Struggling to Thrive as a Large Team Working Remotely? This Exec Has the Field Guide You Need, as seen on FirstRound

April 3, 2020

With a few weeks of social distancing and remote work under their belts, many teams and companies now face a bigger challenge: Can they thrive while telecommuting indefinitely? NerdWallet VP of Content Maggie Leung says they can — if they adapt, learn and iterate.

As she’s shared on the Review before, Leung has encountered every kind of management challenge in her career as an executive and news editor, sharpening her tools for tackling sticky situations. But for this particular hurdle we all face, she’s an especially helpful guide to turn to. That’s because over the past six years, Leung’s built out the large team charged with crafting the personal finance coverage that has helped her company stand out — and they’ve been fully remote from the very beginning.

“I joined NerdWallet when we were still early-stage. I needed the best talent and I knew they wouldn’t all move to the Bay Area,” she says. That doesn’t mean Leung was some kind of remote work crusader, though. “I’d seen it done badly. My husband is an engineer and I’d seen his mediocre work-from-home experiences. I also had managed or worked with many distributed teams at places like CNN or The Wall Street Journal and there were a fair share of bumps in the road,” says Leung, who spent nearly 20 years in the news world before joining NerdWallet in late 2013. “But I knew that it was possible to do much better and set out to reverse a lot of suboptimal things I’d seen. And we kept iterating as our team expanded — we grew to about 30 in year one, to 60 in year two, reaching 100 people at our peak. Now we’re about 80 full-timers all across the country.”

Her content team was also in the unique position of being the only remote team at NerdWallet for years. “Many of the remote guidelines and practices that we started on our team have since spread to other teams at NerdWallet,” Leung says. “That doesn’t mean that everything transfers, but it’s always good to take a look at what others have done. Don’t reinvent the wheel when you don’t need to.”

In that spirit of sharing and making sure others don’t have to start from scratch, Leung sat down with us to pass along tactical tips and key takeaways from leading a large remote team. From mistakes that are easy to make and lessons she wished she’d learned sooner, to the team-building tactics and leadership techniques that have paid off, Leung shares a practical playbook for founders and executives in these unprecedented times.

Remote work doesn’t require any special sauce. It’s about having high intent as a leader and then pushing your team to relentlessly — and consistently — take small steps toward your North Star, trusting them all along the way.

MEETING THE MOMENT: START OFF BY RECOGNIZING THIS ISN’T BUSINESS AS USUAL

“Telecommuting can work really well. We have six years of metrics on throughput, morale, engagement, talent retention and business results to prove that across our large content team,” says Leung. “But a lot of people are struggling with working remotely right now because they had to switch overnight without any prep. And there’s the stress of a worldwide pandemic on top of that. So my first pointer is that no one should judge the merits of remote work based on these kinds of conditions.”

Even with all its experience, her team is in the exact same boat. “To be fully transparent, our team has excelled at telecommuting for six years and we’re still facing significant challenges now,” says Leung. “We have people suddenly at home with young kids or trying to help college-age kids who are stranded or struggling. Folks are worried about how to help loved ones who are immunocompromised, or who are dealing with loved ones losing their jobs. All those things impact humans, so they impact our team, no matter how long or how well we’ve been working remotely.”

With this important caveat in place, Leung addresses remote work detractors more generally. “When people say that telecommuting isn’t as efficient or as effective as working co-located, it’s probably because they don’t know how to do it well, not because it’s not doable. The thing is, it’s all learnable if people want to learn it. And I’d say it’s important to learn. Even before coronavirus, I’ve always felt that knowing how to manage well remotely was a competitive advantage,” she says.

“But now it's becoming all the more clear that remote skills will be table stakes for managers who want to win and retain top talent. So despite all the hardships with this mass plunge into remote work, I’d encourage managers to view this as an opportunity to learn new skills or to prove themselves. That extends to individual contributors who want to work more autonomously or remotely even after the world returns to ‘normal.’”

There are no silver bullets. Strong remote teams are built on building trust and communicating consistently and effectively. There are many ways to get there — even if you have a team that’s in the deep end struggling to work well now.

