Chapter & Lesson #14

“Better to remain silent and be thought a fool than to speak and to remove all doubt.” 


One of my favorite stories from this era is from a meeting I had with Steve Ballmer, the then CEO of Microsoft, while I was enrolled in Microsoft’s special Executive training program they called “The Bench”.  The Bench program was put together in 2000 shortly after Ballmer took the reigns of the CEO spot after Bill Gates decided to step away from the CEO job and become the Chairman.  Microsoft was becoming increasingly concerned that their young managers were not up to the task of leading the company to whenever it was they wanted to go, and decided some good schooling for young talent might be the right answer.  Most people did not take the training very seriously, but I found a lot of the content in the courses at least somewhat valuable, and the access to the other people in the company and the networking provided by the program was definitely worth the price of admission – which was free if you were nominated to it!

It was spring of 2001, via the program, I had received an invite to go and meet with Ballmer, the topic for the meeting was undisclosed, and the entire setup of the meeting was very odd as we were told that no preparation was necessary- this was highly unusual when meeting with the CEO at Microsoft, as it turned out that was all by design.  The meeting was setup in Steve’s personal conference room in Building 34.   Ballmer had a special wing in building 34 dedicated to him and his support staff.   To get in there you had to pass through a special security area where there was a guard at the door of the wing and you had better be coming with an invite or you would be swept out of there quickly.  Apparently, all the windows in the CEO wing are bulletproof as well (and no I am not making this up).  As you walk through the wing there are all kinds of handlers and special staff in there who are dedicated personally to seeing out every detail of Ballmer’s every move.   It is a bit intimating to even step foot into the place.    

After receiving the odd invitation to meet with Mr. Ballmer, I asked twice if there was any prep required for the meeting and was told it was not necessary.  This had me concerned as most meetings with Steve Ballmer or even any of his VP’s would require pre-meetings, and sometimes weeks of planning to get the exact powerpoint deck, messaging and every other detail ironed out before getting in the room with one of these guys.  So this was for sure going to be a somewhat different and odd meeting with the CEO.

When I arrived at the conference room there were about 6 other people who also were assembling at the same time, these were other Bench Program members, but none of them were in the same class group I was in, so I had no knowledge of these people and only slightly knew a couple of the people in the room.  We were told to go ahead and go into the room and wait for a while by one of Steve’s assistants.  At this point, it still was not clear why we were there.  Then a gentleman came in and introduced himself as the monitor for the meeting, he was not a Microsoft employee, but some consultant Microsoft had hired to run this little dog and pony show.

It soon became clear that this meeting was really going to be some weird young executive meat market or talent show for Steve Ballmer.  The moderator asked us to come up with key issues for Microsoft that we wanted to talk to Steve about when he got there.   As a group, we were to identify the topics and present to him why we thought they were important to discuss.   The moderator told us we would have 30 minutes to pick the topics and who will present them and that he would be back just before Steve arrives.

Moments like this is when shit got really weird at a place like Microsoft.   Figuring out who is going to talk and what about, agreeing on the topics, it was like an instant chess match unfolding before your eyes.   Game of Thrones style, everyone was working through the right way to look good, please the king, and not come off looking like a total jackass.  Most everyone was failing miserably at the task. 

Unfortunately for me, I was a young and overconfident fool, so I opened my fat mouth and said I thought we should talk about competing with Google.  My reasoning was that Google seemed to be enjoying a strong connection with technical Reviewers and Press analysts I had been visiting as of late, and many of them had told me that we should be looking more closely at them. Some were suggesting that Microsoft should start forming a partnership with them or be looking to buy them.

At that time Microsoft had a product called MSN Explorer which was essentially a customized version of Internet Explorer with a bunch of buttons and chrome on it that pointed users exclusively to MSN properties.  As part of my job leading MSN PR, I had recently been out pitching the product to the press.  Most of the press basically liked the product but they did not like how it handled the Internet search function.  The search functionality was locked to use only MSN Search at the time.   I had several reviewers tell me that they would never use or recommend a product where they could not use Google as their primary search engine.  The cognoscenti of the tech media had already made up their mind that Google was important, and it was the best Internet search engine available on the market.   It was concerning to me and I felt like Steve should know about it.   This was the VERY early in the days of search.  It is hard to believe that Google didn’t really get started in search in any serious way until about the year 2000.  Adwords had just been invented and were just starting to roll out on Google. 

