Dear Businesslady’s Guide to Getting Promoted

Have you ever gotten a promotion? Occasionally you’ll luck out and one will just get bestowed on you, and (if you’re like me and this happens at a formative early stage in your career) you might internalize the erroneous notion that such an occurrence is commonplace. Then you’ll spend the next several years realizing that such sudden elevations are rare, and that being encouraged to apply for a higher-level position is much more likely.

Pursuing a new job — whether at your current organization or a different one — is the easiest and simplest way to get a promotion. It’s also basically identical to the process of job-searching (especially since most people are looking for something “better” if they’re going to bother prepping application materials). That’s a topic I’ve already covered quite extensively, although my inbox is always open if you need help with a variation on that or any other theme.

This column is for folks who are performing at a high, above-and-beyond level, but who aren’t particularly interested in leaving their current role or organization. It’s about the kind of promotion where you convince the powers that be to create a new position that reflects your uniquely valuable contributions.

The first step in making that happen is, obviously, being an extraordinary employee. If you’re just okay, you’re going to have to work much harder to make a compelling case for your own advancement, and if you’re even a little bit below-average then you’re facing seriously long odds. But please know that I’m delineating these categories dispassionately, and without any judgment. There are plenty of reasons to approach your job from the standpoint of “I do most of what’s asked of me, and nothing more.” You know who’s totally justified in having that attitude? Someone whose employer is unwilling to reward hard workers. Gives hard stare directly to camera at an imaginary audience of inept managers.

But how can you tell if you’re one of the standout staffers who might have a shot at a raise and/or a new title? It can be hard to self-assess. There’s a kind of Dunning-Kruger effect, where the strongest employees are often the humblest and most self-effacing — although this isn’t exclusively true. Nor should it be the case that high performance is directly correlated with quiet acceptance of any and all workplace conditions. A cheery whatever-the-boss-wants attitude may serve you well in junior roles, but it becomes a liability as you get further along in your career. For one thing, the more experience you have, the more qualified you are to offer productive counterpoints that protect managers and companies from their own ill-conceived plans — and if you fail to mobilize that skillset, you’re missing out on the chance to seize more authority (and, eventually, earn yourself a promotion). Many good employees are more circumspect with their criticisms than their cranky/slackery counterparts. Which is too bad, because it’s the inverse of effective collaboration. Leadership teams thrive on feedback that’s looking out for their organization’s best interests.

The best reason to get comfortable speaking out, though, is that it’s essential to becoming your own advocate. While you can do a complete 180° flip between stoic obeisance and vocal critique, it’s a lot more effective to slip “I’m being under-recognized” into an ongoing litany of other insightful observations. If you feel uneasy about initiating the promotion talk — or about bearing bad news to your boss in general — practice by bringing up lower-stakes stuff that’s irrelevant to your own personal gain.

Of course, even within the context of open communication with your manager, there’s not usually a seamless segue into “I’d like a promotion.” Before you even raise the issue, you have to prepare your case. Not only will that ensure you’re well prepared for the conversation when it happens, it will also provide you with psychological support: as you’re gathering evidence, you will increasingly convince yourself that you deserve more, which will help you overcome the awkwardness of asking for it. (And if your research results feel less than compelling, you can always pause that project and pivot your efforts toward finding ways to enhance, and visibly demonstrate, your value.)

Even if you’re not prone to dramatic shifts in perspective (like this “mood swings” cartoon I saw on Twitter the other day—which as the kids say, made me feel extremely seen), you probably have days at work where you feel like a rockstar. When your inner monologue is cheering you on — whether it’s the positivity of “I am CRUSHING IT” or the irritated self-aggrandizement of “you fools would perish without me” directed at your coworkers — harness that energy as you compile a list of reasons your promotion is warranted.

For anyone who hasn’t read my book cover-to-cover or memorized my entire archive, I’ll reiterate one of my favorite pieces of advice: create a folder in your work email where you copy-save complimentary messages. (The copying is so that you don’t lose track of whatever other info they may contain. The saving is, I hope, self-explanatory.) A repository like this is valuable for many reasons — it helps cheer you up when you’re on an emotional downswing, for instance — but it’s essential when you’re trying to remember what makes you so great. You can even grab quotes to include in any write-ups you prepare to support your promotion case. Just make sure they’re specific enough to be meaningful — “I couldn’t believe how much effort you put into solving my complex problem” is vastly superior to a generic “great job, thanks!” But it’s also fine if you can’t find any movie-poster-level blurbs about your phenomenal performance — reviewing a collection of accolades will help jog your memory about long-forgotten work wins of yore.

The goal here isn’t to provide an abstract argument that your role is important, regardless of who might inhabit it. You want to provide proof that YOU — with your distinctive arsenal of talents — are helping your organization thrive, and that no one else could do it as successfully. Here are some other points to ponder as you’re doing this preliminary preparation:

  • What sets you apart from your colleagues in similar positions? Or if you don’t have peers, why is your specialized role so essential?
  • When have you made an unequivocally positive impact — money saved, processes streamlined, et cetera?
  • How does your salary/title compare to other people doing comparable work? (Needless to say, if the answer here is anywhere from “fine” to “way better,” then you probably still have some dues to pay.)
  • Without putting it in exactly these terms… how screwed would your workplace be if you randomly decided to quit? What would they lose? Be precise. (“Those jerks would lose everything,” while therapeutic, doesn’t exactly capture what you bring to the table.)

