Challenging Conversations

Updated: August 18, 2016


Simulate and practice challenging conversations.



Asking generative questions

Listening actively

Navigating power

Challenging conversations


  1. Identify a challenging conversation you’ve had recently or need to have with somebody.
  2. Take 10 minutes each to describe the person involved (anonymize her or him if necessary, and try to be fair), the goal of the conversation, and the context. Specifically:
    • What made or will make this conversation challenging?
    • What will the outcomes (both positive and negative) be of having this conversation?
  3. Pick either your or your partner’s scenario, and role play. You will play yourself, and your partner will play the other person. (3 min)
  4. Debrief. What happened? How did that feel? What could you have done differently? (5 min each)
  5. Replay the scenario. What happened this time? How did it feel? (10 min)
  6. If you have time, switch to your partner’s challenging conversation, and repeat these steps.

Design Notes

Certain kinds of conversations are incredibly difficult because they trigger all sorts of scary emotions, both within others and ourselves. We fear other people’s reactions and sometimes our own. We struggle with how to communicate constructively in light of these potential emotions.

The best way to have these kinds of conversations successfully is to practice them. We can do this by finding friends or colleagues we trust and by role playing. Doing so lets us practice and fine-tune what we’re going to say.

More importantly, role playing enables you to experience and navigate around emotions that may come up in a way that simply strategizing about a conversation does not.

Sometimes, these role plays can be emotionally challenging. Find a safe, comfortable time and place to practice, and do these with people you trust.