Member preview

What I Learned Working for Steve Ballmer

Bill Gates, Steve Ballmer, Jim Allchin, Mark Zbikowski — at Mark’s 25th Anniversary party. The author is seen entering stage right.
“The reason that God was able to create the world in seven days is that he didn’t have to worry about the installed base.” — Enzo Torresi. 1945–2016.

A few months ago, I published a story called “What I Learned Working for Both Bill Gates and Steve Jobs.” It was a re-published piece I’d written two years ago. The original had been read by a few hundred people, mostly friends and family and colleagues, received some positive reviews, and was quickly forgotten in the digital onslaught for your attention that is the internet.

When I re-published the blog post, I took the time to clean it up a bit, added a few sentences summarizing my thoughts, and highlighted a couple of key lessons in bold. Perhaps even more importantly, I updated its bland title to one that included the names of two icons of the industry. I figured a little advertising never hurts.

Within a couple of days, the new version caught fire. It had tens of thousands of views, it was picked up by the editors of Medium (the blogging site I use) and marketed on their front page, it was translated into half a dozen languages, it was offered by multiple publishers in syndication. Medium even paid for a professional artist to record an audio version. Editors of several online journals contacted me breathlessly asking to publish my other blog posts which had so far languished.

Suddenly, thousands of people were taking the time not just to read what I’d written but also to “highlight” almost each and every sentence in the story, a feature of Medium used by readers to draw attention to key parts of an article. Articles in totally unrelated fields were quoting me! To this day, it gets more views, “claps”, shares, and retweets than most of my other blog posts.

I was surprised by the response, to say the least. I felt like yelling from the rooftops: “But I said all this two years ago and no one even bothered to read it!” I guess I had something to say, I just hadn’t found the audience the first time around.

The key phrases from the article that were most often quoted and retweeted were the two lessons I attributed, respectively, to Steve Jobs and Bill Gates: that you should never fight a battle in a war that has already been lost and that everything in life is interesting, if you just pay enough attention to the details. I won’t repeat the stories here, you’re welcome to go read them for yourself:


Here, as a follow-up, I want to relate a few stories about Steve Ballmer and the lessons I learned from him. I worked at Microsoft for a dozen years, beginning in 1998, and the experience afforded me quite a few interactions with Steve.

Lest I be accused of name dropping, let me be clear upfront. I was present at perhaps a hundred or so meetings with Ballmer or Gates or both during my tenure at the company (averaging perhaps one a month) but I was by no means in touch with either of them on a regular basis. I don’t intend to glorify my own role nor do I wish to imply “inner circle” standing. What I learned, I learned by watching them do — as much or more so than through any words they said in private or public interactions.

Steve has gotten a bad rap recently and has been blamed for some of Microsoft’s missteps while he was at the helm. But I suspect most of his critics haven’t been in his shoes, responsible for running the world’s most valuable company or managing 100,000 employees. Few seem to give him credit for his many successes: almost quadrupling the company’s revenues (from $20B to $75B) even in the midst of an antitrust lawsuit, the construction of several multi-billion dollar businesses, not to mention delivery of 75% gross margins.

Ballmer was the peanut butter to Gates’ jelly, bringing business savvy to the technical battlefront. One without the other would never have been as successful as the combination of the two. For that, he deserves much credit.

I once participated in an executive offsite where, as one of our exercises, we were offered a chance to “Be SteveB for a day”. What would you do, given the opportunity, if you were in his shoes for a day, to move the needle, to increase revenues by even a tiny amount, say 1%, or to win 5% more market share in a given competitive arena?

What we all found out very quickly, even given our deep knowledge of Microsoft businesses and technologies, was that even the most outlandish proposals were unlikely to make a dent in the Microsoft P&L, given its gigantic size and market dominance, or to deliver substantial value to shareholders. So I give him a lot of credit for what he did accomplish and I refer his critics to my favorite Teddy Roosevelt quote:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs with the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” — Theodore Roosevelt. Citizenship in a Republic. April 23rd, 1910.

I, for one, prefer to dwell on the positives, on the lessons I learned from Steve. I found him to be sincere to the extreme, passionate in everything he did, and loyal — almost to a fault. Steve was famous for emotional and over-the-top speeches, one of the most cited examples being his “Developers! Developers! Developers!” chant at a company meeting. His enthusiasm knew no bounds and his passion was contagious.

Ballmer is a math whiz and had won math tournaments as a kid. He also seems to have photographic memory. One story I heard, from two people who were there, is about Steve at a company offsite with roughly 25 executives in attendance. He walks in and mingles for a few minutes, then heads to the stage for a “fireside chat”. During the interview, as part of a response to a question, he mentions that he knows what type of shoes each person in the room is wearing — and then proceeds to list them one by one!


The first story I want to relate about Steve is when we went in to see him as part of an acquisition we were doing. We’d spent months working in a cross-company effort, including representatives from Sales, Marketing, Program Management, Engineering, Legal, HR, Finance, and every other team you can imagine, as we put together the case for the acquisition.

The process had been going on for several months and we were ready for a final go/no-go decision. We’d had several earlier meetings with Ballmer and other executives but this meeting was special. We thought we had all the data ready and wanted a final decision. The price was pretty high, so we needed to go all the way to the top for a decision.

I distinctly remember this meeting because it happened on September 11, 2001. We had all staggered into the office after watching our world disintegrate on TV that morning, not even sure whether the meeting was going to take place or not. We considered rescheduling the meeting given the circumstances but we all knew that it would take an eternity to align the schedules of all the executives who needed to be in attendance — and we needed a decision pronto.

