Know When To Skip A Difficult Conversation By Asking Yourself These Questions

Know When To Skip A Difficult Conversation By Asking Yourself These Questions

Difficult conversations are a pain for everyone involved. They’re not always as necessary as we think they are though, and Harvard Business Review put together 11 questions to ask yourself before you bother heading into that difficult chat.

Photo by Akuppa John Wigham.

Sometimes, a difficult conversation is a necessary evil to get through a rough spot in a relationship. Other times, it’s a pointless exercise that just leaves both sides feeling worse. Ask yourself these 11 questions to figure out if that conversation is worth having or skipping:

  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. How long ago did it arise? Is it a repeat or recurring problem? Could it become one?
  8. How “material” is the issue to our relationship or to the job?
  9. How committed am I to being “right”?
  10. What reasonable, actionable solution can I offer?
  11. Is this the right person to talk to about this issue?

If you answer in a way that suggests the situation will resolve itself, it’s not that critical, you’re more interested in placing blame, or it’s just too late to speak up, then you can probably skip out on that conversation altogether. Otherwise, that difficult conversation is probably worth having, so make sure you do it right.

When to Skip a Difficult Conversation [Harvard Business Review]


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