How to work with eccentric people and not go crazy.

About 2% of the population is considered “gifted”. 

We don’t hear this term as much when referring to adults. Instead we hear odd, eccentric, weird.  

And while their numbers are small, I am sure you have come across someone who could be described this way.

Upon first meeting, you knew there was something different about them. It could be that they dressed without concern for convention. It could be that when they talked, it seemed they had ingested the whole Internet. Perhaps they didn’t like to talk and they always seemed sullen and removed. That is, until it was “ShowTime”.  

And then, all was pretty much forgiven because they were just so darn good at what they do. 

While their competence may help your company’s bottom line results, it doesn’t necessarily help your day-to-day because you still have to figure out how to work with eccentric superstar employees. 

Extraordinary people rubbing shoulders with the rest of us.

We always hear about the famous ones. The ones in sports, in music, and of course, in medicine, but we don’t hear that much about eccentric folks from the corporate world, perhaps because they’re not on a big stage or on TV.

These colleagues (or bosses even) may have some of the same annoying behaviors as the people who drive you nuts at work (read about how to deal with people who drive you nuts here), but these folks are ultra-smart and creative. They see the world from a different viewpoint and that can make working with them challenging. 


But let’s face it: on some level, if you’re their boss, they can make you nervous. You’re sometimes wondering what they will do next or what kind of impression they will make at the next meeting.  

As a colleague, you might not enjoy their company so much. You can work with them but that’s about it. 

The Story of Wild Bill

One of the first people I met like that was a guy known as “Wild Bill”.  

One evening, I went to a dimly lit jazz club to meet some musicians. It was the kind of place you’d see in the movies: small, crowded, smoky --hey it was the 80’s-- with little round tables scattered about. At the front of the room, there was a quartet of musicians led by a robust trumpet player.  


They were playing Jazz standards. Standards are a melody with chord changes, and players take turns improvising over the chords. As the band played through their set, I realized this guy on the trumpet was not your average player. Hearing him was a truly memorable experience. 

Whenever “Wild Bill” improvised, it was spectacular – a creative flurry of notes. He would play incredibly fast and then stop, throw out a swearword and put the horn to his lips again - “F” bombs right up there on stage between the onslaught of notes, not super loud but certainly noticeable from where I was sitting. 

When he stopped for a second to catch his breath, he would shake his valve playing hand like he was trying to shake off the notes he didn’t like. Every improvisation was as if he was having an intense battle with his horn to make it do what he wanted.

A year of so later, I put together a Dixieland band (you know with the striped shirts and the boater hats) and I needed a trumpet player. Bill agreed to work for me. He would become my employee and my musical colleague, but I learned that Bill wasn’t just different on stage, he was different, period.

The Ottawa-Carleton Dixieland Jazz Band back in the day.

The Ottawa-Carleton Dixieland Jazz Band back in the day.

I found that the secret to dealing with Bill was to get to know him (as much as he would let me) and I had to manage him – a lot. 

I always tried to spend a little time chatting with him every day we were working to get a sense of what was going on in his life. I also made sure he had my schedule written in his agenda (again, before Internet calendars and emails).

 He was in demand as a player so this was important. I made sure I had subs lined up for him. It’s usually the player’s job to arrange their subs, but organization wasn’t Bill’s forte.  Left to his own devices, double bookings would often happen and we’d be left short. 

Why did I do all that for Bill? Why did I overlook his shortcomings? Because when he was on the gig, we sounded amazing and we would often get other bookings from someone in the crowd. As the expression goes… “He was money!”

They exist on a different plane.

There are people who are unconventional, God love them. They make life interesting, when so many of the rest of us are prone to the safe and secure.  

They don’t see the boundaries or impose limits on themselves. They are about the art - the work. It is who they are. If you’re looking for engaged employees, look no further than an eccentric employee.


But you’ve got to manage them and they WILL test your people skills. 

Some tips to use with eccentric employees:

1) You’ve got to let them be who they are.  

That means, you have to give them some freedom and trust that they will deliver. Whenever Bill played, it was creativity in action and he would push his playing (and his life) so far that sometimes he would crash. But 99% of the time, it was amazing stuff. 

2) Set up good systems around them.  

The other players I chose in the band were really, really good musicians but they were really grounded. They would play exactly what was on the page. (I am not sure Bill ever read the page). Were they boring? Not at all! Solid, you bet! Their ears were always open and they were willing and able to adapt to change. They were able to support Bill as he took us on his amazing musical journeys. 

3) Let them do what they are best at and that’s it.

I never let Bill get involved in any of the nitty-gritty of the gig.  There were bookings to make, venues to be in contact with, instruments and PA systems to move, set lists to be determined.   The other musicians and myself would pitch in to make all those things go smoothly. All Bill did was show up and play.  We were all ok with that and I already told you why… Bill was money!

4) Stuff is going to happen.

Very occasionally, despite Bill’s best efforts and mine, he wouldn’t make a gig. We’d be left without a trumpet player and I’d be scrambling to cover. That’s just the way it was and, to be honest, it was probably something I didn’t anticipate. Don’t beat yourself up over this. Stuff is going to happen. 

When things like this happen, all you can do is keep weighing the good and the not-so-good. You should see that by having an eccentric employee, you are coming out ahead, which I certainly was.

5) If you’re a colleague

I've noticed that when I have been the colleague of an eccentric employee, they would push me to the point where I’d question why the boss kept them around.  As an employee in the trenches with them, it can be harder, so notice how they help the bottom line.  They do help or they wouldn’t still be there, believe me. You’ll have to find your own way to cope.  For me, it often means just keeping my distance and paying attention to what I need to do.

Life goes on

It’s wonderfully creative people like Bill who make us really earn the name “boss” or “manager”. They make life and work more colourful and force us to be more creative as well.  

Keep an open mind as the extraordinary unfolds before you. You know what they say: if it doesn’t kill you, it’ll make you stronger, and there’s no doubt that you will have some stories to tell someday. Everyone loves a good story.  Thanks, Bill.

Enjoy this post?  I'd love to read your stories or comments below about the interesting folks you've worked with and how you managed.