How I work: Slack’s Steve Wood on establishing rapport with a virtual team

All professionals—direct reports, managers and even VPs—know the importance of building out an internal network in the early days of a new job.

Usually you develop those relationships by building trust in person, where you can go for coffee together, shoot the breeze over lunch, and get a feel for someone’s sense of humor in those in-between moments before and after a physical meeting. But for many people who have started new jobs over the past year, those types of chance meetings simply haven’t been an option.

That was certainly the case for Steve Wood, who joined Slack in June 2020 as our VP of Product, Developer Platform. Previously, most interviews—and later onboarding—would have happened in the office. But because Slack has committed to a remote-first approach amid the current public health crisis and beyond, that was no longer an option.

Today, Wood leads a team of 35 that is tasked with making all of the tools we rely on each day work better—by integrating them with Slack. We sat down together (digitally, of course) and asked him to look back at what it was like to step into a VP role without the benefit of meeting a single teammate in person.

The words that follow are Steve’s, as told to Slack HQ.

Lesson 1: Leverage collective intelligence

I rapidly realized how much you rely on being able to see each other in the physical world to help you manage trust and communication in the digital world. Those casual elevator conversations where you start to get to know each other—all of that just completely disappeared. We tried to do the typical Ask Me Anything, but for me, it continued to feel unnatural.

The team did a great job of pulling together everything, so I had a ton of reading to do. It kept the meeting volumes down. They literally gave me a download. And it was enormously helpful to be able to scroll up through Slack and go backward in time and see what decisions had been made before I arrived.

Often in business, you remake a lot of decisions. In the past, people would say, “Yeah, we’ve discussed that before,” but now I can actually see where it was discussed, and I can rely back on those conversations. I can learn, contextually, how we ended up in a place. Previously, I’d have to have the team take me through it all over again and educate me on why something was a dumb idea.

Lesson 2: Let social connection flow

We’ve made it a point to let conversations unfold naturally in our video conferences. I know that a lot of people are like: “Run the meeting. Here’s the agenda. Get it done, get through it.” But we no longer have that downtime. If a casual conversation emerges during a structured time, so be it. If that means we have to organize another meeting to talk about the thing we’re supposed to be talking about, then that’s OK. This isn’t about wasting time, but rather building trust.

It’ll be interesting—when everybody finally does get together in the future—to see the reorientation of, “OK, you’re not a head in a box!” Because people’s actual physical demeanor does affect how you perceive people, and you don’t see that on Zoom.

Lesson 3: Embrace what you do and don’t know

One way I tried to build trust was asynchronous video. The idea was to be present in a way that I couldn’t do one-on-one at scale. And this isn’t to sound like a therapist, but candidly, I tried to be a little more vulnerable and human by saying, “Actually, I don’t know as much as you think.”

I wanted to raise questions, and putting those in an asynchronous video and getting people to reply—or at least be a little more open—was a great way to change posture and be a little less of “the big boss.” Not that I was huge into that to begin with! But by asking people to help me understand, I got feedback along the lines of, “Oh, OK. He’s all right.”

Another thing I did early on was build an app, and I shared it with everybody in the platform group. That may sound like a trivial thing. But it helped show my team: I can code. I’m trying to build a deep understanding. Rather than just doing PowerPoints, I want to get really deep into the product itself.

Lesson 4: Do away with meeting hierarchy

I’ve built a number of startups where we had remote and distributed people. It’s always been something that’s worked for me. We weren’t 100% distributed; we would meet and get together. When I was at Boomi, my engineering group was largely in Pennsylvania, and I was based out of San Francisco. I would Zoom into a meeting, but I’d be the talking head onscreen, and they’d all be in the boardroom.

As soon as we all went remote, everyone’s contribution spiked dramatically. The amount of discussion went up because people were all leveled, regardless of location. Now, everyone is accessing each other through the same technology and has the same constraints around them. They can contribute on the same level.

When you’re in person, it’s easy to grab a couple of people and into a room to quickly brainstorm. In those situations, the first thought isn’t, “Let’s conference in the remote people.” So here, we’re trying to build much stronger personal connections with people by eliminating some of that hierarchy.

Lesson 5: The definition of performance isn’t fixed

Understanding the nature of performance in this environment has been challenging. Particularly in product, we don’t have as many of the easy levers to pull on performance, because a lot of product is the impact of your influence on the organization: your leadership and your ability to align people. You can sense it. You know when it’s happening, but it’s hard to literally put a check mark next to it.

I don’t think we’ve been in an environment where the stresses inside and outside work have been quite so dramatic on people. There’s no benchmark for this. It’s like: “OK, aside from a difficult political situation, a difficult cultural situation, a difficult financial situation and a difficult environmental situation, let’s talk about performance.” Spouses are losing jobs. The children are at home. Loved ones are sick. People are experiencing financial hardship. It’s tough for leaders to understand what being a high performing team means, and tough to know how to support one!

What is a realistic expectation of somebody, in terms of the stress that they should be under versus the stresses that you have to pull off them somehow? Some of these things are quite private, and people don’t always feel comfortable talking about them. That’s where that personal connection has been more valuable—where people understand that they’re talking to a human, as opposed to just their boss.

This is part of what led us to a place where we’ve become more flexible with working hours. In the office, even before this, the culture has always been: “Work hard and go home.”