Episode 26: Steven Sinofsky at Microsoft – how to lead Windows and Office, what happened with Windows Vista , dealing with Bill Gates, competing with Apple and how to write really, really well.


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Sinofsky: There’s a very, very fine line between leadership and manipulation. You have to figure that out to be a great leader.

We have been excited about this guest for a long time- Steven Sinofsky. Steven was the president of the Windows division at Microsoft, both products used by billions of users. He is the author of one of the most popular Substack books – He also happens to be a dear friend and someone we have been thrilled to learn from for a long time. And he didn’t disappoint!

WATCH/LISTEN: You can listen to it on Spotify, Apple or watch it on Youtube (below). If you do, we would love a comment or rating! We also have some highlights below.


Show Notes and links (with timestamps)

03:30- How does Steven write so well
12:20 – Messaging apps vs email 
16:10 – Bill Gates and Steven’s memo and the history of internet at Microsoft 
37:00 – On open source software 
42:50 – Dominance and what could have Microsoft done differently? 
49:30 – Leading the Office team 
55:00 – Microsoft’s culture of being aggressive 
1:00:15 – Startups today vs Microsoft then 
1:04:50 – How to set the right culture for your startup 
1:09:00 – Windows Vista and the history 
1:21:00 – Steven taking over Windows 
1:29:00 – Mac vs PC ads by Apple 
1:31:30 – Shipping Windows 7 
1:39:30 – State of desktop and laptop computing 
1:44:50 – Are we at the end of smartphone innovation cycle? 
1:49:00 – Bill Gates as a leader and traits of a good leader 

Other Steven Sinofsky quotes

  • So you have to have a way of finding your ability to have the conversation with a team that tells them, in the framework I’ve laid out, this one sounds like a good idea. But with having them think that it was their idea, having them own that it was their idea and leading them to conclude that it’s the right thing to do and that they are accountable for doing it all

  • I’m Mac, I’m a PC- Those ads were, were brutal. Just what you would expect from Steve Jobs, they were completely in touch with how the world perceived PCs.

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