If history is any guide, Microsoft (NASDAQ:MSFT) will probably choose the wrong person as its next CEO. Instead of seeking out a person with the skills to lead Microsoft into the future, the CEO search committee will likely be wasting time by trying to recreate the past.

They'll look for someone who is young, trendy, mobile-friendly, and charismatic. In other words, they'll be looking for the exact opposite of current chief, Steve Ballmer.

Back to the future
The Microsoft of old was led by Bill Gates the visionary and Steve Ballmer the operator. Together, they rode the wave of the personal computer to unbelievable success and riches. Once Gates stepped aside, Microsoft's former No. 2 struggled to create a clear vision for the company, and was often forced to play catch-up with smaller, more nimble competitors.

The obvious, if flawed, takeaway for anyone looking at that history is that Mr. Softy now needs to find itself a young visionary like Mark Zuckerberg to come in and run the show. Instead of playing catch-up, it's time to infuse the company with a start-up ethos. Or so it appears.

It's not you, it's me
Corporations are made up of and run by people, so it should come as no surprise that they fall victim to the same cognitive biases that ordinary individuals do.

What happens when a relationship goes bad? The next partner you seek out often has exactly the opposite personality and characteristics of the previous one. Sadly, this isn't always the most successful strategy in the world.

You don't need to look very far to find failed corporate marriages. How about J.C. Penney and Ron Johnson? Or Yahoo!, before Marissa Mayer?

With history as our guide, we can expect Microsoft and its activist investors to roll out the red carpet for a young, tech-savvy entrepreneur with a bold vision of the future. The vision will be strong on buzzwords and light on execution details. And for that, he or she will be paid a king's ransom, upfront.

Boring guys rule
Hopefully, my pessimistic prediction will not come to pass. What Microsoft really needs right now is a capital allocator. That's right, Microsoft's future relies completely on how well it can reinvest the $20 plus billion of free cash flow it generates each year. That's the key question the search committee should be focused on.

With any luck, Microsoft will learn from history and one of its old, familiar foes. Back in the 1990s, Microsoft was a young buck, taking on the tech titans of old and beating them senseless, at a different game than the old guard was accustomed to playing. The old, plodding companies just couldn't keep up. One old-guard player, IBM (NYSE:IBM), was in particularly rough shape in the early 1990s. But then a new leader arrived in 1993. His name was Louis Gerstner.

Gerstner was a consulting guy and, worst of all, lacked a bold vision of the future. In a meeting with Wall Street analysts he coined the phrase "logical incrementalism." The analysts, myopic and fearful of any uncertainty, panned his plan of attack and IBM's stock declined sharply.

But that's exactly the freedom IBM needed to reinvent itself and succeed in an uncertain future. While IBM wasn't (and isn't) considered a hot tech company by any stretch of the imagination, it has generated excellent returns for its shareholders. And that's exactly what Microsoft can do, too.

It's time for the board to step up to the plate and act in the best interests of long-term shareholders. They can take one step in the right direction by seeking out a great capital allocator without a bold vision for the future. For some companies -- at some points in their history -- the boring, operationally minded leader trumps the hip visionary. This is one of those times for Microsoft.

Buck Hartzell owns shares of Microsoft. The Motley Fool owns shares of International Business Machines and Microsoft. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.