The Dos and Don'ts of Getting Drinks or Dinner With Your Boss
Ed. note: Want to learn how to take your career to the next level? Our co-founders, Katherine Power and Hillary Kerr, are spilling the secrets to stepping up your professional game in a brand-new book, The Career Code: Must-Know Rules for a Strategic, Stylish, and Self-Made Career. Decoding all the lessons they learned while building their own company from scratch, the rule book will put you on the fast track to achieving your career dreams—big and small.
In anticipation of the book’s release on May 17, today we’re sharing some bonus material from the book about how to handle a night out with your boss. Are you a manager? There’s some sage advice in here for you, too. Read on below.
The longer you work with someone and the closer you get, the more likely you are to have a real connection with them and feel like you can talk about things outside the office. And you should! How weird would it be otherwise?
Boundaries are a thing, and no matter how great your relationship is, it’s wise to keep some things to yourself. Our rule of thumb? If you wouldn’t say it to your significant other’s parents, don’t say it to your boss.
It’s good to remember that you don't have to mirror your boss’s decisions. A safe way to proceed is to follow their lead but stay slightly behind. You don’t want to order six drinks to your boss’s three—try two instead. And don’t order an appetizer, salad, main course, and dessert if she’s only having a main.
Basically, try to read the room and follow along in kind while retaining a degree of formality (i.e. have fun, but don’t overshare). Some situations will be more relaxed than others, but at the end of the day, this is the person who signs your paychecks and will be your future letter of reference, so don’t do anything to jeopardize either of those.
One of the worst things bosses tend to do is assume that people want to be at their work event or dinner. Don’t get us wrong: Sometimes our employees are excited, but for the most part, our events are not the highlights of their social calendars. If you ask them to attend something, they basically have to go, so be respectful of their time and don’t force them to linger longer than necessary.
We always try to leave on the earlier side of a dinner or event we’re having with our company or team, not because we don’t want to be there but because we know that no one is really going to loosen up or have as much fun when their bosses are there. (Even though we’re totally cool. Totally.) Our point is this: When you have essentially forced attendees on your hands, realize that they want to get back to their off-duty lives and try not to take up too much of their time.
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What other tips would you add to this list? Share with us below.