Chapter and Lesson #8

Chapter 8 

“You will never understand bureaucracies until you understand that for bureaucrats procedure is everything and outcomes are nothing.”  

Thomas Sowell

The hyper growth years of Microsoft were pretty much official over after the year 2000.  The company was still in great financial shape and an excellent place to work, and there were many tremendous opportunities to advance personal computing and to advance my career.   But Microsoft had become a big, fairly slow, bureaucratic machine, it was now playing defense.  The DOJ case and ensuing settlement, the declining stock price, and the overall size and bureaucracy of Microsoft was settling into the company culture.

Microsoft was now afraid to be aggressive competitively which was core to it’s culture.  It seemed that everything had to be checked and double-checked by a growing legion of lawyers, lobbyists and PR experts at the company.  It felt like lawyers were involved in every decision the company made, big and small.   Every product move, every marketing message, even internal communication emails were being reviewed for DOJ compliance.  The company was wounded and just did not want to take on any additional risk.  In hindsight, the company needed to change the culture and grow up.   So in many respects, that company was just evolving to a more mature and responsible corporation.  Personally, I found the changes hard to deal with, working at Microsoft was less fun, it took way longer to get less done.  Work started to really feel like a lot of work!     

The bureaucracy It slowed things down, it made jobs much harder, and getting stuff done was way more difficult than it had been in the past.   But the worst part was, Microsoft was losing its focus on the customer, and it was losing its drive to innovate.   Fear had taken over.  Fear of being sued, fear of losing your job, fear of another stock price meltdown.   More than ever bureaucrats were running the show at Microsoft, there was an attempt to take the risk out of everything.  It was suffocating.   

I vividly remember one of my favorite managers at Microsoft, Lora Shiner, telling me that once the lawyers and the bureaucrats take over it is better to leave and find a new place where you can focus on doing stuff that matters over just covering your ass all the time.  She was of course right about that.  But it is very hard to leave a good thing, and I had a family to think about – so I took the risk-averse path and stayed with the company.    I mostly regret staying at Microsoft as long as I did.   I took a comfortable route that was good for me financially, but it slowed my learning and stunted a lot of growth that I think I would have enjoyed had I left to try new things.  It also landed me ended up landing me into a spot where I was branded a “lifer” at the company.  Not that there is anything wrong with spending a lifetime at a great company like Microsoft.  But for me personally, my dream was never to be a lifer at some big company.  I just didn’t fit what I wanted to do with my life.       

Lesson #8  When the lawyers and bureaucrats start to take over at your company, getting stuff done gets way harder, it’s a good sign that it is probably time to leave for your next opportunity 

I will never really know if I would have been better off leaving Microsoft when it became obvious to me that the company was becoming a “big slow corporation”.   I do know that most of the real fun of showing up to work and getting a lot of stuff done was fading pretty fast.   The company was becoming excruciatingly slow.  Important decisions took countless meetings with “stakeholders” from so many different divisions and groups all over the company that often times a decision would just never get made.    Worse, many decisions were made for internal political reasons, to protect a senior manager’s turf, or to make sure a certain group or Corporate VP would make their fiscal year numbers.   Microsoft had gone from a company that encouraged their people to take risks, break rules and focus on customers; to a bloated organization that made a lot of internal backroom decisions to protect the growing layers of middle management,   too often at the cost of creating badly inferior products.   The signs were there for me, and if you see them at your company consider leaving!   

As a footnote: It appears that Satya Nadella has done a lot to change the culture at Microsoft.   I have not been at the company for a long while, so I really don’t know first hand how different things are today.  But certainly Nadella deserves a lot of credit for turning around Microsoft and by most reports he has changed the culture significantly.


Chapter and Lesson #7


If you buy things you do not need, soon you will have to sell things you need. 

Warren Buffett 

Once it became clear that Microsoft was going to win the web browser wars against Netscape, it became less and less clear what to do with all the resources and the people that had been built up to fight the war.   By 1998 the DOJ was fully engaged in trying to dismantle Microsoft’s power over the PC industry and put an end to the aggressive tactics used by Microsoft to beat down competitors like Netscape.  The browser wars were being used by the DOJ as a prime example of how Microsoft played unfairly with their market dominance of PC operating systems.   Ballmer’s famous “Ham Sandwich” quote, where he said that Janet Reno (the Attorney General in charge of the lawsuit against Microsoft) had it all wrong and that if Microsoft wanted to integrate a ham sandwich into Windows it was within their rights.   That quote highlighted the arrogance of Microsoft back in that day.  Microsoft employees were riding high, the stock was booming, lots of people were getting very rich at the company, Porsches, Ferraris, Hummers and lots of other expensive cars lined the parking lots.   

