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Steven Sinofsky on Leading Office & Windows at Microsoft and The Art of Writing Well | Aarthi and Sriram’s Good Time Show Ep. 26

Check out the Episode Page & Show Notes 

Key Takeaways

  • Steven Sinofsky doesn’t write immediately when he has an idea; he will stew with an idea for days at a time so he can really think about it
  • The Darwinian element of early Microsoft was the ability to do email 
  • Microsoft had to realize that TCP/IP was not something it had to make go away, but something that the company would have to pivot around  
  • After getting back from a recruiting trip at Cornell, and only three months on the job as Bill Gates’s technical assistant, Steven wrote a memo explaining why Microsoft had to adopt the “internet thing” 
  • People celebrate the winner for a short time, and then go onto to dislike the winner for a long time
  • “My whole career at Microsoft I thought we were on the verge of going out of business.”Steven Sinofsky on only the paranoid survive 
  • The Mac vs PC ads were “brutal”, according to Steven Sinofsky; they were 90% accurate, but the 10% that was inaccurate drove him absolutely bonkers
  • Have a “Strong opinion, willing to change” operating framework 
  • “Leading is giving people a picture upon which to decide things so that you are not the limiting factor, the gatekeeper, or the micromanager.” – Steven Sinofsky 
  • Leadership requires the fortitude to create the picture for those following you and then let it go 
  • “There is a very fine line between leadership and manipulation.” – Steven Sinofsky 

Intro 

  • Steven Sinofsky (@stevesi) was president of the Windows & Office divisions at Microsoft. Today, he writes Hardcore Software on Substack, a collection of personal stories detailing the rise and fall of the PC.  
  • In this conversation, Steven Sinofsky, Aarthi, and Sriram discuss the lessons that Steven learned while leading Office and Windows at Microsoft, the art of writing well, Bill Gates, Steve Jobs, effective leadership, the future of computing, and more 
  • Check out these Podcast Notes from Bill Gates on Founders, Mistakes, & Philanthropy 
  • Hosts: Aarthi Ramamurthy (@aarthir) and Sriram Krishnan (@sriramk)  

How Steve Writes So Well 

  • Steven sticks to a five-paragraph essay format, except he does five paragraphs for each paragraph 
  • It is common for writers to over-index on being concise at the expense of telling the whole story 
  • Steven doesn’t write immediately when he has an idea; he will stew with an idea for days at a time so he can really think about it
  • He had thought about writing Hardcore Software for eight years before starting it on Substack    
  • For better or for worse, early Microsoft culture was email-heavy: “You were either varsity email or you weren’t”
  • The Darwinian element of early Microsoft was the ability to do email 
  • Early Microsoft treated email like instant messaging 

Messaging Apps vs Email 

  • Microsoft’s culture was long-form writing; the company had a word processor and spreadsheet product
  • Bill Gates was a voracious reader, which contributed to his attention to detail in his emails

Bill Gates and Steven’s Memo & The History of the Internet at Microsoft

  • Microsoft had to realize that TCP/IP was not something it had to make go away, but something that the company would have to pivot around  
  • It either had to adopt TCP/IP or withdraw itself from the internet 
  • After getting back from a recruiting trip at Cornell, and only three months on the job as Bill Gates’s technical assistant, Steven wrote a memo explaining why Microsoft had to adopt the “internet thing” 
  • Every person that Steven did an “internet demo” for thought it was the stupidest thing
  • Many people thought that the internet couldn’t work because no one owned it 
  • Steven created the slide that Bill Gates presented which basically announced Microsoft’s official foray into the internet (April 3rd, 1994) 

On Open Source Software 

  • The Walled Garden approach to building the internet was never going to work, regardless of how hard Microsoft tried to make it work initially 
  • There were “open systems” at the time, but no open source
  • Not understanding open software was one of Microsoft’s three biggest failings in the arc of open software
  • Google hacked the open-closed system debate when it created the Search 

Dominance and What Microsoft Could Have Done Differently 

  • People celebrate the winner for a short time, and then go onto to dislike the winner for a long time
  • People mostly like the underdog 
  • It is hard to be liked in the middle of an antitrust trial 
  • “We grew into the monopoly that we had.”Steven Sinofsky 
  • The pessimistic view was Microsoft was trying to lock people into its walled garden; the optimistic view was Microsoft was trying to make its customers happy and give them the products they needed 
  • “My whole career at Microsoft I thought we were on the verge of going out of business.” Steven Sinofsky on only the paranoid survive 

