Why Is This Man Smiling? — A day at Microsoft, early 1990s

The buttons and posters appeared one day and then were quickly taken down, but some of us snagged the swag before it could be recalled. Apparently, some lackey in the marketing group had prematurely pulled the trigger on an elaborate campaign to launch… whatever was being launched.

A couple of days later the items reappeared: buttons bearing the grinning mouth and nose and bottom rims of the glasses of the famous founder of Microsoft, and posters that said “why is this man smiling?”

We, the denizens of early-90s Microsoft hallways and rabbit-warren offices — about 10,000 of us — had no idea. Until we opened our email later that day and saw an invitation to an event on one of the ballfields in the center of campus.

What exciting program was being announced? Speculation flew. Bonuses for all? Some kind of award? A trip to Hawaii? Our expectations were high. This was a company, after all, that gave generous bonuses every six months along with stock options that were zooming skyward along with the company’s valuation; that had an actual “morale budget” for every group to spend as they saw fit for parties, outings, beer and snacks at meetings, whatever we wanted, just to keep us all happy and productive.

We trouped out to the ballfield at the appointed time. A stage was set up at one end. Music boomed over loudspeakers. Tables around the perimeter were laden with buckets of beer and wine and sodas and massive trays of sandwiches, cookies, and snacks. We helped ourselves, clinked bottles and congratulated ourselves on doing whatever we had done to deserve this, and then waited.

After a while, Mike Maples appeared on stage. Mike was the head of marketing. At the time, his sister, Marla Maples, was married to Donald Trump. He got asked about her all the time, and always admitted that yes, he was related to that Marla. He made a few introductory remarks but didn’t reveal our purpose in gathering. He left that to BillG, as everyone called him.

Bill Gates took the mic.

Bill shared the exciting news that, in the plaza between buildings 16 and 17 and even as he spoke, paving stones were being replaced with plaques commemorating every product the company had shipped to date. As each new product shipped, he told us, new plaques would appear. Walking the plaza, which he dubbed the Walk of Fame, would afford a person a chance to tour Microsoft’s illustrious history of shipping great software.

The silence was deafening. If we hadn’t been standing on a grassy field, you could have heard a pin drop.

Then Bill held up an oblong slab of Lucite and announced that, in addition to the awesome Walk of Fame, every time we shipped a new product, everyone on the product team would be given one of these plaques and a metallic sticker with the name of the product and the date, which we could then affix to the plaque. The more products you had a part in shipping, the more stickers you would amass.

Stickers? This all came down to stickers? The disappointment was palpable. We waited for the other shoe… the cash awards that came with it, the trips, the big stuff. Nope, there was nothing else. The Ship-It Award, as some genius in marketing had decided to call it, was nothing but a piece of plastic with spaces for stickers.

And that was it. We were encouraged to party and enjoy the treats, and then to make our way to the Walk of Fame to look at the plaques and bask in the glory of shipping cool stuff. Everyone drank as much beer as they could get their hands on and laughed at the anticlimactic event.

When we got back to our offices, we found an email from Mike Maples with the subject line “Shit-It Awards.” Yes, someone had made a monumental typo in the subject line. It seemed the perfect end to a bizarre day.

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