Asking for a pay rise. Pushing back on a deadline you know you can't hit. Telling your manager something isn't working, or that you're thinking of leaving. These conversations matter, and most of us either avoid them or walk in underprepared and leave wishing we'd said it differently.
Good preparation doesn't mean scripting every word. It means knowing what you want, how you'll open, and how you'll handle the moment it gets uncomfortable. Here's a simple way to do that, drawn from how high performance coaches prepare athletes for the moments that count.
If you manage people yourself, this works both ways. It's also how you'd want your own team to come to you.
Step 1: Get clear on the outcome you want
Write one sentence that finishes: "By the end of this conversation, I want..."
Be specific. "I want them to understand how stretched I am" is a feeling. "I want us to agree which of my three projects gets pushed back a month" is an outcome you can both work toward.
Then write your fallback: the smaller result you'd still count as progress. Maybe it's an agreement to revisit it in two weeks. A fallback stops the conversation feeling all or nothing.
Step 2: Separate the facts from your story
Before a hard conversation, most of us have built a story: "they don't value me", "they always dump work on me". The story may be partly true, but leading with it puts the other person on the defensive.
Make two lists:
- Facts: things anyone could observe. "I've worked past 7pm on 11 of the last 15 days." "The project was scoped for two people and I'm doing it alone."
- Interpretations: what you've concluded from those facts.
Lead with the facts. Hold your interpretations loosely, and offer them as questions if you need to: "I'm reading this as... is that fair?"
Step 3: Think about what your boss needs
Your manager has their own pressures: targets, their own boss, a team to keep running. Spend five minutes writing down what they're probably worried about and what they'd need in order to say yes.
If you're asking for a pay rise, they need evidence they can take to whoever signs it off. If you're pushing back on a deadline, they need a plan for what happens instead. Bring that with you and you've turned a complaint into a proposal.
Step 4: Plan your first two sentences
The opening sets the tone, and it's where nerves hit hardest. Write your first two sentences and practise saying them out loud.
A simple shape that works:
- Name the topic plainly. "I'd like to talk about my workload over the next quarter."
- Say why it matters to both of you. "I want to keep delivering well, and right now I don't think I can do that on all three projects."
Then stop and let them respond. Don't fill the silence.
Book the time properly too. A hard conversation squeezed into the last five minutes of a one on one, or raised in a corridor, rarely goes well. Ask for 20 minutes and say what it's about.
Step 5: Prepare for the tense moment
At some point it may get uncomfortable. They might push back, get defensive or say no. Decide now how you'll respond.
High performance athletes rehearse the hard moments, not just the good ones, so they stay steady when it happens for real. You can do the same:
- Have a reset line ready. "Let me make sure I've understood you..." buys you time and shows you're listening.
- Slow your breathing. A long, slow breath out helps you settle. Take one before you answer anything that stings.
- Know you can pause. "Can I think about that and come back to you tomorrow?" is a strong answer, not a weak one.
Step 6: Agree next steps and follow up in writing
End by summarising what you agreed and who does what by when. Then send a short, friendly note the same day: "Thanks for the chat. As discussed, we'll..." It keeps you both honest and gives you a record if things drift.
If it didn't go the way you hoped, that's not the end. You've raised it, you know where they stand, and you can plan your next step from there.
Try it in Pocket Mentor
Pocket Mentor is built on a framework from high performance coaches in AFL and F1. Before your conversation, open a chat and talk it through: what you want, what your boss needs and how you'll open. Your mentor helps you get your thinking straight, and the chat summary gives you your key points to look over before you walk in.
START WITH POCKET MENTOR.