When to Skip a Difficult Conversation

by Deborah Grayson Riegel

Quick Takes

  • Ask yourself questions to consider whether to delay or skip
  • Avoid the conversation if your answers indicate the problem will resolve itself
  • Delay the conversation if you don’t have details or concrete examples
  • Focus on the current situation if the problem is part of a larger issue

We all occasionally need to give tough feedback to employees, colleagues, clients, family members, and friends. Yet, no matter how skilled or experienced we are at it, most of us would do anything to find a way out. As Douglas Stone, Bruce Patton, and Sheila Heen explain in their book, Difficult Conversations, this internal struggle is natural: “If we try to avoid the problem, we’ll feel taken advantage of, our feelings will fester . . . and we’ll rob the other person of the opportunity to improve things. But if we confront the problem, we may be rejected or attacked, we might hurt the other person in ways we didn’t intend, and the relationship might suffer.”

In a 2016 Globis survey of more than 200 professionals on the topic of difficult conversations, 95% were worried about damaging the other person’s self-esteem, 92% of respondents said they were concerned about the associated levels of stress for the other person, and 92% were fearful of causing upset. And, while 80% of respondents reported that these conversations were a part of their job, more than half indicated that they didn’t feel as if they had adequate training on how to conduct them effectively.1

In my role as an executive coach, I often help clients overcome their hesitation and anxiety so they’re able to handle tough but important conversations, at work and at home, in the right way. But sometimes we discover that their avoidance instincts are actually valid. Not every conversation with our boss, our partner, our kid’s little league coach, or a mother-in-law needs to be had immediately, had by them, or had at all.

How can you assess whether you’re making a strategic choice to avoid a difficult conversation or just chickening out? Here are 12 questions designed to help you consider what to say, delay, or skip:

  1. Based on what I know about this person and our relationship, what can I realistically hope to achieve by having the conversation?
  2. What is my “secret agenda” or “hidden hope” for this conversation? (Long-term harmony? Revenge? That they will change?)
  3. What concrete examples do I have to share of how this issue has shown up?
  4. What’s my contribution to the situation?
  5. Do I tend to look for problems with this person or about this issue?
  6. Is it already starting to resolve itself?
  7. Have I done a “H.A.L.T.” check—Am I hungry, angry, lonely, or tired?
  8. How long ago did it arise? Is it a repeat or recurring problem? Could it become one?
  9. How material is the issue to our relationship or to the job?
  10. How committed am I to being right?
  11. What reasonable, actionable solution can I offer?
  12. Is this the right person to talk to about this issue?

If your answers tell you that the situation is likely to resolve itself, that your concern isn’t critical to the relationship or to your work, that you’re more committed to placing blame or being right than to really listening or seeking solutions, or that the appropriate time to address the problem has passed, then you probably shouldn’t speak up.

I worked with one leader who was angry about the fact that she had gone through a time-consuming process to help her company apply for a prestigious industry award, only for her boss to take credit when the organization won. He didn’t even invite her to the awards ceremony. When we discussed how to confront the problem, she acknowledged that she had been frustrated with her boss’s pattern of claiming responsibility for her ideas for more than five years. But she ultimately decided that she wouldn’t bring up all those incidents, only the most recent, arguing that she deserved to accompany him to the event. She also decided that she would continue to address these concerns in the moment, rather than letting her anger build up, poisoning her relationship and her credibility.

Another leader with whom I worked wanted to talk to his direct report about being “less defensive” when he gave her feedback. But when I asked him to identify specific behaviors, he couldn’t articulate them beyond “it’s just how I feel when I talk with her.” He therefore decided to delay the conversation until he could offer concrete evidence and offer more useful advice on how to do things differently.

A third leader decided that she should stop trying to have difficult conversations with her teenage son as soon as he came home from school when she realized that all conversations felt challenging between 3 and 4 p.m., regardless of topic. After doing a H.A.L.T. check with him, she realized that he was hungry and tired right after school, and wasn’t his most patient, reflective, or rational self. She also discovered that she, too, was hungry and tired during that time frame, and so she was more likely to focus on frustrations. She found a time after dinner and some TV time when both of them were more relaxed, and satiated, to bring up touchier topics with less stress.

Deciding carefully and strategically about whether to speak up or let it go isn’t an abdication of responsibility; it’s taking responsibility for making sure that the messages you do communicate are delivered for the right reasons and generate the desired results.

Adapted from content posted on hbr.org, March 1, 2016 (product #H02OY9).

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