Figuring Out Job Offer Negotiations: Lessons Learned from Kym Possible

As regular readers know, I recently changed companies. After all the interviews, the next part of that process was the offer negotiation phase.  To be incredibly transparent, I hate that part of the interview process like almost nothing else in my life. It’s gut-churning and mind-numbing and terror-inducing all at the same time. I always feel like I’m doing it wrong, and at the end of the process, I’m certain I’ve made horrible mistakes that will haunt me for the rest of my career.

In the 35+ years I’ve worked in tech, I’ve changed jobs several times, each time interviewing with several companies before making a career move. After some back-of-the-napkin math, I realized I’ve received dozens of offers over the course of my career.

Anyone who’s worked in tech understands this is pretty typical, and not just in this current period of marketplace unrest, with the “great resignation/reshuffling/whatever”; weekly announcements of layoffs and companies getting acquired, spun off, or shut down like it was a game of whack-a-mole where the moles were actually Russian nesting dolls.

Moving around like that means I’ve negotiated my salary, benefits, days off, and so on a bunch of times. And you’d think that after so much practice over so many years, it would feel like old hat. No big deal. A walk in the park.

Nothing could be further from the truth.

There are, of course, plenty of resources to learn how to be a better negotiator and to take control (not to mention ownership) of one’s career. I’m a big fan of Chris Voss’ book “Never Split the Difference.” I’m an equally big fan of Josh Doody, who I’ve enjoyed hearing from on | three | separate | appearances | on Corey Quinn’s Screaming In the Cloud podcast.

But even with the information I gleaned from those (and other) resources, I’m still uncomfortable with the entire process. Negotiating the purchase of a car or house is so much easier emotionally, because objects aren’t tied to yourself worth the way a job offer objectifies your value as a professional.

This makes it more important than ever to take a principle we hold true in our data centers and apply it to our careers: Namely, if something isn’t a core competency for the business, don’t spend huge amounts of time, effort, or budget on building it internally. And it’s an indisputable fact that – while salary negotiation is important to my career – it’s utterly irrelevant to my day-to-day job.

This is why, when my friend and former colleague Kymberlee Price (aka “KymPossible” on Bluesky, hence the title of this blog) offered to help with the negotiation phase during my last job search, I jumped at the chance.

If you are currently in the negotiation phase of your own job, stop reading this and contact her. If you are hunting for your next job and know that negotiations are on the horizon, write down her info and contact her after you finish reading this. And if you aren’t looking for a new job at this moment, I’d remind you that – in tech at least – your transition to turning on that green “Open to Work” banner in LinkedIn can happen at any time. So, grab her info and put it somewhere for safekeeping.

If you’re thinking, “I’m just not comfortable with being super aggressive to my future employer”, you need to move over and make some room because I’m not either. In fact, almost every one of Kym’s clients says the same thing. And the truth is, nobody is saying you need to be. In fact, aggressive is the very LAST thing that you need for effective negotiations. Firm? Absolutely. Confident? 100%. But aggressive? Never.

Like any great tech practitioner, helping people negotiate their salary is Kym’s SIDE HUSTLE. By day, she’s a kick-ass product security leader. Kym relies on data and analysis to identify how the offer on the table stands up to industry standards, your current compensation, the likely movement of the market in the next few years, and more. Kym’s process takes the emotion completely out of the conversation. Her view of “total compensation” goes way beyond what I’m used to considering. Not only did she factor in the usual elements like stock options, bonuses, etc., but she also included out-of-pocket healthcare costs, 401k matching, PTO, and a projection of how the complete offer will “age” over five years, based on average raises, bonuses, etc.

The approach is hard to argue against. It’s not a fierce contest of wills where one side insists they are “worth more,” and the other does their best to convince them otherwise. It’s a frank and fact-based discussion of how the company’s offer compares competitively to other options available and proposes adjustments to close any gaps so you can happily accept.  A company can still choose to say, “That’s not something we can do.” However, this is a far cry from the standard pushback of “We don’t believe we (or anyone else) should do this.” Which, I gotta tell you, is a breath of fresh air.

Now, all of this implies that you’re always going to get a lowball offer – which isn’t the case. Kym tells me that when clients get a phenomenal offer straight out of the gate, she provides them with a few key questions to ask the recruiter to confirm it really is a great offer and ensure there aren’t any surprises later. Sometimes, the base compensation is great, but you’re losing $50-100k a year in benefits, retirement matching, etc. Maybe you’re okay with that tradeoff, but you need to know about it upfront.

As a Tech professional, I need to build and maintain my skills as a developer, sysadmin, and engineer. I need to stay up to date on the latest tools, techniques, and technologies. But I don’t need to spend precious time learning the fine art of salary negotiation, even when I will probably have to do it several more times before I retire.

Not when there are amazing folks like Kymberlee Price around to do it and do it far better than I could ever imagine.

Also published here.