I remember one day three of the top managers of the IE Marketing team went out and bought brand new Porsche 911’s during their lunch break.   They were young guys, making a ton of money, on top of the world.  The machismo and bravado of that group in those days was unstoppable.  Looking back now, it all seems completely out of hand and foolish.    There was one guy, who for a short period was my boss, who had bought a brand new BMW in the early 90’s with his Microsoft stock options, he regretted it for many years to come, he had a spreadsheet where he would track how much the stock would have been worth had he held on to it.   At one point he was the not so proud owner of a BMW 3 series sedan that had cost him well over $1 Million in lost opportunity had he only held onto his Microsoft stock.    

In 1998, the stock was continually reaching all time new highs.  Money and stock options were flowing like water to middle managers and above.  The top brass already knew that it was the beginning of the end of the “best of times”.  Mike Maples the head of HR and Steve Ballmer had already started cutting back on the big elaborate parties– in an effort many folks internally coined the “Shrimp to Weenies” set of cutbacks.  Made famous by the infamous Mike Maples memo sent to employees back in 1993.

Unfortunately, most of the rank and file were blinded by their fast made money, and many thought the party would never end.  In reality, the company was getting too big to have all the lavish benefits and elaborate parties that could include all the new employees.  Microsoft was famous for their massively extreme Holiday parties.   These parties were blow your mind type events, where they had real A list rock bands, mountains of fresh shrimp, open bars, magicians & entertainers, chocolate fountains and anything you can think of that would make for the most insane party you had ever witnessed.   It was a sign of the times, and all that exuberance led many people to think the party would never end.  It did.  

It was hard to predict back in the mid-1990’s, that at the end of the decade  Microsoft would hit an all-time high — closing at 58.71 on December 23rd, 1999. (Split adjusted- I think there may have actually been a daytime high of near 120, but can’t recall exactly.  The next decade would prove to be much more difficult for Microsoft and the stock.


The beginning of the new century was not great time for Microsoft.  The stock plummeted off the high it had hit in 1999, by the end of 2000 Microsoft had lost more than half of its value.  The .com bubble had burst, and a big tech slowdown was on underway.  Microsoft had benefited both from a  PC purchasing cycle that was completed for the big Y2K computer glitch scare and booming sales of PC’s from the big dot-com boom.  The potential Y2K glitch had many companies scared to death that their systems and software would not be able to handle the year 2000 with their various business software programs.  For some reason, when many of these systems were built in the late 1900’s the engineers did not look out far enough and plan for the flip of the date to the new century.  Going from 1999 to the year 2000 would break many different programs, some of this was because many of the systems relied only on the last 2 digits of the year.  Going from 99 to 00 as the year could cause a lot of potential problems.  Because of this, many companies decided that not only would they need to make sure they fixed these software problems, they would also take the opportunity to upgrade a lot of their aging infrastructure.  This pushed a lot of tech spending forward, and helped to contribute to the overall bubble in the tech space.    

Additionally, In the few years leading up to year 2000 there was a general euphoria around almost every new .com company.   Dubbed the Dot-com bubble, Silicon Valley was funding startups based only on an idea and a name.  You didn’t even need customers and revenue was an afterthought.   It was a moronic time, and everyone thought their idea was going to work, no matter how stupid it was.    

As the bubble burst, employees across the tech sector lost millions in “paper” wealth, watching their stock options evaporate into being worthless paper and never returning.    

Stock options – are a right to buy a specific number of shares of your company’s stock during a time and at a price that your employer specifies.  If that stock is going up fast, you can make a TON of money very quickly with Stock Options.  Options were the crack that fed Microsoft employees for many years.  When the bubble burst, it was devastating to many at the company, and it started to change the culture of the company dramatically.   

From Microsoft’s IPO in March of 1986 all the way up to the year 2000 all of the employees were being lifted by the rising tide of the stock price.  It was not at all uncommon for secretaries or administrative assistants to become overnight millionaires.  People did not have to knock themselves out, or others at the company to make great money.   Making the stock go up was a unifying mission that everyone was benefiting from, the lowest level mailroom employee to those in the C level suite were in on the game.   Unfortunately, when the stock run ran out of steam, intense infighting for the fewer available rewards started to set in.  It was a long dark decade in the halls of Microsoft.  

