Project Management Humor: Four Of My Own Personal Work Stories

Sometimes we just need to laugh. We’ve been producing a lot of longer-form content lately that’s either technical or instructional in nature. While project management is both of these things most of the time, there’s plenty of chaos mixed in for good measure. From this chaos emerges some pretty funny stuff, even if it doesn’t seem too funny at the time. This article will be focused on project management humor, as seen through four of my own personal work stories. There’s definitely a few nuggets of wisdom in each story of what not to do in the future! Enjoy.

PROJECT MANAGEMENT HUMOR - My Boss Skipped His Own Meeting

1. My Boss Skipped The Urgent Meeting That He Set Up

For several years, I was the project manager on a complex renovation project. We’d been working on the building for a couple of years, and the most crucial stages of the project were beginning to heat up.

During this time, we had nowhere close to the amount of managers we should’ve had to run all our projects. We had a project superintendent who was spread across several large projects, and we had no assistant project managers to help out with the daily grind of paperwork and logistics. Just project managers, field crews, one office admin, one project engineer and a really horrible bossto make us miserable all the time. These projects were in the multi-million dollar range.

To spare you the details, this project was what you’d call a dumpster fire. Nothing went right from the get-go and no one was too interested in stepping in to make it so.

My boss decided he’d had enough. We got an email late in the evening summoning us to our main office the following afternoon for a super-important, several hour, once-and-for-all meeting so he could “clean up the mess”. Myself, along with our project engineer, the super and our field foreman made our way to the office for a fun afternoon scream-fest.

At 1pm, we shuffled in to our conference room, and my boss shut the door. He sat down, at first not saying a word.

We were then berated for all of the issues and problems that he’d largely been responsible for creating in the first place. For years, I battled to get some more help on the project. Our office had been a revolving door of employees up to that point – the average lasting 6-8 months. We were given lectures, scoldings and a lot of “you need to…”s for the first 30 minutes of the meeting.

Then around 1:30pm, my boss gets up. He starts putting on his coat. I thought he’d just gotten into the office when we did, but I was wrong. “Well, you guys know what you need to do“, he said. “Where the **** are you going??”, our faces must’ve said. “I have a meeting I need to get to“, he replied, “but you guys are all together in the office at this point, so get started on fixing everything we just discussed.

My boss turns to me. “Meet me in the office early tomorrow morning and give me a report on what you guys came up with.” Exit stage left.

None of us knew whether to scream or laugh our asses off. 

2. A Subcontractor & I Drove Through A Blizzard To Meet Each Other, Only To Find The Other One Missing…

On the aforementioned restoration project, we had a specialty subcontractor that was making some pricey replicas from the original building for us. We had removed and stored all of the original pieces, and this contractor was tasked with taking them back to the shop and making exact replicas of each one for the rebuild.

We were a few months away from actually needing these replicas onsite. It was the middle of winter in the northeast, so this particular subcontractor had a lot of time available to work inside their shop. They began working on some of the replicas.

How’s everything coming along?” I said on the phone one afternoon. “Pretty well, I have a few pieces made already“, our subcontractor said back. “Great. Well, we’d like to be able to pay you for what you’ve done so far, but we’ll need some photos and specific information from you in order to bill the client. How about we meet tomorrow morning to go over it?“. “Sure, sounds good“, he said. We agreed to meet first thing in the morning.

After hanging up, I remembered that I didn’t know which of their two addresses he’d be at. We confirmed the address of their shop via text.

I woke up to several inches of snow on the ground with more still coming down. In the major northeast city I was living in at the time, I knew the normally 30-40 minute drive to his shop would take a couple of hours. Even though I left home around 6am, it was somewhere around 8am or later by the time I got to this company’s shop.

Except no one was there. No one in sight even. No cars in the parking lot.

I called the subcontractor, and he told me he was five minutes away – traffic was crazy that morning, he said. I agreed.

Five minutes go by, then ten minutes. “I just spoke with him“, I thought. Suddenly, he called.

I’m out front, where are you guys?“, he said. I looked around and saw no one.

He went all the way to the job site – two hours away considering snow and traffic. I was at his shop.

Needless to say, we both were pretty angry at one another. I barely knew this guy, too – I had only really known their owner up to this point. He said some nasty things to me, I said some angry things back.

