Memories from Working at Microsoft in the Nineties

Life in the fast lane: the days of sleeping at the office

Carlos Arguelles
9 min readMay 20, 2021
21-yr old, fresh out of college, and first job at Microsoft!

I was a Software Engineer at Microsoft for 11 years, between 1998 and 2009. Being at Microsoft in the nineties was a unique experience, and I knew I was part of something special.

Over the decade-plus I spent at Microsoft, life there opened my horizons in so many ways. I was born and raised in a small town in rural Argentina, and went to high school and college in a small town in the Midwest. Coming to the West Coast, moving to a metropolitan area with three million people, and being dropped at the epicenter of the computing world, Microsoft in the nineties, was an amazing experience.

In front of Building 25

If I could magically choose a time and a place to go back to, if for only one day, I would choose Microsoft circa 1998. There was so much energy in the air. We were all young, single, and had no life outside work. We happily worked 80-hours per week. I often slept in the office, even though my Redmond apartment was just ten minutes away. In fact many people slept at the office, many nights. We were going to change the world. It was not uncommon to walk the hallways at 2AM, and they were as lively as they were during the day.

Since we worked 80-hour weeks in a high stress environment, we needed to relax by doing crazy things as well. “Work hard, Play hard” was the motto. One of the ways in which it translated was, if you went on vacation, your office was pranking grounds. One time, we removed the door of somebody’s office, and replaced it with drywall, essentially closing off our friend’s entire office. You can imagine his surprise as he came back from vacation and couldn’t find his office! (and the only way in was to break through the drywall). Another time, we filled every possible square inch of the surface of somebody’s office with turf: floor, chair, table, we even made a little mouse pad out of turf. You can imagine what a messy job it was to remove all the dirt from that office!

Ah, that bulky CRT monitor and the giant tower desktop machines from those days!

And there was the wealth. So much money. Everywhere. It just seemed to rain on the streets of Redmond. It was not unusual to see Ferraris, Lamborghinis, Maseratis, in the parking lots of Microsoft campus. Some of my co-workers that had been there for a while were sitting on millions of dollars of stock. Even I, an entry level kid, was sitting on over a million dollars of Microsoft stock, 18 months into my tenure (spoiler alert: this would not last…). And oh boy the company parties were lavish, always five star hotels.

That excess cash everywhere also led us to become spoiled and entitled. When money got tighter in 2002, Microsoft removed the free towels provided in the locker rooms. Apparently somebody did the math and determined that we were spending hundreds of thousands of dollars in towels and laundry. But when the towels were removed, there was a huge uproar and bringing them back became a crusade for many. After thousands of microsofties rebelled, Microsoft gave in. The towels were back. Microsoft probably lost more money in the decreased productivity of thousands of engineers whining for weeks than it ever would have saved in towels.

I remember there was an outdoor summer party once. Bill Gates and Steve Ballmer were sitting on silly inflatable pool floaties shaped like chairs, on stage. After the party, I sneaked backstage with one of my engineers, Matt, and we ‘acquired’ Bill Gates inflatable floatie. It became the guest chair in my office for years. It wasn’t high quality, so I ended up patching it many times. But in my mind, the fact that Bill Gates’ ass had been there for 2 hours made it a fun trophy and a good conversational piece.

My first building was Building 8, right next to Bill Gates’ building. I’d often see his helicopter landing on the helipad of Building 9. Occasionally I’d see him driving his convertible Porsche on campus on a sunny day. He seemed so approachable, but there was actually a fair bit of security around him, just very discreet. I went up to his office one day and snapped a photo for the hell of it, and within 10 seconds security guards showed up and confiscated my camera.

Hiring was a very unique process. Strategy was simple: we went to the top schools in the nation and we tried to get the top graduating kids. MIT, Carnegie Mellon, Stanford, Berkeley, Cornell, Harvard, Princeton, the list continued. If you were in the top 10% of the graduating class, Microsoft was going to pay whatever it needed to pay to get you to join. Microsoft was the Big Dog, and the expectation was that you were going to be a millionaire by age 30 so it was not that hard to snatch up talent. I was self-conscious because I did not have that pedigree: I had gone to the University of Missouri Columbia, whose Computer Science program ranked 110th (the story of how I actually made it to Microsoft is for another blog!).

Our interview process was somewhat unorthodox. You flew to Redmond and had a full day of coding interviews. These were hour-long, stand-in-front-of-the-whiteboard-and-write-code sort of deal. While today, in 2021, this is standard practice with the FAANG companies, in 1997 it was definitely unusual. In addition to coding, we gave our candidates brain teasers. High IQ was a requirement. I remember practicing brain teasers until 2am the night before my interview! When I look back at this twenty years later, it seems strange. We did not (at all) probe for leadership skills or culture fit. We just did coding and IQ tests essentially. I learned years later than IQ has nothing to do with actual success at work!

