Working (and Communicating) With Difficult People

Sometimes, you have to work with people that aren’t nice, that are just really, really hard to work with.

I try to be self-aware enough to know that it is frequently me. I’m not always an easy person to get along with. I used to be really bad at interrupting people so I got in the habit of wearing a rubber band on my wrist. If I caught myself interrupting I would snap the rubber band. This eventually evolved into I would snap the rubber band once at the beginning of the meeting, and it would snap me (see what I did there?) into focus so I wouldn’t interrupt people during the meeting. Lately, this has evolved even further into me snapping the band to just try and remember to be a nicer person in general.

When it comes to working with difficult people, there are entire books written on this subject, but here are a few quick thoughts to keep in mind, some quick ideas that might help you.

Communication Style

A common theme, one that is deeply explored in Dale Carnegie’s How to Win Friends and Influence People, is the idea that every person has specific ways that they are best communicated with. Some people like small talk, some people like friendliness, others just want direction in a clear, black-and-white manner, and so forth. Figuring out the communication style that works best with that person, and then following it, can at least help improve the communications that have to occur between you and that person.

Use Email

If working with the person is causing issues to where you are feeling anxiety speaking with them, or there’s so much tension and antagonism that speaking with them has the potential to escalate, then simply don’t speak with them unless absolutely necessary. Instead, if you have to interact with them see if you can just send them an email or an instant message. Also, include other people on the email or in the chat messages. Sometimes, the presence of other people forces people to behave more civilly. Also, by taking the time to write things down you can review what you are going to say and make sure that your communication is clear, concise, non-inflammatory, and professional.

Don’t Take It Personally

I learned an extremely valuable lesson from a book called The Four Agreements, by Don Miguel Ruiz. One of the agreements is Don’t Take Anything Personally. The reason is, no other person really knows the true you; instead, they have a mental model of “you” in their head, and that is what they are reacting to. And, to be honest, their mental model of “you” is highly influenced by their own thoughts and feelings and thus might be very inaccurate. So if someone is antagonistic towards you, this might be because they are perceiving you as, for example, distrustful. But you may not have done anything to warrant it…maybe they just have a bad history of distrustful coworkers and so they assume every coworker is distrustful. There’s only so much you can do but ultimately this is in the other person’s head, so there is no reason to be offended by it. I’ve found that keeping this idea in mind can be helpful because I’m no longer questioning myself as to how I’ve wronged this other person, instead I can focus on just continuing to be professional, civil, and even kind.

Tactically Decide to Compromise

One of the challenges of working with difficult people is when decisions need to be made together, or when job functions require you to perform tasks in a certain way with another person. Sometimes, you can make an intentional decision that the time and effort to “win” the situation just isn’t worth it, and to just go along with the other person’s way.

I’ll give you an example. One time, I was working to modernize the software development lifecycle processes at an organization, and one thing I wanted to do was implement automated unit testing and system testing via the CI/CD pipelines, with automated report generation to be available via a web portal. But the organization had a strict configuration management policy that required all SDLC artifacts to be in a specific Microsoft Word template with a specific cover page. I went back-and-forth with the CM manager on adjusting the policy to allow the automated HTML reports to be accepted, even offering to submit a Word document as the Test Report that contained links. But the CM manager wouldn’t budge and insisted on the test reports being copy/pasted into the Word document. The situation was rapidly becoming antagonistic. I probably could have gone higher up the management chain and “gotten my way”, but eventually I just instituted a manual periodic process where I or the scrum master would manually copy/paste the report output into a Word document and deliver it to the CM team. The task only took about 15 minutes, and I would only do it once a month or so, so it was not worth automating, and in my opinion not worth arguing about. Eventually, the CM process was indeed replaced with a new process that was more innovative, but for about a year, once a month I would take 15 minutes and put together a report for the CM team to “check a box”. This is obviously not an ideal situation but I knew it wouldn’t be permanent and it wasn’t that much effort to work around, so I chose to just deal with the situation and save my energy for addressing other issues.

Throwing Down the Gauntlet

To follow along with the last example, there are times, however, where you decide to not “just go along with it”, and take a stand. I call this, deciding to “throw down the gauntlet”. There are some issues that I will not just deal with. One example is when helping an employee deal with an HR issue, or there’s an ethics or legal issue, or if an employee is being bullied or mistreated by another team member. There are certain times where I’ve had to take a breath and steady myself, and take that stand with another person that I am not going to back down or budge on an issue. One of the most important criteria I’ll ask myself in this situation is, am I willing to go three, four, five levels up the management chain, even to the top of the organization, and defend my decision and actions? If the answer is yes, then these are the situations where I choose to take my stand. This has only occurred a couple of times in my career, but there are times when the situation is not something I’m willing to back away from or compromise.


Using these approaches above can help provide you with some tools and ideas on how to work with difficult people. The main thing to remember is just to maintain both your professionalism and your ethics. Because when it comes down to it, those are the two most important things and everything else is secondary.

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