How I Chessmastered Myself Into a Promotion at Work

Those of you who follow us on Twitter already heard that I’m up for a promotion at work.

It feels unwise to talk about it because it’s not official yet. There’s no contract in place, and we haven’t gone through title or salary negotiations. It’s possible that circumstances could fail to come together. But I’ve interviewed for the role change with all stakeholders and each one has given a green light to the promotion. The woman who will become my boss has already added me to her regular staff meetings and tasked me with a new project. It feels like a done deal, so I’m taking the karmic risk of telling you all about it now.

Plus, I just couldn’t pass up the opportunity to give you all rolling updates!

It’s the first promotion I’ve ever received while working at a large corporation. (I was promoted in my first job from unpaid intern to intern with a stipend, basically. After I cried in front of my boss about money issues. A STORY FOR ANOTHER TIME!) I’m not entirely sure how to navigate the promotion gracefully, but I’ll certainly invite you all along upon my journey of discovery.

The better part of getting this promotion was luck. And I think that’s likely true of any promotion.

But luck is boring to blog about. And it ain’t everything. I Underwooded a good portion of this shit. So let me tell you what I tried and rate how well it worked.

Choose your battlefield

The nice part about being the attacking party is that you get to choose the time and location you strike. Like that poor horny hopping bird from that one episode of Planet Earth, you are about to make a large investment of time and effort. So you want to start by choosing your site carefully.

I came out of my last job with a very clear vision of the kind of company I wanted to work for. It had to have a good culture; I did not care if the people or the duties were dull as long as they had a positive, respectful culture overall. It had to be large, too. I’d learned that it’s much easier to set your own pace in large companies. I needed to report in to a mature senior manager who was able and willing to position me correctly to coworkers and other leaders.

And it had to pay well, obvs. Check the title of this blog, yo.

Most importantly, I needed to find a stable company with an unstable team. And I found exactly what I was looking for working in a sales enablement role for a small department within a huge Fortune 500 company.

Seek chaos

I had a pretty lousy manager in my first corporate job. Let’s call her “Tina” because her name was fucking Tina.

She was indiscrete, gossipy, and shortsighted. I wouldn’t consider her a high-performer either. She was bizarrely loyal to her director, whom she called her best friend. (Tellingly, her director never once used that term in return.) But Tina never displayed much of a sense of loyalty toward her own employees. I’m not sure she ever understood what a powerful team she had. She was every inch the person about whom you wondered, “How did you end up managing people?”

So one day, I asked her.

Turns out that early in her career she was on a team of about twenty people. One day, out of the blue, layoffs hit. Almost all of her fellow coworkers got the axe. She was spared along with one other employee (another young woman). They moved to a new department and each received a promotion to manager.

You can infer a lot of interesting things from this story. For one, she likely was not the best qualified in her group to manage. Suddenly axing a large team is a cost-saving measure. And since both employees saved from the chopping block were young women in the 1970s, it’s likely they weren’t the best candidates for the management track—they were just the cheapest.

So Tina got lucky in her promotion, right? Right. That is a true statement.

But she was also correctly placed in a somewhat chaotic environment. Chaos is the mother of opportunity.

Chaos is the mother of opportunity

If you work for a company where profits are modest and steady, everybody’s happy, and there are no major industry disruptions or aggressive competitors out there, your odds of a promotion aren’t great. Roles may still open up, but it’ll be at a much slower pace. Headcount expands in drips and drabs and you may be stuck waiting for someone to retire or leave the company to slip in behind them.

If, however, your company has reason for instability—a recent acquisition, legal action, big shake-ups in executive leadership, major industry shifts, whispers of impending layoffs—attrition will be much higher.

Let me put this into terms with which our readers will really connect. If you were trying to land your ass on the Iron Throne, when would you choose to enter Westeros and make your bid? During the peaceful and prosperous fifty-five-year reign of Jaehaerys I the Wise? Or during the War of the Five Kings?

Infighting, ousting, dethroning, budget slashing, and cutthroat decisions are a double-edged sword, to be sure. But if you take a long view, it’s entirely possible to use institutional chaos to your advantage. Sometimes it pays to run toward the rolling heads. Their decapitated bodies no longer need the sweet chairs they were just sitting in.

(This is not to say you should ever seek out dysfunction or destruction. We’re talking about temporary institutional instability—events and circumstances that will prompt major change. You’re looking for the death of Jon Arryn, not the Red Wedding. Do not construe this as advice to seek out poisonous cultures or outright failing companies. Toxicity can prompt change, but it almost always changes into a slightly different flavor of the exact same toxicity.)

Find the best chess pieces

I met and worked closely with about thirty leaders in my new role. I immediately honed in on three who I felt could help me advance.