“One of the biggest risks at times like this — when there’s a lot of change or uncertainty — is for leaders to pretend to have certainty or all the answers. That can lead to inflexibility. You choose cookie-cutter solutions or attempt quick fixes that don’t evolve as circumstances change,” says Leung.

“For instance, it’s not possible to make blanket declarations about how we can support people at this time. Even among people with children, that can vary widely. A single parent with young children will face different struggles from dual-parent households with high school-age children. And while some parents are overwhelmed by having their kids home all the time now, at the other end of the spectrum, others who live alone or those who have existing mental health issues might need a different sort of support.”

In her experience, it’s important for leaders to put in the leg work to identify what their teams need to thrive. “Who’s introverted or extroverted? Who needs more guidance, check-ins or emotional support? Who thrives on autonomy? Whom do you pair up for best results? What are the best opportunities for each individual to shine? How much scheduling flexibility can you afford or productivity can you trade off, depending on their personal circumstances now? Such answers are driven by who’s on your team, not just by what you wish for or need as a leader,” she says.

Cookie-cutter won’t work. It’s knowing your team members’ personalities, priorities and motivations that will help you bring out the best in them in remote work.

To get into the nitty-gritty details of how to do just that, Leung shares a series of six tactical takeaways that have helped her level up as a leader of a large remote team:

1. Create space for conversations — and try to cultivate that “we’re all in this together” feeling.

The first line-item on the newly-minted remote leader’s checklist is to make sure you’re spending enough time listening to your team and their individual concerns. “All the managers on our team normally keep an eye on morale and challenges, but that’s especially acute now, with so much turmoil going on around the world,” says Leung. “You don't want to end up with people feeling isolated or burnt out. If they’re feeling trapped or losing their sense of support, that can easily show up in their work, in how they interact with others, in their health — and none of that is good for individuals, teams or managers.”

To address this, Leung recommends creating space for such conversations. “You can do it 1:1 or in small groups if your team is large and has different needs,” she says. Here are a few specific ideas:

  • Pass around a survey link or online sticky note link and ask everyone to anonymously write down three adjectives for how they’re feeling, right then and there. Gather the results and read them out loud to show how everyone is feeling similarly. “One of the worst things is when you’re struggling alone,” Leung says. “You can also use interactive tools that let you create word clouds that reflect your team’s current mood or concerns.”
  • Break your team or company into separate Zoom breakout rooms or Slack channels to discuss specific challenges. “Parents could pool ideas. Or you could do a virtual panel or brown bag, with parents who’ve successfully worked at home for years sharing tips and strategies, mistakes they learned from and things they’d do differently,” she says.
  • It’s also helpful to nudge others to bring up topics and challenges in meetings or Slack channels. “Sometimes, if someone raises an issue with me during a 1:1, I’ll ask whether they’d be comfortable sharing it on a Slack channel to help other teammates who might be grappling with similar challenges,” says Leung.

“As leaders, it’s easy to forget that folks on our teams often default to thinking they are the only ones who are nervous or anxious. So whatever tactics you use — and the possibilities are endless — the key is to get people comfortable with talking to both managers and teammates. Then people can empathize and share ideas about how to deal. And managers can better target their efforts to help.”

You have to anticipate and try to calibrate emotions as much as workload. FOMO, anxiety and isolation are all things managers must take into consideration if remote teams are going to perform sustainably over months or years.

2. Invest in relationships and set a cultural North Star.

It’s especially easy for remote relationships to fall into a trap of cutting the small talk and getting straight down to business. “That creates an unnecessary ceiling for the team and the company. Managers can never help bring out the best in people if they don’t get to know them as individuals. People with stronger relationships tend to be more willing to be candid, to give each other the benefit of the doubt and offer goodwill, and to help even when things go wrong. And people rarely run through walls for transactional leaders,” says Leung. “Strong relationships also help with remote retention, which saves the costs and churn of unnecessary turnover.”

Relationships, a willingness to communicate and flexibility are huge sources of strength right now. No matter what comes up, teams that nurture those elements have a better shot at figuring things out.