I also volunteered for a program to take the candidates out to dinner after their interview. I had a budget of $250, and I actually received updates on how the candidate was doing throughout the interview day. If the candidate was a strong hire, I was to blow the full $250 budget on a lavish meal for them and “close the deal.” It made for awkward conversations sometimes, as I knew whether the candidate was getting an offer or not — sometimes candidates were feeling so good about having nailed the interview, yet I knew they hadn’t (but wasn’t allowed to say anything).

We targeted young computer science graduates that were malleable. The ability to be shaped was critical, because your first job at Microsoft was sort of an indoctrination. You came in without a preconceived notion of what a job should be, and the Microsoft Ways were imprinted onto you. The process was almost like a xerox machine, faithfully creating mini-mes with half the DNA from Bill Gates and the other half of the DNA from Steve Ballmer. I can still recognize an old-time-microsoftie within 10 minutes of talking to them.

Something unexpected happened circa 2000 or 2001: as the stock growth slowed down, Microsoft found itself made out of two distinct socioeconomic classes. There were the people that had joined prior to 1995: they were rich, as in, really rich… in the millions of dollars of vested stock. They had benefited handsomely from the Microsoft stock wild ride (it split twice in my first 3 years!). They had Ferraris, mansions, and did weekend trips to Belize for the hell of it. Every other day some 35-yr old guy retired. Then, there were the engineers that had joined circa 1999. Their stock grants were stale, or sometimes, even underwater (2002–2003 they definitely went under-water!). Those engineers were just as smart and successful, but they looked at the older generation with a fair degree of envy and frustration. So there was a lot of tension between these two classes. Me? I was smack in the middle: having joined in 1997, my initial grant was worth over a million dollars by the year 2000, but by the time I actually sold it in 2003 it was just about two hundred thousand dollars. Clearly, unlike the prior Microsoft generation, I was not going to retire by age 35.

Microsoft in the nineties was aggressive, competitive, cut-throat, adrenaline-charged, testosterone-filled. I think it would most likely fail every single DEI (diversity, equity and inclusion) test you would ever apply to it. At the time, I was young… barely 21 and fresh out of college! So it seemed fun and I failed to see what was wrong with that. Looking back, I can see just how toxic some of that culture was.

Here’s one (painful) example. Because Microsoft performance worked on a bell curve, it was clear to all of us that our co-workers of the same level were directly competing for limited resources (promotions and raises). It meant that it was actually in my best interest for my co-workers to fail, because that would help me succeed. I remember one time I was trying to collaborate with a jerk in my team, and he point blank told me, “you’re my competition, I want to get promoted so I don’t want to do something that is going to help you!” That’s right, we were neck to neck in performance calibration so he needed me to fail.

As a second example, the Microsoft company meetings were a crazy affair. Microsoft would bus thousands of engineers across Lake Washington (from Redmond to downtown Seattle) and we would fill the Kingdome, a stadium Seattle had back then. And Steve Ballmer was a showman. He would literally run around the stadium to an adoring crowd of microsofties chanting and cheering and some inspirational song like “Eye of the Tiger” blasting at full volume. As he got older, those jogs around the stadium got slower, and he ended up more winded and sweaty at the end. The last company meeting I attended, he was drenched in sweat and panting like a dog! I thought he was going to have a heart-attack right there. What jumps out at me is what toxic culture he was fostering. After he caught his breath, he would start yelling about how “we needed to destroy the competition!!!!” In 1998 his message was “We must destroy Sun! We must destroy Netscape!” Eventually towards the end of my decade+ it shifted to “We must destroy Google!”. When I stated, I was 21, young and full of testosterone so I would wildly (and blindly) cheer like everybody else. It wasn’t until years later that it sort of dawned on me that It was never really about creating great technology to help people… it was always about some company that was the enemy and we needed to destroy. It was such a toxic message, and eventually, towards the end, I realized this is not something I wanted to be a part of, despite how much I loved many aspects of Microsoft.

I have another early-Microsoft memory: when the President of China came to talk to Microsoft executives. He clearly was not popular among the Chinese-American, so there were concerns around security. I noticed a bunch of mean-looking buff guys with giant weapons (military? paramilitary?) walking around my building. They were looking for good vantage points to defend this guy’s drive into campus. I thought, gee, it’ll be fun to drive around campus and could I see the president’s motorcade? So I hopped on my convertible, put the top down, and drove around trying to time it just right. There was a huge motorcade with some heavily fortified vehicles, tinted windows, limos, the whole works. Apparently I timed it a little “too right”. I ended up stuck between 2 of the cars in the motorcade! Next thing I know, there’s a little red dot on my dashboard. I followed it up to the building’s roof. Sure enough, there was a guy with a rifle trained on me and just waiting for me to do something stupid. I got out of there nice and slow, with no sudden movements!



Carlos Arguelles

Hi! I'm a Senior Principal Engineer (L8) at Amazon. In the last 26 years, I've worked at Google and Microsoft as well.