How to Get Along with Your Boss, Even if They’re Difficult

Years ago, I went for a walk with a co-worker because she needed to decompress. She was a friend and was unbelievably stressed. You see, she was about a year into her role and did not have a good relationship with her boss. They’re time together was purely transactional, and they didn’t trust one another at all. Most of what my co-worker was doing was simply documenting so she could cover herself if the boss ever threatened performance actions. As we walked, I listened to all she had to share. I listened to her frustration. I supported her thinking that she needed to be prepared if things went from bad to worse. Then, I challenged her. Every relationship you’re in is 50% you, I told her. I can help you get along with your boss, but only if you want to.

I’ll let you in on a secret, most managers, supervisors, and leaders of all sorts are doing the best they can. They are under their own stress and pressure. Most of them haven’t learned the best way to lead people and are treading water in their own pool. This makes it incredibly hard for them to set the best examples, because they just don’t know it. That doesn’t mean that it’s your responsibility to fix them. It does mean, that just like my friend, you’re 50% of that relationship. You can impact the relationship with your boss for the better, but only if you want to. There are 4 steps to improving your relationship with your boss. Read on if you’re curious how they could impact your relationship. If you’d rather learn through video, click here to watch the YouTube video.

Get them to open up

I can all but feel you cringing at me. Our first thought when we hear about ‘opening up’ is sharing personal information. Not only can that be awkward, but in a work situation it can also be inappropriate depending on how deep you go. When I say the first step to getting along with your boss is getting them to open up, I mean about work. Ask them about their background and what their biggest lesson was to get them where they are today. Maybe ask what their career goals are or goals for just this year. If they could achieve just one thing this year, what would it be? Any of those questions that you wonder about your mentors, ask them of your boss.

Not only will this help you develop rapport with your boss but it will also likely give you insights into their stories. Maybe you’ll develop more empathy for how they interact with you. Potentially you could learn some golden nugget that helps you work with them or helps in your own career journey. With one boss of mine who was particularly tough to work with, I asked him what his favorite project was he worked on. His eyes got stary as he remembered back to his years in a project management role. He shared about his first big project and everything he learned from it. Some of his story explained a lot of why he behaved the way he did. It didn’t excuse it, but it did help me understand it and respond in different ways. It also gave me a chance to share stories that aligned with his and build connection based on similar experiences.

Connect with your boss

Again, I get it. You don’t really want to connect with your boss if they’re difficult. I for one have worried in the past that I would pick up on their bad habits if we connected too much. Odds are though, if you’re intentionally connecting to improve the situation you’re much less likely to drop below your standards. As you’re getting your boss to open up you’ll likely naturally find commonalities you can connect on. Just like when they’re opening up, your connections don’t necessarily need to be personal. Perhaps you went to the same school years a part or maybe you did similar roles in your past as you were growing in your career. More likely than either of those, you’ll have had similar experiences in people you’ve worked with over the years. This will be the most valuable area to connect on.

You won’t want to share openly everything you notice, ‘Oh wow, Bad Boss Brenda, I too have had a toxic leader. Isn’t. That. Interesting.‘ You will however find things to share. Maybe both you and your boss value family time and you can clarify that they reserve time in the morning with their spouse and you value dinner time with your kids. Or maybe you can share a time you were both amazingly productive at work. You can then share that for you, it was because you took 30 minutes to work out every lunch hour. Finding commonalities with your leader will help you agree with them conceptually while advocating for your own needs.

Help your boss

One of the great things about connecting with your boss is that you have to speak with them anyway so you can skip the awkward part about setting the meeting. My co-worker’s boss that I mentioned before loved to set random update meetings. She had a specific thing she wanted to better understand or question, but she didn’t share exactly what it was. She would just put a weekly or bi-weekly meeting on the calendar that would eventually fall off when her schedule got too full. As the manager would ask for updates, I encouraged my co-worker to inquire about what the boss was working on too.

Asking what your boss is working on continues building rapport and connection, it also creates opportunities to streamline efforts. A perfect example of this is when one of my bosses asked me to create presentations. I would build the slides based off of his outline and he would give the presentation. Once I began asking about his workload and realized how much time he was dedicating to learning the presentation I suggested that I present on some of them. This was like a silver bullet. He was happy because it took something off his plate. I was happy because it did away with a week’s worth of questions and minor revisions as he learned the presentation. Then, it gave me more facetime with other leaders and helped me build my network.

I had an employee once ask me what I was working on and when I complained that I had to find all of the project statuses in my email she saw a fix. She created a shared project management sheet where I could check for status on everything rather than waiting on emails. This was a win-win too. We both reduced emails and I could get answers any time of the day or night regardless of her schedule.

Communicate better about work

You may have sensed that we were getting to this point. Improving the relationship started with verbal communication and the solutions to help your boss often center around improving communication in some form as well. Communication is everything. This is your opportunity to get creative, find what works for both of you and supports each of your needs. I have had bosses that I gave my personal cell phone number to because I thought that would be the best way to connect. There have also been bosses that I’d rather not speak to at all so any means of automating the information and take me out of it was ideal. Emails will work great for people who want to refer back to the full story. Chat works well for those who just want quick responses.

There is no one right way to do this part because it is about learning more about each other, developing trust, and then finding the communication mode that will best support you and your boss in doing the work you need to do. Understand what you both need and look for tools and ideas that support it.

Will you get along with your boss?

I’ll be honest, very few people want to take ownership for their part of a dysfunctional relationship. Even less are willing to take steps to fix it. I totally get that. Especially because in a work situation it can feel like the leader’s job to make sure the relationship is solid. To that I’ll say, I agree. It is the leader’s job to make sure that we’re doing our best work and achieving what we need to achieve. That is what this community is though right? A group of people who strive to lead in all areas of life. You are the leader in this situation. Take the opportunity to coach and lead the leaders you work with.