On Leung’s team, there are a number of people who’ve never met in person. Yet many say they feel closer to their virtual teammates than many people they used to work with in person elsewhere. “Before this era of social distancing, many folks on our team went out of their way to meet up with their colleagues while on vacation, which is of course entirely voluntary,” she says. “That’s because they’ve grown close while working together. I’ve found you can get to know and trust each other online just as well (or even better) than in person if you build the right expectations and culture on your teams.”

For Leung, this isn’t a happy accident in remote work adventures, but rather the result of years of intentional effort. Here are two specific tactics that have been helpful in this arena:

  • To work on that benefit of the doubt muscle: “Assumptions of negative intent — that someone doesn't care or is being obstructionist — are especially risky for any remote worker to have. That’s because they tend to skew your interactions, behaviors and approaches, which can impact how professional you appear or cause situations to spiral out of control quickly,” says Leung. “Remind yourself that we usually know facts, not intent. Ask direct, open-ended, nonjudgmental questions. It’s often helpful to do discovery by asking someone to ‘Please help me understand X.’ If you think you know someone’s intent, check yourself by asking whether that’s the only possibility or whether there might be other good or benign ones. If you can brainstorm even just a couple of potential options, there’s a decent chance you were wrong.”
  • To set expectations: On Leung’s team, the North Star for a healthy culture includes her entire team working toward a set of expectations for cultural norms and deliverables. (Take a look at the chart below.) “When it comes to working remotely, messaging expectations for deliverables is important, but that’s only half of the equation. It’s just as important to consistently message and reinforce work norms — how you all treat one another and behave,” she says. “On remote teams, you can’t observe signals in person and you have fewer interactions than you might in an office. Without a cultural North Star, everyone on your team ends up setting a variety of expectations on their own. Not only will some of those conflict with each other, it’s unlikely you’ll end up with the culture you want as a leader.” You can also extend this ethos to future teammates if you’re continuing with remote hiring. On NerdWallet’s content team, a boiled-down version of its North Star values are included in a deck that they share with finalist job candidates. “We start messaging our expectations before they even join us,” says Leung.

3. Fight fires with candor.

Candor and directness are vital for any thriving team, but they’re often overlooked when working remotely. “Don’t wait for fires to catch, because with telecommuting, they might reach the full-blown conflagration stage before you even realize it. If you’re worried about something or something’s bugging you, say so,” says Leung.

Nuance and tone can be easily misread or overlooked, so hoping that someone will eventually pick up on what you wish for — either as a manager or an individual contributor — isn’t a winning strategy. “If someone isn’t forthcoming enough, I call it out,” she says. “As an example, I’ll often say: ‘I’m having a hard time understanding how you’re prioritizing or approaching X. Can you please walk me through your thinking?’ Or, 'I can’t read how you’re feeling or what you’re thinking. Please give me more to work with here.' You can push persistently and still be collegial about it. Don't get judgmental, because that can create a chilling effect. But don’t miss those opportunities to ask.”

It’s important to stick with facts and do your own detective work as you hear about issues. “I once caught wind that a couple of cross-functional partners were finding it frustrating to work with a leader on my team. So I talked to those people directly to get their perspective,” says Leung.

“During a regular 1:1 meeting, I brought up the issue with the leader in question and asked him what he thought was going on. We peeled it back, and I walked him through what I thought was going off track. It turns out he wasn’t communicating at the right level. He was super tactical, and his emails and other communications could be read as off-tone, especially if someone didn’t normally work with him and already know that he’s company first,” she says.

“That was important to surface and fix, because he works remotely permanently and will constantly be working with different teams and new hires. For that person, it was important to show right off the bat that his intent was to help deliver for the company — that he wasn’t trying to be obstructionist by raising issues — a key step he’d been missing. Sometimes you just need to be explicit, like saying, ‘I get what you’re trying to accomplish here and I want to help you succeed. I have some suggestions on how I can do that (or, I have concerns).’”

