Jack Dorsey: Twitter CEO, Square CEO . . . and possible CIO role model?

If Jack Dorsey can find the time to innovate while running not one but two high-profile companies, it’s going become harder for CIOs to suggest they can’t do the same.

Of course, there is a difference between leading an IT department and overseeing something like Twitter, where Dorsey was confirmed as permanent CEO on Monday, or Square, his mobile payments startup. Yet Dorsey’s triumphant Twitter story arch — to co-founder to ousted leader and back again — is instructive for CIOs who want to better understand how to navigate the challenges of corporate politics.

Time rewards managers who are willing to keep learning: Dorsey’s first tour of duty as Twitter’s CEO is not generally considered successful. As detailed in profiles at Vanity Fair and elsewhere, Dorsey was either aloof, inscrutable and generally unable to really loyalty or the best efforts of those who surrounded him. That’s all changed now, with hashtags like #IdworkforJack cropping up on Twitter. Re/Code, which got the scoop on Dorsey’s appointment as CEO, does a great job of detailing the faults he’s shown in the past and how he’s worked to overcome many, if not all of them. CIOs who lack the so-called “soft” skills they need should take hope.

It’s all about UX: Twitter may not be the most diversified organization in terms of what it offers and sources of revenue, but many experts have suggested Dorsey’s reputation as a “product guy” makes him the ideal candidate to turn the social media company’s fortunes around. The Telegraph recently showed a picture of Jack’s initial sketch of the Twitter interface, and it’s interesting to see how much it holds true today, yet makes room for so much more. For CIOs, technology is usually more something that either allows the product to be created or helps market and sell it. It could be argued, though, that today any company’s digital presence represents a part of its brand and is therefore a product, too. Channel your inner Dorsey if you want to thrive.

True leadership is treating everything as a work in progress: CIOs are often accused of doggedly sticking with IT initiatives that are doomed to fail, and unwilling to shift course even when there’s still time. Dorsey has proven he is willing to question everything. As CNBC reported, he killed off Square Wallet when it was proving ineffective as a competitor to PayPal and similar products. Even Twitter’s legendary 140-character limit is reportedly being reconsidered. Such changes can be painful, but they’re also sometimes the only sure way to grow and improve.

The biggest question, of course, is how can one person do justice to both Square and Twitter and not become completely torn at the seams? ABC News suggests it’s a combination of relentless scheduling and choosing “themes” for various days. CIOs might want to treat Dorsey as a kind of case study, thinking of his dual CEO duties in light of how they’re tasked with meeting business expectations while managing the demands of IT infrastructure. If you really think such things can’t be done, then maybe you don’t know Jack.

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Jim Love, Chief Content Officer, IT World Canada

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Shane Schick
Shane Schickhttp://shaneschick.com
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