Somehow he thought I was confirming the shop’s address just to make sure where it was, not to meet there. He swore that he thought the meeting was onsite.

Eventually we cooled off and just tried to forget about it. Both of our mornings were completely ruined.

Oddly enough, he ended up being one of the most valuable people on this project. 


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3. The Assistant Engineer Who Was Hired For A Position We Didn’t Need

Our office was under-staffed relative to the amount of projects we had in the hopper. This started to become obvious the moment our projects really got into full swing. We needed people, and fast. A couple project managers and I recommended hiring an assistant project manager to help with the administrative work and to learn the ropes.

Even our project engineer agreed with this. Our boss thought differently. We were told as much.

I’m not going to just hire more people to make up for mistakes and inefficiencies“, he stated. We went on with our projects and lives.

A month or so later, we received an email from our boss. The subject line read “New Hire: Assistant Engineer“. My jaw almost hit the floor.

We don’t even need another person in project engineering. Even the project engineer himself had agreed about our office needing more managerial help. Apparently our boss thought differently.

He hired someone with zero experience in contracting to be our assistant project engineer. None of the PMs were consulted.

After about two weeks after the assistant engineer started, our project engineer told our boss that he didn’t see the need for the new guy.

In order to fire him, though, my boss would need to let our corporate headquarters know about it. He’d look pretty silly for selling them on the idea of hiring this person, just to fire them shortly after.

What did he do instead? He made this assistant engineer – who had ZERO construction experience – into a project manager, too. It went as well as you’d expect it to. Several months later, he was fired.

Where does project management humor fit in? After all that, we stilldidn’t have an assistant project manager!

Project Manager Humor - We Helped Design A Building For Free

4. Our Team Helped A Property Owner Design Their Building For Free – We Just Didn’t Know It

Several years ago, our company decided to bid on a portion of an upcoming mega-project. This is in a major northeast city and it’s a gigantic project. You’d probably know of it if you heard it.

We spent a couple of weeks putting together a proposal based on early detail documents. We turned it in and awaited feedback.

We got back questions and requests for additional information. We worked on a revised proposal and resubmitted again.

Next time, we got even more requests back. “Can you give us a price on ‘x’, but an alternate price for ‘y’? Separately, what if we didn’t have you work on ‘x’ at all but only did ‘y’? Also, include a price for ‘p’, ‘q’, ‘r’, ‘s’, and ‘t’.

Having so much time and energy invested, our boss and upper management decided to continue bidding this project.

In fairness to them, it would’ve been a gigantic contract if we didget it, so it makes sense to need to get pretty detailed in the bidding process. No pain, no gain right?

We then were asked for our own ideas on certain aspects of doing the work, such as how we’d install the steel structure, what kind of scaffolding and work access we’d provide, how many different ways we’d do this-or-that. Things we saw as flaws in the design, specific fabrication/installation means and methods, installation prices for differently-sized components – the list goes on and on.

We chased this project in this fashion for months. 

Our estimates were sliced and diced on various bid forms, checklists and spreadsheets so many times, we were starting to lose track of what the **** we were actually trying to do.

This process continued intermittently for eight or nine MONTHS on top of . We surely sunk a six-figure amount of overhead costs into bidding this project, all while charging zero in the process. Just chasing after the potential dollar signs.

The project’s final design was literally developed based on the feedback and bidding iterations that we had went through – for free.

Weekends, nights, stress and about 50 trees’ worth of paper later, we were told that another contractor was getting the project. They were about 10% lower than our final price ended up being.

Now THAT was a tough pill to swallow. Even tougher to explain. If we lost the job but were paid for a portion of our time, it wouldn’t seem so bad.

There was a heaviness in the air after we found that out. We really thought that project was going to be the big breakthrough we were hoping for. In hindsight, I don’t know what our company, or any of us, were thinking. Actually I do – we began to think about how silly it was only a fraction of the way in!

The building is done now. It looks pretty nice! 

In Summary

While project management is stressful, difficult and not always fun, there’s plenty of humor to be found. Whether it be straight-up funny stuff that happens, dark humor and ironic situations, it’s best to keep things from getting too serious – at work or in life. Humor is the spice of life!

I truly hope you’ve enjoyed this article. If you have some funny project management humor to share, feel free to leave a comment below. Thanks for reading!

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