Are you skilled at handling tough conversations, or do you tend to avoid them?
I prefer to avoid them altogether. I’m tough conversation-avoidant. Some are tough conversation-relishers. (It’s my article, and I can make up words if I want to.) I dread conversations like when you have to address someone about subpar performance; you need to fire someone who’s not meeting expectations. The time you must apologize for your own mistakes. Or when you have to make the case for yourself despite perceived shortcomings.
Underlying these conversations are things like pride, shame, right, and wrong. For those of us who identify as avoidant, those are difficult emotions when what we really want is to connect with others. To belong. And the bridge to connection is always the story we tell.
When Avoidance Feels Easier
Think about a time you’ve had to do this. Just thinking about these kinds of conversations gives me a heavy-weighted feeling, like a concrete box closing around my heart. Everything constricts. I contract. My first instinct? Push away what I hate. Avoid it. Focus on literally anything else.
But here’s the problem: it’s nearly impossible to focus well on other things when you’re carrying the weight of an unaddressed conversation. That avoidance becomes its own burden.
Which brings me to the stories that break down barriers, the ones that transform tough conversations into moments of breakthrough.
When I was in my mid-20s, I was almost fired from a supervisory role at a luxury hotel in Aspen for a stupid thing I later regretted. Because I otherwise had a great performance, they gave me a second chance, suspending me for three days instead.
Several years later, I sat in a job interview with the food and beverage director at the Four Seasons Seattle. I had made it to the third round of interviews, and I was feeling confident until he asked: “What would your boss in Aspen say about you if I called her for a reference?”
An hour’s worth of dialogue ran through my mind in milliseconds as I pondered how to respond. He could very well know her; hospitality is a small world. Did he already talk to her? Does he know what happened? Is this a bluff? Why phrase it exactly like that?
But I knew what I needed to do. I chose transparency.
“They would tell you I was reliable and a great employee overall,” I said. “But there was one time I made a bad judgment call, and I’m sorry for that.”
I got the job.
Later, I discovered that he did, in fact, know my former boss, and the question was a test. My answer, choosing honesty over deflection, determined whether I’d be hired. Getting that job was pivotal for reasons I won’t go into, but let me just say that was a big deal.
Every Conversation Is a Test
What if we treated every difficult conversation as a test? Whether you’re delivering or receiving the difficult news.
The question isn’t whether you’ll face these moments, because eventually, you have to. The question is: How will you show up?
Will you contract and avoid? Will you deflect and minimize? Or will you lean into transparency, even when it’s uncomfortable?
Transparency doesn’t mean oversharing or being unnecessarily harsh. It means addressing difficult topics head-on with honesty, respect, and genuine care for connection.
Because on the other side of those tough conversations – the ones we dread and delay – lies the very thing we’re seeking: authentic connection built on trust and truth.
If you’ve had a time you’ve seen this in action, I’d love to know.
Take care out there.
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