How to negotiate like a boss


Last week, a friend pinged about an upcoming salary negotiation. In advance of the discussion, she’s talking to lots of folks so she can learn from all our mistakes. I wish I’d been clever enough to ask for this type of advice in my twenties. Might have ended up with fewer dumb mistakes to cover in my posts.

As I talk about how my approach to salary negotiations has evolved since my twenties, I’m mortified. So many of the things I thought were fixed or non-negotiable turned out to be the opposite. And so much of what freaked me out turned out to be no big deal.

And here’s the terrifying part: the thing I thought was no big deal was the biggest fuck up of all. A perpetuating inequality and wage gap type fuck up. We’ll get there.

But first, let’s check in on 20-something me and see how she’s doing…

Mistake #1: The quiet wait. The budding resentment.

Early in my career, I dreaded asking for a raise. I figured it was easier to do great work, keep my head down, and hope that someone noticed.

In 2014, the CEO of Microsoft, Satya Nadella went to the Grace Hopper Conference and told women in tech not to ask for raises. He basically quoted 22-year-old me. And if we’ve learned nothing else through The Co-Pour, it’s that 22-year-old me was an idiot.

Keep your head down. Work hard. Hope someone notices. I developed that approach in 2002. It was wrong then. It was still wrong in 2014. Satya’s mea culpa tweet quickly followed his onstage comments.

This approach is busted for so many reasons. To stand up as the CEO of a major tech company in 2014 and deliver this advice on stage at the GHC. Pretty sure gobsmacked is the word I’m looking for.

If you got hired in 2010 and haven’t had a raise since, chances are good you’re well out of sync with market rates.

For startups who are notoriously crappy at both mythical meritocracy and HR as a function, this advice is a recipe for disaster. In this environment, if you fail to get a raise or get ahead, you don’t know if it’s because you didn’t work hard enough. Or if it’s because of the irregular and unstructured performance reviews. Or the woefully vague and unactionable feedback. Or compensation reviews that don’t adhere to a schedule.

Without a clear sense of the process, people spend a bunch of time wondering when, exactly, is the right time to bring up their salary.

TODO: Schedule the awkwardness.

Set a time to meet to talk about compensation. And at the end of that discussion, set up the next discussion (typically six to 12 months in the future). And then go put a reminder on your calendar. That way you don’t have to worry that you’re pestering or nagging or otherwise annoying anyone. You’re simply following up. The same way you always do. Because you’re amazing.

Mistake #2: Everything has changed. Except for your salary.

My murky startup job meant that I got to take on a bunch of new responsibilities. My role then changed from individual contributor (IC) to manager. I went from being US-focused to covering a global business. I completed major projects, on time, and with awesome outcomes.

Despite big changes in my roles and responsibilities, my salary stayed the same. I would get a knot in my stomach every time I thought about approaching my boss. Ugh. Maybe I’ll just wait until the end of next quarter.

Inevitably, another quarter would come and go without any movement. I would swear to myself I’d bring it up next time. And then chicken out.

This cycle continued for years.

Photo credit BonninStudio, Stocksy United

I started to lead bigger teams and hire more people. That process taught me a ton about how people negotiate, what the HR folks have in mind, and how salaries are set. With that knowledge, it was no longer this opaque, terrifying process. It was actually pretty straightforward.

I had always felt super weird about asking for a raise. The asking part felt odd— as though the raise were an allowance or my parent’s car keys on a Saturday night. And the raise part felt weird — what if they say yes but we have different amounts in mind?

And then I learned the most amazing phrase. Ready?

COMPENSATION REVIEW (or comp review or comp assessment or salary review)

Let’s hold these gems up side by side and see if we can spot the difference:

ASKING FOR A RAISE: Please let me have jumped through the right hoops at the right moments. Please let now be the perfect day — where my boss is in a good mood, the sun is shining, and I have had stellar performance on a recent project.

COMPENSATION REVIEW: Well hello there formalized HR approach. Your salaries are set by the market and assessed every so often to make sure to pay similar rates for similar roles at similar companies? Where have you been all my life?

Once I figured out that comp reviews were pretty commonplace for most grown up organizations, the whole mess of salary negotiation got a lot easier.

Other handy ways to indicate you think you might be underpaid without having to say that you think you are underpaid (or an offer is too low):

  • I want to make sure my comp is in step with market rates for this role. This is useful if you have a well-defined role (designer, engineer, sales associate) and are in an area where there are many people doing that same job. In San Francisco, there are zillions of senior engineers. Their salaries may vary but you can at least get a sense of market rate by doing some online research.
  • My responsibilities have changed and I’m excited about this new and challenging role. I’d love to set up a time to update my job spec, make sure we’ve got the same things in mind, and conduct a comp review. Early stage startups will struggle with this. They may not have job descriptions. They may not know what a comp review is. But unless they are a super tiny shop, chances are good there was a job posting that they used when they hired you. If you take a look and everything is different, it’s time for a chat to get on the same page.
  • Can you share the salary band or range for this position and how you anticipate an employee will progress through the band? Basically what you’re asking for here is for them to tell you the high and low end of salary for the role. And then you want to know how they think about the job criteria at the low, middle, and high points of that salary.
  • TODO: Check in on the market.