4. Shine a spotlight on what good looks like.

Leung has also noticed that managers of remote teams tend to miss opportunities to elevate role models or highlight strong examples of best practices or key wins. “It’s not just that someone did well, it’s the explanation of how they did it that often goes missing on remote teams. If you’re only calling out those people by name and not asking them to share their approach, problem-solving chops, challenges and failures with your team, you’re leaving money on the table,” she says. “Make all the ‘experts’ or sources of help on your team as visible as possible.”

Leung’s team constantly pools know-how by sharing problems and solutions. Tactically, they have a #shoutout channel on Slack where they can call out examples of people who live the company values teamwide. They’ve also instituted a bimonthly initiative called “What Good Looks Like.”

Here’s an example of this practice in action: “We routinely make decisions about new initiatives and prefer to keep those decisions localized, so higher managers don’t become micromanagers or bottleneckers. But for a certain type of initiative, we were seeing inconsistent approaches that were creating unnecessary work and wear and tear. So an individual contributor on our team proposed producing a decision tree to help his pod and others make decisions faster and more consistently,” says Leung.

“He quarterbacked by getting input and buy-in from a few others on our team. Once he was done, he rolled it across our entire 80-person team. He was living one of our company values, to act like an owner. So we called out his accomplishment, had him walk our team through how he thought through the problem, worked to get different perspectives and launched it. And we explicitly tell team members that that’s the kind of initiative we value. That’s especially important for new hires to see, because it helps to set expectations. We want everyone to see beyond job descriptions.”

There’s no limit to what your team can do — even remotely — if they know they’re empowered to think and act like owners.

5. Connect the dots, relentlessly.

This is one Leung recommends underlining and returning to, especially for remote teams. “It’s a realization I wish I had a lot sooner. When you telecommute, it’s much easier for information to become siloed, for team members to have missed certain meetings because they’re in different time zones or are off working on other initiatives,” she says.

Here’s how she recommends translating your work as a leader and connecting those dots virtually:

  • Share the “why” and "how" constantly. Showing how you think strategically or problem-solve helps your team members build stronger judgment and deal with greater complexity on their own. “That would give you leverage as a leader under any circumstances, but it’s particularly important when you’re managing remotely. You’re not going to be there for most of what they’re doing,” Leung says. “You’re not always going to be available for a consult. And you shouldn’t be. Managers who make themselves indispensable turn themselves into bottlenecks or crutches.” Leung consistently practices this with her large team, explaining not only decisions or strategies, but also the “why” behind them. “I almost always write those kinds of things down and share them as widely as relevant in a combo of Slack channels, email and internal wiki pages. We have a huge, robust wiki that we constantly use across our team. We’re relentless about keeping it updated,” she says. “That’s because with a large remote team, you want everyone to have access to the same info if relevant, and you want it to scale — that way even with new hires, you can share stuff you’ve previously written. We also record most of our team meetings and training sessions, so people can catch up if they missed one, or if they’re new hires.”
  • Create touchpoints — more than you might think you need. “You might be surprised on how much you’ve come to rely on the ‘Swing by my desk’ or ‘Let’s grab a conference room to catch up,’ methods in the office. If someone is tackling an initiative they’re not familiar with, you can schedule early checkpoints, say even one early in the thinking or planning phase so that you can check for alignment or gaps,” Leung says. “Sometimes it can be as easy as saying on Slack: ‘Please let me know how you’re thinking about the first (or next) steps. You can grab 10 minutes by phone or Zoom, or just Slack if it’s relatively straightforward.’”

6. Don’t unintentionally undermine your team.

It’s crucial for managers to share information consistently — and avoid doling it out randomly. “Information is power,” says Leung. “If you share it in ways that look like you're playing favorites, you’re telling the rest of your team that they can’t be fully recognized on merit alone; they have to win some kind of popularity contest with you.”

This is even more important than on co-located teams, because when working remotely, everyone’s insecurities can loom larger. "You have fewer signals to read so you can't tell where you stand. Managers who don’t realize this can unintentionally create divisions, unhealthy competition or jealousy on their remote teams."

