4 Real Leaders Share How They Negotiated Big Wins (And What Actually Worked)
Real stories from real women who negotiated big wins — and what made the difference.
Welcome to Reframed! I'm Ashley Rudolph and I write this newsletter for high-achievers ready for the next level in their careers. Reframed readers describe the experience best: “I read all of your posts and there’s something to learn from all of them! I love the personal stories of leadership and work the most.”
Listen to the audio version of this week’s post, press play.
I love the thrill of negotiating.
The tension that builds before I hop on the phone or walk into a room.
Putting together my case, my proof points.
Rehearsing them.
Questioning whether I’m crazy enough to make the ask. An ask that’s so brave that it makes my stomach do backflips.
I love it.
IN CASE YOU MISSED IT →
These days it’s less about me negotiating and more about how I support my clients when they’re negotiating job offers or promotions/raises.
For me, the key to negotiating effectively is the combination of:
Leveraging the right frameworks, tools, and tactics (which I covered in depth in this newsletter)
Creating the conditions for the best version of yourself to show up in the conversation
Last week, one of my clients got a job offer.
Mid five-figure increase.
The company upgraded the role from a senior manager to a senior director and increased the budget for the role (by more than $80k), just to win her over.
She created the conditions for the best version of herself to show up in every single conversation. She prepped, connected with every interviewer, showed her expertise—and when it was time to negotiate, we collaborated on a strategy that matched her situation. The end result?
They loved her.
They had to have her.
They upgraded the role to match her level and comp.
She got the job.
Her experience wasn’t a one-off.
This week, I decided to cosplay as my own version of a corporate Carrie Bradshaw (a la those Season 1 woman-on-the-street interviews) and reached out to a few women in my network. I asked them to share their negotiation success stories (they’re really good).
It feels more important than ever to have these conversations. This job market is rattling people’s confidence. I'm hearing questions I've never heard before from high-performers - "Should I even negotiate? What if they rescind the offer? What if I'm lucky just to have gotten this job?"
When everything feels unpredictable, asking for more is terrifying. And yet the people who negotiate well—even in this market—consistently do three things well:
They research
They know their number, and
They make the ask at the right time
Every. Single. Time.
One more thing before we get into their stories: context is everything. You can prep the perfect pitch, rehearse every line, have the data at your fingertips — but if the other person isn’t ready to have the conversation, it won’t land. If you aren’t on the same page with your boss about your performance or there are budgetary constraints, no clever script is going to override that.
The women I spoke to understood this. They didn’t just prepare their asks — they had great timing.
I hope these stories give you the nudge you need to do the thing.
THE TACTICS: FOUR WOMEN SHARE HOW THEY NEGOTIATED
These four women all negotiated successfully and they did it their way.
A former customer experience and strategy director turned business owner who built a case so strong it didn’t need defending.
A senior people leader who turned a nerve-wracking ask into undeniable proof she was ready.
A marketing exec turned consultant whose mindset shift changed everything.
A trusted friend working in big tech who shared how she pivoted from higher ed/non-profits into tech.
Enjoy!
Dr. Jen Pardi-Cusick, former customer experience and strategy director turned business owner
What I love about Jen's story is how she turned a moment that could have easily led to being stuck in frustration into an opportunity. She built an ironclad case that spoke for itself and got what she asked for.
I was in a group of people in my field and they were all directors, VPs, and SVPs and I was a manager. However, they were all running programs that were way less sophisticated than mine and I was like, "Well this isn't right.".
So I put together a package of my current job description, marked up with everything that wasn't factual, as well as several open jobs at other companies at the director level (and comp) and highlighted all the things on those job posts that I was already doing at my current org.
I ended up getting a 30% raise, the director title, doubled my bonus and quadrupled my stock grants, and got a more appropriate seat at the table in executive conversations.
Putting together a packet of facts made me feel way more confident because it wasn't my opinion that I was undertitled/underpaid, it was right there in black and white. I barely had to say anything other than explain my approach and say that I didn't want to wait for the comp cycle because this was obviously an error.
Annabelle Sullivan, Head of People and Ops
What stood out to me about Annabelle's story is that her win helped her go from seeing negotiation as scary to seeing that it can be a signal of competence.
I was moving from a manager --> director role, and had been undercompensated relative to my duties for years, so I took this as an opportunity to ensure I was being paid the market rate for my skills & experience. I had also just read Chris Voss’s masterclass on negotiation.
I was offered a new job but the salary was below market, so I asked for a base comp that was more in-line with market - 40% above their initial offer. They accepted my counter with no issues.
I knew I also wanted a sign-on bonus, as I was missing out on a $40k bonus at my consulting firm by moving into this new role - so I asked them to provide 1/2 ($20k) & they agreed.
It really taught me that negotiating is not some scary thing & that, quite frankly, when you negotiate, often times they think you are MORE equipped for the role, because they see you know your worth.
Kate Citron, False Start & former marketing exec
I've been admiring her content on career development for marketers (this letter making yourself indispensable is one of my favorites), so I reached out to Kate Citron to dive deeper into one of her career wins. What I loved most about her approach is how she went into her negotiations informed. She owned her number from day one - she didn’t apologize and was prepared to not back down.
