I Was Terrified to Lead This Billion-Dollar Negotiation—Here's How It Changed My Career Forever

A decision to say 'yes' to something new feels terrifying.

Right?!

That’s exactly how I felt when I agreed to lead a multi-billion-dollar negotiation with one of the biggest health tech corporations in the world.

I would probably be the most inexperienced person in the negotiation room.

Everything about it was intimidating, but I said yes anyway!

Out of My Depth, but Committed

I was in my early thirties back then.

By that time I had handled hundreds of smaller deals. So, I wasn't quite a rookie.

But this was THE DEAL!

My team had prepared the data, crunched the numbers, and mapped out scenarios. But as the lead negotiator, I felt weighted down. Lots of what-ifs whirling around in my brain! I kept replaying possible conversations in my head, imagining how I’d respond to all the objections and/or counters.

I wanted to appear confident, even though inside, I was second-guessing everything.

A Room That Swallowed You Whole

The boardroom was big! Definitely an architectural flex - a panoramic view of the city, glass walls, and a table so massive it seemed designed to make people feel small. I was on home ground sure but I had only been in that room once or twice before and always trailing some big C-suite leader.

Only this time I was supposed to own this entire thing?!

And then the other team walked in! From where I stood, they looked self-assured, confident, and pretty much acted like they belonged from the get-go! Sharp suits, measured steps, faces set in controlled seriousness.

I was, of course, experiencing an endless series of mini-panic attacks! But thankfully all on the inside.

Finding My Feet

The opening minutes are a blur to this day.

I launched into my prepared points. Any pause in the conversation felt twice as long, every question like a test I wasn’t sure I was ready for.

When we broke for a recess, I practically ran to the breakout room. I called a few cross functional leaders, asking for guidance on a few topics. My notes were scattered across the table, a great visual of how I felt—barely holding it together.

But something shifted as the day progressed.

My preparation started to carry me.

I leaned into the discomfort, trusting that I knew what I was doing. I didn’t have all the answers, but I had enough to move the conversation forward.

By mid-afternoon, I stopped feeling like I was barely surviving...phew!

The negotiations went on for several weeks. As the days went by, I started to relax more and more. And focused on the mission. I observed their strategies, course-corrected when needed, and slowly built confidence.

Steady progress!

Why This Experience Matters

That negotiation changed how I saw myself.

I used to think confidence came from feeling prepared and ready. That is true of course. But what I learned that day is that confidence adds up later as well, after you’ve done the thing that scares you.

It is true what they say - the moments where we grow the most is when we dive into discomfort. It feels like sitting in an oversized boardroom, surrounded by people who seem more powerful, more experienced, more everything. But if you can push through the nerves, you’ll come out on the other side with a new kind of self-assurance!

I’ve never been afraid of a negotiation since that day. I know every negotiation will not be successful but I know I will show up, not being driven by fears and insecurities.

A Challenge for You

Think about something you’ve been avoiding because it feels too big.

It can be a project at work that pushes you beyond your current skills, a pay-raise conversation with your boss, or even applying for a role that feels just out of reach.

What’s one step you can take this week to say yes to it? No perfection required. It just has to move you closer to the thing that scares you.

You might feel unprepared, nervous, or like you’re in over your head. That’s okay. I can tell you first hand growth happens when you push through that brain chaos!

And on the other side, you’ll be stronger for it.

If you take on this challenge, I’d love to hear about it. What’s your “uncomfortable yes,” and how are you preparing for it? Let me know in the comments or shoot me a message.

Dorothy Mashburn is on a mission to empower women of color (and allies!) to steer their career journey and confidently negotiate their value. She can be reached here.

OR

Get the secrets to commanding top offers with my book, Executive Edge - Finding Golden Nuggets. Discover how to tap into hidden insights, position yourself as the must-have candidate, and secure the offers you deserve. Get your copy now!!!