The key to turning tough workplace conversations into wins is the right preparation.

We all face tough conversations at work. We might need to give someone critical feedback about their performance, ask for a long-overdue raise, or even let a colleague go. Too often, professionals think that if we know where we want to end up, and we keep our nerves in check, we are prepared to navigate anything that comes up in a conversation.

But in addition to knowing where you want to end up, you have to plan for the steps that will get you there. That’s why, to win in tough conversations, it’s essential to prepare. Here are three things you must do to start managing a conversation before you even walk into the room:

1. Map it out (and not just in your head)

Create a mind map to organize your thoughts. This helps you hone your message, and also provides you with a script you can fall back on. Don’t underestimate the power of doing your planning on paper. Research shows that when you write things down, the process of evaluating and organizing the information helps it stick, even when your notes are not in front of you.

If you force yourself to put the hardest part first in your outline, there’s also less chance you’ll give in to the temptation to make small talk or dance around the issue once the conversation begins.

2. Design a conversation, not a monologue

When you prepare, knowing when you’ll stop talking is just as important as knowing what you need to say. If you want the other party to hear, understand and act on what you tell them, then give them a chance to be a good conversation partner by building in pauses. This means not only planning for the points you have to make, but also anticipating what they might ask.

Especially when tensions or stakes are high, it’s essential to plan the moment you’ll stop, check in and give the other party a chance to think and respond. If you repeat yourself, over-communicate or nervously fill in silences, you won’t know whether they are getting the message.

3. Once you’ve prepared, practice!

You’re not truly prepared for a tough conversation until you’ve tested what you need to say on someone else. If there’s one step you might be tempted to skip, it’s this one. Role playing and saying things out loud can feel uncomfortable—but that’s exactly why practice is essential. Your delivery will improve each time you talk through your map, so it makes no sense to let the real conversation be the first time you say it all out loud.

A neutral party can also give you feedback on your nonverbal cues and the clarity of your message. They’ll be able to tell you if you’re getting to the point, and if the words you’ve chosen strike the right tone. Make sure the person you practice with is crystal clear about the takeaways you intended: could they tell when the conversation was over? Did they have a clear sense of what would happen next?

Don’t count on your attitude, your people skills, or even the fact that you’re ‘right’ to get you to a win. Instead, enter tough conversations prepared, with a listener-tested script in mind, and set yourself up to stay on track, communicate clearly and listen intentionally.


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  • Jessica

    Good insights . /the key is not to react but to slow down and work though the process. easier said than done

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