Why I Let My Employees (Literally) 'Ask Me Anything'

Originally published at Forbes.com on November 23, 2016.

Former President Barack Obama broke with convention back in 2012 when he agreed to do an Ask Me Anything — AMA — on the Internet forum Reddit. Since then, AMAs have gone from an obscure online ritual to a rite of passage: everyone from Apple’s Steve Wozniak to Elon Musk has signed up to respond to crowdsourced questions, live, while the Internet watches.

But if you think it takes guts to expose yourself to a half hour of inquiries from strangers on the web, try fielding regular sessions of no-holds-barred questions from your own employees — live and on camera. Welcome to our normal routine: the internal AMA.

My company, Shopify, a commerce platform for retailers, has been riffing on Reddit’s idea since our early days. While facing questions from my team is tough when I’m in the hot seat, it’s become a crucial tool for building trust as we’ve scaled from hundreds to more than a thousand employees. Here’s how and why this technique works:

Anatomy of an AMA

A lot of businesses claim to have a culture of transparency without realizing it’s a two-way street. You might regularly blast out quarterly reports and other updates in a mass email, but unless your team has the chance to respond to that information, or clarify what exactly it means for them, it’s a meaningless action. Internal AMAs are a streamlined mechanism that lets us do that in simple, repeatable steps. Here’s our not-so-secret formula:

• Staff submit questions through an online forum — anonymously if they want. There are lots of free, no-nonsense tools out there that enable employees to do this, from Facebook Workplace to Google Forms — no special technical skill required.
• Our entire team then votes on which questions are the most relevant (just like Reddit’s system of upvoting and downvoting). This lets us know which questions are high on people’s minds. I’ve found time and time again that the top five questions absolutely reflect the prevailing mood and paramount concerns of the company. There’s really no faster way to get a feel for the zeitgeist.
• At least once a month a member of our executive team then answers the top 15 or 20 questions. This happens during our regular town hall meetings, which are streamed in real time to all our offices and online to every employee.
• The most important part: No cherry-picking or skirting the issue is allowed! A live moderator asks the questions — we don’t see them in advance — and holds us to account. In other words, this isn’t some carefully choreographed corporate show: The goal is to make it as raw, honest — and even sometimes uncomfortable — as possible.

The Payoff

Do I ever end up squirming up there? Sure. There are plenty of times when I’ve been caught entirely off-guard. But that’s precisely the point. The element of surprise is the secret ingredient that makes the internal AMA such a valuable tool. Here’s the big payoff for us:

• A pressure-release valve: A key advantage of internal AMAs is that they offer an early-notice system for simmering issues. For example, after we learned we’d be going public in 2015, I was stoked to share the news with our team. But subsequent AMAs showed not everyone shared the enthusiasm of the executive team. The questions I got reflected anxiety about what the move would mean for company culture, how it would impact day-to-day duties, even confusion about what it means to be a public company in the first place. When your company scales beyond a certain size, it’s easy to lose touch with what’s relevant for people at different levels of your organization. In this sense, the AMA is a powerful way to collapse corporate hierarchies and ensure that all perspectives — not just those from the top — are heard.
• Vulnerability doesn’t need to be a weakness: As the top-down decision-making of yesterday goes by the wayside, it’s important that leaders aren’t afraid to be vulnerable in front of their teams. There have been lots of times I’ve had to admit I don’t have all the answers, and I’ve learned that that’s OK. Part of the unexpected beauty of the internal AMA is it shows my imperfections and limitations. You might be thinking that this hardly sounds like a payoff. But contrary to popular belief, exposing your vulnerability doesn’t need to be a weakness. When I get up to field questions, I’m showing my team that I’m really willing to listen to them: that their feedback is valuable and their experience matters just as much as mine. It’s truly one of the most important things I do in my job. Too many companies still have an us vs. them mentality between senior management and the rest of the team. The AMA is an occasion to show we’re all in it together, facing problems and figuring out solutions as one.

Creating a culture where it’s safe to ask literally anything can lead to some awkward moments, but just taking that step helps instill a sense of ownership at every level. Sitting in that hot seat might make you sweat, but that just means you’re doing it right.