For me personally, I went from being a paper millionaire to much less than that in a very short time span.   It was personally painful to see options on paper that were once going to be worth a lot of money turn into worthless numbers on a spreadsheet.    

I still felt very fortunate, however.  First of all, I was lucky to keep my job in the tech industry at that time.  When the bubble crashed and many Dot-com companies went bankrupt, a lot of people lost their jobs entirely.   I still had a good job and was still moving up the ladder, so I was thankful for that. 

I also had a lot of friends at Microsoft who had implemented a “buy and hold” exercise on their stock options.   This was a way to leverage options where you could essentially take a margin loan when you exercised your options and “hold” the stock you had that was previously just an option to buy it.  This was an extremely risky thing to do, think about taking out a huge loan to buy shares in a single tech company – hoping that the stock will continue to rise.  What many employees did not understand was using loan debt for leverage works aggressively both on the up and downside for stock gains and LOSSES!

If the stock goes up, doing this type of strategy is very rewarding.  However, if the stock goes down, you can lose a lot of money very quickly.   Without getting too technical, a very bad thing can happen when you buy and hold stock utilizing loaned money from your stockbroker.  If the stock goes down dramatically, you can receive what is called a “margin call” from your stockbroker.  Basically when you receive a “margin call” it means that the broker who loaned you money to buy shares of the stock is now forcing you to either sell your remaining shares to cover your losses in the stock or put in more cash to hold the borrowed shares you have in your account.  The broker does this because they have certain requirements for the dollar amount of stock you must have as collateral for the loan they have given you to “buy and hold” your stock.  This can result in forcing you to sell your shares at a very low price, just to pay off the loan you had for the stock.   The result for many people who did this at Microsoft was that they went from being paper millionaires to being totally broke.   

For many people, they were even worse than broke, they were in debt because of this strategy.  Not only did they lose all the value of their stock holdings, they also ended up with big income tax bills on the income realized from their exercised options that were used to “buy and hold” their stock using those margin loans.  Unfortunately, to the IRS, it didn’t matter if you suffered big losses on your stock after it was purchased on a margin loan.  As far as they were concerned, when you exercised your stock options, that was a taxable event.  They still wanted to be paid on the gain of the stock option.  So a lot of people suffered a double whammy when they had margin loans called from their broker, causing them to lose most or all of their stock money, and they still would have a big tax bill, with no money left to pay it.

I knew quite a few people who went from being paper millionaires to bankruptcy in a matter of only months.  Merrill Lynch ended up getting sued for the practice of recommending the strategy.    It was heartbreaking to see friends and colleagues lose all their wealth in such a short timeframe, all while betting on the company that had brought them so much wealth and security over the years.  It shook many people to the core.  

So while I saw much of my paper wealth disappear in that terrible bubble bursting year of 2000, I never spent any of the money, I dreamed of what it would be like, but I never actually had the chance!  Very lucky for me, my career was moving forward pretty well at that time, and there was always at least the hope of a stock rebound.  Which finally after many dark years seems to be taking place!      

Not long after this time, Microsoft abandoned stock options altogether and replaced them with stock awards.   Stock awards are essentially a form restricted stock in the company, they work exactly like regular stock, but you are restricted on when you can sell them – they vest over a period of 4 years where you can sell them as they vest, they were much better suited for a slower growing company than stock options. Microsoft was becoming more like IBM, a solid company with no debt, an increasingly diversified revenue stream, much of it coming from enterprise customers on multiyear agreements.

The executives knew that the days of rapidly increasing stock price were over. They still wanted employees invested in the company, but they saw the damaging whipsaw effects stock options could cause, and the tax consequences of stock options were also starting to become an issue for the company.  So a move to giving employees smaller, yet significant grants of restricted stock took over.   Restricted shares work out better for the employees as the stock does not need to move up at all and they still retain their value.   And even if the stock drifts lower, they are still at least worth something, whereas stock options are worthless if the price goes below your buying strike price.  I ended up with 10’s of thousands of shares of worthless underwater stock options.  That was always a big bummer to look at on the employee stock page!   

