Microsoft's Ballmer on his biggest regret, the next CEO and more

Microsoft's Ballmer on his biggest regret, the next CEO and more

Summary: I had 15 minutes today to ask Microsoft's outgoing CEO Steve Ballmer a few questions. We talked his biggest regrets, his thinking on what's next and more. Here's Part 1.


It's been 20 years since I was allowed by Microsoft to interview Steve Ballmer. (Yeah, I don't know why, either.)


But today, the day Ballmer announced he'd be retiring within a year as Microsoft's CEO, I got my (most likely last) 15 minutes with Ballmer to interview him.

I asked the usual questions that most might. And I asked a couple of the thousands of questions I have saved up over the years, hoping against hope I'd be granted an audience with SteveB.

Here's what we talked about (from our transcript, which I've edited for length):

Q: What was today like for you? After all, you've been one of the most public faces of Microsoft since 1980.

Ballmer: Somebody said congratulations to me this morning, and I've got to say that surprised me, probably shouldn't. When you retire, it's a perfectly reasonable thing. But, of course, my mind's been all around this notion of it never really being perfect time. ...

So I guess it's congratulations. On the other hand, this is my life. I love Microsoft. I love everything about Microsoft. I own a lot of Microsoft stock. I'm going to continue to own a lot of Microsoft stock. But given that my personal plans wouldn't have had me here forever, this seemed like an appropriate time to me to move forward with retirement.

Q: You think this CEO search is going to take a year?

Ballmer: We've (with the board) have all been working together and the board wants to be able to look, and John (Thompson, the lead director on Microsoft's board) can talk about its needs, but a year is a nice long time. And if it winds up being less, but, you know, it just means that we can do things in a very planful and orderly fashion.

Q: When did you actually decide you were going to retire? Was this a sudden decision?

Ballmer: I would say for me, yeah, I've thought about it for a long time, but the timing became more clear to me over the course of the last few months.

You know, we worked hard. We worked hard on our strategy process, our org process. And frankly I had no time to think about it during all of that.... I would say my thinking has intensified really over the last couple, two, two and a half months, something like that.

Q: So when did you finally decide?

Ballmer: Officially, a day or two ago. We had a board call. When was that, two days ago? And it was really two days ago ... I would say that we really -- I finalized and we finalized that this was the right path forward.

Q: Did Chairman Bill Gates ask you to stay or go?

Ballmer: No. Bill -- I mean, no. Bill respects my decision. I mean, it's one of these things when if it's -- you know, ultimately these kinds of things have to be one's own personal decision.

Q: What's next for you now?

Ballmer: Frankly I don't know. I haven't spent a lot of time -- I don't have time to spend actually even thinking about what comes next. I'm not going to have time to do that until the board gets a successor in place.

My whole life has been about my family and about Microsoft. And I do relish the idea that I'll have another chapter, a chapter two, if you will, of my life where I'll get to sort of experience other sides of life, learn more about myself, all of that, but it's not like I leave with a specific plan in mind.

Q: Single biggest thing you are proud you did at Microsoft. You can just pick one:

Ballmer: I'm proud of being I would say a significant part even of the birth of intelligent personal computing, the notion that people use computing technologies, whether that's phones, PCs. I mean, we kind of birthed that over the course of the '80s and the '90s, and that's had such an unbelievable impact on people's lives. I would say a billion plus people and now more with phones, even if they're not all our phones, I'm very proud of what we've accomplished there.

If I had to sort of couple it, I'm very proud that we were able to make this incredible impact on the planet and at the same time do a good job for our shareholders.

Q: Your biggest regret?

Ballmer: Oh, you know, I've actually had a chance to make a lot of mistakes, and probably because, you know, people all want to focus in on period A, period B, but I would say probably the thing I regret most is the, what shall I call it, the loopedy-loo that we did that was sort of Longhorn to Vista. I would say that's probably the thing I regret most. And, you know, there are side effects of that when you tie up a big team to do something that doesn't prove out to be as valuable.

For more, check out Part 2 of my convo with Ballmer (and Thompson). We talk CEO succession planning, why Microsoft doesn't want to 'just' be an IBM and more.

