One of the hardest parts of any job is working with difficult people. No matter what your assignment, if there are other people who make it hard for you to get your work done or who make you feel unhappy, unsupported, or misunderstood while you’re doing your work, it can turn going to the office something you dread.

If you think you can just run away from the problem, well you can’t.  Trust me, I have left several jobs thanks to the difficult people around me. But reality is that difficult people will pop up everywhere throughout your life.


So it’s in everyone’s best interest to learn how to work *with* the difficult people in their lives and not running away from them, and to manage your interactions with them in a way that helps you both be successful. You can’t avoid difficult people, but you can improve your relationships with them and your work life overall by exerting a little positive effort.


To that end, here is part one series of posts on how to manage difficult people in your career.

First up? Bad bosses.



A bad boss can make everything harder. Every project, every interaction becomes harder when you have someone who’s not on your side or who is difficult to work with. And when that person is in a position of authority over you? Well, now you’re not just frustrated but you also feel powerless to do anything about it.


I once had a very successful whom I found endlessly frustrating, and ultimately was the reason I left the company. He was horrible. A great example of his frustrating behavior is that during calibration (the already awful process where managers are forced to stack rank employees across their organization) he would force everyone to talk about people as bulldogs, collies, or poodles.  I was so upset I ended up having to excuse myself, and then ended up playing along only to get my team’s the reviews and rankings they deserved.  It was his team and you had to play by his rules.

In retrospect, there was a lot more I could have done and knowing what I know now I could have triumphed and risen higher in the organization.  There are lots of techniques and strategies to work around people like this – and with a dash of patience these things tend to right themselves.

I think a lot of people who have bad bosses feel that their only option is to quit. After all, you can’t exactly call your boss into your office and tell them you’re giving them a negative review this year. But there are realistic actions you can take to improve this relationship without having to jump ship.

I have talked a lot on this blog before about the importance of managing upwards. Your boss is potentially your biggest asset in your career and movement to the next level, so it’s worth your while to try to improve this relationship. You’ll get not just the short-term benefits of daily interactions being easier, but you’ll also get also the long-term win of an ally for your big picture career ambitions (and hopefully won’t be forced to talk about team members as breeds of dogs).


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Focus on building a relationship

I once took over a team with a person who made my life incredibly difficult, and who did not want me as their manager at all. It was one of the more difficult moments I have had at work.  They would make snarky comments during my meetings (if they showed up, which wouldn’t have been on time), and took advantage of any opportunity where they could undermine me.  They made it clear they didn’t think I was doing a good job and looked for ways to make my job harder. I wanted to quit.  But instead of shutting down or writing them off, I took knowledge and lessons and saw it as a challenge: “You don’t know it yet – but I’m going to be your new best friend at work.”

Instead of avoiding them I seized any chance I had I work closely with them.  I setup weekly one-on-one meetings, some over lunch or coffee.  During that time I focused on them, what they wanted to see the team do, what they wanted to do with their career, and who they were.  I listened intently, and asked them for feedback on my ideas, and small favors to help see them though.    Over the months I built a relationship and this person is one of the people I miss most from that job.

Relationships take time, and the more energy you put into making a negative relationship into a positive one, the better that relationship will naturally become. Find ways to help; do favors; ask for advice. When people see each other as real people with good intentions, they can’t help but start to let bad feelings melt away.


Get to know your boss better.

It’s really easy for someone to become a caricature in your mind (the pointy hair guy in Dilbert comes to mind). Like, when you see your boss you immediately start thinking about what a self-centered jerk he or she is, or how they never recognize your work, and suddenly that emotion colors all of your interactions with them. Everything they do confirms all the horrible things you think about them, compounding all of your bad feelings over again.

(And be honest, there is something a little satisfying about thinking terrible things about someone you are sure is just an awful person. A lot of us can be reluctant to give up our 100% negative perceptions of people, for fear we’ll have to develop a more nuanced understanding of them and cut them some slack.

But, I’m sorry to say, even self-centered jerks have soft sides sometimes, and spending more time with someone gives you the chance to see them as a more complete person. Maybe you’ll learn that your boss is masking their own insecurities by critiquing others harshly. Or you might discover through conversations that your boss is being micromanaged by their own boss, and they’re stressed under the pressure.

And you might just realize that it’s not that they’re rude, they’re just bad on the phone.

I also tend to think that no one wants to be “bossed”, “managed” or “told what to do”.  Who liked their parents when they were the ones standing between you and something you wanted?  It is the nature of authority – smart people tend to rebel against it.  And learning to like the person with the can be a bitter pill to swallow.  However, that relationship can be one of your most important – leading to promotions, raises, mentoring, and references.


By having a bit of empathy, and taking the time to understand your boss’ motivations and fears, it lets you into their heads, and helps you perceive their actions and words more accurately.


