September 19, 2013, 1:22 PM — Microsoft will host financial analysts on Thursday for an afternoon of executive presentations and question-and-answer sessions. Here are four uncomfortable issues CEO Steve Ballmer and his lieutenants should address when they face the Wall Street crowd at the Meydenbauer Convention Center in Bellevue, Washington:
-- Will Ballmer's successor be expected to toe the line and execute on the exiting CEO's vision and strategy, or will the replacement get some leeway to rethink the current plans?
A sweeping and controversial corporate reorganization plan was one of Ballmer's last major moves before announcing he would retire at some undisclosed point in the coming year. While the wheels are already turning on the implementation of the changes, it's very possible Ballmer will be gone before the process is complete.
Since Ballmer's reorganization has the blessing of the board, one would assume that the incoming CEO will be told to carry it out without major revisions. However, the reorganization plan hasn't exactly prompted a consensus endorsement from outside observers. After all, it seeks to unify the company even more than it is today, mesh all of its parts and make sure that, for example, the Xbox team is aware of and has input into what the SQL Server team is doing, and vice versa. Ballmer calls this the "One Microsoft" vision.
The problem here is that many believe that's the wrong direction to take in order to fix Microsoft's problems and make it more agile when innovating and responding to market opportunities. This camp thinks it would be better to infuse more autonomy into the company and possibly even spin off some of its parts, because the product lines have become too diverse to be contained in the same corporate bottle.
-- What does Microsoft plan to do from a product perspective if Windows 8.1 and the second-generation Surface tablets fail to ignite enthusiasm?
Windows 8 and the Surface tablet were not a hit and that is a big problem for Microsoft, which is rushing out a major update for the OS due in mid-October and is also working on a second generation for the Surface tablets.
Windows 8.1 is expected to address the main complaints lobbed at its predecessor, whose radically redesigned Modern user interface freaked out many consumers and IT pros. Likewise, the new Surfaces -- both the RT and Pro models -- are supposed to be faster, more battery efficient and all around better.
However, it's not entirely a sure thing that Windows 8.1 and the Surface 2 tablets will be able to undo the damage, in which case Microsoft's tablet problems remains: Windows and the company will still be chasing on foot the runaway train of tablet sales that Apple and Android vendors have been riding to the bank for several years.