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4 Ways to Avoid Difficult Conversation Traps

Michele McGovern
By: Michele McGovern
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About the Author

Michele McGovern writes. A lot. These days, she covers HR, digging deep into company culture, DEI, leadership, management and the everchanging world of work. In the years between getting a BA in journalism from a state school and writing about HR, she wrote about big-city crime for a wire service and small-town life for local newspapers. She’s a mediocre mom, decent wife, wannabe athlete and consummate pursuer of fun - on land, snow and water. Find her on LinkedIn @michele-mcgovern-writer.

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Last Updated: October 6, 2025
5 minute engagement

Some conversations are difficult before they start. They become even more of a nightmare when they take a turn for the worse — and you end up in difficult conversation traps.

It’s so bad, some leaders would rather not face difficult conversations head-on. Instead, nearly two-thirds are willing to go out of their way to make difficult conversations more comfortable for the other person, according to research from Fractl.

While that’s an interesting tactic, most difficult conversations usually never enter the comfort zone.

Say or do the wrong thing in the heat of the moment, and your employees’ emotions might escalate. And no one can easily dig out of a difficult conversation trap.

“Even with the best of intentions, conversations about performance or behavior can provoke defensiveness and veer off track,” says Marlene Chism, author of From Conflict to Courage, in her blog.

Address Difficult Conversation Traps

Despite the uncomfortable verbal volley that can follow, it’s still better to address difficult subjects than ignore them.

Several researchers and professors from the Harvard Kennedy School find that the benefits of addressing awkward, difficult and uncomfortable subjects outweigh the short-term comfort of ignoring the issue.

“That means that we need to enter into these conversations with a high level of sensitivity, realizing that not everyone stands on the same ground,” says Cornell William Brooks, the Professor of the Practice of Public Leadership and Social Justice at HKS, in a panel discussion on the research.

So address the issues that feel weird to bring up. But be prepared to avoid the four biggest difficult conversation traps.

No. 1: A Rehash of the Past

  • What it is: You or the other person starts to slowly or quickly bring up a laundry list of infractions from the past, whether they were previously addressed or not.
  • Why it happens: It often happens because you never addressed issues that should’ve been handled (so, yes, the boss is sometimes partly to blame for this trap). At the same time, the other person in the difficult conversation might bring up old issues in defense of the current situation.
  • How to escape: Assuming you set the intention, you can continue to give honest, difficult feedback without digging up bones. How? “Talk about what you want rather than what you don’t want,” says Chism. Instead of saying, “I don’t want you to arrive late anymore,” say, “I want you to arrive on time and ready to greet clients.” Or instead of, “I don’t want you missing goals anymore,” say, “I want you to hit the goal this quarter and surpass it next quarter. Now let’s devise the plan.”

No. 2: The Perception Game

  • What it is: You and your employee (or colleague) enter the difficult conversation assuming you both know why the other has come to this point and what the other will say, do or expect.
  • Why it happens: It’s often fueled by resentment. Perhaps you resent the behavior or situation you want to correct because it directly affects you. Or maybe the other person resents you for even bringing it up or trying to change him or her.
  • How to escape: Address the observed behavior or situation — not why you think it exists. And ask the employee or colleague to also address the exact behaviors. For instance, instead of, “You’re lazy and everyone has to pick up the slack for you,” say, “You’ve been late four days this week and Janice had to take your first 10 calls.” Or avoid something like, “Your lack of attention to detail caused you to miss goals.” Instead, say, “There were 14 miscalculations on the Smith report, so we had to scrap the deal.”

No. 3: Passive Aggressiveness

  • What it is: You say there’s a problem and you express some discontent about it. But you don’t lay out what is really bothering you, and indirectly express negative feelings through disregard.
  • Why it happens: You’re still afraid to have the difficult conversation and address the real issues. Or you think the other person should know what’s wrong and should be doing more to address it without you having to spell it out.
  • How to escape: Try this three-step approach:
    • Be curious. Ask a point-blank question such as, “Is there a reason you arrived late four days this week?” You might get a legitimate answer that leads to a quick, legitimate solution.
    • Share your perspective. Let the other person know why it bothers you. For instance, “I understand you’ve had a transportation glitch, but it’s frustrating for me and members of the team who have to answer your calls.”
    • Make a firm request. Ask for compliance with exactly what you need. Say, “Since we all have demanding schedules, please make arrangements to be on time and ready to work.”

No. 4: Verbal Ping Pong

  • What it is: It’s a back and forth of accusations and defenses — and it’s usually off the intended subject.
  • Why it happens: The person on the other end of the difficult conversation triggers you — perhaps pointing out a shortcoming, accusing you of causing the problem or getting irrationally defensive. So you start to defend yourself, and the other person continues a defense, too.
  • How to escape: Start difficult conversations with an intention — and if you veer away from it into a trap, you can reiterate the intention and get back to it. Examples: “My intention is for us to discuss why you’ve been late 10 times this month and what we can do to help you arrive on time and ready to work.” “The intention for our discussion is to get realigned on your goals and ways to achieve them.”
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