More coverage:

Topics: Microsoft, The Year's Best Tech for Work and Play


Mary Jo has covered the tech industry for 30 years for a variety of publications and Web sites, and is a frequent guest on radio, TV and podcasts, speaking about all things Microsoft-related. She is the author of Microsoft 2.0: How Microsoft plans to stay relevant in the post-Gates era (John Wiley & Sons, 2008).

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  • Lot of internal pressure

    Only a guess but I imagine that some internal things were going on to kind of nudge Steve out.
    Microsoft as a stock has gone nowhere and I think much of that blame will go to the CEO. Some business news media seem to think that Microsoft needs new blood and not someone from inside Microsoft. It will be interesting to see what the board does. Microsoft has not so much been on the wrong paths. Just that they have fallen so far behind everyone else. I think Windows 8 was another case of rushing through a tablet ideal and nothing goes well when your playing catch up.
    • Windows 8 & Metro are NOT a mistake...

      While uptake has been slower than Microsoft may have liked, one can't really say that "Microsoft is falling behind in mobile" and then criticize the OS that actually pushes the envelope for what a mobile OS is.

      When you have a billion users, and then make drastic changes to it in order to compete in tomorrow's market... of course there are going to be growing pains. I'm sure Microsoft knew this before Windows 8 ever launched. Ballmer called it the "riskiest" thing Microsoft has ever done. But with great risks can come great rewards... and, I believe, over time, the "new Windows" will prove successful and the thing that saved the company from obscurity.
      • RE: Windows 8 & Metro are NOT a mistake...

        Agreed. There are always issues with growing pains. People are always resistant to change. Sometimes it just takes time for people to quit being idiots then learn to appreciate when companies try to innovate.
        Those who hunt Trolls
        • Windows 8 is very ambitious...

          Windows 8 is very ambitious... but it makes perfect sense from Microsoft's point of view. Their strength is the desktop, so it makes sense that they'd try to bring the power of the desktop to mobile. In the long run, I think the enterprise will get onboard with this vision, and that's when Windows will really gain some traction in tablets.

          I suspect that eventually (maybe for Windows 9) that RT will power Windows Phones, and that RT will lose "desktop" mode. It's pretty clear that Microsoft is headed in this direction. If they manage to pull it off, then they're actually ahead of Google & Apple.

          Only time will tell if Microsoft's strategy is the best one. Clearly, Apple's strategy is failing (if the measure is market share). Android is approaching 80% market share, and iOS is almost down to 10%. Meanwhile, Windows Phone is steadily clawing its way towards 10%.
      • No they're proof

        Microsoft refuses to listen to customers. "Metro" started with the zune, and the kin phones. Both were complete failures. Microsoft's top fools were so enraged they put that abomination of a UI on everything, no matter if it doesn't work.
        Troll Hunter J
  • >>the loopedy-loo

    I like it. :)
    Ram U
    • I like Windows Vista SP2

      in spite of its bloat.
      Rabid Howler Monkey
      • Vista wasn't a failure

        it was ahead of its time, but the major issue I think was MS HAL was not readily accepted by its partners and some of the interesting parts of Longhorn were either dissed out like WinFS or reduced to limited functionality like WCF, WF and WPF. In my opinion Microsoft shouldn't have released WPF first of all, they should've waited it to evolve internally, and should have worked on Silverlight+WPF issues. The HAL implementation was not ready for the requirements of WPF until Vista SP2.
        Ram U
      • Vista ran extremely well.

        Don't know why people complained about it.

        I like it less than 8, but more than 7, mainly due to its interface.

        Instead of icons, the taskbar had text, which is very useful when you're multitasking.
        • Windows 7 can too

          You can also have text on Windows 7 taskbar, go into taskbar properties and in the Taskbar Button dropdown select "Combine when taskbar is full". When an app is opened now the icon expands to show text and each copy of the app (i.e. two browser window) shows as separate icons until the taskbar is full.
        • Unix had that 20 years ago

          but no surpise
      • The problem with Vista was hardware...