In the course of this exercise, a picture of You, With Promotion will emerge. What do you want your title to be? Think of a first choice to propose, along with some backup options you’d be happy with. What should your new salary be? This is an extra level of difficulty in terms of securing your boss’s buy-in (title changes are free; raises are not) but unless you think it would seem absurd to ask for more money, it can’t hurt to try. That means coming up with a number you’d be pleased with, then bumping it up a few notches so there’s room to negotiate.

The last step is checking in with yourself to confirm that you really do want to stick around for a while. If you’re unsure, spend some time contemplating the possibility of leaving, and maybe even send out a few applications to see if that helps crystallize your feelings. A promotion doesn’t obligate you to unending fealty to your current job, but you risk burning bridges if you bounce right afterward — so make sure you’re not subconsciously planning to do just that.

With all that background in place, then you’re ready to broach the subject with your boss. The best strategy will depend on the usual rhythms of your office, but in the absence of any obvious procedure, I’d recommend mentioning it verbally during a generally chill meeting, then asking what kind of documentation (if any) they’d like to see. If you need to produce a memo or other formal communique, all your prepwork means you can turn it around with a quickness. And if your manager jumps immediately to “sounds good; let’s talk numbers,” you’ll be equipped to discuss details.

You should also be prepared to hear “no,” regardless of how airtight your case may be. You don’t have to pretend to be indifferent to the news and take it in breezy stride, but you do have to figure out a way to move forward without feeling like you and your manager are now permanently in a fight. Try to change that “no” into an implicit “not yet” by asking what you can do to improve your prospects. Get as much information as possible about the rationale behind the decision—both so you can understand it better for your own peace of mind, and so you can use it as ammunition during a future appeal. Make it clear that you’ll want to revisit this issue and get your boss’s buy-in on a reasonable waiting period before you put it back on the agenda. That way, it won’t be a surprise when you release Promotion Request Two: Back in the Habit of… uh… Advocating for Appropriate Compensation. (Two totally unrelated fun facts: I saw the Sister Act sequel in a theater, and I am one thousand years old!)

In all other scenarios, there’ll probably be some debate over the exact form your promotion should take. Be flexible (you may not get everything you want, and that’s okay) and thoughtful (what do you want most, and what are you willing to give up?), but don’t be shy about pushing back as needed. If your manager is willing to consider promoting you, that means your value has been noted. Don’t give up that bargaining power just because it’s sometimes uncomfortable to assert yourself.

Even in the ideal outcome — where your boss says, “Brilliant idea! I should’ve promoted you years ago!” or something similarly utopian — your work still isn’t over. In most offices, there’s a swamp of bureaucracy to wade through before your promotion can actually be conferred. (The exception would be extremely small and/or anarchic organizations, which can have downsides that balance out their speedy implementation of personnel changes.) Warn your manager, HR representative, and any other relevant decision-makers that you will be following up on this, and then proceed to bug them about it — politely, professionally, and reasonably — until the thing gets done. Everyone’s busy, and putting through a promotion is extra work. It’s unlikely to be the top priority of anyone involved in making it happen, except for you. And no matter how supportive your supervisor is and how assiduously you issue reminders, the promotion process is also likely to take F O R E V E R. Or at least, it’ll seem that way. Paradoxically, this is the upside to having your request turned down at first — it at least gives you something to work toward, with all the motivation and satisfaction that accompanies a major goal. Checking in about the still-uncertain status of something that all parties agree should happen is as fulfilling as trying to get a bunch of toddlers ready to go play outside in the snow, and about as tedious. Yet it’s a necessary final step.

It’s a lot of effort, but it all becomes worth it when — at long last — hooray, you get promoted! Look at you, with your fancy new title that better captures your contributions and a paycheck that makes you feel appreciated. If you think there’s a case to be made for your own advancement, I highly recommend making it. Resolve to create a career situation you can feel Good As Hell about (and if you didn’t recognize the lyrical reference in this column’s subheading, add in a bonus resolution to familiarize yourself with the amazing oeuvre of Lizzo). Then, use your newfound professional power for good: work toward elevating everyone else in your organization who’s equally deserving.

Postscript: I wrote this before I learned The Billfold was shuttering, but I suppose it’s an excellent note to end on. I’ve weathered one website closure already, so I’m sure Dear Businesslady will reappear eventually on an internet near you. If you follow/like/subscribe via the links below, you’ll be the first to learn about my new home. (And if you are a media entity interested in publishing a career-advice column, please get in touch!) I’ve loved being part of this community, and if any of you need help with a work conundrum, you know where to find me.

Courtney C.W. Guerra is the author of the fun, funny, fulfillment-focused career guide Is This Working?, and she’s been giving advice as Dear Businesslady since 2014. Her first postcollege “real job” was at an HR consulting firm, after which she steadily worked her way through administrative positions until she found a role that truly suits her — and now she tries to help others do the same.

Email me at, and keep in touch (seriously, I mean it!) via Twitter,  Facebook, my TinyLetter, or my website.

Photo by Nastuh Abootalebi on Unsplash.

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