Have you ever walked out of a one-on-one with your boss feeling like you just gave a verbal status report, but nothing really moved forward for you or your career? In this episode of Speaking with Confidence, we’re tackling one of the most underused and most valuable meetings in your entire week: the one-on-one with your manager. I break down why these touchpoints often get wasted, and how you can turn them into your best shot at getting the recognition, resources, and growth you deserve.
I’ve seen it happen again and again with the people I coach: You work hard, you want more responsibility or a raise, but when you get 30 minutes of your boss’s time, you end up listing what’s on track and what’s been checked off and that’s it. I used to believe the work speaks for itself, but as I’ve learned (the hard way), it simply doesn’t. If you don’t use your one-on-one to tell your side of the story, something else will fill that space.
This episode is a solo one just me, sharing the hard-won strategies that help professionals go from being invisible to being seen and valued. We’ll walk through three actionable phases to make your one-on-one the most powerful meeting on your schedule, and I’ll give you the tools to prepare, build momentum, and make your big ask with confidence.
Here’s a quick overview of what we covered:
Why status updates belong in quick emails, not in your precious one-on-one time
The importance of preparing for your one-on-one like it’s your meeting, not just your boss’s
How to create and use a simple “brag file” to capture wins, progress, and impact as they happen
The 3-line agenda that keeps your meetings focused and shows up with clarity every time
Why the sequence of your ask really matters and how to build up to the big things you want
The difference between asking for more resources or support, and outright asking for a raise or promotion
How to have the money and title conversation, including the crucial “power of the pause”
The role of timing and how to find out when pay decisions are really made
How to separate the ask for money from the ask for scope or title and why you want to keep those threads clear
Strategies if the answer is “no” and how that’s not always the end of the road
What to do when following up after your meeting, and how to keep a shared record that helps your boss go to bat for you (or helps you make your case elsewhere if you ever need to)
The weekly challenge to get started and show up like your one-on-ones are there for you because they are
By the end of this episode, you’ll have a playbook for turning your one-on-ones from routine updates into compelling opportunities for growth. Start your brag file, send your three-line agenda, and remember: you’re not just working hard, you’re making sure your hard work gets seen. Let’s make your next meeting count!
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