I’m not surprised to see that Jon and Grant are leaving Microsoft, though I don’t know that this constitutes “wrath” on the part of Terry Myerson. More on that in another post. Now just a few comments on Jon and Grant.
I interacted with Jon a little in his time in Online Services and then we worked together extensively (on Quests) when he was running the Core OS group during Windows 7. Steven Sinofsky got the public credit for how good Windows 7 is, but most of the improvement that you see (over Vista) is because of Jon. The quality improvements, the focus on improving memory usage and boot time, bringing the relationship with OEMs on OS support back from the dead, etc. are Jon. Even the Service Pack work that made Vista usable is Jon. I’ve rarely found executives in our industry that were as devoted to producing great software as Jon.
I can’t recall if Jon was a VP when I joined Microsoft, but if not he became one soon thereafter. It seemed like all of his peer executives left Microsoft long ago, and ever since the online services days I wondered if Jon would “retire” after completing a particular project. This was especially true after Windows 7 and then Windows 8, but in each case it appears there was another big thing that interested him enough to continue on. So I’m not surprised that a reorg that left him searching for something that would make staying at Microsoft worthwhile would lead to his leaving. Or, was it some indication from Jon that he wanted to leave part of the trigger for Terry’s reorg decisions? We may never know.
I never worked with Grant though we met back in the 90s when we were teammates as part of one of Microsoft’s leadership development offsites. Grant lead the two largest and most critical test organizations in his career at Microsoft, and the results were obvious to any observer. The quality of Office and then Window 7 and 8/8.1 were outstanding. With my limited visibility I’d say Microsoft has lost a great test leader. But it is also clear that having lead the organizations he did there were likely no roles of similar scope available in the current org structure.
With the departure of Jon and Grant Microsoft has lost a significant portion of its senior leadership talent. This may be a natural part of the evolution of the company, but that doesn’t make it any less sad. I wish them both well in their future endeavors.
Hal's (Im)Perfect Vision 
I wonder if the stock price has anything to do with these decisions. Now that MSFT is trading in the high 30’s, are these folks deciding it’s time to cash out their stock and move on to other endeavors? Personally, after I’d saved a decent amount of money, I’d love to teach or do something different to end my ‘career.’ Also, leaving now is a decision. After the new CEO takes over, it will look more like being forced out.
I doubt it. Both of them, and particularly Jon, would have made the bulk of their money years ago when Microsoft did options rather than stock grants. Recent price movements might have slightly influenced their timing decision. There is also a possibility they received an exit package offer that expired at the end of the year and they decided to take it rather than risk an appropriate opportunity not appearing and leaving without the package.
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As a junior MSFT watcher its always difficult to tell whether theses changes will ultimately hurt or help the platform. The loss of institutional sources like DeVaan and George could be a serious issue for Windows especially with Threshold coming. But the situation could also lead to new voices that could bring new changes that can be positive long term.
Well, both good and bad. But in truth Windows gained back institutional memory into the Windows team with recent moves.