How much of an increase did you negotiate?
I negotiated a $40k base salary increase through a new opportunity — the exact amount I earned in my first job in 2013, which made it feel even more meaningful.
What do you think made you successful?
I was crystal clear about my compensation requirements from the first conversation I had with the recruiter. My ask was pretty far above the range listed for the role, which naturally garnered some pushback. Instead of avoiding the conversation, I welcomed it and was always prepared with talking points to support my why.
I also believed, perhaps irrationally, that I could get the salary I wanted, whether in this role, my current company, or elsewhere. As such, I was ready to turn down an offer that didn’t meet my requirements.
How did you feel after?
Proud — less because of the final number, and more because of how I handled the process. Negotiating has historically made me uncomfortable, but this time I felt calm and confident. I had the experience to know my worth, and that made all the difference.
What are some of the biggest mistakes that women make when negotiating?
At the risk of generalizing, women are more afraid than men to ask for the number they want. I could psychoanalyze this all day (and I have with myself), but I don’t think the reason matters much. What’s more important is that we go for it anyway.
First, validate whether your number is reasonable: check Glassdoor, Levels, and this comp report; talk to friends, family, coworkers, and even your partner to find out what others are making.
If your number is fair (even if it’s not — I support aiming high, too), practice asking for it. State your salary target out loud until it sounds confident, even if you don’t feel that way yet. And have talking points prepared to support you. You may not need them, but you’ll feel better knowing they’re there.
A very smart and high-achieving friend in big tech
Ever have that one friend who always has a plan, can talk you off any ledge, and somehow makes it look easy? That’s [redacted]. We spoke anonymously because, well… #bigtech. What I didn’t know until now: just how courageous it was for her to walk away from a safe-but-draining career in higher ed/non-profits, ask for more than she’d ever asked for before, and prove to herself she could thrive in an entirely new industry.
What was your most meaningful jump?
Moving from higher ed and nonprofits into tech.
It amounted to about a 15k pay increase from one job to the next, and while I have had larger pay increases in the years after, it was definitely a huge milestone for me and helped give me the confidence to get where I am now.
What gave you the courage to do it?
I had been working with the same boss for a long time, only 27 and feeling completely burned out from the long hours (regularly pulling 60 hour weeks and coming in on Saturdays) for the type of pay that only afforded me a tiny, creaky studio apartment.
I knew exactly the number I had in mind to be able to start really living my life and not feel so trapped in the 9-5 grind.
The offer came in and was the exact same pay as my current role. Initially I was a bit crushed - it just felt so obvious that I wouldn’t be any closer to my own goals if I didn’t just ASK for what I wanted, and what I knew I deserved. So I responded to it a bit above where I really wanted to be, and the counter nailed my expectations. I signed the offer letter that day.
What do you think made you successful? How did you feel after?
When I spoke to the recruiter about it I came armed with information. I built my reasoning around what current market trends were, highlighted my subject matter expertise, and left some wiggle room between what I told them I wanted vs what I’d actually accept to try and set us both up for success. I said something to the effect of “you are offering me what is below my expectation and this is what it would take to get there.” I don’t think I had really ever asserted myself in that way before, and it felt great to have actually stood up for myself in a way that made an immediate and material difference in my life. Turns out shooters do, in fact, shoot!
What are some of the biggest mistakes that high achievers make when negotiating?
One thing I see a lot (and try to coach out) in high performers is that they can often fixate on the volume of work they can do vs the impact of that work. I think [that] can be a mistake because ultimately good companies want to hire people who are uniquely talented at what they do, and quantity does not really convey quality in a way that motivates an employer in negotiations.
The most critical mistake, to me, is being extremely rigid with your expectations, especially with no clear “why.” If you are trying to negotiate higher pay, but are getting negative signals with regard to salary, pivot! There are plenty of ways to find more total compensation by focusing less on a specific number and more on what you want the money for.
In the example I shared, part of my calculation included knowing I wanted to be able to take more time off of work, and going from 10 total PTO days annually to somewhere with “unlimited” time off was a huge part of the package. No more unpaid days off! My current job offers incredible benefits for people who are looking to start a family, which is something I’m hoping to do in the next few years. The generous parental leave, medical and fertility benefits are worth more than what I made in any of the first several years of my career, and are a huge contributing factor for why I’m planning to stick around.
If you’re sitting on an ask right now — a raise, a title, a role — this is your reminder: stop waiting until it feels less scary. It won’t.
Negotiation doesn’t get easier. But every time you do it, you prove to yourself that you’re worth it (and you are).
Good luck! See you next week.
Ashley
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Great lessons, thanks a lot Ashley and everyone who has shared their stories. Chris Voss’ book is indeed a masterpiece, I used it to negotiate my salary too and now use the learnings to coach people to negotiate! A must read.
This was so helpful Ashley! Thanks to everyone who shared their stories, I'm saving this to refer back to later and just put Never Split the Difference on hold at the library.