The first one was a director I pegged immediately as a kindred spirit: a totally badass Slytherin battle-axe with a secret heart of gold. We liked each other immediately. She gave me an alley-oop to the second key leader on the premise that he would make a good mentor for me. This was Slytherin misdirection. She knew he’d be able to recommend me for roles in an area of the business aligned with my skill set.

The third was a bright-eyed new manager who joined the company just a few months after I did. I set up a 1:1 with him in his first week and basically told him what I’d figured out about the company’s organizational quirks. It saved him a bunch of time and guesswork, so he was grateful. Plus we vibed on each other’s brand of nerdiness; I mentioned the sunk cost fallacy in our first meeting and we were off to the races.

So those were my three choices in the promotion chess game. Besides having the right priorities and personalities (and being high-performing managers themselves), they were diverse in key ways. All three were at least two levels above me, but only one was in my direct chain of command. This gave me access to a much broader swath of potential roles and contacts. It also gave me an exit strategy for if I ever realized I wanted to be on a different team.

Once I’d identified them, the next step was to ally myself with them.

Make them your allies

The hands-down best thing I did for myself in seeking promotion was to build good relationships with my leaders. And this sounds harder than it actually is. Really, I started by just saying “hi” to them.

When someone is two levels or more above you, there is an unspoken social expectation that you will behave deferentially toward them. Don’t fall for it. Do not ever show social deference to a good leader.

I repeat: do not ever show social deference to a good leader. You know what, hold on, let me pull-quote it too:

Do not ever show social deference to a good leader.

Sorry, I just really needed to get that particular note through. You have a leg-up if you’re in the Millennial age range. We famously hate highly-stratified office organizations.

See, good leaders understand that we are human beings first, members of our separate families next, and workers like… seventh. We don’t live in a caste system. (Although on a serious note, this advice does not apply if your leaders actually do come from highly hierarchical cultures, such as India or Japan. That requires different tactics. I’ll write a separate promotion guide for you one day, I promise.) If a leader appears to appreciate or expect deference, they are not a good leader. Walk away from them.

Rather, good leaders care about their team members on a human basis. They will appreciate being approached and spoken to as though there is no hierarchical distinction between the two of you.

Socialize your way into a promotion

So when you notice your boss’s boss is in the office, swing by. Knock on their doorway and say “Hi, how are you, how’re things going with you?” Establish a regular and friendly rapport. Make sure they know your name and say hello to you in the hallways. If they’re part of your direct chain of command, ask if you can set up a monthly chat to get their insights on your performance. If they’re outside of it, ask if they’d be willing to serve as your mentor or meet with you occasionally to give you visibility into their team’s work.

These meetings are opportunities for you to frame yourself as high-performing and successful. Don’t fail to mention all the tough, meaty projects you’ve been working through. The point is to continuously keep yourself in front of their eyes and remind them how much potential you have.

If the thought of doing this makes your skin crawl, you’re not alone. I once worked with someone who coordinated major events for the company. This role brought her into contact with the company’s CEO, a rarified individual with a borderline household name. She talked for weeks about how thrilled she was to get to work directly with him. And when she finally got her chance, she… deferred. Deferred like a champ. She stood by silently while he browsed his emails, brought him water when he asked for it, and held back the curtain for him to walk onstage.

Meanwhile, her ambitious junior boldly said hello to him and asked him for his opinion on the previous night’s football game. They got into an animated conversation together, to the horror of the senior. She scolded the junior later for wasting his time. (Yes, really. I can’t make this shit up.)

When the three met again at another event six months later, the CEO remembered the ambitious junior’s name. To the hardworking and accomplished but socially deferential senior, he said the five worst possible words:

“Hi, nice to meet you.”

Talk to people like you’re their equal, and they will remember you as their equal. Talk to them like they’re royalty, and they will forget you because that makes you a fucking peasant.

Ask for a promotion

Everything seemed like it was in place.

I was in a good company with a good culture. I was on a team experiencing a lot of turbulence and plenty of veterans were leaving because of it. I’d found three cool leaders and gotten chummy with each of them. When a department-wide reorganization was announced, I knew I had the perfect storm of promotion potential. I sat back and waited for my invitation to the big kid’s table.

… it never came.

They passed me over.

Because I had failed on this last and most important step: I didn’t explicitly ask.

My leaders all agreed that I was bright and capable. They gave me plum assignments and heaped me with accolades. I was visible, appreciated, and they talked about me as a key player in the department. And when they handed out management jobs, there wasn’t one for me because I didn’t freaking ask for it.

You have to reap what you sow

As I’ve written before, promotions don’t come simply by virtue of being good at your current job. They also don’t come solely from having a good network. You have to have the balls to put both to work for you. And I’d been too timid to pull this particular trigger. I was now stuck reporting to the most junior manager on the team… a man whose job I’d expected for myself.