Find out what makes them tick at work.

Coming to see your boss as a complete person will help you better understand how to work with them in a work context. In your next meeting ask about their work life; what are their biggest priorities, problems, annoyances, and perhaps even goals? 

How do they see their career growing and changing within your company?  What keeps them up at night?  Learning what is driving them can help you contribute positively, but if you don’t know, or haven’t asked you could be looking in the wrong places for these opportunities (if not missing them entirely).

Everybody has a certain way they prefer to get things done. If you learn what this means to your boss, you’ll do better at giving them the key things they’re looking for and show that you take their needs seriously.

(It’s kind of like love languages. Some people show love through words of affirmation, and others through quality time. Understanding what your partner’s love language is helps you show them affection in the way that is most meaningful to them. What’s your boss’ “work love” language?)

Having empathy for their preferences allows you to see, “Oh, my manager’s biggest pet peeve is _______. In the future, I’ll prioritize that thing over others when I’m working/meeting/speaking with them.”


Show them you are listening.

Everybody likes it when other people do things their way and care about what they have to say. So do that! Sometimes it’s as simple as demonstrating that you are hearing what your boss is saying, and you’ll find that they in turn become more receptive to your ideas too.

As an introvert, I don’t always communicate my positive feelings about other people to them – which is sometimes all they really want. People often incorrectly assume introverts are stuck up and judgmental because we don’t naturally smile and nod along, so it’s important to consider what messages your body language and conversation style are sending to your boss too.

Find ways to demonstrate respect and listening, even if they don’t come naturally, like nodding, smiling, saying “thank you”, asking questions, and making eye contact when speaking with your boss. Do you get the impression your boss thinks you have an attitude problem? If you think your boss might think *you’re* the one who’s not listening or being helpful, try a couple of those simple tricks and see if it helps. You may not be communicating as much as you need to.

One of the best pieces of career advice I ever received was to ask advice of people and get them invested in helping you.  By enlisting them on your journey as a mentor that will be rooting for you and helping you succeed.  So perhaps look for an opportunity where your boss can help you or teach you a thing or two.



Solicit feedback and understand expectations

Asking someone’s advice does two things: it helps you get their opinion on an issue, and it also shows them you care about their opinion. Asking your boss for feedback, therefore, is killing two birds with one stone; you’ll get advice on improving your job performance and you’ll show your boss their opinion matters to you, all in one meeting. Not bad!

Ask for feedback (even if it’s not offered).

Bad managers come in many forms, but one of the most common is the manager who doesn’t have time for or interest in coaching their team as much as their team might want or need. You can remedy this by proactively asking for feedback yourself. If your boss isn’t good about scheduling 1:1’s with you, schedule them yourself.   If they aren’t making the time, then be proactive and seek the time with them.

Managers often don’t have a lot of time to do really in-depth performance reviews or regular 1:1’s with everyone on their team. This can be really frustrating when you’re looking to improve, but you don’t have to leave all the power in your boss’ hands. You can take charge of your own feedback, though, by asking your own, better questions that force more precise answers.\

Instead of asking a general “how am I doing?” question, bring a list. Control the meeting and get what you want – by asking for it.


  • What could have gone better in the last project?
  • How could I have made that meeting more useful?
  • Can you give me an example of what you’re looking for?
  • Who is someone who does this exceptionally well?


[ Extra tip: you can get feedback in little ways without even calling a meeting. Try closing your emails to your boss with questions like: Do these look like the right priorities? Is there anything missing from this list? If I have extra time, where can I make the biggest impact this week? ]


Give them your feedback too.

As you may have heard me say before: no one comes to work to do a bad job. And I guarantee in almost every situation your bad boss wants to be doing a better job (and probably knows they have room for improvement). Your relationship with your boss is a two-way street, and even though you can’t sit them down and give them a performance review per se, you can offer them suggestions on how they can be a better boss *for you*.

For example, I know that as a manager, I don’t give people a ton of direction. Usually, people who need more information or clarification from me need to ask for it or else I won’t give it.

Another example is an engineer on one of my former teams who I knew felt underserved by me. I didn’t know what he needed from me, though, until one day he came into my office and told me, “I want you to coach me more. Give me more feedback and tell me how I can keep improving.” And that was all it took; we set up regular 1:1s and I started giving him the feedback he was looking for to improve.  Knowing that he wanted me to pay more attention was a trigger, and I sent him feedback on everything from how he conducted himself in meetings to the comments he made on team member’s checkins.



Managing upwards


Managing your manager isn’t easy, and there aren’t many guidelines for how to handle a superior who’s underperforming. At the end of the day, though, the one place I think every successful relationship negotiation starts with is with communication.

How have you dealt with a bad boss in the past?   Please leave tips, ideas or links to other articles in the comments since I am sure there are plenty of other strategies and examples of these sticky situations.

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