Every once and a while, I stumble into a workplace that feels more like middle school or high school drama than an actual work environment where adults gather. O.k., I lied. It’s not every once and while. Reliving the dynamics of middle school and high school drama in our working years is more common than any of us would want or like to admit. But, alas, it is reality. And in keeping with that unfortunate reality, sometimes it matters if our boss likes us or not. So, what are the big “Do’s” and “Don’ts” in getting our boss to like us? Here are some of the most effective (and disastrous) approaches that I’ve seen:

“Don’ts” for getting your boss to like you

  • Be like one of the “cool kids” – I had a client recently tell me that the problem with his workplace is that there seems to be a “cool kids” clique in his office. As he describes it, the cool kids like to “make fun of other people in order to show how smart they are.” He was tempted to try to fit in, but opted to be true to himself. Follow his lead. In middle school the “cool kids” sometimes end up in the principal’s office. In real life, they end up in jail.
  • Kiss up to your boss – There is the natural tendency to tell your boss he or she is the greatest thing since “sliced bread.” You compliment them at every turn: “great idea boss, nicely said boss, you are the greatest, boss…” The problem with this approach is that a healthy boss will see right through this and perceive you as possessing low self confidence. An unhealthy boss will also see you as possessing low self confidence, but then they will proceed to bully you. Neither ends pretty.
  • Try hard to be your boss’ friend outside of work – This is a common approach that often ends in confusion and disaster. You know the drill: invite your boss out for drinks after work, invite him or her on vacations or sporting events, go golfing or shopping with him or her. In general, the strategy is to blur the lines between friend and boss so they like you enough to make things more comfortable for you. The problem I’ve seen with this approach is that it is not uncommon for the boss to separate the two roles in his or her mind (or to be told to do so by their superior). They come back from a great vacation with their employee and start Monday off by letting him or her go.
  • Dress like your boss – Just like in middle school or high school, this strategy entails dressing like the “cool kids.” The downside to this strategy is, just like in high school, everyone knows what you are trying to do… and it looks just as pathetic now as it did then. Have some self-respect.

Those are the big “Don’ts” when it comes to getting your boss to like you. Here are some of the better “Do’s”.

“Do’s” for getting your boss to like you

  • Focus on your work – A great strategy to get your boss to like you – get your work done consistently well and on time. Shocking, I know.
  • Add value in every interaction with your boss – In every interaction with your boss (casual conversations in the hall, meetings in his or her office, etc…) look to be adding value. What do I mean by that? Ask good questions. Provide updates. Don’t waste his or her time with a rambling story about your golf game that weekend.
  • Look out for your boss – Be on the lookout for things that might help or hurt your boss and let he or she know. They’ll appreciate the fact that you’ve “got their back” and will likely return the favor. Just be careful to not make up those problems just to get in his or her good graces. That kind of manipulation will eventually swallow you whole.
  • Dress like your boss – “Wait, didn’t you just say I shouldn’t dress like my boss?”  Here’s where you do want to pay attention to your boss’ appearance. Bosses do care about “how” things get done. So, notice your boss’ style and try to modulate your style to fall in line with how he or she approaches work. The same goes for attire. If he or she is business casual at work, I would not recommend coming into the office in torn jeans and a retro Motley Crue tee shirt.


Just like the wonder years of middle school and high school, getting your boss to like you can be an unpleasant and self-sacrificing experience if you let it. Stick to your guns, stay true to your values, and be the consummate professional and I promise, the right people will like you in the end.