The answer to that question is crucial to the health of the struggling tech giant and the revitalization of the company's stock. A series of missteps - not the least of which was Microsoft's failure to recognize the mobile revolution until it was too late - had left the stock languishing for more than a decade.
And while Microsoft stock is up more than 40% in 2013, that climb was stifled over the summer by numerous downgrades.
With the company at a crossroads, whoever becomes the next Microsoft CEO will need to possess the ability to shake the tech giant out of its doldrums so it can better compete with the likes of Apple Inc. (Nasdaq: AAPL) and Google Inc. (Nasdaq: GOOG).
Not that it will be easy. The next Microsoft CEO would only be the third person to hold this position in the firm's 38-year history.
Microsoft's situation calls for one of two leader types: a turnaround expert capable of changing the culture and focusing on business development, or a technology visionary capable of guiding the firm in a rapidly changing world.
So far, the Redmond, Wash.-based company has cut down the list of potential candidates from 40 to "about five."
As talk on the Street continues to heats up over who that will be, I had a chance to speak with Money Morning Defense & Technology Specialist Michael A. Robinson about the narrowing list of candidates.
Robinson says there is one person with the turnaround experience and leadership knowledge to lead the software giant into the next decade.
And that person is going to need every ounce of experience and wisdom to rejuvenate this tired tech titan...
Challenges Facing the Next Microsoft CEO
The truth is, Microsoft is desperate for change.
Ballmer's looming departure has fueled negative views about the company's future. And it's deeply affecting business decisions.
Concerns about a CEO transition has factored into company downgrades by a number of Wall Street analysts, including Bank of America Merrill Lynch and UBS. Numerous reports suggest the company won't even make final decisions on major capital investments until it selects its next CEO.
But this is a short-term problem. It's the long-term transition to new consumer markets - primarily the red-hot domain of smartphones and tablets - that poses the greatest challenge to Microsoft and is delaying the search.
"The big question for MSFT is how to go mobile," Robinson told me. "Android and iOS pretty much own the market."
Robinson argues that the company has finally got mobile right. But now it's a question of implementation...
About the Author
Garrett Baldwin is a globally recognized research economist, financial writer, and consultant with degrees from Northwestern, Johns Hopkins, Purdue, and Indiana University. He is a seasoned financial and political risk analyst, with a focus on stocks, hedge funds, private equity, blockchain, and housing policy. He has conducted risk assessment projects for clients in 27 countries, and consulted on policy and financial operations for some of the nation's largest financial institutions, including a $1.5 trillion credit fund, a $43 billion credit and auto loan giant, as well as two of the largest Wall Street banks by assets under management.
Garrett joined Money Map Press as an economist and researcher in 2011, specializing in alternative strategies with an emphasis on fundamental and technical analysis.