        The problem with Vista was the hardware partners. They pushed/sold machines that weren't really capable of running Vista... which made Vista look bad. Similarly, they've been slow to release innovative, touch-based tablets/hybrids at the launch of Windows 8... and now they're paying the price.

        The PC market was bound to take a hit eventually because: (1) it's a mature market, (2) PCs last longer than they used to, and (3) fierce competition from phones & tablets. Even so, the OEMs could've mitigated their losses by creating "must-have" devices. They didn't... not at first, anyway. Hopefully that will change.
  • Good luck

    Enjoy your retirement and congratulations from me too.
  • Regret

    His biggest regret should have been that virus, Melissa.
  • His mistake

    I am not sure if I would say it was his mistake, but certainly, Microsoft's mistake was to underestimate the interconnectivity (which began with the consumerization of the Internet). In that sense, their biggest loss was to Google and not Apple. As some have posted above, MS can probably ride out Apple and other device manufacturers. But their weakness remains connectivity and all that goes with it - with a special focus on Search. Which is also why, if you notice, they have been frantically ramping up on their online services, which they are now trying hard to pair up with the devices - thus Skydrive, Office 365, the revamped Outlook webmail - and this is only on the consumer side of things. I am sure on the Enterprise front they are also working on connectivity, collaboration and other related stuff. Also notice their recent emphasis on Search, which they apparently plan to give prominence to when they release Win 8.1.
  • Excellent answer Steve Ballmer

    "the thing I regret most is the, what shall I call it, the loopedy-loo that we did that was sort of Longhorn to Vista. I would say that's probably the thing I regret most. And, you know, there are side effects of that when you tie up a big team to do something that doesn't prove out to be as valuable."

    Yes a thousand times. While Vista itself was a fine OS, it could have been a fine OS years earlier. Then those people could have been freed up to work on Windows 8 and I would have had my fantastic Surface RT tablet years earlier.

    "I'm proud of being I would say a significant part even of the birth of intelligent personal computing"

    Absolutely yes. People tend to forget that if the apples of the world had their way, there would not be any such thing as a personal computer for anyone but the very wealthy. Think about cutting the population of the Internet by 95% and how much benefit we would have lost as a civilization. Thanks to Microsoft, the inventor of the truly personal computer, we have greatly benefited, even if Microsoft hasn't always been the financial benefactor, as Steve Ballmer also wisely pointed out.

    The entire PC revolution is thanks to Microsoft.
    • I hated Vista

      But that probably had more to do with the fact that was my first 64 machine, at a time when 64 bit OS were just becoming popular on the desktop, and there were no drivers for anything... not the OS' fault really.
    • MS dream was (and is) the same as Apples.

      No systems but Windows.

      Unfortunately for both of them, computer technology was very widespread. MS just lucked out and got exclusive contracts with vendors to only include Windows. Apple was not directly affected as they made their own, but all the other software companies were.

      And it wasn't MS that made PCs. It was the manufacturers. And the inventor of the truly personal computer was Apple. Not MS. If you want to include anyone else, then it was IBM that made them popular - after all, it has always been the "IBM PC architecture". And the core faults also belong to IBM. Poor interrupt structure (only 15??? I was working systems that had more than that and were the equivalent processing power in 1975). Interrupt vectors limited to 15? The lowly PDP-11 had as many as you had device controllers (which would usually top out at about 80), and a 4 level hardware interrupt priority. Where the PC only has two - one non-maskable, the others are all multiplexed through the same wire (as decoded externally).

      Blame the hardware on IBM. NO problem there.

      MS is responsible for all the virus, worms, email, and the other security failures.
      • Nope, apple did not invent the personal computer

        apple simply copied many others in providing computers that cost at minimum thousands of dollars.

        It was Microsoft that realized personal computers should not be reserved only for the wealthy.

        Kudos Microsoft. Thanks for inventing the true PC.
        • Again Matt

          You're wrong. Just because you're a Microsoft MVP, and a member of Microsoft's möbius Mobile Evangelist club, does not give you license to lie, no matter how your Imam feels.
          Troll Hunter J