2020-03 10 HR Examiner article Jamie Resker Before You Engage In A Difficult Conversation photo img cc0 by volodymyr hryshchenko V5vqWC9gyEU unsplash 544x363px-v101.jpg

Putting off difficult conversations can have consequences. But, sometimes the best course of action is doing nothing. Jamie Resker explains how to evaluate whether you should have a discussion with an employee, and if so, the best way to handle it.

Consider These Three Things Before You Engage In A Difficult Conversation:

Importance, Motive, and Signaling Positive Intent

At work, at home, and in life, people fall short of our expectations and do things that irritate and disappoint us. The behaviors and actions of others can trigger feelings of anger, irritation, and anxiety.

It’s easy to put off a difficult conversation, but there might be consequences. Avoidance can lead to the deterioration of an important relationship, obsessively thinking about an unresolved issue, and imagining worst-case scenarios. But, sometimes, the best course of action is doing nothing. You need to determine whether the problem is significant enough to raise.

Before engaging in a difficult conversation, you’ll want to examine your intent. Are your motives positive and constructive? If so, move ahead to the next step, what to say. How will you begin the conversation? What words should you use (and not use) to engage the other party?

STEP 1: Consider The Importance

Is the situation critical? What is the range of potential outcomes? Should you ignore the issue?

Examples Of Conversations To Skip

Look the other way when the issue is: trivial, is more about your personal preference or style, or when the risk could outweigh the benefit (like criticizing your boss or alienating a neighbor).


  • Your boss snapping their chewing gum gets on your nerves.
  • You’re at the movies, and the person sitting nearby is loudly chomping on popcorn.
  • Your neighbor’s Halloween decorations are still on display in January.
2017-03-27 HRExaminer photo img jamie resker profile photo 200px

Jamie Resker, HRExaminer.com Editorial Advisory Board Contributor

Safety issues, the possibility of a failed project, and heading off problems are good reasons to engage in a conversation. If the issue is hurting an important relationship, consider a conversation. Your in-laws, immediate family, neighbors, and co-workers usually represent important-to-maintain relations. The criticality of the relationship or situation is your judgment call.

On the flip-side, the person who cuts you off in traffic is not an important connection, which is why people feel comfortable honking and making rude hand gestures. You’ll never see this person again. Can you imagine doing this at work?

STEP 2: What Is Your Motive?

What is your reasoning behind addressing a perceived problem? Is the intent constructive or destructive?

Destructive Intent

If the aim is to hurt, humiliate, discredit, or prove someone wrong, then the outcome will be poor. Placing blame, belittling, or seeing someone get what they deserve can feel cathartic, but confrontational approaches usually backfire.

Most people, when provoked, don’t respond with, “Thank you so much for telling me this. I’m sorry, I’ll do better next time.” Instead, you’re apt to trigger an emotional flight or fight response: Defensiveness, counter-attacks, deflection, rationalizations, or shutting down.

My advice is to hold off on initiating a conversation rooted in wanting to hurt or punish.

Constructive Intent

Initiating a difficult conversation makes sense when you want to help, improve an outcome, arrive at a solution, create shared understanding, strengthen coordination, or salvage an important relationship. If your intent is positive, then the next step is finding the right words to begin the discussion. You’ll want to start with your positive intent.

STEP 3: The Best (And Worst) Ways To Begin The Conversation

Start with your positive intent and use non-judgmental and open-to-listen conversation starters:

  • “I have an idea on how we can work better together, can I run it by you?”
  • “I think we have different perspectives on whether to get snow tires on the truck. Can we talk this through?”
  • I’d like to see if we could have a better understanding of ___________. Can we discuss our perspectives, common objectives, and work toward steps that will help get the project on track?

Stay away from sweeping judgments, blame, and argumentative starters:

  • “You never…”
  • “You always…”
  • “Why did you…”
  • “I have some feedback for you.”


When considering a difficult conversation, first reflect on whether the matter is important. Look past insignificant issues and things you can’t change (like movie-goers eating popcorn). Avoid things that might get you into trouble (like using your car horn as an “anger management tool” to signal your annoyance with the other driver).

Blaming, passive-aggressive behavior, and mean sarcasm might feel liberating, but these words and actions can’t improve relationships and resolve problems. Instead, destructive intent weakens relationships and perpetuates problems.

Ensure that your reason for engaging in a difficult conversation is constructive. Use conversation starters that show you are initiating a conversation for the right reason and are open to hearing new perspectives.

There’s no way to rehearse for a discussion as we can’t predict what the other party will say and how they will react. But we can thoughtfully enter a discussion with a mindset and approach that gets the conversation off to the right start, allows for listening, perspective sharing, and has the best chance for a successful outcome.

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