Bullish Q&A: My Boss Thinks of Me as “Sweet and Cheerful.” How Can I Move Into Management?

When Your Boss Thinks You're -Sweet,- But You Want to Be CEO

I happen to be lucky enough to have a generally sunny disposition and get along with most folks I interact with. I’m comfortable in the workplace, and do my best work, when I’m being myself, making jokes and making friends. I find that a little self-deprecation also lubricates relationships across project teams.

Still, I have a career track record of being praised for being cheerful and sweet rather than producing great work. In my current position, I’ve seen colleagues who are equally qualified get picked out for stretch opportunities and advancement ahead of me and I think my attitude is at least partially to blame. I’m a (white, cis, heterosexual) woman in a company of majority women, so I don’t see any gender discrimination at play here.

So, my question is, how do I get people to stop thinking of me as the office cheerleader/goofball and start thinking of me as a strategic thinker who can get business in the door and get the job done? And ideally, how can I do that without changing who I am? Putting on a formal face strikes me as cold, and really stresses me out.


I see your issue here. Being considered “sweet” at work isn’t usually a way to get ahead (perhaps because of internalized misogyny!)

First thought: Your in-person persona might be cheerful, but is your writing style more serious, strategic, or at least “just like everyone else’s”? If so, perhaps you could start generating more reports, documents, hard-hitting emails, etc. Perhaps with numbers, charts, and firmly-recommended recommendations. In person, a lot of us say, “Soooo maybe we should try X?” But in a report, you can write “Conclusion: The data clearly indicate X is the superior solution.” Maybe you can become known for hard-hitting, useful, actionable writing. Maybe when new people join the company, they’ll encounter your emails and reports first – and be shocked that you’re so nice and approachable in real life.

You could also consider changing your look a little. Maybe a sunny personality AND a lighthearted approach to workplace attire is pigeonholing you a bit. If it doesn’t bother you, you could consider dressing more formally (if anyone at your company even does that), wearing more structured “serious” clothing, getting some Very Serious glasses, etc. Obviously this is all highly situation-dependent, but if changing your look is a lot less stressful than changing your personality, it’s a thought.

But more importantly: JUST TELL YOUR SUPERIORS that you want more responsibilities, and that you aspire to move into management. Literally just tell them. You could certainly say, “I notice some of my coworkers at the same level have been picked out for stretch opportunities, and I asked for this meeting to make clear that I’m more than ready to contribute more to the company.” You could also find a way to talk about your sweet and sunny disposition in more favorable terms – for instance, “I’ve gotten positive feedback for my collaborative style and for making people comfortable, and I’d like to parlay those skills into eventually managing a team.”

Thought experiment: imagine your inner bro. I mean, you probably don’t have an inner bro, but we can still steal a page from someone we don’t like very much! That dude who graduated from Dartmouth five years ago and is boycotting the new Ghostbusters literally tells people all the time that he wants to make partner or director or whatever by 2018. That guy has no trouble saying, “I really admire your career, Mr. CEO. I, too, would like to be a CEO one day. What do you recommend as a next step for me?”, by which of course he is offering himself up for opportunities.

So, that’s my big message. Even in a female-dominated environment, it can still help to rinse out all the gendered training most of us have received, and the most damaging aspect of that is the idea that good girls wait to be picked. Whether by a hot guy or a boss or the artistic community or the publishing world, etc., nothing good comes from waiting to get picked. At least half the time you get picked for something, it’s by someone who’s looking to exploit you. I use the word “exploit” loosely – of course all companies are looking to “exploit” their employees by making money off of them, otherwise jobs wouldn’t exist in the first place. Sure. But waiting to get picked is not only slow and nerve-wracking, it means you end up in situations designed by others for their own benefit.

Hell, maybe repeatedly and straightforwardly telling your managers that you’re ready to move up will activate their gendered conditioning. I mean, it just wouldn’t be nice to turn you down more than once or twice, right?

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