The next CEO choice will say so much about the new Microsoft

I was stunned to get the news Ballmer had stepped down. Some will says forced but no one really knows. I think it was some external pressure since why now? He could have left some time ago on his own accord if it was simply a stepping down. The market cheered the news with a nice stock pop – I sold my MSFT a long time ago cause frankly I had given up on Ballmer. I know there are lots of people on twitter praising some portion of the Ballmer era – I won’t argue with it. I didn’t work at Microsoft and I have never met the guy but as a customer – Ballmer is one reason why I gave up both using anything from Microsoft, besides office (they screwed that up to), and why I didn’t care to be a developer of anything Microsoft. Steve had a bad habit of just saying too many dumb things. Who wants to be associated with a guy who says dumb things, puts down things that are winning and overall pretends to know what he is doing on all fronts. He doesn’t. It was this attitude that bugged me more than anything.

So some years ago – I won’t pinpoint a date. Steve should have stepped down or someone should have called for his head. Would this have fixed Microsoft? Hard to say since I think Microsoft’s problems are bigger than the CEO but changing the CEO can help to outwardly tell folks that things need changing. So whoever is picked next could signal big changes or more of the same. I don’t know if Microsoft should break up to win again – maybe there is no winning again. Choosing a new CEO who gets how the world works now, is slightly humbler and open to change – could create a better attitude across the board. Just look at Yahoo! for an example of how the fundamentals have not really changed but that a new CEO has created a new life in the company. Sure – Yahoo! has not turned around but it looks like it is has a better chance than it did before.

When I think about how I view Microsoft this tweet comes to mind:

Ouriel Ohayon (@OurielOhayon)
24/8/13 12:03 PM
ballmer. a wonderful enterprise CEO, a catastrophic consumer internet/mobile CEO

It sums up for me how on one hand Microsoft is able to print cash around some core businesses but yet fail to meet new markets. I think it is tough for anyone to say – hey how did Microsoft miss the iOS and Tablet evolution? Let’s be honest – not only Microsoft missed it. Google was the only one to stay in the game with Android. All of the phone guys missed it. It is not like one can just easily invent something to compete. Apple bowled one over on everyone. Windows – I won’t get into it but I think it is just a mess and it should have been redone some time ago to better compete. Win 8 does nothing for me but I guess it is enough to stay in the game but I don’t think it converts or wins over anyone new. My gut tells me that the desktop hold will keep weakening over time and Microsoft will have to find other ways to keep people in the fold. Bottom line is they missed some waves – tablets, mobile, purpose built OS’s and how to talk to a new type of developer.

What can Microsoft do now? I don’t know. I have a few ideas.

They should quickly cement Office as the productivity stack for everyone by making it work everywhere and cheaper. I see they are kind of doing it by they are not going full bore. Otherwise I could buy it on my iOS device outright with no funky hooks to other things within Microsoft.

They need to understand that the living room is still up for grabs but that constantly approaching it from a gaming angle isn’t the answer. I don’t play games. So I tend to never consider the Xbox and their recent Xbox release mess has only confused me more. Microsoft should strip out the hardcore stuff and ship a TV box with a hand gesture remote that works. Make it as simple as Apple TV but blow past Apple with a better UI, the open interface around all sort of media outlets, open up the billing system for all takers and work with a couple of different media backends for secure content. Meaning don’t force us to use shitty PlayReady – more on that later. The living room is so wide open – Microsoft should double down on it quick since Apple is moving too slow, Google scares everyone and the Smart TV guys are just well – dumb.

Micrsoft should keep pushing Azure – I haven’t used it but there is more room for other players here. However this is where they need to start beating Amazon with price, service and ease of use. For most of us AWS is good enough, is totally self-service and the prices keep getting better. I have had first hand experience working with trying to work with Azure and what I found is Microsoft still treats it like an enterprise sale. None of us want that – ever. That is the beauty with AWS – it’s self service. Enough.

Yes Microsoft must try to win in Mobile but I am not sure how. Windows Phone does nothing for me. They should have bought up Rim, Nokia and anyone else left before it got this bad. Then they could have cornered everything but iOS and Android trying to make sense out of a third messed up pillar. In lieu of doing that they still have a messed up third pillar but yet even smaller market share than if they hard forced the consolidation. I see no easy way for them in Mobile.

In the enterprise I assume Microsoft is doing well but I am sure over time it will slip cause the cloud providers, the other Mobile stacks, the other productivity stacks and the general open Internet will keep chipping away at the core of Microsoft and over time I think they will start lose in the Enterprise as well. Since the rest of the world is smaller companies and startups – none of us look to Microsoft for anything. Anything. Why would we? They belittle most of what we do use and they try to pretend that they are cool but offering hip services or by getting Gruber to praise their stuff. None of us are falling for it cause in some sense we just don’t feel cool using Microsoft. It’s just that simple.

However let’s pretend for a minute that there is something you wanted from them – I was in that situation of actually needing, or thought I needed, something from Microsoft. I actually had a pretty good contact in Seattle for the stuff I needed as well. So I emailed. Was told that based on my location I would need to talk to someone in BizDev in Japan. Okay. That took a few weeks to get nailed down. They only wanted calls versus email – this is typical of people stuck in the “enterprise” mode. Who has time for calls when you already asked the questions in email and most could have a simple answer? Cause in the “enterprise” mode all questions have more question versus answers. This is why self service always wins. So the Japan calls lead to calls in Singapore which lead to calls with Japan, Seattle and Singapore all at the same time which finally lead to complex pricing structures that changed based on the moon phases and time of day. This finally lead to lots of offers for using Azure, using a 3rd party and to using Microsoft directly. It took a few months to get the big picture which lead me to deciding to try and do it without Microsoft cause it was just too complicated. As developers the complicatedness should be in the problems we try to solve – not in the vendors we choose to work with.

So this is leading to an entire generation of developers and startups who have erased Microsoft from our tool belt which means down the road – Microsoft’s hold will continue to get weaker. I know they make a lot of money. I know the downfall won’t happen fast but it is already happening. Microsoft could optically change a lot of this by picking a CEO that matters to the rest of us.

Let’s see who gets the job. In the meantime I will keep not using Microsoft – apart from Office for now.