WRITING THIS BLOG often makes me reflect on people I’ve encountered during my career.
Sometimes people ask, “Who was the oddest person you ever had working for you?” and although quite a few pop into my head, there’s one that tops all others.
It’s a guy named Larry who I worked with in San Diego a number of years ago, but labeling him as “odd” doesn’t even come close to describing what a character he was.
There were two head-shaking encounters that I remember, and they make you wonder — are there other employees out there like this?
Encounter 1: Sleeping on the job
IT WAS BACK WHEN I was Editor of the San Diego Business Journal, and one morning around 9:30 am, one of my editors popped into my office and said, “I need to talk to you about Larry.”
It wasn’t unusual to be greeted like that, because it’s not unusual for editors to ask for guidance while managing reporters. That’s often because editors and reporters frequently have a different perspective on what’s important and what is not.
Larry (not his real name), had those same issues as well, but the challenges with him were usually less about his reporting and more about the odd things he did at work and how they impacted everyone around him.
I asked my editor what was up with Larry, and I was told something I had heard before.
She said, “Larry is sleeping in his car out in the parking lot.”
I assumed this was a general observation, and I told her that people sometimes nap in their cars on their lunch break. It didn’t sound like a big deal to me.

Her response? “Yes, I know people sometimes do that, but Larry is out napping in his car right now — and he started work at 9 am.”
TAKING YOUR LUNCH BREAK 30 minutes into your work day in order to nap in your car was a new one for me, and it made me do something I had never, ever done during my long managerial career
I went out to the parking lot to wake an employee up.
When I got to the car, I knocked on the driver’s side window. Larry popped up and rolled it down. Here’s a rough version of how the conversation went:
ME: What are you doing out here, Larry?
LARRY: Taking a nap.
ME: It’s 9:30 in the morning and you started work a half hour ago. Why are you taking a nap now?
LARRY: I had a bad night and thought I would take my break early and catch up on my sleep.
ME: Why didn’t you tell your editor?
LARRY: I never tell her when I’m taking my lunch break.
ME: That’s probably because you normally don’t take lunch 30 minutes into your shift. You should have asked her if taking a break at 9:30 was OK. You need to come up to my office so we can talk about this.
LARRY: Can I finish my lunch break first?
You can probably guess what I said.
The three of us met in my office where we talked about the obligations of an employee. They included checking with your supervisor if you were doing something out of the ordinary — like taking your lunch break at 9:30 am so you could take a nap.
The big concern was that although Larry apologized and agreed that he should have cleared his early lunch hour with his supervisor, he didn’t seem to understand what he had done wrong.
It wasn’t an act for Larry. He actually DIDN’T know what he did wrong because we had previous instances where he didn’t seem to understand normal (and acceptable) workplace protocols. I didn’t truly understand this until my second head-shaking encounter with him.
Encounter 2: Bagels and cream cheese?
BUSINESS JOURNALS TEND TO HAVE lean staffs, and that was certainly true when I was Editor in San Diego. There were about a dozen journalists in the newsroom, and when you add in sales staff, production staffers, and administrative people, the office head count was no more than 30 people.
It was lean and mean and the Publisher was a retired Marine who was always trying to do small things to build camaraderie. One way he did this was by bringing in bagels and cream cheese for the staff every Friday morning.
I’m not much of a bagels and cream cheese guy, so I didn’t really focus on the Friday ritual until one week when Larry’s editor — yes, the lady who brought the sleeping in his car to my attention — flagged me about another issue.
She said that Larry was pulling the used cream cheese cartons out of the trash at the end of the day on Friday, taking them home, and then bringing them back to the office a week later. He would then remove the fresh and unopened cream cheese cartons intended to be used that week and replace them with the used ones he had fished out of the trash the Friday before.
How did my editor know Larry was doing this?
Well, when you work with reporters you quickly find that they’re pretty nosy, and a couple of them who were usually first to the bagels wondered why the cream cheese cartons were half full some weeks before anyone had even eaten one.
That led them to start watching more closely over a couple of Fridays. Guess what? They found it was Larry fishing the used cream cheese cartons out of the trash, taking them home, bringing them back a week later, and then pocketing the new, unopened cartons for himself.
Non-acceptable workplace behavior
THE STAFF KNEW Larry was quirky — they all had heard about the 9:30 am sleeping incident — but this was way beyond that.
Once again, Larry and his editor ended up in my office. We had a conversation similar to the one over his morning nap, but this time, one thing clearly stood out — Larry was truly puzzled by the notion that he had done something wrong.
Here’s what he told me:
- He said he didn’t know that there was anything wrong with taking the used cream cheese cartons out of the trash;
- He also didn’t believe there was anything wrong with him saving the used cartons to swap the next week for the brand new ones.
I told him that this was stealing, about the possible health and safety issues that could develop from doing something like this, and how it could make others sick. I also told him that his conduct had made everyone in the office distrustful of him, and that a great many of them were concerned about what crazy thing he might do next.
The more I talked with Larry, the less he seemed to understand. And just like with the sleeping incident, he had no understanding of acceptable workplace protocols and behavior, nor how something like this might alarm and anger the entire Business Journal staff.
I had talked to the publisher before sitting down with Larry, and we agreed he should be suspended for a few weeks so we could do a more thorough investigation into his work practices. Larry didn’t seem terribly bothered by this, and he left that Friday as if nothing had happened.
A week later, before the HR investigation was finished, he quit … never to be seen again. No one was sad to see him go. They were just happy to know the cream cheese wasn’t being pulled out of the garbage and recycled any more.
Good managers do the tough stuff
ONE MORE THING: The “Larry” story has come up a number of times over the last 20 years, and the main reaction I get is disbelief that any person would actually do things like this on the job.
But dealing with Larry and his odd behavior was something that I had to cope with, like it or not — and that is the essence of being a manager.
Some think managing isn’t all that hard, but all that shows is that they probably never had to do it.
I worked for a guy who used to brag that he never had to fire anyone, and I wrote about him a few years ago in Good Leaders Give Bad News, While Bad Leaders Avoid Doing the Tough Stuff. My insight then is still applicable now.
It’s this: Good leaders have to give bad news.
I still believe this, but thinking back about “Larry” reminds me that dealing with odd people issues, although not in the same league as telling someone they’re losing their job, can be tough for managers too.
And if you can’t do the really tough stuff — with kindness and empathy — you’re really not much of a manager at all.