With this in mind, guidance for new hires on Leung’s team includes this section:

There are cases when information isn't shared widely for business reasons. When there's no such reason, info is shared teamwide. If you see instances when key information wasn't widely shared and aren't clear why, please ask. This is part of our culture for specific reasons:

  • It's hard to feel invested if you think information is being shared selectively and you lack info that might help you do your work more effectively.
  • You've invested part of your future in this company. You deserve to know how we're doing.
  • We scale more effectively if we keep sharing information and avoid creating pockets of best practices and other info.

TROUBLESHOOTING TEAMS: HANDLING ISSUES REMOTELY

Of course, with even all the best practices in place and good intentions in the world, performance issues and thorny team challenges will still rear their heads virtually. “Problems crop up all the time, so you want to have shared resources whenever reasonable. If you have processes, make sure you document them so they’re self-serve,” says Leung.

“It’s better to think through different challenges you might encounter as a leader right now so you’re not caught flat-footed when they come to pass. Consider the scenarios that scare you, whether it’s the first tough performance review you’ll have to deliver or the first person you’ll have to let go remotely. Think about the issues or questions your middle managers might face if you have a large team. If you have a problem emerge and think it might repeat, spread word so you can limit that on your team or among cross-functional partners.”

Expect issues to come up and have consistent hygiene for dealing with them. “Winging it” keeps remote teams from working at scale.

Here, Leung outlines three specific sticky situations she’s encountered as a remote executive:

1. People who aren't working well remotely.

When hiring remotely, you need to flex (a perhaps newfound) muscle for sussing out someone's ability to do the job virtually. “You want to ask about initiatives they drove, how they managed time, how much guidance they needed, how self-starting they are, how they got buy-in from various stakeholders and took into account different perspectives,” says Leung. “You want to assess how well someone communicates and builds trust or handles friction or problems. That’s because thriving while working remotely requires hard and soft skills over and above what’s needed in an office setting.”

Her team screens for this when they hire, Leung says, but obviously you might not have had the opportunity to test remote skills before your team was plunged into a new setting. “You can turn things around together. Ultimately, you might have to reset expectations and norms, but you can do it transparently and humanely,” Leung says. One thing she urges managers to avoid: If you’re worried about underperformers or slackers on your team, don’t send mass messages or lay down the law in a team meeting. “You’ll only alienate team members who’ve been doing the right thing. If you have problems with individuals, talk to them individually,” she says.

For example, if an individual has been performing well and is now struggling to thrive remotely, it’s important to take into consideration the stresses that everyone is facing generally because of new restrictions and challenges. “Don’t forget to do your discovery. If someone is now not delivering or seems troubled, you want to ask open-ended questions to get them talking. Hopefully, you’ve been nurturing trust all along, so you can have those types of conversations,” says Leung.

If not, you can still open the door. “You can say, ‘I notice that you don’t seem like yourself. We’re all struggling with different scenarios with everything that’s happening. For example, I’m seeing X, Y and Z on our team. How does that compare to what you’re facing?’” Leung suggests. “It’s a nonjudgmental question that’s more likely to get people talking. And if they’re not forthcoming, keep pushing as needed, persistently but collegially. You can even say something like, ‘It worries me that I don’t know how to help you.'"

2. Teams that were already struggling before the shift to remote work.

Even managers with inherited teams or uneven performers have the opportunity to turn things around. “If things haven’t been going well even in the office before the coronavirus outbreak, teams now have a chance to be honest with one another and to call for a ‘reset,’” says Leung. “You could say, ‘Look, we all know we were struggling with X, Y and Z before we suddenly switched to social distancing and working from home. We have a chance to turn things around, to come up with new approaches that will work for us all. As a manager, this is what I’m worried about…’”

Leaders have a chance to be honest and direct like they never have before. If you can’t bond when things are tough, you’re missing an opportunity.

“On the individual level, if I had a poor performer, I’d try to incentivize them to want to improve by clearly signaling that they have a chance now to help turn things around. In a virtual 1:1, I might say something like: ‘I’m worried, because I need to trust you to handle X, but I don’t have the confidence that it will necessarily go well. Can you help me come up with ideas for how we can make things work?’ But no one’s going to believe you if it’s all BS — if they lean in, you actually need to recognize those efforts. Even if their first attempts aren’t strong, make sure that you acknowledge the intent and the effort. That’s the only way to get them to the next stage of progress if they don’t already trust you,” Leung says.

