Microsoft is no spring chicken. Perhaps like you and me, it has been through the various stages of life, from a cool 20-year-old (Windows 95), an established mid-30s adult (Windows 7), and a 40-something in a midlife crisis (Windows 8: "I'm a desktop, I'm a tablet ... I don't know who I am anymore"). Now, we're looking at a mature, 50-something Microsoft that's growing comfortable in its own skin.
Like any self-confident, mature adult, Microsoft isn't afraid to push the envelope a bit, but it does so with more thought. You see that trend in Microsoft's cloud migration via Azure and Office 365, compelling but grounded products like the new Surface Book, and the ambitions of still-to-come products like HoloLens.
Some Microsoft initiatives may seem to be about capturing the cool, but they're really about driving toward the future with confidence.
If anyone embodies that new, mature confidence it's the company's new CEO, Satya Nadella. What you see from him and his Microsoft are stability, maturity, and experience.
At the same time, it's obvious Microsoft is also looking to remain relevant -- to resonate with the youth, too. The next generation of workers is mobile- and social-focused, practically born with a smartphone in their hands and an almost obsessive use of apps for messaging, photo sharing, and so on. They write with acronyms and emojis in 140-character spurts. Email, though not dead, is decidedly not "cool."
So Microsoft is looking to create an email/social blend with Outlook 2016 and Outlook on the Web. Recently, Microsoft announced the addition of likes and mentions built into Outlook on the Web. I'm a dinosaur, so I think this is stupid, but I'm also not in the generation Microsoft is trying to appeal to.
Even a dinosaur like me can see some utility in liking emails as a way to quickly vote. I work with a group of 20 people. When an email goes out to all 20 seeking suggestions, only five will respond. It sure would be good to know what those other 15 are thinking.
The mentions feature is a modern version of adding someone to the thread as a cc:, using the @name convention pioneered by Twitter and adopted in tools like Slack and HipChat. Where it differs from a cc: is that you can do so in context and sort messages by mention to ensure there was follow-up.
Add-ons to Outlook like Delve for card-style topical exploration and Sway to create videolike presentations also appeal to the newer generation's style and sensibilities.
Applications like Word, Excel, and PowerPoint are already bursting with features, and long ago reached the point of diminishing returns. It's better for Microsoft to look to new methods and create new applications for the new generation of enterprise workers; that's the wisdom you'd expect from a mature adult.
I'd almost say that 50-something Microsoft is trying to appeal to its grandkids, although it's really about creating a legacy for the next generation.
None of this forward thinking makes Microsoft cool again. Microsoft understands that being cool is a dumb goal given its history -- it would be like a 50-year-old man dying his hair and driving around in a 1969 Mustang. He thinks he's cool, but we think he's pathetic and hopeless. Instead, Microsoft is like that 50-year old undaunted by his graying hair who dresses smartly and drives a BMW.
Ironically, that makes Microsoft cool again to me.