Difficult Conversations Don’t Age Well

November 27, 2024

By Dave Bushy, PCC

“Bad news doesn’t age well,” someone once said to me.  I couldn’t agree more.  The same can be said about difficult conversations.

In all aspects of our lives, we human beings have a tendency to avoid talking about the negatives that might emerge in any situation and to just accentuate the positives – or not talk about the issues at all. 

While that can serve us at times, it can often lead to a number of problems for leaders who regularly choose to hold off on delivering challenging news about their organizations, outside influences and, most especially, about interpersonal and performance issues by subordinates.

“I’m going to set up a meeting to tell him,” is a common phrase I hear in coaching.  It is often linked to a situation the client describes to me about another person in their organization who may have made a poor decision, failed to deliver results that were needed or a possible myriad of other circumstances where communication was not only warranted, but desperately needed. 

In one recent session with a client, a senior leader related to me an observation about one of his direct reports that had occurred just that morning.  I could see that he was frustrated and emotional about what he had seen and it was important to let him vent. 

After a few minutes, my client paused.  I gently prodded: “Tell me more.”

“Well, he really was inappropriate in how he spoke.  He belittled the young analyst and, to be candid, made him feel shamed and upset.  It was just a minor performance issue, but it was blown all out of proportion. I think he even made the guy cry”

I waited as my client let out a long sigh and then asked “What did you say to him?”

“Well, I’m planning to speak with him, I promise.”

“And to whom are you promising this?”

“I guess to myself.”

“And when might that conversation take place?”

“I think in our next one-on-one.  It shouldn’t be more than a week, I assure you.”

“What’s getting in the way of an immediate conversation with this individual?”

“Well, we’re all busy and I…”.

Then came another pause which I allowed to marinate for a while.  Inevitably the silence allowed the client to reflect a bit more.

After a still longer pause he said  “Well, he gets a bit prickly when I bring these things up.  I’d rather wait.”

“And how has that worked for you in the past?”

“Not so well, but I hope he can finally see the light someday.  I guess I just hope he realizes what he’s done and self-corrects.  He’s a smart guy and I know he’s got it in him.”

“You used the word ‘Hope’ a couple of times, did you notice that?” I asked softly.

“Yeah, I know, it’s not much of a strategy, is it?” the client responds.

“What intentions do you want to have for this person?”

“I’d like to be able to help this person improve.  I really would.”

“And what choices can you make with those intentions?”

“Well, maybe begin with having a conversation about my intentions and what I want for my direct report.  And then tell him what I saw and felt and then see what he has to say.  I might even try some of the techniques you use with me in coaching, Dave.  I especially like ‘tell me more.’  From that conversation, maybe we can begin to build a foundation of trust that makes it even easier when either one of us wants to deliver bad news.  We need to be able to engage in challenging dialogues right away, not wait until the next day or week.

I smiled and said: “Bad news or difficult conversations don’t age well, I guess.”

A smile came across his face, “Yeah, they don’t.  And I’m going to talk with him as soon as we finish this session.

From that commitment my client began to make small steps on improving his approach to challenging and difficult conversations. In our current sessions, he continues to reflect upon how that works for him.

Dave Bushy of Boston Executive Coaches – bostonexecutivecoaches.com – is a an ICF-certified coach who was trained at the Gestalt International Study Center (GISC).  Dave is a former U.S. Army officer and senior airline executive who works with leaders throughout the world.

Image by Cristian Ferronato from Pixabay

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