From the Collective

On Remote Teamwork: 6 Challenges & 6 Strategies - Part 1

Anna Jacobson

Welcome to the first post from the one and only Anna Jacobson, Operations & Data Partner at OpCo. Anna is a cross-functional business leader, data strategist, and operations veteran who is passionate about combining technology with process and organization design to ensure outstanding collaboration across technical, business, and creative teams. Her strong leadership and communications skills combined with hands-on technical proficiency have enabled her to lead across a wide variety of contexts, bringing breadth, creativity, process, and innovation to every endeavor.

Outside of work, you can find her eating and photographing her way across the world with her husband and son. She’s also an avid nature fan and spends as much time as possible in the forest and on the water in her adopted home of Vancouver, BC. 

Anna is known for her operational expertise, and in this two-part series, she will take us on a deep dive into her perspective on internal operations to offer practical advice on building remote teams effectively and with empathy.


I spent the first chapter of my career in one of the most in-person, co-located industries there is - construction management. Even so, at the time I left my prior job, my team had been fully remote for over a year due to the pandemic. We were thrown into remote work without any planning or preparation; the company did not have a work-from-home policy, and many people on my team had never even used Zoom before. Although necessity can drive innovation, these were the worst possible conditions for any kind of intentionality about our new workplace culture, remote operations, or communications practices. Most of us, myself included, were barely hanging on, just trying to survive in a frighteningly uncertain time.

By contrast, here at Operator Collective, our team has been fully remote and fully distributed by design from Day 1 (which was pre-COVID). Like any startup, though, our internal operations practices developed organically and on an as-needed basis at the beginning. As we enter our third year, our organization has matured and our team has grown, and so has our need to take a more intentional approach to how we function as a team. One of many things we focused on last year was identifying our challenges as a remote team and designing actionable solutions to address those challenges.


Remote Teamwork Challenges

Enabling visibility. 

Remote teams have to find the right mix of tools and processes to ensure everyone has access to the information they need, understands what’s happening, and is empowered to do their job well. 

Navigating flexible schedules and different time zones. 

When teamwork is being conducted across different schedules and time zones, careful coordination is necessary so progress doesn’t get stalled.

Maintaining boundaries. 

When work is always accessible and team members are reachable 24/7, misaligned expectations around availability can cause frustration and delays.

Finding emotional context. 

To ensure healthy interactions, remote teams need to create practices to gain emotional insights about their colleagues that don’t rely on nonverbal cues such as body language, intonation, and facial expressions.

Creating spontaneous social interaction. 

The chance encounters that happen naturally in an office environment are few and far between for a remote team, potentially making it harder to form emotional bonds or know the whole person.

Reducing FOMO. 

The emotional component of lack of visibility, FOMO is the sense that things are happening that a team member is not aware of, with the negative perception of being left out or left behind (a bad feeling, whether or not it is actually the case).  

Remote Teamwork Strategies: Building Visibility


Because remote teamwork relies heavily on asynchronous communication, which tends to be slower, it needs to be timely and high-quality to avoid significant back-and-forth that could mean losing days between unclear messages. 

Overcommunication is the strategy that addresses all of the challenges described above and enables all of the other strategies described below. Though I chose it, I don’t love the word “overcommunication” since it implies communicating too much. Really, what I mean by it is communicating more than what people were used to in the past - but just the right amount to optimize the team’s productivity.

And it’s not just about quantity, it’s also about quality - which usually means clarity. For example, instead of ending a message with “What do you think?” (something I have been guilty of doing many times in the past!), our team now strives to state clearly the goal of the communication, usually one of these five things:

  • Providing visibility (“FYI”)
  • Asking for input (“Do you have any suggestions?”)
  • Asking for collaboration (“Could you please do X, Y, and Z?”)
  • Asking for confirmation or authorization (“Yes or no?”)
  • Asking for direction (“Let me know how you want to proceed.”)

Each of these use-cases requires a different type of response; in order to be efficient, team members need to know from the outset what is being asked of them.