You can be explicit about the challenges of managing remotely as well, framing things positively, of course. “If I were nervous about a particular direct report working remotely because I couldn’t keep as close of tabs, I might ask for suggestions on how they can make their contributions more visible, so I can better recognize them,” says Leung. “For example, one of my early hires would send me bullets by email to recap her progress at a regular cadence.”

It’s key for managers to strike the right tone here. “You need visibility and it’s okay to say that as a manager. Just remember that you don’t want your idea of visibility to feel oppressive or demoralizing,” she says. "You can even say, ‘I need to know what’s going on, but I don’t want to smother you. Please help me come up with ideas on how we can make that work.’"

In an office setting, you might be able to dance around issues by making check-ins seem more casual or avoiding them altogether. If you work remotely, you have limited interactions, so make them count.

3. Middle managers who aren’t delivering:

With large remote teams, Leung notes it’s especially important to have strong middle managers. That’s because it’s unlikely that most individual contributors will interact with the top layer of leadership frequently. “Most of their daily work life — good or bad — is shaped by their direct managers,” she says.

For Leung, this was a lesson learned the hard way. “I wished I’d known how to better coach other managers sooner. I learned on my own, so I didn’t have a coaching or training pattern to model off,” she says. “Looking back, I would’ve done it more systematically and saved my team time and individuals wear and tear.”

When I look back across my career, my regrets all focus on people on my team who were mismanaged by managers whom I should’ve trained better and faster. That’s always going to be my responsibility. I’m never going to feel good if someone was short-changed.

Here are some examples of how Leung has since strengthened that system for her remote middle managers:

“I now have a mental checklist of questions that I ask myself about all the managers on my team. The questions include: Do they try to gloss over things or are they upfront with issues? Do they know how to smell for smoke early? How well can they manage people who aren’t like them? People who might think differently or need different support or guidance? Do they knee jerk into protecting their team members? How will they know if something is off about one of their team members? What kind of questions are they asking their direct reports — are they loaded for confirmation bias or avoiding necessary confrontations?” she says.

“To make sure middle managers are guiding career development for individuals working remotely, we now have expectations across our team that every fourth 1:1 meeting should involve discussing career development,” she says. “To backstop, senior leaders also do skip-level 1:1s. They ask qualitative questions to gauge how well individuals know what skills they’re supposed to be strengthening and whether they’re being given opportunities to do that.”

“We do 1:1 coaching with managers, and also have all-manager training sessions via Zoom. We’ve modeled hard conversations, for example,” she says. “It’s not to be a cure-all, it’s to help stimulate conversations and thinking, and reinforce that we care about progress. It also allows managers to share challenges with each other directly.”

TYING IT ALL TOGETHER: QUESTIONS TO ASK BEFORE TRYING OUT A NEW REMOTE WORK TACTIC

“What works for our remote team are things that work for all humans — trust, transparency, clear communication, clear expectations, mutual respect, accountability and camaraderie,” Leung says. “When it comes to remote work, there’s no huge secret or magic potion. To make our large remote team work, we do a lot of small things consistently and we know that every element matters. It’s like going to the gym every day — everyone knows it’s healthy, but not everyone does it consistently. We also know we’re not perfect, that we’ll screw things up along the way, that we’ll fall short. That’s okay. We know what our North Star is, and we all have a chance to do better every day,” Leung says.

“Every team can figure out its own North Star and pool, copy or borrow tactics for working remotely. The tactics themselves can vary endlessly,” she says. But when considering implementing a new remote work practice, Leung recommends that leaders always ask themselves the following questions:

  • Would doing this make our team trust each other more?
  • Would doing this make people trust their managers more?
  • Would doing this make people feel that they’re growing or that they’re appreciated?
  • Would doing this make people feel like we’re doing something worthwhile?
  • Can I explain this to my team and reasonably expect them to follow my rationale, even if they disagree with me?

“The same things that make sense when managing in the office usually still matter when working remotely, and are often magnified. Your bond, your trust and your communications are more important than ever — so adjust and iterate as needed.”

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