Our perspective

Return-to-Office: How Stripe Manages Remote & Hybrid Work and Culture

Sadasia McCutchen
27 Jul 2021
stripe user operations team

Our most recent conversation in part 3 of our Return-to-Office series is about best practices and technology enablement for hybrid work environments. With so many companies facing new configurations for employees and work planning, it’s vital to put the right tools and programs together with fresh thinking about productivity and an evolving work culture.

Need to catch up on the RTO series? Here’s part 1 and part 2.

Our guest for this session was Jay Shirley, Head of Tech Enablement and Remote Hub Site Lead at Stripe. Jay has worked remotely for 15 years and managed teams at Stripe for the past six years, including growing the company’s Seattle office. Attendees included leaders from Crowdstrike, Dataiku, Everlaw, Lyft, MX, Newfold Digital, and Strive Health.

Here are the central themes from our conversation, with Jay’s commentary.

Design meetings to be more participatory.

The last year-plus gives us all a good reason to break out of old routines and question why we stick to familiar patterns that may not work well anymore, Jay said. One routine that’s ripe for change is the design of meetings. As he put it, “Being intentional about meetings is like the secret sauce to effective remote strategy.” He recommended preparing agendas and any background reading ahead of time to make everyone in the meeting fully engaged and intentional. “When you don’t give people an agenda and pre-reads, you’re incentivizing good improv skills — but not good judgment- and problem-solving skills, because people need time to think through and do stuff ahead of time.”

Another key to meeting hygiene: everyone should understand what recurring meetings are for, and eliminate those that aren’t effective. Jay advised that each recurring meeting have a page, on an intranet or other shared workspace, describing its purpose, and naming the agenda-setter for each session. As he suggested, “You can’t have a recurring meeting without somebody owning the meeting and being responsible for the quality.” Ideally, make meeting quality (and ownership) part of performance reviews, because “nobody likes to be in bad meetings, but very rarely do people feel like they have their name attached to the quality.” That doesn’t mean that one person has to facilitate each session; there may be a rotation. But whomever designs it, he emphasized, “it has to have a purpose.” Further, if you institute a simple way for attendees to score each meeting, you encourage quality, and reward those who produce good meetings. “You can say, ‘this meeting is a three out of five.’ Not every meeting has to be five out of five, but just giving a score could be helpful.”

Make sure there’s a protocol for group decision-making — and that everyone knows what it is.

Perhaps we’ve all been blindsided by an internal decision we didn’t see coming, or one that seemed to switch our course. In a world where not everyone is in a physical room together, it’s vital that everyone understand the rules of decision-making. An additional benefit of having pre-announced meeting agendas is that the group knows whether a decision is needed. Jay noted that if instead you require a decision from an unprepared group, chances are “somebody who’s very confident and good at speaking extemporaneously are going to be the ones that drive that decision — but there are other people, if you give them 24 hours to sit and percolate, they’re going to come up with the better quality decision.”

In a distributed meeting where people are scattered between phones, meeting rooms and webcams, you can avoid another decision-making pitfall: making decisions after the meeting is over. In an office as people leave the meeting, Jay said, there’s a certain amount of talk on the way back to your desks, and maybe some “alterations” to the decision emerge. “But everybody who wasn’t walking with you are caught by surprise, and the people who were remote were completely excluded from that,” Jay pointed out. Here having webcam/phone booth meetings can actually prevent some of that happening — “either force the meeting quality to be better, or if there’s follow-up discussion to build some kind of catch when you do that.”

Help teams collaborate better with the right tools and creative hacks.

Jay has discovered a great hack for making project work with remote teams more effective: limit the timezone spread. He observed that it’s easy to say, “Hey, we’re remote, we can hire for anywhere.” But once you go beyond four time zones, he said, it’s probably not worth it. “I’ve worked with engineers over in Europe, and it’s really hard to get them to fit nicely with American time zones,” he said, “and 40 hours is pretty much the ideal spread, because you get enough time where people will be having real-time interaction.” He added that in-person working sessions are great, ”but don’t overlook real-time collaboration, whether it’s over code and pairing sessions or design doc edit sessions. That real-time collaboration does really build trust.” Just watch your timezone spread!

A good bit of our conversation was about collaboration tools for both meetings and individual productivity. Jay reported he’s a big fan of shared Google Docs for meetings. Using the comment feature, for example, encourages individual input ahead of a meeting. He reminded the group to be sure someone is in charge of accounting for the comments and subsequent decisions that arise from the meeting prep work.

Establish new ways to create connection and community, especially for remote teams.

A big question in our pandemic era is how to avoid “Zoom fatigue” and other symptoms of weariness around remote working and connecting. Jay advised varying your video call protocols to shake things up; for broadcast meetings, as an example, everyone but the speaker turns their camera off. Or for live events, provide pre-recorded content that’s enjoyable instead of standard business visuals — just explore different approaches and see what the effects are.

Similarly, social-only meetings and social elements to regular meetings can help lift spirits and limit always-on fatigue. At Stripe, Jay reported, one practice they have for remote meetings is Question of the Day. “We just tag a random person to ask a question” to help everyone learn about something new. Another tactic is asking everyone to post a photo of a favorite thing (example: from your neighborhood) as a pre-meeting slide show. Even that simple task “can get people connected,” Jay said. Although being in-office with snacks is nice to have, “really what we want is a place for innovation and collaboration that you wouldn’t expect. You have to make people collide with a little bit more focus.” Another gambit for cross-team (or all company) meetings is what Jay calls contextual trivia, featuring stories or quiz questions about the early days, product specifics, or even crazy incident reports. “When you bring those things, you get somebody who is good at storytelling, and it pulls people together,” he said.

