One way Pinterest aims to keep its 5,265 full-time employees both informed and engaged is through one-hour sessions where they can ask executives whatever they want.
Pinterest uses a platform called Slido, which allows employees to post questions and upvote the ones they want business leaders to answer at the company’s next gathering, which they call an AMA (ask me anything) session.
“Whichever questions have the most likes is what ultimately goes in those AMAs,” said Ali Colangelo, director of executive communications at Pinterest.
The submission window opens soon after the previous sessions ends, giving employees time to post questions as soon as they think of them. The window closes about a week prior to the AMA session, giving execs time to prep their answers and make sure the right people are available to address specific questions only they can.
Why does Pinterest let tough questions rise publicly?
Questions range from inquiries about specific benefits to the rise of AI to deeper dives into earnings reports to rumors, such as when some speculated OpenAI would acquire Pinterest.
“It could literally be anything,” said Colangelo. “It’s just a matter of what gets the most upvotes.”
Because the Slido platform is public, where every employee can see the questions and which ones are growing in popularity, Pinterest can’t filter out the tough or controversial ones.
Colangelo noted that while employees are not always going to be happy with the responses, Pinterest isn’t an organization that shies away from hard questions.
“Bill Ready, our CEO, wants to answer them,” said Colangelo. “He is somebody who wants to address it head on. He knows that not answering them will build up more challenges and sensitivities.”
Each AMA session generally addresses 10 questions. The total questions submitted on Slido, however, can range from 20-50, according to Colangelo. It all depends on what’s happening and what’s top-of-mind for employees.
An internal moderator, usually someone at the VP level, relays the questions to the executives, often adding context and their own perspective to what’s been asked and why it matters.
“Our best moderators are those who read the questions, but also add their own color,” said Colangelo.
Although some questions are answered on the spot, others require some follow-ups and additional attention.
“Comms is obviously monitoring and taking notes during these, so if there is something that we think a follow through needs to be made on, we’ll follow up,” said Colangelo.
How do in-person AMAs support a remote-first workforce?
While all Pinterest AMAs are live-streamed and recorded for staff around the world, the company makes a point of doing them in person at one of its 24 global offices whenever possible. When business leaders are travelling for work and client meetings, the team aims to carve out time for them to visit a nearby office to show up for their local team.
Pinterest also remains a remote-first company, meaning working at the office is fully optional. Having an in-person event, such as an executive AMA, is a good reason to bring everyone together. It’s something out of the ordinary that also makes leadership feel more accessible to everyone.
Colangelo described it as an opportunity to maximize executives’ time on the ground when visiting different locations.
The sessions have proven to be popular. While they’ve been around for years, their cadence has increased from about one per quarter, as part of an all-hands meeting, to twice per quarter — one standalone AMA session, plus another baked into a quarterly all-hands meeting.
“Given the overwhelmingly positive response and the fact that questions were coming in so frequently, we upped the ante and we started doing them more frequently,” said Colangelo.
Some business leaders have even started doing their own breakout groups that follow a similar format. Pinterest’s Chief People Officer Doniel Sutton, for example, did her own session in New York last week. Since joining Pinterest from Amazon earlier this year, Chief Marketing Officer Claudine Cheever has hosted her own small-group discussions.
“I think we are very lucky at Pinterest, where our C-suite just gets the value of comms,” said Colangelo. “Some C-suites are not as bought in; ours is.”
