Professional athletes don’t just show up to their games without practicing.
That would be a recipe for disaster. Similarly, you wouldn’t show up to a test without studying. There’s a time and place for showing up and “winging it”.
Difficult conversations aren’t those times.
But – I also recognize that you don’t always have hours to prepare for every conversation.
So I’ve distilled my entire preparation routine into the 10 most important questions that will help you get ready for any difficult conversation.
Unlike other guides that narrow it down to 3 questions, this checklist will let you get deeper so you can better handle any obstacles during the conversation.
So take these 10 and feel free to ignore ones that aren’t relevant, but I know you’ll find them vital to your next conversation:
Let’s get into it:
| Question | Considerations |
| What is my goal for this conversation? | Be as specific and concrete as possible. |
| Why is this important to me? | This will help you define and explain why you’re even bringing it up to them. |
| How flexible am I willing to be? | Another way to phrase this is – “Would I rather be right or be successful?” |
| What examples/data will I need to back up my point? | Especially with employees and performance issues, you’ll need to come with receipts |
| When is a good time/place to do this? | Make sure it’s a time both of you won’t be rushed or interrupted |
| Do I need to be the one to deliver this? | Sometimes, the message or conversation might be better received from someone else who has more influence/trust with that person. |
| What assumptions am I making? | What are you overlooking? What biases may be creeping in? |
| What will I need to keep myself calm? | Figure out your emotional triggers and make sure you have calming tools to keep yourself grounded during the conversation. |
| What’s the other person’s communication style and triggers? | The more you understand about the other person, the more you can phrase things and bring up things in a way that they can receive it. |
| Who holds more actual/perceived power? | Reflect on if one of you has more positional authority, but also take into account who has more perceived power (for example, an older team member may hold more perceived power, even if you’re their manager) |
I truly believe the more you can answer these questions going into it, the better prepared and better capable you’ll be to handle whatever comes your way.
If there’s another question you love using, but don’t see up there, reply back and let me know what it is!
Cheers,
Chris
