Bosses are tricky. While there will always be a power dynamic, in today’s flattened power structure, it can be challenging to balance between manager-employee and coworker-friend. Also, it’s incredibly intimidating to get to know a boss or manager. But don’t get tripped up waiting for him or her to make the first move. There’s so much you can do in your role to manage upwards.

Work off the Workplace

If you’re not sure where to start with a manager, look to your office environment for cues. Is it common for coworkers to grab lunch, or run out to get coffee? Do teams do happy hours, or are most people chained to their desk during the lunch hour? When you begin to notice these practices, it’ll be easier to discern what next steps to take with a manager. You might be able to casually ask if he or she wants to run out for a coffee together, or it might be a more formal lunch invitation.

In addition to picking up on office out behaviors, take note of the conversational environment. Do coworkers keep things light, or is your water cooler a heated location for political debates? You can always err on the side of caution and broach neutral topics with your boss, but it helps to have an understanding of how personal office conversation gets overall. Take note of how other relationships might work in your office, which often leads to the right avenue to approach friendship with a boss.

It Take Two to Review

Taking initiative to set up check-ins or employee performance reviews more regularly can also do wonders for your relationship with your boss. Setting up a regular time for the two of you to meet will not only help your performance as an employee but likely also foster a friendly relationship between the two of you.

Of course, employee performance reviews can be a vulnerable time for you, but it’s also a time to be honest with your boss. These meetings can be the ideal time for giving feedback to your boss. Naturally, reviews are a time to build trust and communication. While the content of these meetings is likely more career or performance-based, you will develop some familiarity with your boss over time.

Go for Guidance

So you’ve got a regular meeting, and might’ve grabbed a coffee or two with your manager, but still feel like you can do more? A surefire way to connect with them is to ask them for guidance or advice.

Why will this benefit your relationship? You’ll get brownie points for asking for help from a boss - a sort of ego stroke - and you’ll also be learning from him or her. Remember that bosses are humans too, and they’ve likely been through the same tribulations you’re experiencing now. Their seniority is a benefit to you; you need only ask for advisement to unlock a ton of experience and knowledge.

Need some good questions to ask? Ask what steps were taken in their careers to get there or what was a regret from early on in their career.

A Bad Boss in the Batch

You might try again and again to build a relationship with your boss, only to be shot down. It’s discouraging and can be a strain on your working relationship. If your effort and advances are going unnoticed, you need to consider why this might be happening. It could just be scheduling issues or a particularity private boss, but if neither of these options sounds likely, it might be worth talking to HR.

Not all bosses were meant to manage, and if you think your relationship with your boss is borderline hostile, then you need to work with HR to ensure that the negative relationship doesn’t sour your experience with the company overall.

Small steps are often the key to a better boss-employee relationship. Pick up on cues around the office, take opportunities to ask questions and learn from bosses. Use systems that are already in place, like employee performance reviews, as a tool to better your relationship. Many of us want a friendship or camaraderie all at once, but acknowledge that building trust or a relationship with your boss will be slow moving. That being said, remember there are always actions you can take to grow it.


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