How to Prepare for a Big Conversation at Work

Big conversations are never easy. Whether you're asking for a pay raise, resolving a difficult situation, or trying to clear the air, the lead-up is often the hardest part. What actually causes stress isn't usually the topic itself; it's the uncertainty about how to approach it.

As a coach, and as someone who’s had my fair share of challenging conversations, I’ve seen how powerful it is when people prepare thoughtfully. Not by scripting every line, but by getting grounded in your own perspective, considering the view from the other side, and entering the meeting with a clear sense of purpose. I have a Sales Director for 5 years who always asked to send over 3 bullet points as an agenda before every meeting - at first I thought it was too much, but over time I saw how easy it made every tricky point in the discussions we had, as he knew what was coming, and I’d had to think about it before.

This new worksheet is designed to help you. You'll work through:
• Your view of the situation and why it matters.
• Their possible perspective using a simple two-column exercise inspired by Gestalt thinking.
• A clear meeting agenda, including the powerful line I learned at LinkedIn: “This meeting will be successful if…”
• Your opening sentence so you don’t freeze at the start.
• One practical step you’ll take in the next 48 hours.

You can download the full worksheet here: Preparing for Big Conversations

If you try it, I’d love to hear what stands out for you.