I remember Steve walking in and sitting down. He seemed shaken by the World Trade Center attacks and made a few comments as we waited for others to arrive and then announced: “But we can’t afford to be distracted. The show must go on. Let’s proceed.”

So we started presenting our case, talking through the dozens of slides that we’d put together covering every topic from competitive pressures to product-market fit to revenue projections to engineering team integration and more.

I did a large part of the presentation as it was ultimately my team that would host the arriving R&D team. I noticed, as I was speaking, that Steve started flipping through the printed copy of the slides in front of him. He was listening to the pitch and simultaneously flipping through the spreadsheets that presented the target company’s sales forecasts, costs, profits, etc. Half a dozen pages in, he slowed down and started running his finger down the page. Then he looked up, waited for a pause in the presentation, and said in a soft voice: “This number is wrong!”

You could hear a pin drop in the room. I was floored and lost my entire train of thought in that instant. He had just scanned dozens of pages worth of numbers, data that an entire team of thirty or more people had worked on for over a month, and instantly pinpointed a flaw in the math. I knew he was a math whiz but never saw this coming. Later, I heard from others that he had a habit of doing this in meetings.

I admit, in hindsight, to not having paid great attention to every single number on every single page of the spreadsheet. I was the engineering leader and not responsible for the business angles of the transaction. Besides, I was more interested in the strategic synergy, the competitive pressure, the customer value prop, the engineering team integration, and a dozen other angles. I’d trusted the finance guys to get the math right. In my zeal, I’d wanted the deal to happen, so I’d been happy with the nice numbers and didn’t question them enough.

We spent the next few minutes scratching our heads, mumbling, and re-working the math in real-time. He was right! There was a serious flaw in one of our formulas and no one else had noticed it. The deal didn’t make any sense once you corrected the math. We were done.

The fact that he noticed the error while simultaneously listening to my pitch, not to mention the distractions caused by the day’s ghastly news, gave me pause. Any other executive would have assumed his finance people could write Excel formulas and delegated the task. But not Steve. That level of attention to detail was impressive, to say the least. The lesson I learned from Steve that day was simple: Every single detail matters; Trust but verify.


I was once informed, upon inheriting a project during a reorg, that it had recently caused a massive outage at a major Italian bank. No one at the bank, it seems, was able to log in to their systems for… er… a couple of days thanks to a bug in this particular piece of software! As is typical with reorgs, I hadn’t created the mess but I’d have to clean it up.

The component in question implemented a distributed file replication protocol as part of Active Directory and needed to function properly before a user could login and use the system. In their zeal to expose cool functionality, the team had exposed one too many knobs in this component, one of which the Italian bank had used to shoot themselves in the foot.

The software worked great when everything was in order but gave up in the face of the simplest of errors and required an expert in digital forensics with a PhD in distributed computing to diagnose and repair it. Needless to say, the bank had run into one of these error conditions and was basically up the creek without a paddle.

I suppose things could have been worse. Imagine the run we could have caused on the Italian banking system as panicked citizens were told they couldn’t withdraw money from their accounts because the tellers had all been locked out of their computers. Thankfully, that didn’t happen.

Meanwhile, back at the ranch, we got busy addressing the root cause. We had to offer immediate bug fixes to customers who had deployed the problematic code base while also simultaneously building a replacement component from the ground up with a more robust design and better error handling — which we did over the next few months, but that’s not the point of the story.

A few days after the initial meltdown at the bank, Steve personally went onsite to apologize to the CEO and employees. He could have sent an emissary to represent Microsoft in a difficult and contentious situation but instead chose to go himself. The lesson I learned from Steve that day? A leader falls on his sword for his team if and when needed.


When it was finally time for me to leave Microsoft, after we’d completed Windows 7, Steve was the one executive who kept meeting with me, at least half a dozen times, repeatedly asking me to stay and setting up meetings with executives around the company — trying to play matchmaker. He didn’t have to do that. I was flattered that he seemed to think I was worth saving.

To Steve, loyalty to Microsoft was paramount. His father had been a Detroit man and refused to drive anything but American cars. Steve was famous for flying into fits of rage if he saw an employee using a competitor’s products. He’d been known to grab iPhones and smash them on the ground. I never saw this in person, but did hear of cases where he had done so. At the time, I used both an iPod and an iPhone. I remember him wagging his finger at me a couple of times but nothing more.

It made sense that he wanted us to use our own products to show not just loyalty to the company but also so we could feel, first hand, the pain we were causing our customers through bad design decisions or when we introduced bugs into the product. We had to be the first and the most critical users of our own products, even before we subjected our customers to them. Eating your own dogfood is a required step in delivering high quality products:

On the flip side, though, this also meant we didn’t really spend much time wallowing in what the competition was doing. Of course, we had folks performing Competitive Analysis and tear-downs and some employees took the time to play with competitors’ offerings but, for the most part, the rank and file used Microsoft products for their daily tasks.

Count the number of Microsoft employees at the time (early 2000’s) and then count the number who used products from competitors on a regular basis — MacOS instead of Windows, Linux instead of Windows Server, Gmail instead of Exchange and Hotmail, Yahoo! Instead of MSN, Sony Playstation instead of XBox, iPod instead of Zune, etc., and the latter would be a much smaller number than the former.

I enjoyed my time at Microsoft but if I had any of it to do over again, if I were in Steve’s shoes, I’d exhort the employees to do both: by all means, use your own products but also relentlessly use those of your competitors. Don’t just play with them or read about them on a slide. Use them every day to get your job done. That’s the only way you get to know thine enemy.