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The downside of Zuckerberg’s exalted status within his company is that it is difficult for him to get genuine, unexpurgated feedback. He has tried, at times, to puncture his own bubble. In 2013, as a New Year’s resolution, he pledged to meet someone new, outside Facebook, every day. In 2017, he travelled to more than thirty states on a “listening tour” that he hoped would better acquaint him with the outside world. David Plouffe, President Obama’s former campaign manager, who is now the head of policy and advocacy at the Chan Zuckerberg Initiative, the family’s philanthropic investment company, attended some events on the tour. He told me, “When a politician goes to one of those, it’s an hour, and they’re talking for fifty of those minutes. He would talk for, like, five, and just ask questions.”

But the exercise came off as stilted and tone-deaf. Zuckerberg travelled with a professional photographer, who documented him feeding a calf in Wisconsin, ordering barbecue, and working on an assembly line at a Ford plant in Michigan. Online, people joked that the photos made him look like an extraterrestrial exploring the human race for the first time. A former Facebook executive who was involved in the tour told a friend, “No one wanted to tell Mark, and no one did tell Mark, that this really looks just dumb.”

There seem to be three communication gaps outlined here in Evan Osnos’s revealing profile of Mark Zuckerberg: one is getting unvarnished feedback from your employees. Speaking as a fellow CEO and founder, it’s certainly hard to pop that bubble — see “the bear is sticky with honey.” There are a few techniques like skip-level 1:1 meetings, anonymous feedback forms, interviewing new hires, and 360 reviews you can do to try to counter this, but there’s no panacea and this one requires constant work as you scale.

The second gap is getting the unvarnished truth from your users — much easier, as they’re quite happy to tell you what’s what. I’ve recently started cold-calling (yes, on the phone!) some of our Jetpack customers just to understand what they love and don’t love about the experience and about how we can help them solve their business challenges. There’s a casual intimacy to phone conversations that just can’t be replicated in other user feedback forums. Pair this with good instrumentation throughout your product so you see what people do and not just what they say and you’re golden.

The third and last communication gap is the connection to the world as most people experience it. If your status, wealth, or celebrity reach a point that they are shutting you out from “real” experiences, take some risks and get outside of your comfort zone. As it turns out, this new GQ profile of Paul McCartney offered a tip on that:

McCartney tells me a further such story of a time he took the Hampton Jitney, the slightly upmarket bus service that runs from the Hamptons into Manhattan, because he was deep into Charles Dickens’s Nicholas Nickleby and he wanted to finish it, and how he then took a local bus uptown, and when a woman blurted from across the bus, “Hey! Are you Paul McCartney?” he invited her to sit next to him and chatted all the way uptown. “It’s a way of not worrying about your fame,” he says. “It’s a way of not turning into the reclusive rock star. I often say to Nancy: I get in their faces before they get a chance to get in mine.”

Makes me wonder if Jack Dorsey still rides the bus to work every day. I think this is what Zuckerberg was attempting with his 30-state tour, and hopefully it was helpful even if the optics didn’t appeal to everyone — the daily habit of his 2013 resolution to meet someone new every day feels more powerful than the touristic 30-state one. But for an entity as large as Facebook maybe it’s moot, as Casey Newton pointed out in his newsletter last week it can be quite hard to pin the answers to Facebook’s real problems, and our democracy’s real challenges in the face of targeted online propaganda, to just one person.