Microsoft’s Culture of Being Aggressive  

  • The aggressive culture at Microsoft was rooted in the personalities of Bill Gates and Steve Ballmer 
  • Steve Ballmer has the classic teams-sports competitiveness 
  • Bill Gates was about winning technically, and being the most right
  • Steve Ballmer was about winning in the market with sales and the customer 

Startups Today vs Microsoft Then 

  • Young people say, “No, it’s just different” when they don’t want to hear what you’re saying 
  • Slack vs Teams was a very old-school competition 
  • The most competitive thing you do in old-school enterprise software is writing a 30 page white paper with a ton of references explaining why your competitor stinks
  • The crypto world and ChatGPT are completely over their skis right now, much like Microsoft was  

How To Set The Right Culture For Your Startup 

  • There are two types of founders:
    • One is completely convinced that she has no competitor, the company is unique, and the world will come to her 
    • The other is obsessed with her competitors and knows all of their features 
  • Even if you think you’re unique, the industry will bring competition towards you whether it is bogus or not 

Windows Vista and The History 

  • Second System Syndrome: a team that is successful in launching a complex system takes a step back and decides to build a second system to fix the first one, and then the team vanishes for a decade and nothing happens
  • Code was shipped over much longer time horizons in the Windows Vista days, and the developers had to think of what the world would like two years out and build that world
  • Today, software developers think of an idea and ship it by 4 PM 

Steven Taking Over Windows

  • “I could not stand how everything in Windows was some executive escalation.” – Steven Sinofsky    
  • There had to be a meeting with VPs each time two teams disagreed on something
    • Steven couldn’t stand this dynamic and immediately changed it when he took over 
  • Fixing these bureaucratic issues requires individuals to make definitive decisions 

Mac Vs PC Ads 

  • The Mac vs PC ads were “brutal”, according to Steven Sinofsky 
  • The ads were completely in touch with how the world viewed PCs and were 90% accurate 
  • The 10% that was wrong drove Steven absolutely bonkers 
  • It’s only been in the last two years that Macintosh was even registered as a competitor to Windows 

Shipping Windows 7

  • Checkpoints are not reviews; it’s your fault if you come to a checkpoint meeting and you leave doing different stuff than when you came into the meeting
  • Windows 7 kept the operating system relevant in terms of just running programs
  • Windows 7 kept the “buying a PC wasn’t horrible” thing going 

The State of Desktop and Laptop Computing

  • The phone completely dominates computing 
  • The number of people operating a computer is the population of earth – and that computer is a smartphone 
  • All the best PC usage in the world is about 1/8th of smartphone usage, and it’s never going to become half 
  • Apple has been relentless in developing its operating system on the mobile while simultaneously jettisoning old things from the Mac   
  • The Mac has become more phone-like as Apple has forced applications to incrementally modernize over the past decade
    • This has made Apple’s laptop a moderate step function in computing

Are We At The End Of The Smartphone Innovation Cycle?

  • Think about the evolution of automobiles when you think about the evolution of smartphones
    • Today, people all around the world are getting access to cars for the first time 
  • A “mother of all technology disruptions” will be required to disrupt the smartphone
    • The only thing that has faced this is the discovery of fire 
  • Nothing has penetrated all of Earth like the smartphone 
  • Replacing 7 billion smartphones with some innovation that no one has thought of before is a monumental task 

Bill Gates As A Leader & The Traits Of Good Leaders

  • Bill Gates’s “Strong opinion, willing to change” irritated Steven at the time but he has since grown to appreciate this intellectual framework 
  • It is a nightmare to work for a manager who only criticizes; Steven calls this crux “Leading Is Not Editing” 
  • “Leading is giving people a picture upon which to decide things so that you are not the limiting factor, the gatekeeper, or the micromanager.” Steven Sinofsky 
  • Leadership requires the fortitude to create the picture for those following you and then let it go 
  • Sweating over every management detail sounds like a cool management book about Steve Jobs but it isn’t for 99.99% of leaders 
  • However, a hands-off-eye-off leadership style is also ineffective, as echoed by Ben Chestnut’s conversation on 20VC
  • Empower the team to think that it was their idea so they own it  
  • “There is a very fine line between leadership and manipulation.”Steven Sinofsky 
  • Empower your team, but don’t empower them to do stupid things
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Notes By Stan Rizzo

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