You’re bound to encounter them at some point in your career. Here are some survival tips for dealing with the tough ones in a professional manner.

Getting Along with Difficult People

You’re bound to encounter them at some point in your career. Here are some survival tips for dealing with the tough ones in a professional manner.

Few of us have to look very far for the empirical evidence on what it’s like to work with difficult people. That’s because, unfortunately, difficult people are nearly everywhere. This month I’m going to share case studies about different kinds of difficult people who have crossed my path. I’ve changed their names. What I haven’t changed are the insights I picked up in the course of working with these various individuals. Perhaps my experiences will prove comforting to you.

The Client

I’ve concluded that I need my difficult clients. They make me a better practicing MCSE. I call it, “The pipeline theory”: The Trans-Alaska pipeline was ultimately built to a higher standard because of relentless environmentalists. If it weren’t for my nagging and unreasonable clients, I would never have discovered some amazing workarounds and solutions. I have two strategies with difficult clients: path of least resistance and conversion.

My path of least resistance strategy in working with difficult clients has been to “just get it done” and get ‘em out of my hair. And in the end I discovered some pretty good workarounds. One such workaround was for the traveling biotech CEO who needed a reliable dial-in solution at a reasonable cost. Well, the reliability requirement killed any idea of using RAS, so I went with PCAnywhere. But when you’re calling in from overseas, PCAnywhere, with its remote control orientation, is hardly the cheapest solution. Remote control solutions take place in real time. The CEO couldn’t just compose email messages off-line, when it’s inexpensive, and then connect to the home office for mail and file transfer activity.

The solution? I trained him to compose his email in WordPad and then simply copy and paste the text into his email application while connected via PCAnywhere. This lowered his long-distance charges dramatically. And it’s a solution I might not have otherwise discovered.

My insight:
Look for ways to train the end user in some new tricks. Overcommunicate, even if it bugs you to work with the recipient. Consider the possibility that the difficult person is simply in a difficult position.

By its very nature, my conversion strategy is more optimistic: Today’s difficult client is tomorrow’s referral source. For this, I need look no further than Debbie, the construction company controller. Over the course of a year, I “converted” Debbie from a critic to a fan by overcommunicating with her. Each step of the way, be it verbally or in my written site reports, I purposefully told her more than she probably wanted to know about the project. Ultimately, I gained her trust (a key success factor in consulting), and I educated Debbie in basic network troubleshooting. Not only did I add yet another member to the Brelsford fan club, but I reduced the number of service calls I needed to place at this site. And along the way, I learned a thing or two about Debbie and her company. (It turns out Debbie wasn’t really the problem. It was her boss. Debbie was simply responding to the pressures from above.)

The Boss

You’re reading the words of somebody who scored high marks for being “unmanageable” on the Myers Briggs assessment tests. This is a useful diagnostics tool that allows you to discover what your gifts are or aren’t. It’s often used for employment screening and counseling purposes. That said, my recent scores showed high marks for independence and defiance. This isn’t always the stuff that successful Fortune 500 careers are made of, but it is the stuff of consultants and entrepreneurs. (Such gifts always score high back home in my native Alaska, where every second car has this bumper sticker: “We don’t give a damn how they do it Outside.”)

So have I had a difficult boss? You bet. And here’s what I learned. First, get the work done. Focusing on results has helped me get through, around, and away from difficult bosses. Second, find a communication channel that allows you to remain on speaking terms with this difficult boss. I remember one working relationship where our communications amounted only to email and voicemail; but at least we had that.

My insight:
Leave your resentments at the door. Bosses, who have their own resentments, don’t need to deal with yours. Be professional; keep your “issues” at home.

Try compliments, not criticism. I’m not suggesting you become a walking PR agency; just try out a different attitude than that curmudgeonly techie persona. Endear yourself to your stakeholders (bosses, clients, coworkers). Compliments, not criticism, may well follow.

Last, try being a boss yourself. Perhaps the biggest mindshift occurred when I actually became the boss. All of a sudden, my boss wasn’t such a bad guy after all. And knowing what I wanted to see from my own employees, I’m now more sympathetic to his plight.

The Co-worker

My strategies for working with difficult co-workers: fight, flight… or wait. Most recently, a difficult co-worker named Linda proved to be a more formidable fighter than I imagined, so fighting wasn’t going to solve my difficulties with her. And flight isn’t a viable option; I like my job!

My insight:
Patience can be
a virtue.

So here, I adapted a strategy of waiting it out. It took nearly two years. But ultimately Linda, by her own miscues, was asked to leave the firm. I no longer have a difficult co-worker problem.

The Employee

My insight:
Practice that difficult skill of listening. And when working with a difficult employee, remember: There’s usually plenty of blame to go around.

In this era of the free agent, junior consultants come and go at will, I’ve seen the good, the bad, and the difficult. Let’s take Sam, a recent loss from my staff. Toward the end, Sam’s usually reliable performance dropped off, and his communication wasn’t as sincere and open as before; in short, he became more difficult to work with. It turns out that our firm wasn’t the right long-term fit for Sam. The go-go pace of billable hour consulting didn’t work for him (he took an in-house position with a client). Perhaps these “difficulties” could have been avoided if I’d done a better job of recruiting. I was so eager to obtain Sam’s services, that perhaps I didn’t hear him express his need for stability—a foreign concept to plenty of us MCSEs.


I think back to the “blaming” environment caused, in part, by the difficult co-worker I mentioned earlier. Up until the end, the “goodness of fit” difficulties were always someone else’s problem, according to Linda. Why was it ultimately Linda who suffered her own untimely demise?

Now you’re probably wondering, have I ever been that difficult person? Regrettably—yes. In my college summer hire days, I was probably a walking case study in collegiate know-it-all-ism. (I’m probably overdue to make amends with some of my co-workers from those carefree days of my youth.) However, I now actively hire college kids during the summer at my consulting practice, and having been in their shoes, I do believe I’m a more accommodating and understanding boss.

My insight:
Don’t congratulate yourself so much that you overlook one possibility: Perhaps you’re the difficult person.

A second experience bears mentioning. When I was a sole proprietor computer consultant a few years ago, I made an interesting discovery: I had days where working with myself was a chore. That is, I was that difficult person. Then and there my awareness heightened towards being a more compatible person to interact with. If you can’t work with yourself, who can you work with?

A Final Insight

Believe it or not, just saying things like, “Good morning,” and “Thank you,” can make a big difference in working with difficult people. Maybe it’s because they hear it so rarely. Got any better ideas? Send me some mail with your war stories.

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