    If you got hired in 2010 and haven’t had a raise since, chances are good you’re well out of sync with market rates. Market rates don’t usually swing too wildly. But for emerging technologies (AI, big data, VR), what was once a nascent skill set may suddenly be in very high demand. Check in on the market yearly.

    Find mentors in your network that you feel comfortable asking for advice. Senior folks have usually hired for every stage of your career. They can give you a rough idea of what to expect along the way.

    Many venture capital firms have people on staff to help portfolio companies set salaries for various stages of investment (seed on up). Find one of those people and buy them a coffee.

    Mistake #3: The biggest fuckup of all

    For the bosses reading this, I need you to take a moment. Imagine the spreadsheet that HR sends out. The one with the hidden columns. The one that lists everyone on your team’s salaries and their start dates and the last time they got a raise.

    Now imagine you’re in the middle of a bunch of tasks. In addition to your usual 50 open tabs, you have a bunch of open emails. You are trying to respond to HR with the updated salary data but instead of sending it to your internal contact, you accidentally send it to the entire editorial team at the New York Times. They print the spreadsheet on the front page of the next day’s newspaper.

    How do you feel? Are you okay with what your staff will see in the news? Or do you cringe? Are you panicked about that glaring disparity between employees who are doing the same job with the same level of experience. The one you’ve been meaning to fix but haven’t.


    Conversations about money are uncomfortable. And negotiations, even when they aren’t about money, are also uncomfortable.

    You may not ever have your salary data show up in The New York Times, but it’s a useful test for how you’re doing. You should assume that people talk. That after spending day in and day out with their colleagues, people will get comfortable. And at some point, that conversation may turn to discussions about salary. That’s okay. They aren’t doing anything wrong. It’s their personal information and they are allowed to share it as they wish.

    Your job is not to prevent those discussions. Your job is to make sure that everything passes the sniff test when those discussions happen.

    TODO: Take the time to make it right

    You inherited the team. You didn’t hire them into those weird salary ranges. They were like that when you got there. It’s not your fault, per se.

    But if you’ve managed that crew for more than a month without a plan to address it, you’re complicit. Your inaction has perpetuated a salary structure that isn’t defensible. It’s going to be a giant pain in the ass to fix it. It will require input from HR, from senior management, and a bunch of your time to chase down the details. But it’s your job. And you will sleep better at night for knowing you pass The New York Times test*.

    *The amazing part about this test is that The Actual New York Times did not pass this test.

    One last thing: Samba not combat

    Here’s the secret truth about salary negotiation that anyone who’s done a bunch of it can tell you:
    At the end of the negotiation, you still have to work together.

    If you are the hiring manager and your inbound employee feels totally screwed, that’s a terrible way to start things off. And if you are trying to close a candidate with unrealistic salary expectations who won’t budge, that also sucks.

    In the best circumstances, salary negotiation is a dance. Not a fight. It’s a back and forth — a step forward, a step back, one to the right or left. And finally, a decision to go forward together. Or to part ways.

    Conversations about money are uncomfortable. And negotiations, even when they aren’t about money, are also uncomfortable. Depending on your upbringing, background, and relative privilege in the world, that discomfort can range from mild to paralyzing. Everything in this post is something I wish I’d known at some stage in my career. But if you’d told me some of this in my twenties, I probably wouldn’t have known what to do with it.

    And not only because 22-year-old me was an idiot. It took me awhile to find my voice, to feel confident, and to have the awkward conversations along the way. And even after all that, I still had to get over my imposter syndrome to finally get paid what I was worth.

    Wherever you are in that cycle, I hope this helps. If you have tips about what’s worked for you, I’d love to hear them. Please share them in the comments.

    This article was syndicated with permission from The Co-Pour


    Melissa Nightingale

    Melissa Nightingale is a founder and partner at Raw Signal Group. She is co-editor of The Co-pour and co-author of a book about modern leadership (coming fall 2017). Melissa’s been a startup warrior since the first dotcom boom and has the branded t-shirt collection to prove it. She has held senior leadership roles in marketing, pr, and strategy at several fast paced startups, including Wattpad, Edmodo, and Mozilla. Melissa moved to Toronto after more than a decade of working in senior tech roles in Silicon Valley. She is gradually adjusting to seasons.

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