Dennis Woodside, the Google exec chosen to rebuild Motorola after the Intrernet giant acquired the struggling company, is bolting his post for startup Dropbox. Will this hurt Lenovo as it prepares to take over the business in a $2.9 billion deal?

In a blog post announcing his departure last Thursday, Woodside said he would leave as of March 31 and that he was leaving Motorola “in great hands” of Jonathan Rosenberg, a “longtime Googler and SVP of Products from 2002 to 2011.”

It’s hard to believe, however, that Woodside’s departure could not have come at a worse time for either Lenovo or Google or Motorola Mobility. Lenovo shares were hammered since the deal was announced with many financial analysts questioning the wisdom of the deal. Chair and CEO Yang Yuanqing assured investors that the deal will pay off. Those assurances came the same day Woodside said he was bailing.

Lenovo already has a full plate, absorbing IBM’s troubled x86 server business. How can a potential management/transition challenge at a likewise troubled Motorola help?

Despite introduction of new smartphones, Motorola Mobility’s market share is declining – consistently and sharply. It’s losing major money. Now the company is being sold. And its CEO is quitting, How can that help employee morale with staff already worried about layoffs? 

Stability through a transition is always crucial. How many other executives will follow Woodside’s example and bolt?

Perhaps Woodside’s departure was already in the works before the Lenovo deal was announced. This quick a departure after the big deal was announced is suspicious. If not, then Lenovo has the right to ask: “Hey, what’s going on here? We bought more than phones and engineers. We also bought thought leadership.”

Motorola’s December Gaff

As The Verge noted:

“Woodside had actually been an executive at Google for years before taking the Motorola job, and made such an impression in Silicon Valley that Apple’s Tim Cook actually tried to hire him away from the company at one point. However, despite overseeing phones like the Moto X, Woodside was unable to jumpstart Motorola’s mobile business, which eventually lead to the Lenovo sale.”

Motorola Mobility committed a huge gaff in December as Woodside admitted in a blog: A promotion for new, custom-designed phones went off the tracks when customer demand overwhelmed and derailed the website set up to handle orders.

Woodside certainly gave no signs of wanting out when the Google-Lenovo deal was announced Jan. 29.

“Since being acquired by Google in 2012, Motorola has transformed itself, focusing on solving real consumer problems and providing amazing experiences built on a foundation of pure Android. The result has been Moto X, Moto G, and a reinvigorated Droid line. Together, these devices have won over consumers and critics alike and helped re-establish the Motorola brand around the world.

“Now, as we set our sights bringing the mobile Internet to the next 100 million people, Lenovo is the perfect partner to help us achieve that goal.”

Oops … 

For the record, here’s what Woodside wrote in the departure blog:

“Lenovo Will Bring It Scale …”

“This was not an easy decision to make, but I leave knowing that Motorola is in great hands – now and in the future.

“In the last 18 months, Motorolans have built two of the company’s best loved phones ever, introduced customization to the industry, brought unprecedented quality and performance to a value-priced smartphone, and created experiences that changed how people use and interact with their smartphones.

“It was a reinvention the likes of which many 85-year-old brands could not have achieved. And it was astonishing to be a part of.

“I’m excited about what the next chapter in Motorola’s storied history will bring under the new ownership of Lenovo. While Google imbued simplicity and software sensibility into the company, Lenovo will bring it the scale it deserves. I have no doubt the two companies together will be a force for good in the mobile industry

“To ensure that Motorola maintains its current momentum and successfully transitions to Lenovo ownership, Jonathan Rosenberg, a longtime Googler and SVP of Products from 2002 to 2011, will step in as COO at Motorola Mobility as of April 1. Jonathan worked very closely with me to build the leadership team at Motorola and has been intimately involved in steering business and product decisions alongside with the current leadership team. Google Chief Business Officer Nikesh Arora will remain Executive Chairman of the Motorola Operating Board, and continue to oversee the strategy.

“With their support, the entire Motorola management team remains focused on our current strategy and on creating great mobile devices that deliver the mobile Internet to millions more people around the world.

“That’s something we can all rally behind.”

We shall see.