My Boss Asked a Question About My Potential Promotion. Uh, the Answer Is Obvious.

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How do you escape the promotion catch-22? I’ve asked for a promotion for the last two years. Even with my boss pushing me to do so, I was turned down because it “wasn’t in the budget” to do more than one for my group. The first time, they promoted a teammate who had been at the company a few years longer than me (which was frustrating because I felt I deserved it more than the other person, but I understood based on seniority), and the second promotion went to another member who is transitioning to another team (so it stung that, as they’re leaving our team, they take up our promotion budget, since they joined much closer to when I did). I think a large part of the reason I haven’t been promoted is purely budgetary, but also part of it might come down to the promotion application we have to fill out.

When I first expressed interest in a promotion, my manager said a big thing the higher-ups looked at was what I did outside of my normal workload. Being good at your job is expected in your current position, not something that would get you promoted. So over the years, I’ve added extra things to my work. I joined the team that creates and reviews the guidelines and procedures that all my co-workers and I use to do our jobs, leading several projects to refine and update them. I took over a chunk of the responsibilities of training new hires and getting them access to the systems they need. And I’ve taken on several other one-off projects or longer-term things.

However, the promotion applications focus mainly on what more I will do after I’m promoted. How will the promotion let me do more at the company? While I try to answer with specifics, I feel that this is the most annoying question and leads to my weakest answer. I did all this extra work because I was told that it would lead to promotion, but to get a promotion, they basically skim over all that, only asking about past/current achievements in one question, and ask several questions about the future. So they ask us to do the work of someone in a higher position, but then want you to do even more to actually get the title and pay to go along with it. The promotion wouldn’t really come along with any specific new responsibilities baked in that I can reference; I’d just be expected to do more. My manager once asked about my answer, “What’s stopping you from doing this stuff now?” And the answer is (though I didn’t say this): Why would I do all this extra work voluntarily for no more money? If promoted, I’m willing to step it up another level, take on more responsibilities, and earn the bump in pay, but when I’m already doing everything in my job description at a high level plus taking on extra tasks and projects, it feels self-defeating to do even more for no reward. I work to live; I don’t work to make my company money.

So I’m wondering how to get over that hump. From everything I’m hearing, I deserve a promotion: I get excellent feedback from my manager (and he almost forced me to apply for a promotion the second time) and from people on the extra teams I work on; I’ve been given retention bonuses beyond our yearly bonuses at different times, so the company obviously values me beyond just my boss; we moved to a grade system for our full year reviews this year, and I received the second-highest grade, specifically being told I only didn’t receive the highest because the managers must put a certain percentage of their team at each level. But it’s not happening. I obviously can’t just say, “Pay me more, and I’ll do more,” can I? I feel like the company is saying, “Why would we pay you more when you’re already doing even more than your job description for your current pay?” when the reason I’m doing more is to get paid more.

(Side note: I constantly have my eye on other job openings and am totally willing to change jobs, but with the job market like it is, I don’t expect to find anything any time soon, so it’s not as simple as moving to a new job to get a pay bump.)

—Stuck in a Loop

Dear Stuck in a Loop,

I’m sorry you’re stuck in this accelerating hamster wheel. As you’ve discovered, the promotion system is designed in part to make people work even harder for the same amount of money. You’ve done all the right things by applying for promotions, taking on new responsibilities, building your network, and looking for other jobs. And your analysis of the situation seems sound: There are real budget constraints, the encouragement you’re getting seems genuine, and the system is exploitative.

So, how can you position yourself for a promotion next time? Start by using the connections you’ve made through your extra projects to learn more about how the promotion process works. Do you know anyone who holds the job title you’re seeking? Ask them how their work differs from what they did before their promotion. Ask what ideas and kinds of experience seem to impress the promotions committee. Do you know who is in charge of making promotion decisions? Introduce yourself to those people and ask for their guidance on your next promotion application. Does the promotion application have a section for letters of recommendation? If so, be bold in asking your colleagues, especially those who are higher in the organizational chart, if they would be willing to advocate for you. If it doesn’t, offer to provide endorsements anyway.

Before you fill out the promotion application form again, review the organization’s mission statements and other aspirational language from leadership. You don’t mention what sort of company you work for, but I suspect they value leadership, strategic thinking, creativity, and innovation. Maybe service or a side order of vision. Translate what you’ve already accomplished to those sorts of qualities: “I led the strategic plan to develop a new training program that set new hires up for success,” or some similar chest-thumping language. Include “deliverables,” especially anything that added to the company’s financial success, reputation, customer service, or personnel development.

A promotion is about money, sure, but it also sets you up to have more influence. To address questions about what you’ll do with your new position, say that a promotion would allow you to have even more impact across the company. Use any intel you gathered from other people at or above the job level you’re seeking to name some strategic goals. Talk about your demonstrated leadership abilities and how you would use a promotion to participate even more in strategic planning, ambitious initiatives, and team-building. Talk about big picture stuff, mirroring the language the company uses about itself. Show ambition, confidence, and eagerness. And don’t give up. Coming close to a promotion twice is frustrating, but two years isn’t that long in company time.

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I was hired a couple of weeks ago by a small business that seems to be highly dysfunctional. The owner and receptionist/office manager just snap and snarl at each other all day like a pair of angry weasels, and rarely give me any actual work to do.

