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Agile optimism: Inside the mind of great growth leaders

Agile optimism doesn't turn on hope for a positive outcome but instead seeks new insights along the way to that outcome, writes Nick Tasler.

5 min read

LeadershipStrategy

agile optimism

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One early spring day in 2016, engineers at Microsoft unveiled a curve-jumping piece of technology. “Tay” was one of the world’s first AI-powered chatbots, and this big bet on AI represented many of the hopes and dreams for the future of the Redmond Giant. In the two years since Satya Nadella had taken the helm as CEO, optimism had been soaring hand-in-hand with the stock price. The lumbering giant finally seemed to have found its footing once again. Now, Tay would signal the beginning of a proud new era of growth and innovation.  

Then disaster struck. A few hours after Tay’s release on Twitter, internet trolls began bombarding Tay with sexist and racist remarks. Within a day, Tay churned out over 96,000 tweets that became increasingly offensive with every passing minute. The media lambasted Tay as a “failure” and a “humiliation.” At the company whose famous founder was notorious for telling his brightest people, “That’s the stupidest f*%#ing idea I’ve ever heard,” the future did not look bright for Tay’s creators. 

But Satya Nadella was not Bill Gates or Steve Ballmer. After Microsoft publicly accepted blame and apologized for Tay’s lewd remarks, Nadella wrote a personal message to Tay’s engineers, saying, “Keep pushing and know that I am with you.”  

Nadella leads with what I call “agile optimism.” There are two kinds of optimism: Agile optimism and fragile optimism. 

Fragile optimism is about expecting a positive outcome — to land that deal, win that race or hit a home run with this new product. 

Agile optimism is about expecting insights on the way to outcomes — pursuing this deal will open a door I didn’t see before; running that race will build important new muscles; launching this product will teach us invaluable lessons about what our customers really want. 

Fragile optimism works great in well-defined situations when there is a well-paved highway leading to your desired destination. It can make people feel empowered and excited for a while. 

But when you’re trying to do something new, like break into a new market, meet a new customer need or grow faster with fewer resources, the “road” is often little more than a barely noticeable strip of trampled grass winding between the trees. Believing that you or your team can accurately predict all the details on the road to your desired outcome without making any missteps ensures that it’s only a matter of time before your fragile optimism shatters into a thousand little pieces. 

Six months before Satya Nadella was handed the reins to Microsoft, I had the opportunity to speak to Microsoft’s global salesforce. I was told that Microsoft had become too defensive. Their salespeople had become “compliance cops,” policing companies that were using versions of Windows and Word without the proper license. Instead of finding creative ways to service customers, Microsoft’s people were looking for more efficient ways to sanction them.  

This problem was no secret to anyone, including the salesforce. This way of doing things had to change. And yet, it wasn’t changing. Why? As one leader told me in private, in a culture where outcomes are everything, “the risks to my career of trying something new far outweigh the reward.”  

In companies defined by fragile optimism, you’ll often find arrogance at the top and insecurity everywhere else. Everyone knows they are just one stray ball away from causing a crack in their boss’s expectations for perfection. 

After spending his entire career at Microsoft, nobody understood this dynamic better than Nadella. He knew that Microsoft didn’t have a talent problem. It had a mindset problem. Breaking through the company’s 14-year slump meant transforming its infamous Know-It-All culture into a Learn-It-All culture. In other words, Nadella had to change the way his leaders thought about change. 

So when the chatbot Tay “turned into a Nazi,” as one CBS News headline read, Nadella didn’t just see a public embarrassment and a shattered hope. He saw a trove of insights to be gleaned about how to help this infant technology of AI learn to walk and how to set a tone of agile optimism for Microsoft’s army of managers.  

At Nadella’s Microsoft, failures would still be failures. But they were to be expected and embraced as fodder for insights that would propel the company to exciting new heights. It’s no wonder that later that same year, Tay’s creators launched a new troll-resistant chatbot named Zo and have gone on to lead the way in AI.

The lesson for any leader wanting to foster agile optimism in their team is to make it clear that you will embrace the Tays on the way to every Zo.

Opinions expressed by SmartBrief contributors are their own.

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