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Make Your Work Conversations Better & Your Work Life Worse

Bob Goldman on

"We have to talk."

If you work for a company with two or more employees, these four words will strike terror in what's left of your nervous system. But before you reply with a thoughtful response, like "Do we? Why?" or "I think not," or my personal favorite, "Not tonight. I have a headache," consider the possibility that someday, the person initiating the convo could be y-o-u.

The talk you need to have may be with a co-worker, a manager or the CEO; it doesn't matter. Like most things at work, there's a right way and a wrong way to go about it, which brings us to "How to Have a Difficult Conversation" by Jancee Dunn in "The New York Times."

The problem with initiating a difficult conversation, writes Dunn, is rarely the subject that you want to discuss. The problem is that you're afraid to discuss it. There could be a major business disaster on the horizon, a firestorm in the balance sheet, a competitor who is about to introduce a product much better and much cheaper than the junk your company sells, but you don't have the courage to bring it up, up the org chart.

Or it could simply be some garden-variety friction between a co-worker at your level, or lower, if that's possible. Either way, talking up, across or down, there's something about initiating the conversation that makes you want to stop before you start.

This isn't cowardice -- well, it is, but not always. It can also be optimism.

"It's tempting to delay a difficult conversation, especially with someone you care about or see often," says Matt Abrahams, a lecturer at Stanford Graduate School of Business. "We do this hoping and praying it will get better on its own."

It's a lovely thought, but very unlikely, especially considering the people with whom you work. Will your immediate manager suddenly realize that you can't be expected to respond to 3 a.m. emails before the sun rises? Can the IT dudette suddenly come to the realization that it isn't possible to manage your contacts on a 1991 version of Lotus Organizer? Would the jerk in the next cubicle ever grok that eating mountains of sardines at their desk is not conducive to their mental health?

I think not.

Fortunately, turning around the cowardly lion in your work convos can be done. Let's talk about it.

No. 1: Choose an Appropriate Moment

A major meltdown is never the right time to initiate a difficult conversation. But what if your department is always in meltdown mode? That could keep the problem festering until you get to retirement age. Which, in these exciting AI days, has moved from 65 to 25.

It's not only the timing that counts. It's also the location

"Chatting in person is best," opines professor Abrahams, "because you can read cues and clues in a way that you can't on a device."

 

It's true. When you're on the phone, you never can be really sure the person you're talking to isn't tearing up and breaking down. Moving the convo to Zoom won't help. With recent advances in AI slop, you could be making your case to a chatbot.

And nobody wants to cross a chatbot.

No. 2: Give that Person a Heads-Up

Author Jefferson Fisher recommends starting your difficult conversations with a friendly "heads-up sentence" like "Hey, I'd like to get something off my chest." Heads-up sentences that I prefer are a touch more dramatic, like "Something's bugging me and if you won't talk about it, I'm holding my breath until I turn red."

If the target tries to put you off, stalk them in a friendly way. What a co-worker won't discuss in the office will be unavoidable when you show up at their house on Saturday morning with donuts and a sleeping bag.

No. 3: Keep Calm and Stay on Message.

Write down the outcome you want to achieve. This will be useful if tempers fray and the conversation derails, which is almost certain to happen, especially considering that your point of view on the matter is almost certainly wrong.

Once the difficult conversation is finished and you have achieved absolutely everything you want and the other person is totally vanquished, move on to the next person in the company who is bugging you and start another difficult conversation.

Do endless demands for heated confrontations damage your reputation or reinforce your image as management material?

Let's talk about it, but not tonight; I have a headache.

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Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at info@creators.com. To find out more about Bob Goldman and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.


Copyright 2026 Creators Syndicate, Inc.

 

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