If I approach either of them to ask if there’s anything I can do, they act like I’m just bothering them. The office manager has actually said a couple of times that showing me how to do something would be harder than doing it herself. I’m honestly not sure why I was even hired. I do at most an hour or two of work out of my eight hours, and often none at all. And I’m getting pretty sick of being snapped at every time I try to take any initiative.

However, coming from a series of food service jobs where I was running around every second of my shift, it’s actually kind of … heavenly? The yelling is nothing new, the pay is surprisingly good, and I have a nice private desk in a back room where I can happily read a book or write on my phone all day. How wrong is it to just give up, do this, and collect the paycheck for as long as I can? I’m thinking I might actually be able to finish my first novel here.

Finish your novel. Please include the line “snap and snarl at each other all day like a pair of angry weasels.” Send proofs to me for a blurb when the time comes; I want to read it.

When you’re not writing or doing actual work—or if you need to look busy—use your office hours to prepare yourself to advance your career. Read up on the industry this small business is part of. Take online classes that are relevant to the job, or to a future job you’d like to pursue. Ask the owner to tell you more about how they started this business and how it runs. Get to know the office manager, with your shields up. If nothing else, it’s all material for your novel.

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I left an office-based job just short of a year ago. My line manager was a bully who chipped away at my confidence, and over time, without me noticing, my confidence was mostly gone. I’m in my 50s, so the workplace isn’t exactly kind to someone my age.

So I decided to go into business for myself, doing more or less what I did in my last job. It’s 90 percent set up and good to go, but I’m dragging my feet for the last 10 percent because I’m basically terrified to launch. I don’t think I can do it, but I don’t understand why, because I was actually really good at my job before leaving, and the new business is essentially the same thing.

Why am I so frightened to take the leap? How can I believe in myself again? Do I just go for it and hope for the best, or just scrap it all and go back to an office? I need either guidance or courage.

—Am I the Cowardly Lion?

Dear Am I the Cowardly Lion?

If you haven’t watched The Wizard of Oz in a while, you might have forgotten that the Cowardly Lion had courage all along. And so do you! You freed yourself from a bullying boss, which takes a lot of nerve. Kiss-up, kick-down managers can do so much damage to someone’s ambition, self-esteem, and ability to sleep through the night. (We hear from a lot of people whose managers belong in the Bad Boss Hall of Fame.) Good for you for getting out.

Congratulations on setting up 90 percent of your new business! It’s fine to take a breath, look around, and steel yourself for the final 10 percent. Are you worried about any specific parts of the new business? You probably didn’t handle all of the relevant tasks directly at your previous job, like marketing, bookkeeping, taxes, or legal. If you’re hesitant about any of those responsibilities, read up on them, ask someone with expertise to double-check your plans, or take a class on small business management.

If you already know what you need to do, sometimes chunking a huge task into smaller ones can make it less daunting. Set up a checklist with every small item and cross them off as you go. Include things like “take a walk” to give yourself time to reflect.

Have you had enough social interactions since you left your job? Working on a big, independent project like this can be isolating. Seek out other people who have started their own business, maybe by joining a local small business network. Ask them how they handled the final stages of setting up their shop. I suspect a lot of them had jitters before launching.

Finally, think of being in your 50s as a feature, not a bug. You have decades of experience. You are good at this kind of job. You know yourself, you know this industry, and you have good judgment in the people you will and won’t work with. You’re thoughtful and thorough, and you’re brave to start something new. You’ve got this.

I am a software engineer. Recently, my boss has become enamored with a co-worker 20 years younger than me, and he offered her a promotion that I have been trying to get for the past 11 years. My wife just gave birth to our eighth child, and I am losing the ability to financially support my family. Should I report my boss to human resources? He is clearly acting biased toward this young lady.

—Prejudiced Against By a Boss With Pride

Dear Prejudiced Against By a Boss With Pride,

You may well be correct that your boss has a crush on your co-worker and gave her a promotion to impress her or spend more time with her. But it’s possible she has experience, skills, or leadership abilities that aren’t obvious to you, and the promotion was well deserved. Unless you have evidence of inappropriate behavior, there’s nothing you or the human resources department can or should do about it.

Rather than worrying about your boss or co-worker, let’s talk about how you can advance your career. Have you been asking directly for a raise for the past 11 years? Have you talked with your boss about how to position yourself for a promotion? If not, it’s time to start. If you have asked but have been rebuffed, it’s time to try a different approach. In either case, it helps to realize that good work doesn’t speak for itself.

Ask your boss for a meeting to discuss your future at the organization. Ahead of it, make a list of your accomplishments and how you’ve grown in your job. Focus on things that have served the company or your boss by beating deadlines, improving procedures, saving or making money, training other people, or otherwise contributing to your team’s success. At the meeting, share this list, tell your boss you’d like a promotion or raise, and ask him what more you can do to qualify for those goals. Don’t mention your family’s finances; the point is to show your value to the company. It might feel awkward to advocate for yourself, but part of your boss’s job is to retain and support his direct reports.

Go in with modest expectations. If you’ve been reliably doing your job for 11-plus years, your boss might be content to keep you in your current role, and he might be surprised that you’re asking for more. He probably can’t grant you a raise or promotion right away, even if he wants to, but this is a good start to the conversation and can allow him to budget for a higher salary in the future. If he says there’s no opportunity for a raise or promotion this year, ask for other perks, like a performance bonus, more paid time off, or paid parental leave.

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