A few days after completing an insurance claim for my dog, who had knee surgery three weeks ago, I got the nicest email.
Subject: Checking on Birdie
Hi Sasha,
We were wondering how Birdie is recovering from her major leg surgery? We’re sorry to hear she had to go through that and send wishes for a quick recovery!
Please send a quick email letting us know how she’s feeling and give her a great big hug from us!
This pretty much blew me away. Not only did they reimburse me for the surgery, they actually care!
So, I replied. It’s been a stressful time, and I was touched that any company would even bother to ask.
Hi Leslie, it’s a big surgery but she’s coming along all right, thank you. 10 days in and she is walking with a limp and annoyed at her confinement!
And in reply I got:
Hello,
Thank you for your email. We’ll review your claims submission and contact you shortly.
Please visit us online for Frequently Asked Questions and answers about the policy at…
Cue the record scratching and the music stopping.
Here’s the thing: there is no such thing as “personal-ish,” it just doesn’t exist. There are two and only two paths:
The path of efficiency: in a modern, email-driven world, what we care about is a scaled approach that will work enough to hit the bar on our ROI calculations.
The path that’s personal: your experience matters to us. There’s no math to be done because I can’t calculate the value of trust on my spreadsheet.
Now, there’s an interesting question that emerges in the world we’re just entering. Soon, AI will be able to create an experience that feels personal but isn’t. It will walk and talk like trust-building at scale.
I don’t know how we’re going to manage through all of that.
How soon until we cross the uncanny valley, when we can no longer tell the difference between something that was programmed to act like it cares and human caring? My guess is that we will manage to give more people the experience of feeling trusted, and, when we see the wizard behind the curtain, the sense of betrayal and disappointment will be even larger, unless we are very, very transparent.
Regardless of how AI plays into all of this, if the last 30 years have been any indication, there will always be a space for personal—not in spite of its inefficiency but because of it. Raising the ante on trust, doing something surprisingly wonderful…these are the things that make you stand out.
And if you’re like the person at my pet insurance company who had the idea to make something personal, but then couldn’t line up the ducks to deliver that experience, your job isn’t to accept that something’s better than nothing.
Your job is to say “there are only two paths here, we have to pick one of them.”

On the bookends of this trip, I got to spend some time talking to Lily. Lily works at The Parking Spot at LaGuardia airport.