For remote socializing, Stripe runs monthly events using multiplayer drawing games like Skribbl or Drawasaurus. It’s an hour without a lot of prep, and you see that people are carving out time for this. He also recommends trying remote events, such as cooking classes, or using audio only, which taps different ways “so that people don’t have to show up live all the time.”

Jay reminded the group that when possible, there’s no replacement for in-person gatherings, even if they are infrequent. They can help seal connections between people — but only if you provide time for socializing and big-picture thinking, not task work. One of Jay’s favorite group questions is “what are your favorite parts of this team?” followed by “Okay, how does that go wrong?” When a very senior engineer admitted that what went “wrong” was his own over-collaboration, the group coined the word “clobberation” — where somebody’s so excited to partner that they just take over all the work. That exchange formed a bond.

Learn to be attentive to remote employees, and honor work limits.

With so many people not gathering in person — or even having met their colleagues — managers must become attuned to the working and communicating styles, as well as the participation and productivity, of their team members. It’s too easy, especially in larger groups, for individuals not to be noticed, and for managers not to make an extra effort. Jay has found that 30–35 people is where the inattention can take root. He advised that managers make sure to go through their roster to really assess each person’s well-being. With his team, he notes how much (or little) they engage on their company’s public Slack channels, for example, in advance of asking, “How are you doing? How are you holding up?”

Keeping track of who engages or appears on videocalls is not enough, either. Jay emphasized that managers must understand whether a “lack of signal” from a remote colleague might be due to concentration — or might be trouble focusing. “Everybody’s a little bit different,” Jay said. He himself works in 90-minute spurts before taking a break. “In an office, you could look over and say hey, how’s it going, are you stuck on anything?” But absent everyone being together, he said, it’s about “developing that muscle to ask those types of very explicit questions about work style that seem kind of too small to really care about — but with the lack of a signal, you’re going to need that knowledge.”

Jay recommends building in ‘focus hours’ so that employees know they can have uninterrupted periods that reflect their own work flow. It’s especially important for remote workers to know they’re not obligated to take on more tasks from a different time zone: “If you’re remote, it’s easy for that boundary to just get fuzzy so people just work around the clock. It really erodes that deep thought time.”

Encourage people to build their personal networks across the company.

Establishing new connections across the company should become an ongoing personal OKR. Jay’s own goal: talking to four people each week who he doesn’t normally encounter, and he encourages the people on his team to do the same. And it should be purposeful, to tie to work in some way, because that is what makes for a functional network. As he described it, “Forward-looking accountability works really well for this, especially for remote workers. ‘What are you going to do this week? You’re going to talk to two people.’ The accountability loop is about following up.

Consider establishing and maintaining an OKR-style system to keep everyone going.

Having shared understanding of what you (individual and team) are working toward helps everyone — and everything — move forward. Especially as companies grow, being able to document goals and milestones consistently helps new hires acclimate and get on the same page with old-timers. Jay has found that more companies encourage newcomers to prepare for meeting project leads by pre-reading, and even contributing comments to, existing documentation. For example, he said, “Before you can talk to a [senior] person you need to read these. So people can avoid having uninformed one-on-one meetings by first reading the docs, and that has become a cultural norm.”

Beyond documentation, an understanding of shared goals is a key to success. Jay observed that without them, “it’s really easy to get stuck in our own heads. You ask a couple of people what they think our top three priorities are, and you will get vastly different answers.” He firmly believes that having OKRs is the right tool to help that. “The key thing from the top all the way down the ranks, is do you see the goals being reflected? Can anybody anywhere in the company see how they fit into the goals?”

Understanding the shared goals helps you know where you are deviating, and why that might matter. As Jay put it, “It’s really good for somebody to think, ‘I am doing something completely on my own. I know it’s not a priority but I’m making that bet,” versus “I thought this was a priority — and now you’re telling me that it isn’t. You moved the goalposts on me.” He noted that OKRs can especially benefit remote workers, “because it’s harder for people who are remote to look up at their leaders and say, ‘Do you know what we’re doing?’”

Jay also noted that an OKR process does not require anything more elaborate than shared Google Docs, or Slack Ally, or another widely accessible internal tool. “I really hate when we reach for technology to fix what is really a behavioral gap,” he said. At Stripe, the internal intranet rule is that everybody needs to have their goals or OKRs linked. “Nobody gets to say, “I couldn’t find them for this team.” He keeps a spreadsheet that updates from a script that continuously pulls everyone’s goals and progress in. He or the CTO can nudge those who have not responded. The main idea is to be looking at goals and outcomes all the time, not just during performance evaluation season. A regular cadence of assessment and adjustment keeps everyone on board whether they are in office or remote.

Tech enablement is another way of saying “keep things simple.”

In closing, Jay mused aloud: “Perhaps we don’t need more technology, we just need better technology” — easy for everyone to use, and therefore more equitable. He also believes in the power of technology to make processes and systems fairer. “When you’re relying on serendipity or coincidence or charisma, you are excluding people.” Even when urgency is required, don’t sacrifice input for speed. Just take a beat, he advised: “are all the right people [aware and aligned]? You can get input via Slack, or time-limit comments in Google Docs. These collaborative tools work well because people don’t feel they’re as left out; they always have an opportunity.

Enabling technology to help all employees stay focused, productive and authentic has perhaps never been more important for companies to get right. We’ll continue to look at trends and best practices in this critical area.

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