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.  

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