men adn woman at a conference table (Lise Gagne; Getty Images)

We spoke with Jane Buckingham, one of the foremost experts on Gen X (defined by the Pew Research Center as those currently ages 37 to 48) and Gen Y (also called millennials, roughly ages 21 to 36), about how to deftly navigate conversations with your Gen-X boss.

Buckingham, who authored the Modern Girl‘s series, is a pro at handling sticky work situations. And (drumroll, please) she’s Glamour‘s new contributing editor! Buckingham will be the first one to tell you that communication between the two generations isn’t always easy—and with good reason. Gen Xers were raised with a “chin up” mentality, while millennials are said to be the “everyone gets a trophy” generation. (Google it—the phrase is everywhere.) So how can you bridge the gap when talking to your boss? Here’s what to do (and not to do!).

Don’t say, “I can’t do this!”
When you’re overwhelmed, the temptation to go to your boss and tell her you’re drowning can be hard to resist. But be careful how you present yourself-—almost every week it seems, there’s new research that casts millennials as more entitled than the generation before them. And your boss might be reading those studies. “Unfortunately,” Buckingham says “the bad rap that millennials get is that they are entitled and they don’t want to work hard. And even though that’s not true, it may be what your boss is thinking about you too.”

Do approach her with a plan
“The first thing is, figure out if you legitimately have too much to do. Because if you don’t, [your boss] won’t be as sympathetic. If you do, the best thing is to go in with a solution, versus a problem.” In other words, don’t tell your boss that she needs to fix something. Gen X sometimes feels like “Everything is a problem, so they get really frustrated,” says Buckingham. If you present a solution, “Gen Xers can’t say the Y’s are just whining about problems.” Pow!
“Go in and say, ‘Right now, I can’t get everything done that needs to get done. Here’s how I’d like to prioritize it, but that means this particular thing won’t get done in the timeline we laid out,’” Buckingham advises.

Don’t confuse her for your best friend
When you’re at work all the time, it can sometimes start to feel like your boss is your friend—especially if she’s warm and approachable or close to your age. It’s fine to be friendly back, but that doesn’t mean you should share with your boss that you had an amazing OKCupid date last night. Ditch the status update, and instead develop a real connection with her that’s actually going to help your career.
“You have to remember that your boss is your boss first and your friend second,” Buckingham explains. “Don’t get as personal with [her] as you would your friend, but it’s great to say what you did over the weekend.”

Do (discretely) let her know if something’s affecting your work 
f you are dealing with a sick parent, a bad breakup, or something else that is distracting you, it’s OK to pull your boss aside and let her know you’re having a hard time. Just leave out the details—she doesn’t need to know the play-by-play of how you left your ex.
“Gen Y is definitely more accustomed to sharing, and Gen X is still a little nervous about public and private. So when a millennial overshares, her boss doesn’t always feel totally comfortable with it,” says Buckingham. Avoid the awkwardness and impress her by continuing to keep up the quality work, and you’ll be the first person she thinks of when it’s time to move up.

Don’t live up the the “entitled” stereotype
It’s the most uncomfortable conversation of all at work: asking for a promotion or a raise.
“You have to frame this as why it is time and why you deserve it,” says Buckingham. Cite how long you’ve been there, how your responsibilities have changed, and how you’re looking forward to growing. Always frame it as ‘I’m committed to the company and to you,’ not as ‘I’m entitled to this.’”

Do remember she’s human!
If you always remember your boss probably wants to go home and have a glass of wine just as bad as you do and you treat her with respect, your working relationship will grow over time. Oh, and don’t forget the part about kicking ass at your job. The more invaluable you are, the more your boss will count on you—and that makes every conversation easier.