10 hacks to help you prepare for a difficult conversation

Whether you need to talk to your boss about something that’s bothering you or chat with a loved one about a sensitive subject, here are a few tips to help you prepare:

  1. Know your end goal or outcome. Conversations can weave and bend in all kinds of directions. Often we talk around something – for many reasons, like nervousness or fear of hurting someone else – rather than getting to the point. Knowing exactly where you want to steer the discussion or what you want to achieve can help you keep on track.
  2. Consider the timing. It’s unfair to spring a difficult conversation on someone who isn’t ready for it (e.g., they just walked in the door or they’re rushing from a meeting). If you can, let the other person know you want to talk and ask when it would be best for them. Even better? Schedule something in their calendar and let them know what it’s about so they can prepare too.
  3. Think about location. Pick a spot that’s free from distraction, especially by others. But also consider choosing a place where you not only feel safe but can easily exit if you need to.
  4. Get your emotions in check. Having a conversation when you’re angry or upset is not ideal and generally won’t end well. Allow for some distance first. Sometimes our emotions can cloud our judgment, other times they can make things clear.
  5. Think about your “I” statements. A difficult conversation will only be harder when there’s judgement or blame. Using “I” statements is a good way to let someone know how you feel without shaming or accusing them. For example, “When you do X, I feel/think…”
  6. Explore your assumptions. Going into the conversation, what are you assuming – about the situation, about how the other person feels or will react? What are your assumptions based on and is it possible they could be wrong?
  7. Anticipate questions. What might the other person ask? Make a list and figure out a response so you’re prepared – even if the response is that you don’t have an answer.
  8. Put yourself in their shoes. Consider how they might be feeling, what they may be experiencing or going through. Bring along some empathy and compassion.
  9. Keep an open mind. Often we run scenarios in our head or get caught up in old stories that prevent us from providing space for other possibilities. Are you walking into the conversation with your mind already made up? Or with your back up? By definition, a conversation is a talk, between two or more people, in which ideas are exchanged. Are you ready to allow for that exchange?
  10. Practise active listening. This is when you listen to someone without being quick to jump in with your own thoughts. You’re fully present and immersed in what the other person is saying. Try practising with someone else first before you have that difficult conversation.

Want more strategies or support to prepare? Book an appointment with Jennifer.