Friends, in case you were wondering, it didn’t feel good! I can’t recommend it!

I gave myself a few months to lick my wounds. Then I decided that late was better than never, so I reached out to each of my chosen leaders. I told the two outside my chain of command that I wanted more than what I had, and both promised to put out discrete feelers for me on other teams. They were my back burner strategies.

Because no matter how discrete those feelers, they had a risk of getting back to the leader inside my chain of command. So I decided to hit him first. I stopped by his desk, struck up one of our regular chats, observed that he’d been super busy with all the changes lately, then asked him if he’d be up for sneaking out early one day and grabbing a couple beers.

(I should note that a female employee asking her male director out for drinks is something that could be easily misconstrued or backfire horribly. But I knew him, myself, and our team’s culture well enough to know it was a safe move for me. Lunch, coffee, or a 1:1 is a safer move, but I wanted to frame the conversation as something more personal, so drinks it was. Also if you do this, make sure you eat a huge meal right before you go so that you remain mentally sharp. That’s called “setting a bottom,” according to our lovely international readers.)

Make your move

This time, everything was actually in place.

I had a sympathetic director who greatly respected me sitting in front of me with Fat Tires in him. We shot the shit about our shared nerdy passions for ninety minutes. Then in the final half hour, when a work-related topic came up naturally, I went in for the kill.

I started by complimenting my current manager on his strengths. After all, this guy chose him over me. I’d be insulting his decision if I didn’t. I noted that he was a good guy, an honest guy. I even mentioned that I had his back when a particularly tricksy coworker tried to backstab him to demonstrate that I was honest, canny, and willing to play ball with whomever I was given as a coach.

But then I gave my honest opinion that he was too green to know how to use me and that I felt underutilized.

This is a wise way of phrasing it that you’re welcome to borrow—it frames my ask around its business potential, rather than personal gain. Asking for a promotion because “I really need the money” or “I think I deserve this” is a good way to get shut down. Focus on the business and your potential within that business. And keep your financial needs to yourself, as they’ll only hurt you in the bargaining process later.

My director replied, “Our VP is looking for a chief of staff.”

That’s right. I’d been alley-ooped again—this time all the way up to my boss’s boss’s boss.

Climb that promotion ladder, bitches

My director was true to his word. Within two days, I had two interviews with the other stakeholders and all three gave their blessing to move forward with making the new role official.

The hardest part of this final step is the knowledge that I could’ve failed. My director could’ve mumbled something about what a great opportunity it was to shape a fledgeling manager, and skedaddled out like a crab trying to catch the tide. He came through—but there was no guarantee he would.

I think what makes this scary, particularly to young women, is that we’re so sensitized to our own ambitions. It felt as weighty as saying “I have a crush on you.” Like once I’d said “hello, I am hungry for a promotion” in the workplace, I was revealing something shocking and personal that could never be taken back.

But friends, as much as we talk about unlearning bad advice, some Golden Age advice is as true today as it was when our parents and grandparents learned it. And this is just such a situation.

“If you don’t go after what you want, you’ll never have it.”

“If you don’t ask, the answer is always no.”

Or my favorite:

“If you don’t step forward, you’ll stay in the same place.”

However you phrase it, the sentiment is very true. You have to be able to look your leader in the eye and say “I am ambitious and I want more.”

What might help is to remember that they should already know. The good work you already do announces both your capabilities and your intentions. And few people join the workforce hoping to stay in the exact same role all their lives. Wanting more is a pretty obvious and well-known facet of the human experience. So you’re not exactly laying new and shocking information on them.

What you’re doing is passing the final test. If you have the backbone to ask for more for yourself, you’re demonstrating you have the backbone to ask for more for the team that might one day report in to you. And that’s something many good leaders watch for.

Finally…

Make friends with the office gossip

It never hurts.

Here’s more of our peerless advice on navigating the workplace:

• Salary Range: Are You Asking for Enough?
• A Millennial’s Guide to Growing Your Salary
• The First Time I Asked for a Raise
• You Really Need to Ask for a Raise. Here’s How.
• Santa Isn’t Coming and Neither Is Your Promotion: How To Get Promoted
• My Secret Weapon for Preparing for Awkward Boss Confrontations

And that’s it, friends! That’s a pretty comprehensive inventory of all the things I did to get myself considered for a promotion. The next step for me is formalizing a new title and salary. I have never negotiated with a company that fer sher knew what I was making in my previous role, so this should be interesting! I’ll have to part ways with my preferred method of communicating my previous salary.* You can be sure I’ll bring you updates as I stumble through the process.

In the meantime, please tell us what chess master moves have worked for you in the past. Come on, you INTJs, I know you have some maneuvers up your sleeves (which are probably open and robe-like due to y’all being evil viziers).

* Lying.