Searching for Kindness on the Interwebs

From AI to personalized messages — how the tech industry is prioritizing and evangelizing kindness

Elizabeth Reese
Microsoft Design
4 min readAug 8, 2017

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The day before the 2016 U.S. presidential election, when tensions ran high, my husband of 3 months got into it on Facebook with the aunt of my first husband. After he ended the exchange (at my urgent request), she immediately messaged me, apologizing profusely, hoping that she hadn’t offended either him or me, and oh my, weren’t my boys getting big. I reassured her that no feelings had been hurt — that it was a stressful time. We both agreed it would be nice once the election was over and things could get back to normal.

I’ve thought a lot about this exchange in the past few months. It’s such a common occurrence, this condition of online outrage, something that’s only escalated since the 2016 election cycle. There’s a palpable mentality of us vs. them, a feeling of “other” when referencing people of a different political persuasion. It’s a sharp divide, sometimes even among like-minded friends, that breeds unkind words too easily.

So what can we do about it? Recently, I had the pleasure of attending the 2017 Design & Content Conference (D&CC) in Vancouver, BC, an experience that shone a light on the responsibility of tech and the media at large to address the nastiness we see all over the internet.

As a writing manager at Microsoft, it’s my job to think about how we (specifically Windows, Xbox, and Cortana) communicate with our customers, creating positive experiences with engaging designs and inviting language. As the media continues commenting on the stark divide between folks on opposite sides of the political spectrum — the rampant urge to stop listening and dump diatribes into the echo chamber of the Internet — it’s become our responsibility as a tech company to seek goodness and kindness in an increasingly unkind world.

Cortana is always kind.

I have peers who work tirelessly to create Cortana’s tangible personality, and one of her core principles is that she’s always kind (ask her what she thinks of Siri). You’ll recall the minor scandal during the brief life of Microsoft’s bot, Tay. A harmless research experiment gone wrong — brought down by the trolls and bullies of the Internet, who taught Tay in a matter of hours how to be hateful. This was a lesson in the need for ambassadors of kindness; like our Cortana writers.

Hanging out with a few of my colleagues on the Cortana team.

The talk that resonated with me most at D&CC came from Beth Dean, who spoke about Facebook’s efforts to imbue kindness into its interactions. Facebook’s problems are unique, complicated, and usually unintentional, in the same way Tay’s downfall was never intended. A grieving parent sees “memories” collected by Facebook featuring a deceased child. Mother’s Day reminders tear at the hearts of those without mothers. Your news feed shouts out the political diatribes of the day, every day, while your community adds to the stream of angry comments.

As software developers at any tech company become more skilled at using our data to customize and personalize our experiences on the web, we are in turn demanding a higher level of thoughtfulness from our interactions. Are we setting higher expectations from artificial entities because our interactions with people on the web have become more tense? From the venom spewed about immigrants in certain corners of the Internet to the threats leveled at two Republican Senators who disagreed with their leadership over the recent healthcare fights, it’s as though we’ve accepted this behavior as the new normal, and now turn to AI to give us the kindness that’s missing from our human interactions.

I don’t have any answers to this question. But amidst this disconnect that I struggle with — creating a positive, welcoming environment for Microsoft’s customers, while feeling as if I can’t expect the same courtesy from certain parts of the media, or in my political leaders — what I try to keep top of mind in all this is my aunt-in-law. We’ve had different political leanings since I married into the family when I was 22. But in the end, the only thing that ever really mattered was that she loved my first husband, who passed away 5 years ago, and now simply wants to know that his children are growing up into good men who will follow in their father’s footsteps. With her in mind, those on the opposite side of the political spectrum no longer are the “other.”

And maybe the reason that those of us in the tech field are focused now on ensuring that our creations reflect a kindness is to provide a proxy for my aunt-in-law. A techy reminder that if bots and other AIs can be courteous and careful of our feelings, we shouldn’t forget that it’s possible in our human-to-human interactions too. Whether you’re engaging with a bot, your social media audience, your political representatives, or your best friends, your words — and the humanity behind those words — matter more than ever.

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Elizabeth Reese
Microsoft Design

Content Experiences manager at Microsoft. Reader, writer, and small person activity scheduler. (All opinions and thoughts are my own.)