In early 2002, Bert landed a job at Initech, which released its own protocol analyzer tool. Technically, they released a whole slate of protocol analyzers, data loggers, analytics tools, with overlapping features and business cases. Their product catalog had grown over the years, and was a bit of a thicket.

The team Bert joined was a decent mix of talent. Some, like him, were new to the industry. There were some more experienced devs, who knew the product and the low-level internals their software needed to navigate. And then there was Herb.

Herb was every stereotype of the 70s era hacker, aged up into the 00s. He had a collection of buckling spring keyboards, thought 64k of RAM was an incomprehensibly large amount, could code Assembly faster than most of the rest of the team could do C, and he knew every line of code in every product, and knew exactly what it did and why it was there.

Jack, the team's project lead, was Herb's polar opposite. Young, with a shiny new MBA, a focus on the kind of networking skills that didn't involve CAT5 cable, and absolutely no useful knowledge about anything. "Our team exists to serve the business," Jack was fond of saying. "So whatever the business needs, we do. No. Matter. What."

The business decided that their complicated product catalog was hurting their sales. Customers were confused about which product to purchase, some tools were receiving barely any updates, and there really wasn't enough opportunity to "upsell" additional functionality, since every product already had more functionality than most users needed. As part of this process, two older protocol analyzers and an unrelated data logger would be merged into a single product.

Well, the business needed something, and Jack was confident that his team would make it happen. Since this was "just" merging software together, it couldn't possibly be all that much work. It was nothing more than some mechanical repackaging, a little tweaking, and the biggest part of the work was probably updating the help files. Jack didn't need to talk to anyone on the development team to decide how they were going to serve the business.

The new product, Initech's INILYZER, would release in four months. Since it was replacing three existing products, those could be put into end-of-life. Since the INILYZER was definitely coming out in four months, they could be EOLed in four months as well.

Jack's next task was to communicate this to his team at the project kickoff meeting. Jack loved to turn project kickoffs into his own personal motivational speaking exercise, because "That's how you build team morale!" So the kickoff meeting launched with dramatic intro music (provided by a tiny CD player in the corner), a rousing speech, and then the pièce de résistance: freshly made t-shirts for the whole team, emblazoned with: "The INILYZER: August 30, 2002"

August 30th was Jack's predetermined release date.

"Well," Jack said, gleefully doing his best impression of a stadium t-shirt cannon, "does anyone have any questions before we go out and totally crush this awesome project?"

Most of the team cringed, except for Herb. He held up a shirt and pointed at the date. "Yeah. Where'd this timeline come from?"

"It's driven by business need," Jack said.

"Okay, but you're never going to hit this date."

"Um, Herb, we're doers at this company. We have a date, and we are going to hit that date."

This meeting was on a Friday. Over the weekend, Bert and the rest of the team chucked their t-shirts into the rag pile and basically forgot about them. But not Herb. On Monday, Herb walked into the office, proudly wearing his project shirt.

With a small modification, scratched in with red marker. It now read: "The INILYZER: August 30, 20023".

Jack didn't notice it until about 10AM, and when he did, it prompted a meltdown. He started screaming at Herb about insubordination, respect, and team spirit. "I want that shirt off, right now! Or you're fired!"

"I didn't bring anything to change into," Herb said.

Jack stomped off, fuming.

The project continued. August 30th came and went. Summer turned to autumn, autumn into winter. Six months after officially EOLing major products without having a replacement ready to go, there was a management purge throughout the company. Jack got fired, and there was much rejoicing.

Jack's replacement was Emma. It didn't take long for Emma to get a read for the new team, understand the source of the mess, and start working to get it as cleaned up as it could. When upper management started looking at Bert's team as another possible cut, it was Emma who made sure they understood that they were doing the best they could with an unrealistic timeline. Nobody else from the team got fired.

August 30th, 2003, the Initech INILYZER shipped. Emma, having heard about the now infamous t-shirt story, had a small plaque made up to celebrate Herb's accuracy.

Of course, with the unrealistic timeline, unrealistic goals, and management problems, the INILYZER shipped as a pile of barely usable crap. As it turns out, pretty much no customer wanted those products glued together in any way, making the whole effort pointless. It was a technical and commercial flop. The project to replace it started the very same day as its release.

Emma was the PM. Unlike her predecessor, she talked with the developers, especially the most experienced team members, to figure out what the timeline and scope actually were. The project kickoff involved no t-shirts.

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