Bosses

These are the specific conversations you need to have with your boss every month of the year

When you think about those monthly check-ins with your boss, it’s the standing invite on your calendar that likely brews both excitement and anxiety. Even so, being in constant communication with the person who will help you meet your professional goals should always be a priority.

One way to take the heat off of these 30-day mind melds is to come in with a plan, according to motivational speaker and workplace expert Amy Cooper Hakim, Ph.D.

“Some employees wait for feedback or direction from the manager, and assume that ‘no news is good news.’ But in fact, that is not always so,” she said. “To be safe, it is best to have consistent, regular dialogue to ensure that needs are being met in both directions.”

Here, then, is some month-by-month fodder that will build trust, rapport, and loyalty with your boss:

January: The one about focus

Especially if you’re on the East Coast, coming back to work after a long winter’s cat nap over the holidays is a drag. Not only is it usually freezing outside, but fewer hours of daytime mean you barely catch a glimpse of the sun. Hakim says many employees struggle during this season, so it’s extra important to get clear with your manager about the goals of the quarter so you can stay focused and perform at your highest level, even if you’d rather stay at home instead.

“It is easy to get overwhelmed by work, so knowing what to prioritize will help you to focus your energy where it counts. And, without asking, you may be spinning your wheels on a project that really should be placed on the back burner,” Hakim says.

February: The one about prioritizing.

Since some folks don’t consider Valentine’s Day a holiday worth celebrating, February often feels like the official end to the holiday season, where everyone is back in office and ready to tackle deadlines and deliverables. If you find yourself in the middle of three (or more!) tasks all at once, all of a sudden, getting clear about what needs to be completed first and foremost will give your boss the best impression. Hakim also notes it’ll demonstrate your commitment. “Asking about what needs to be accomplished shows that you care about your manager’s goals and priorities. The manager’s response may help you to better prioritize many new and ongoing projects,” she says.

March: The one about promotions and raises

The hard, cold truth about being a professional? If you don’t stand up for your career, no one will — and it’s up to you to have the conversation about meeting your career objectives. In other words: Hakim says if you’re aiming for a raise or a promotion, you and your manager need to be on the same page about what you need to achieve, change or mold to get there.

March makes for the ideal time to start this chat. “Expressing your professional goal and asking for resources or steps to achieve it, shows your boss that you are committed to self-growth and overall goal attainment,” Hakim says. “Managers appreciate this drive and long for employees who are self-motivated and determined.”

April: The one about the second quarter

After nailing it during the first quarter, going above and beyond what was requested of you, keep the momentum going in April by getting specific about how to be even better at your job. Hakim suggests asking your boss about his or her goals for the second quarter and volunteering to take on extra work to make them possible.

“We want to be seen as a go-getter and thought of for special projects that will get the most attention by the higher-ups,” she says. “By showing an interest in these projects, your boss will likely think of you for help. This can benefit you as you progress in the organization.”

May: The one where you surprise them

While, sure, you don’t want to be seen as someone who is bending over backward and brown nosing your way to a fancier title, taking note of your manager’s interests will help you build a professional friendship. Being buddy-buddy isn’t recommended, but if your boss sees you as someone who pays attention, listens, and remembers qualities and tastes, you’re more likely to earn their respect.

Hakim says to seek out an article you think they’d appreciate it and bring it up in the context of an 1:1. “This shows the boss that you have her best interests at heart. When your boss feels that you are thinking of her and of her goals, then she in turn will keep you top-of-mind,” she says.

June: The one about vacation

And no, not the PTO you want to snag before your co-worker does, but your manager’s summer plans. This topical conversations illustrates the emphasis you put on work/life balance and that you understand your manager needs time with friends and family, too. It’s also a way to reassure your boss that when they are jet-setting to Europe or a trendy island, you have their back.

“While it is ideal to keep dialogue solely about work-related topics, it is also important to show your boss that you care. This personal discussion reminds your boss that you see him as a human being and not just as your manager,” Hakim says.

July: The one where you show your commitment

That summer breeze might make you feel fine, but if you let it sweep you away from your deadlines, your manager might be less than peachy-keen with you. Instead of allowing the temptation of warm weather distract you from working at your highest level, double-down and communicate your commitment to your next-up. With half a year behind you, get nitty-gritty with new goals for the third quarter. In addition to putting you in the limelight with your micro-attention to detail, Hakim also says it’ll save you unnecessary busy work in case your priorities are not aligned with those of your boss.

August: The one where you ask for advice

Now that you’ve maintained consistent, constant, meaningful talks throughout the year, it’s time to seek the expertise of your manager. Since they’ve likely been in the game longer than you have, seeking their perspective on books or blogs to read, courses to take, or other advancement advice illustrates respect.

“Bosses love to feel important, and it is a huge compliment for them if you want to emulate their behavior. This question isn’t sucking up either, since you can truly benefit from the insights of someone who is a leader in your organization or industry,” Hakim says.

September: The one where you ask for feedback

A great sign of maturity is being able to ask for critical feedback — and actually take it without getting offended. Roll up your sleeves, straighten your back, take a deep breath, and go for it in September.

“Bosses respect individuals who strive for self-improvement and growth. They especially appreciate those who can take constructive criticism and run with it,” Hakim says.

One way to open this can is to ask for areas of improvement or express places you personally seek to strengthen, giving your manager leeway to describe their experience working with you, too.

October: The one where you show your listening skills

Remember when you inquired about areas of weakness last month? Now is the time to make your monthly meet-up about all of the ways you began working to strengthen those skills or characteristics.

“It’s one thing to ask for advice and another thing to take it and apply it. Bosses love employees who do just that,” Hakim says. If you can dictate with tangible numbers? Even better!

November: The one where you wrap up the year

Since — ahem, thankfully — Thanksgiving falls at the end of the month, the first three weeks of November can be spent getting serious about what needs to be finished by end of year, and setting up timelines to ensure success.

“The months leading up to the holiday season are notoriously slow, even when deliverables are still open and incomplete. By asking this question, your boss understands that you are still focused on work and on meeting department and company objectives,” Hakim says.

December: The one where you express gratitude

As a month that sneaks up on nearly all professionals and then flies by far too fast with endless holiday parties, travel, and responsibility, pausing to say ‘thanks’ to your manager will go a long way, and earn you major bonus stars.

“Gratitude is infectious! When we show that we are grateful and appreciative, then our boss will likely respond in kind. This positivity can make it easier to plow through those final days of the year as we wait for holiday and vacation time,” Hakim says.

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Lindsay Tigar is a seasoned lifestyle and travel writer. When she's not busy writing, she's collecting another passport stamp, taking a boxing class or trying new foods. A full collection of her work can be found at lindsaytigar.com.