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Getting Ahead on ‘Boss’s Day’

Today is Boss’s Day. What, you say, isn’t every day Boss’s Day? Well, sort of. In this Q&A, Lilit Marcus, an editor at the women’s site The Gloss and the author of the “Save the Assistants: A Guide to Surviving and Thriving in the Workplace,” explains how ambitious working women should (and shouldn’t) mark the day, and how to turn a difficult boss into a mentor.

Gabrielle Birkner: What are some appropriate ways to celebrate?

Lilit Marcus: There are two schools of thought about Boss’s Day presents. One is that you should get your boss a little something in order to be professional and thank them for the opportunity of working for them. The other school, which I belong to, thinks it is absurd to buy a present for someone who earns 10 times as much as you do and has the ability to fire you. So if you want to compromise, get them a card and say something and honest and meaningful about how you’ve learned from them or gained insight from working at the company. Keep it brief — you don’t want to go overboard. Save the gushing for when you get promoted.

What’s the worst thing you could do on Boss’ Day?

Don’t try too hard. If you’re lucky enough to have a boss you really like and respect, it is totally fine to get them some kind of thank-you gift. But try to get them something generic like a plant for their desk or a nice bottle of wine. Even if you know your boss personally, buying them a new bottle of their favorite fragrance will be kind of awkward. You don’t want to look like you’re sucking up or that you can’t draw appropriate personal/professional relationships.

How do you turn a boss into a mentor?

No matter how much you dislike your boss, there is always something you can learn from him or her. … Everyone likes to talk about what they are good at, so ask your boss some specific questions about their past accomplishments or notable things they’ve done. It shows that you’ve done your research, and you never know what interesting tidbit you might pick up from your boss’s anecdotes. These questions can then help you segue into a conversation about your own career or things you might be struggling with at the office. Ask for advice; your boss will be flattered that you value their opinion.

What’s the most important thing you learned being an assistant — and how has it shaped your career, post-assistanthood?

The most important thing I learned was how to think on my feet. My job changed constantly, and there were always little crises to deal with. I became good at coming up with quick solutions. If my boss was ranting and raving that his favorite restaurant didn’t have a table for lunch, I would immediately start listing other restaurants he liked and offer to call them. That helped calm him down, and it also worked better than standing around apologizing or trying to beg the restaurant to seat him. Now, when a problem comes up at work, the first question I try to ask myself isn’t “Why is this happening to me?” but “How can I deal with this?”

Your book focuses on the plight of assistant. But is it really assistants who need saving — or is it bosses who need saving? Do you think recent college grads feel a sense of entitlement that previous generations did not?

Yes, there are some horrible bosses, but there are also some great ones. Yes, there are young people with tons of entitlement, but there are also young people who have great work ethics. The problem is when you come into a workplace scenario having already decided what you think people will be like. Marching on your first day thinking “Female bosses are always worse” or “All assistants are incompetent” is a way to guarantee a bad working relationship. Treat every person you work with as an individual with his or her own set of skills, abilities, strengths, and weaknesses. Then decide which ones you can live with.

What qualities do the best bosses have?

The best bosses are willing to teach. Many people who are working as assistants are doing so because they want to move up in a given industry and want to learn about their field and make contacts. A great boss still insists on the fundamentals, but helps an assistant to learn and grow.

And the best assistants?

The best assistants are flexible and organized. If you can keep the day-to-day stuff — scheduling, filing, and other admin tasks — together, it frees up more of your time to work on stuff you find interesting and fulfilling. If all your company records and spreadsheets are so disorganized, you take half an hour to find anything, that is half an hour you aren’t using on the tasks you care more about. My apartment sometimes looks like a bomb went off in it, but my assistant desk was spotless.

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