Thankfully, I was rewarded later on in my career with restricted stock that did very well.  I have no complaints about how my situation turned out with the company.  It took longer than I was hoping to cash in on my tech career and retire early, the learning was valuable, and I enjoyed a lot of interesting things on the journey! 


Lesson #7  If you are lucky enough to score some big money from your job Save That Money Like CRAZY!!  It likely will not happen again!

If you get rich in your job at a high tech growth company, or any company for that matter, the likelihood is you got lucky to be at the right place at the right time. No REALLY!, you probably were not that great or instrumental to the company’s success.  Because you were lucky enough to score some money at the right company, you might get a big ego, and think “I was instrumental in making this all happen, I could repeat this again with the formula I have now!”  The reality is that is not at all likely – lightning will probably not strike twice…   Save that money like crazy! 

Don’t buy stupid shit like cars, boats, vacation houses, etc.. and don’t make a bunch of risky investments.  I made that mistake , and I estimate I wasted at least a half a million dollars on stupid trophy purchases and bad business investments.  It was idiotic.  I bought luxury cars, boats, invested in businesses I knew nothing about.  Almost all of it ended up doing little other than burning through a chunk of my savings.  

All that stuff will bring you very little happiness, and potentially a LOT of aggravation.  Be smart and conservative with your nest egg.  The smartest thing you can do is diversify your money, put it into a few different asset classes of low cost Vanguard Index funds, and forget about it, keep working and make more money as long as you enjoy it. 

This is not an investing book, of which there are many good ones and bad ones out there.  If you have already made your small fortune, go read up on Warren Buffet’s advice on how an individual investor should invest.  If you are lucky enough to win the life lotto more than once – say jumping from one hot tech company to another, good for you!  For most us, getting that kind of lucky, it is a one-time event!   And most never get that lucky!  Remind yourself, you are NOT Bill Gates, Elon Musk, or Mark Zuckerberg – get over your bad self.  Save your money and don’t be foolish with it!    Finally here is some data to prove my point.  

Nobody stays in the Top 1% long.  From a report on the Top 1% of earners.

The Top 1% is often considered an exclusive, monolithic group, but folks actually rise up into it and fall out of it quite often. That’s because their incomes can vary widely year to year.

Some 11% of Americans will join the Top 1% for at least one year during their prime working lives (age 25 to 60), according to research done by Thomas Hirschl, a sociology professor at Cornell University. But only 5.8% will be in it for two years or more.

As for holding onto this status for at least 10 years? Only a miniscule 1.1% of Americans are this fortunate.


Chapter and Lesson #5


One of the things I am best at is riding coattails.  Behind every successful man is me, smiling and taking partial credit.  

Tom Haverfod (Parks & Rec)   

As it turned out, my job in Product Support set me up to grab my next pretty cool job at Microsoft.  The Windows Team at Microsoft was looking to hire somebody into Product Management who had some experience with our Support organization.   At that time Microsoft was spending a TON of money supporting retail and small business customers who were calling in to get phone support on all kinds of different issues they were having with their PC’s.  Sometimes it was a Windows problem, sometimes it was the PC Manufacturer, and sometimes it was a problem with a software or hardware program the customers had added to the PC.

Whatever the problem, a big percentage of people would call Microsoft first for help, and this was taking a big bite out of the profits of Windows.  The Product Management team was interested in finding new and less expensive ways to deal with all of these calls.   So they opened up a new position to hire somebody who could help figure out what should be done to drive down those high customer costs.    

Interestingly, the hiring manager for this role was Suzan Fine – Who is now Suzan DelBene, who has gone on to be a U.S. Congresswoman for Washington State’s first Congressional district.    I loved working for and with Suzan, she had a great way about her, she had an infectious smile, positive attitude and get it done personality.  She was wicked smart, and I think at times overlooked at Microsoft for bigger roles that she likely deserved to have.    

Soon after Suzan hired me, I started working for Lora Shiner who was a group manager on Suzan’s team.  Lora was one of my favorite people I ever had the pleasure of working with and for.  She was an incredibly talented marketing mind and had a common-sense approach combined with a fearless attitude where she could stand up to any Microsoft Executive on any issue.

I remember one meeting we had with Bill Gates where Lora was one of the key presenters.  I can’t recall the issue we were discussing at the time.  But for whatever reason Bill was in a particularly foul mood that day.  He took a shot at Lora and said something to the effect that “you must be the dumbest person I have ever met”.   To which Lora replied with a big smile.  “Bill, while I understand you don’t like my idea, I can assure you that I am not the dumbest person you have ever met, not by a long shot”  That comment shut Bill up for a few seconds, he paused, the room gasped and everyone started to laugh, Bill took the comment with good intent and humor and got quickly  back onto a productive track.    

