How to Make Working With a Boss You Don’t Like Work

I’ve worked for people I didn’t “connect” with.  It was excruciating. Working with someone you can’t get a good read on, or who has a totally different communication style than you, makes it feel like you’re the one who has to make this work.  That’s a lot of pressure!   Over time that expectation becomes exasperating, especially if you’re the only one working on the relationship (because you’re not going to tell your boss you don’t like them… to their face).   This is where managing up can be beneficial.  There’s a lot of assumptions about what managing up is.  The way I define it is setting healthy boundaries for mutual benefit in a professional relationship.
 
Managing up is an important skill to cultivate in today’s working environment, but it is also fraught with concern about authenticity and making sure you don’t stick your foot in your mouth, nor become a door mat.   So, how can you manage up without losing yourself in the process?  Key to this is understanding that it’s possible to build trust with someone whom you don’t like. 

Fortunately, you often end up working with a boss you can connect with on some level, which is what makes it more difficult when you have to work harder at forming a relationship with one you don’t.  I’ve worked with many clients who sacrificed their self-esteem on the altar of “likeability”, it is a soul-shredding process.  Here is the truth, you and the people you work with are not always going to like each other (even with the best intentions).  Over the span of your 30+ year career, you’re going to work with a lot of people you don’t enjoy, and from time-to-time that will include your boss.  Here is the tricky bit, forging healthy working relationships anyway, based on clear communication and mutual benefit.

Finding mutual benefit involves empathy.  Being able to put yourself in another person’s shoes, including your bosses’, is hard work, but it is necessary for building a healthy working relationship.  Examine your own biases about this person; what are they?  Are they conditional (“If you support my ideas, then I’ll support yours…”)?  The best bosses will challenge your thinking from time to time, so that “condition” won’t build a healthy relationship.  Sometimes, your boss may not be able to share details with you or they may be swamped.  This makes them human.  
 
But this is not just about what they need, it’s also about advocating for what you need to be successful in your work.  Boundaries are tricky things, because it feels like if you’re holding your boundaries, you get the results you were after.  Sometimes, but holding healthy boundaries is more about being clear and compassionate about what you need in a timely way: “I understand things are very busy and you and I have not been meeting regularly, but there are some key things we need to discuss before they become problematic and I will need 30 minutes of your time today so we can both stay ahead of them.”  
 
Your boss may still not make time for you, meaning you may not get the results you wanted, but you did hold a boundary.  Now if something goes pear-shaped you can compassionately help your boss to see the value in meeting with you: “I appreciate that you’re upset because you were blind-sided in that meeting.  I made every effort to discuss this with you beforehand.  In the future let’s consider that when I ask for 30 minutes it’s important to make that time so you have everything you need.”  You don’t need to own their anger, nor the outcome – holding healthy boundaries means you can gently remind them of what you did to support them, without judgement or shame (as tempting as that may be). This is more than a cover-your-ass move, it’s about holding others accountable for their actions, with compassion.

Nothing I’ve outlined above is easy or light work, but it doesn’t take long to do when you give yourself some dedicated time to sit and reflect.  Going into reflection with the intention to be open and compassionate with another person, to see what is possible (rather than what you assumed, expected or hoped for) is the starting point to managing up.

The only person you control is yourself and that makes you the best place to start.

“The goal of managing upward up is not to curry favor… it’s about being more effective.”
~ Liz Simpson, Harvard Business School

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