to help, here are three steps to have an effective and transformational difficult conversation:

1. Sit down face-to-face and side-by-side.

One of the best communicators I know was once given this advice: when you’re about to have a difficult conversation, sit next to the recipient, not across the table. Sitting across from someone with an object between you subconsciously creates confrontation.

For example, during her last resignation, she made sure to sit alongside her boss so that it’d feel less adversarial.

2. Kick-off by saying, “I need to have a difficult conversation with you.”

The above-mentioned communication expert used to be my boss, so when she’d occasionally start our 1:1s with this phrase, my heart would race, and my palms would sweat. But at the same time, I learned what a graceful way it was to receive bad news. This verbal cue indicated to me that

(a) she was making the time to talk about it (not email) and

(b) it was a difficult conversation for her too.

Of course I didn’t want to hear bad news (especially about myself – ha!), but she also didn’t want to deliver it. It was tough for both of us, and that introduction got us on the same page to understand that.

3. Start with the now, and articulate the shared vision that you want to achieve*.

Dr. Michelle Buck, who is an expert on conflict transformation, advises that people on different sides – even with the best intentions – often have downward spiral arguments because they’re stuck in the past:

“You did this.”

“No I didn’t…”

Peppered with lots of he said-she saids. Tensions rise, and you circle round and round, getting nowhere.

Instead, start with “Where are we now?”

Get on the same page with the current state, then shift into “What is the common-ground future that we are trying to reach?… Even if we disagree, what actions can we take today that will help us get to the place that benefits both?”

This one takes a LOT of discipline. I’ve recently been in a couple situations where I’m just dying to bring up past missteps that have led to our current tension. I’ve tested this one, and I am reporting back that it is SO. MUCH. WORK. to extract yourself from the what-happened-in-the-past trap.  However, the bright side is: you leave the conversation feeling proud of the way that you handled yourself. You have no “I wish I hadn’t said that” residue. In other words, you acted with integrity.

And if I may, I will leave you with one final thought on a different type of difficult conversation. We’ve been talking a lot about situations where someone believes that (s)he was wronged – in life or work. But what about other difficult conversations that need to be had, not because of anyone’s fault but because, well… life?

In 2014 Dr. Atul Gawande wrote a book called Being Mortal, where he vulnerably examines the correct intersection of humanity and science. He examines this in a situation when the doctor knows that his patient’s future life is limited. In the chapter called “Hard Conversations,” he talks about one of the most difficult conversations of his life. It was with his parents after his father was diagnosed with an illness that would severely limit his life. He concludes,

Those questions were among the hardest I’d asked in my life. I posed them with great trepidation, fearing, well, I don’t know what- anger from my father or mother, or depression, or the sense that just by raising such questions I was letting them down. But what we felt afterward was relief. We felt clarity.

In this intense example, he speaks of something grave: literally life and death. Your difficult conversation may be this important, and it may not be (hopefully, it’s not). It can be political disagreement, financial differences with your spouse, or wanting to get along better with a client.

But have the constructive conversation with a person you care about (personally or professionally) about that thing. The thing that keeps you up at night, causes your heart to race, and is standing in the way of your connection.

*Summarized from Braving the Wilderness

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