Lora was outstanding because of her confidence, her intellect and her very honest and direct style of communication.   She would mentor, support and get out of the way.  She expected the best from people, and when they didn’t deliver she had this magical ability to help them realize they had let her and the organization down.    Lora could fire a person and have them love her all the way through the process until they were out the door.  Sadly, Lora died of cancer at age 47 just before 9/11 attacks.   I was devastated to not be able to make it to her funeral as I got stuck on the East Coast after the attacks of 9/11 and could not get back in time to make her services.   She was a great friend, a mentor, and a great boss.  I still miss her to this day. 

I was very fortunate to have quite a few fantastic bosses at Microsoft.   Lora Shiner was my favorite boss.  Others included  Yusuf Mehdi a long time senior marketing executive for Microsoft.  Bob Kelly the leader of Server and Tools Marketing and now at Ignition Partners, Jeff Price another longtime leader in Windows and Windows Server Marketing now at VP at Oracle, Danielle Tiedt who was the lead marketer for Bing and went on to be the CMO at YouTube,  all great bosses, each was different and each helped me grow and become more successful in my career at Microsoft.

I had my share of bad bosses too, I will talk about some of them later in the book (without naming names).  Most of the bad bosses were bad because they lacked confidence in themselves, they were insecure in their abilities, and they lacked the ability to truly lead and inspire others.   In my experience, bad bosses tend to blame the people around them for their problems.  They have  a tendency to throw up a lot of roadblocks for the people who work for them and around them.   They tend to take away the energy of people in their groups, rather than create energy.   A great boss creates energy and knocks down roadblocks, they want their lowest level employee to have great success, and they never fear the success of their underlings, they embrace it and support it.

I remember I had one boss, who I will not name, I called him the “wife beater”.   This boss would come into my office totally by surprise and just start berating me over some minute detail he was upset about.  He would swear at me, personally insult me, tell me that I was worthless.  It was disgusting, I was still early in my career and in my twenties, and I was afraid to really stand up to him directly.   After his tirades, he would always come back to my office and apologize for losing it.  He would tell me how badly he felt, and that I didn’t deserve to be treated like that.  He would offer to take me out to lunch, which was the last thing in the world I wanted to do.  It was awful, it made going to work a terrible experience.  Luckily there was a reorganization just about every 8-12 months in those days at Microsoft, so I knew I would not be with him long, and sure enough, the nightmare of working for that guy lasted less than a year.  

The point of this is you need a great boss and there is no shame in riding coattails when they are available.

Learning Lesson #5 Picking a Great Boss is MORE important than Picking a Great Job.   This may be obvious to some people, but it took me some time to figure it out.   Having a great boss who can and will support you is so much more important than the job or the content of whatever job you might be considering.   You could have dream job, but if you have a horrible boss, it will ruin anything good about the job.   Bad bosses kill careers, they kill your spirit, and they can make every day a living hell.   Bad jobs, with a great boss, can actually be somewhat fun and satisfying.  Great bosses are extremely rare.  If you have a boss that is supporting you, helping you grow, eliminating problems and allowing you to do good work, you are in a winning situation.   Even if you don’t love the content of the everyday work you are doing, if you have a great boss stick with her or him as long as feasible.   Specific jobs and the work content comes and goes, bad bosses can be forever!  Or at least they can torpedo your career forever.   If you have to make a choice between Great Boss + Bad Job vs. Bad Boss + Great Job.  Pick Great Boss every time.  

Chapter and Lesson #4


“It is not the employer who pays the wages. Employers only handle the money… It is the customer who pays the wages.”- 

Henry Ford, Ford Motor Company 


When I landed the 2nd time at Microsoft, it was first as a contractor.  I had made up my mind that I wanted to work for the company fulltime, and I was going to do everything I could to land what they called a “blue badge” job with the company.   This terminology originates from the different types of employees who had different color badges depending on their employment status with the company.   Blue badges were for fulltime employees.   Microsoft has always had different color badges for temps, contractors, service jobs etc.    Blue was the gold standard, it meant that you were a full-time employee of Microsoft, with benefits, stock and all the nice, and some not so nice, things that go with it.    It took me about a year of hard work, keeping my nose to the grindstone and ears on the phone headset, and kissing a fair amount of ass to finally land my first full-time job.      

