My letter to the Next Microsoft CEO (BusinessWeek)

BusinessWeek asked me to use my experience at to offer advice to the future CEO of Microsoft:

Recently, I spoke with 300 smart and passionate Microsoft (MSFT) employees. Are you as open to change as they are? If yes, read on. I was invited to your company because of my book, The Year Without Pants, which tells my story as a former Microsoft manager who worked for a year at the eighth most popular website in the U.S.:, which is more popular than any Microsoft website, including Bing. These two companies are very different, yet one is on the rise and one is not. As a unique traveler between both cultures, here’s my advice:

Read the full article here / read it as one page.

It was a hard article to write, given how much history I have with the company. They asked me to take an angle that focused on, which forced me to leave out many stories and insights that came simply from working there for a decade and seeing what’s happened since I left. If anyone’s interested, happy to share more thoughts, just ask.


5 Responses to “My letter to the Next Microsoft CEO (BusinessWeek)”

  1. Phil Simon

    Nice piece, Scott. I have a little experience in getting employees at Microsoft to think different. I was pitching an idea for my third book and I had a VP or one division or another say something about not having any money. That might have been true for her budget/department, but at the time the company had more than $40B in cash in its pillars.

    I got the distinct feeling that refrain was common. Different = bad. It’s no wonder that the company is struggling to the extent that is. I know one person, for instance, with a Windows’ phone. He’s a MS employee.

    1. Scott

      Different = bad is how most people everywhere look at things.

      There are many very talented people at Microsoft, the unavoidable problem is there are too many people in power: they have hundreds of executives now. This is a common problem for companies 30 or 40 years old that had amazing runs of insane growth and now have a different profile towards the future. Even if they all agreed big change was needed, they’d never agree on what the change was. Writing a memo is easy – actually changing a culture is very hard.

      Even a CEO has limitations to their power, balanced by the board of directors and the dozens of high profile executives the CEO has to manage. The politics are very complex and I understand that.

      Even back in 1998 they had a strong culture of consensus (despite outward appearances to the contrary). It’s hard to make bold or big changes with a consensus culture. Forget even for the moment what you or I think the right change is, that’s irrelevant if no one has the authority or willingness to make a big change at all. There is no way around the fact that big, mature companies develop conservative cultures, just like older people do.

      What’s fascinating is how critical we all are of companies like Microsoft, or IBM, or even HP – these companies are amazingly profitable. More profitable than most companies in the history of the universe (as most companies go out of business within a few years). Microsoft will make billions of dollars for years to come, as they’ve done so well at maximizing Windows, Office and few other businesses.

      For example: Facebook had about $4 billion in revenue last year. Microsoft earns several times that in a QUARTER. So does Oracle, and many other high tech companies often judged as too old to talk about much. It’s insane when you start looking at some of the numbers.

      The stock market is obsessed with growth and it warps our perspective on what a good company is, or what should be valued and why.

  2. Jean Hominal

    I would personally be interested in any insights and thoughts that you have about Microsoft. I suspect I would not be alone among the readers of this blog or elsewhere.

    Thank you in advance if you end up doing that.



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