When and how we communicate is also important, and consistency helps remote teams to communicate quickly and efficiently. Our team has seven modes of communication with defined use cases:

ASYNCHRONOUS (time-lagged communication)

  • Email: for all external written communication and some internal written communication (e.g. internal discussion about an external email).
  • Slack: for some internal written communication (e.g. standalone conversations, follow-up on verbal discussions). We have a whole separate guide that delves into much more detail about how we use Slack.
  • In-App Comments: for internal tool-specific collaboration (e.g. Google Docs and Slides, Airtable, Canva, etc.). Whenever possible, we have enabled Slack integrations for these tools so that in-app comments get posted to Slack (especially helpful when people are on the go!).
  • Text Message: typically reserved for personal and/or urgent 1:1 written communication.

SYNCHRONOUS (real-time communication)

  • Zoom: for internal and external voice and video communications.
  • Phone: typically reserved for personal and/or urgent 1:1 voice communication (or when we need a break from Zoom).
  • In-Person: for quarterly offsites, community gatherings, etc.

Each of these modes of communication has its place in a distributed setting. Using them consistently is a key to our success as a distributed team. 

There’s an ideal combination of communication types on a remote team: mostly asynchronous, with intentional synchronous communication only as needed - what we call async-first. The goal of being async-first isn’t to eliminate synchronous interaction; an async-first approach aims to shift where we sit on the communication spectrum to find the right balance. We want to maximize the benefits of both async and sync communications while minimizing their problems. To do this, we have async communication as the starting point, make synchronous communication more purposeful and efficient, and enable team members to work on a schedule and in a rhythm that’s best for them.

Clarity around availability and responsiveness. 

On a remote team, team members need to have aligned expectations about each other’s availability for collaboration. 

On our team, we don’t expect each other to be immediately accessible outside of scheduled synchronous interactions such as meetings and 1:1s, even during “business hours” (which increasingly feels like an outmoded concept when we are working across four timezones). However, we have developed some shared expectations so that we can reach each other when we need to:

  • We all have visibility into each other’s calendars and we always keep our calendars up to date.
  • We strive to schedule all internal meetings between 9AM and 4PM PST Monday-Thursday. Although we all work on Friday, we try to protect that day for sustained time for focus and deep thinking.
  • Out-of-office times are calendared. This includes when we’re going to be out for a few hours during a workday and when we’re taking a day or more off for vacation.
  • When we take PTO, our vacation responder is turned on in Gmail and our Slack status is set to “Away”. We respect and protect each others’ PTO, and we manage our responsiveness expectations accordingly (especially for internal communication channels).

Every team has to determine for themselves exactly how they want to work together - for example, a team that doesn’t need to meet frequently might have more no-meeting days each week or a smaller window to schedule internal meetings. But the point is to be thoughtful about what the team needs and explicit in setting expectations.

Default to transparency. 

Keeping everyone in the loop prevents communication breakdowns that cause team splinters and wreak havoc on productivity. By cultivating openness, remote teams can operate on collective trust and mutual understanding.

Having spent a long time in in-person settings, I can say unequivocally that lack of transparency isn’t a challenge unique to remote work. That said, the perception of lack of transparency can be exacerbated by not seeing and hearing conversations going on around you. For many, defaulting to transparency is a mind shift - it’s the exact inverse of the “need to know” basis that many organizations operate on. But once the shift has happened, it’s easy to implement simply by unlocking the doors behind which information is kept - posting to shared Slack channels instead of DM, setting document permissions to be viewable to the whole team, copying team aliases instead of individuals on emails, etc. - and letting work happen out loud, in front of the team, even when all members aren’t participating in it. It also means leveraging team sync sessions - in our case, weekly team meetings and quarterly offsites - to share as much and as openly as possible.

As someone who has handled sensitive financial information my whole career - and more recently developed a focus area in data ethics and privacy - sometimes transparency can feel uncomfortable. But the trick is recognizing which information is sensitive or private - and which isn’t - and trusting the team to use any information that they have responsibly.


The beauty of these strategies is that they don’t just address one remote work challenge at a time - implementing any one of them will help solve multiple issues. Overcommunication, as I said, helps with almost everything. But it’s true for others as well - for example, defaulting to transparency will directly enable visibility across the team, but it also reduces FOMO by creating a sense of openness and trust, supports flexible schedules by reducing the need to spend precious async time getting people caught up, and helps to maintain boundaries by allowing team members to know what each other is up to.  


In Part 2 of this series, I will explore three more remote teamwork strategies focused on optimizing team operations. Stay tuned, and please send me your questions any time at

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