I came up from the bottom, so I had a chance to see the pros and cons of the perma-temps at Microsoft, and the ever-growing legions of contractors the company employs.  Microsoft employs temps and contractors for a few different reasons.  Mostly they want the flexibility in their workforce, it is more efficient for them than hiring fulltime people and having to deal with adjusting that workforce up and down.   For many of the contracted employees, this works pretty well, you can get a pretty decent paying job working as a contractor for Microsoft, and you can have a lot more flexible schedule.   As a contractor you typically can just focus on doing your work, you also don’t have to go to all the bullshit meetings Microsoft has all the time.   

A note about meetings and Microsoft. Microsoft is infamous for holding way too many meetings for just about everything, they have team meetings, group meetings, manager meetings, divisional all hands, pre-meetings, post meetings, meetings to plan more meetings and on and on.  It is an insane “meeting” culture, I don’t know if this has changed since I left.   I can only say that generally if you can’t stand meetings, don’t go to work at Microsoft.  You will have far too many of them and more than 50% of them are total and complete waste of time.   I regularly sat through meetings where there were 100’s sometimes 1000’s of people.  Almost all of them were totally useless and could have been done via a quick email or send a video around.   

For me, it turned out that the little bit of experience I had gained in Aerospace doing sales was useful for landing my first “blue badge” fulltime Microsoft job.  The group I was working for at Microsoft was looking for somebody who had some sales experience, but also some experience working in the Product Support Services group – which was the group I was doing the contracting job in.   That combination of experience landed me in a group that was ramping up a new team to sell a new “paid support” product from Microsoft that they were going to call “Premier Support” at that time.   The “premier” part meant that Microsoft was going to charge significant money to the customer to support their products. 

As more and more big corporations were installing more of Microsoft’s products, quite a few companies were starting to run important parts of their business on Microsoft, and they wanted Microsoft to have more “skin in the game” when selling their software to them.   Believe it or not, back in those days, Microsoft was considered more of a consumer software company, and big enterprise customers did not trust that Microsoft was truly committed to supporting big companies IBM for example was.

Microsoft had previously tried to avoid going deep into servicing customers.   It was expensive to service enterprise customers to the level they expected, and it was not considered a core competency of Microsoft.   IBM, HP, and a few others were considered more credible players in the service business in those days.

Microsoft was a disrupter offering a lower price more flexible PC solution, while others were offering expensive mainframe solutions with very high priced service contracts.   IBM had people inside of all these big fortune 500 companies, and anytime something went wrong they would take the bullet for the CIO who might be in trouble.   It made CIO’s very nervous to have a big deployment of Microsoft software and not have somebody at Microsoft who they could choke when things went wrong.    These dynamics made for the advent of the TAM – or Technical Account Manager at Microsoft.  The TAM was a named technical support expert assigned specifically to a company, or even to a specific department of a larger company.  If for example, a big bank had some sort of serious problem happening with any Microsoft product, they could call on their assigned TAM to make sure their problem was solved, even if that meant the problem required an engineering fix from one of Microsoft’s core development teams.  And a company could ONLY get access to a TAM if they had paid for a Premier Support contract.   It was a brilliant way for Microsoft to charge money to support their products, and customers actually jumped at the chance to get some individualized attention from the fast-growing software company based in the obscure NW corner of the United States.  

For me, this meant a new job was born!   My job was to sell these Premier Support contracts to some of Microsoft’s largest and most important customers.   I was happy and lucky to have a Fulltime spot with the company, many of the young people in the division I was being hired into were already “retiring” as they had enough money in stock options to cash in!  They could “call in rich” as they would say.   I figured if these lucky bastards could be retiring before they were 30 years old, I would be able to knock out enough stock options to be done before I was 30 as well! 

Microsoft was fortunate to have a lot of talent in their support group, they did a good job of working with customers and finding solutions to whatever problems they had.   Microsoft acted like an underdog in those earlier days, it tried to continually go above and beyond to make sure customers were getting good service and were happy and satisfied.   It was a fun group to be part of, and in that work, I learned a lot about what customers wanted from our products and services.  I would hear it first hand from the IT Pros who were doing the actual deployments of Microsoft Software in their environments.   These were the people whose jobs were on the line to make our software work at their companies, you learn a TON from these folks. 