So, like an idiot, I told Ballmer that I thought Google was beating us badly on Search, and that important folks in the industry were telling me Google was going to be a really important company.  Before I could get much else out, he stopped me dead in my tracks.   Ballmer said, I have looked extensively at the Search market and ran the numbers, I don’t ever see search being more than a $300 Million-dollar business.  (Yes he was very wrong, but that really doesn’t matter)

As a young guy trying to move up inside of Microsoft, I was not about to challenge the wisdom of our CEO in a training class where I was supposed to be learning how to be a leader inside of Microsoft.   Steve was a renowned numbers guy, he was the friggin CEO of the company,  and who was I to question whatever math he had done.  I slinked back into my chair, and just sheepishly said,” I don’t know about the revenue part, I only know what others are telling me who I have talked to across the industry”.   He gave me a look like, “who gives a shit what those people are saying, I am the CEO of Microsoft!”.   I failed that meeting.  Big time.

I found out that later that day that Ballmer had called the VP of my division, Yusuf Mehdi, and told him I was a whiner or had a bad attitude or some such thing.  Yusuf caught me later that day in the hallway and said to me, “what did you say to Steve? He thinks you’re a real pain in the ass now!”   I, of course, thought to myself, “oh shit, I must have really pissed this guy off if he took the time to call my boss and tell him he didn’t like me, that went way worse than I thought!!!  I was devastated.  I wondered if my career was over that day, and sort of wished that it was.

I spent the next few years trying to avoid any eye contact whatsoever with Steve Ballmer.  I was just hoping he would forget who I was at that point.   It was an awful experience really, not just the meeting with Ballmer, but the entire Microsoft bench program in retrospect.  By the time I finished the program, half the people in my study group had quit the company, and only a few remained in the program as most just didn’t see the point of going anymore.  It was yet another signal that I missed that I should probably be spending more time thinking what to do beyond Microsoft.    But the primary lesson was more obvious.   As the old saying goes, God gave us two ears and one mouth for a reason.  I wish God would have provided me a muzzle on that day!  

Learning Lesson #14 – When you are a lower level employee in a big, highly competitive company with a cutthroat culture, be very careful when speaking your mind about what is going wrong in front of senior management. 

First, it is important to understand that CEO’s and Senior Executives have probably already heard about the problems you are worried about before.  They are after all running the company and it is unlikely they are totally clueless where the problems lie. 

Secondly and more importantly, in my experience at Microsoft, senior executives honestly don’t really care what you think.  Mostly they want to know that you are loyal to them and that you are not going to rock the boat too much or make them look bad.  

I am sure this is not true in all companies, and Microsoft was for sure a unique culture in those days.   But generally, I think this is true at most big companies.   You are way better off keeping your mouth shut while early in career, continue to try and learn and grow your perspective while trying to move up the ladder. 

When you are early in your career, your job #1 is to make your boss look good.  Just repeat it to yourself, “nobody really cares what I think”.  It hurts, but it will help you move up the ladder and set you up for success later down the line.   

This is particularly true in an environment where the senior management is paranoid.  Which happens to be almost all big tech companies in this age.  Voicing problems and concerns are often seen as a sign of disloyalty or weakness to the leadership in a tech company.  Where the culture is based on fear, you have little to gain by expressing problems.  Even if you think you have a solution to the problem, it is likely not going to be welcomed advice.  Of course, HR departments, and senior managers will tell you they want to hear all your ideas and to bring them forward.  But be very wary of that message, HR will tell you a lot of things in the corporate world that are simply not true, and if you are looking out for your career, you will do better keeping your mouth shut and going along with your senior management.   The fact is the paranoid senior management at your company is likely already very well aware of the problems you see and they have probably already debated them endlessly in meetings you weren’t invited to!  So don’t try and be a hero – it will leave you looking like a zero. 

The ONLY exception to this rule is that if you have a problem that you think could be damaging to your manager, and you have real data, NOT JUST GOSSIP, that will back up your point, it is worth sharing that data with your manager in a private meeting with ONLY your manager.   The problem and the data should be presented in a non-impassioned and straightforward way, and you should not bring a strong opinion to the matter.  Rather, you should simply state that you thought it was important that your manager knows of the issue, and if they need any other assistance that you are there and ready to help!

As you build trust and loyalty with your direct manager, you will eventually be able to extend that trust to take on more responsibilities and your opinion on problems will matter more – not only to your manager – but eventually to others in leadership.  Take it slow, and don’t shoot your mouth off as a young gun, it is a really stupid way to shoot yourself in the foot!