Learning Lesson #4  When starting out in a big company, get a job where you are working directly with customers.   The experience you gain working directly with customers is invaluable for your entire career.  You will get more respect from future bosses, co-workers, customers, and partners if you live in the trenches with customers for a decent period of time.  It may not be glamorous or even all that fun at times, but the experience is the best thing you can do for your career.  I recommend getting the experience as early in your career as possible and stick with it as long as you are progressing in a direction you like.   There are TONS of jobs at big companies where you never actually talk directly to customers at all.  Avoid these jobs early in career.  Jobs that don’t directly touch customers are normally easily replaceable, outsourced, automated and early to be eliminated when times get tough, and they won’t give you the credibility needed to accelerate your career.   Companies are nothing without paying customers, every CEO and senior executive knows that.   Senior Executives have more trust and rely more on people in their organizations who have had a strong direct connection with customers.   And most Senior Executives get their positions because of their focus on customers throughout their careers.  

<<<On to Chapter 5>>>

Chapter and Lesson # 3


Chapter 3 

“Good business leaders create a vision, articulate the vision, passionately own the vision, and relentlessly drive it to completion.”  

Jack Welch 

I decided that when I got my second shot at working at Microsoft I was going to treat that opportunity very differently.  I had a little bit of experience in the real world now.  Even I could now see how PC’s were going to completely transform the workplace.   I was not visionary enough to fully understand how much PC’s were going to change the home, but it was pretty obvious that PC’s were going to be important in many homes very soon.   Of course, Bill Gates had the powerful vision of a PC on every desktop in every home, but that seemed like a distant pipe dream back in 1994.  But when Bill spoke, people listened, and he had a way of making the un-seeable seeable.  For all that has been said and written about Bill Gates, to me at least, he exemplified a bold and strong leadership combined with an amazing vision unlike I had ever seen.  

Gates in my very limited interactions with him, was the real deal, just an absolutely incredible person.  Bill’s vision, intelligence, drive, his massive depth and breadth of so many different areas was just unbelievable to witness. I was amazed and impressed whenever I was fortunate enough to have a meeting with him or hear him speak.  It was just an incredible privilege to be around him.  Whatever you think about Microsoft, its products, its business practices, you can never take away the incredible person that is Bill Gates, and the lasting impact he has had and will continue to have on our planet.   He has made a big dent in the universe. 

So much has been written about Bill Gates that it is hard to come up with anything particularly novel or new to say about the man.  One of the things I always appreciated about Bill was his unique ability to take extremely complex and technically difficult problems and simplify them so that anybody could understand them.    

A meeting with Bill was something that could take weeks to prepare for.  Most of the meetings with Bill were to seek strategic direction, either for a product specifically, or for some kind of directional or strategic advice on the business.  Bill was always amazingly deep on both topics, so much so that you would fear he might ask a question that you had not thought of, and he often would!   When particularly difficult decisions needed to be made, Bill had an incredibly elegant way of weaving his deep technical product knowledge with his insanely good business acumen to come up with what would often be an obvious solution, where he would plainly explain the answer.   

It was amazing to watch Bill lord over meetings with his superior intellect combined with his reputation as the great founder of Microsoft; with his jabbing quick smarts, and his sometimes wicked tongue, he was the only person I have ever seen who could command the respect of Microsoft’s biggest egos and bring them quickly inline.  His leadership was simply unmatched. 

Learning Lesson #3  –  Only work at a company where you truly admire the leadership.   When you truly admire the leadership of the company you work at, the hard times and the difficult things you encounter each day are much easier to deal with.     There were plenty of hard times, bad days, and screwed up things happening at Microsoft during the 20+ years I was there.   When you are lucky enough to have great leadership at the top, you end up trusting that good decisions will ultimately be made about the big things that really matter.   This makes it infinitely easier to deal with all the little stupid things that happen in big organizations all day long.   After Bill left the company, it was clear that Steve Ballmer didn’t have anywhere near the intellect, vision or leadership qualities that Bill did.   You could never be sure if Steve would make a good decision on the big things that really mattered, he was more random, insecure and for my taste and a more difficult personality to deal with.    The longer Steve was in power, the more you could see the company lose its way on so many things.   When a company feels lost at the top, the stupid things that happen every day at all companies seem to feel much worse.  You can put up with a TON of bullshit if you feel like you are heading in a great direction overall.  

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