From the Collective

On Remote Teamwork: 6 Challenges & 6 Strategies - Part 2

Anna Jacobson

On Remote Teamwork: 6 Challenges & 6 Strategies -  Part 2

Welcome to Part 2 of a two-part series focused on remote teamwork. In my last post, I introduced six challenges to remote teamwork (included here again for easy reference) and three strategies to address them by building sightlines. In Part 2,  I will share three more strategies; these ones are focused on optimizing team operations.

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: Optimizing Operations

Clarity around ownership and decision-making. 

Having explicit owners and decision-makers can help close off conversations after adequate feedback and move projects forward.

As our team doubled in size in less than a year, we found we needed to be more explicit about who was doing what. Starting with the “owner”, we adopted Apple’s popular Directly Responsible Individual (DRI) concept to refer to the one person at whom the buck stops on any given project. The DRI sits at the center of the project, responsible for making sure that everyone else on the team understands what they need to contribute and that the project stays on track.

Having a clearly-designated DRI helps to streamline projects by: 

  • Reducing ambiguity and deferred responsibility.
  • Minimizing redundant and counterproductive work.
  • Making communication and collaboration more intentional (everybody doesn’t need to be in every meeting!).
  • Avoiding decision-making bottlenecks and dogpiles.

Planning and organization. 

Thinking through and documenting goals and processes ahead of time plays an essential role in creating trust within the team, as well as promoting clear asynchronous communication and intentional synchronous communication.

One of the most impactful tactics our team has adopted this year is a project-planning framework. Although not every project neatly fits into this process in perfect sequence, it has been surprisingly adaptable to many different kinds of projects across our varied functional areas, including event planning, program design, technology implementation, marketing campaigns, and more.

A key piece of this implementation was creating a template for a project plan that comprehensively covers all phases of the project, including an initial purpose statement (or project charter) and a post-completion retrospective.

Our project plans have proven to be invaluable in a number of ways: 

  • As a tool for thinking through the planning process and anticipating project needs.
  • As the team’s single source of truth for all information related to the project.
  • To facilitate communication between stakeholders throughout the project lifecycle.
  • To promote agility and speed during project execution.
  • As a record after project completion that serves as a resource for future projects.

Design for connection. 

It takes intentionality to build a great remote team culture, and any internal operations strategy needs to address how to foster team connectivity. Just as the team needs practices and tools to execute their work, they also need practices and tools to develop and sustain their culture. 

We have designed and implemented many practices around our team culture, from a non-work Slack channel (#coffee-break, where we share photos from our weekends every Monday morning), to a weekly all-hands meeting, to a robust virtual onboarding process for new employees. All of these practices have been designed with an eye toward instilling connection within the team. Two of the most impactful have been:


Last year we adopted The Birkman Method, a work style assessment tool that focuses on individuals’ needs, usual behaviors, and stress behaviors. It helps optimize our performance as individuals and as a team by giving us: 

  • Non-judgmental profiles of each individual’s strengths, behaviors, motivations, and interests.
  • Predictive summaries of how individuals and teams naturally approach communication, conflict, and decision-making.
  • Ways to help each person manage work interactions in ways that get their needs met and reduce their stress.

As a team, our goals for using Birkman are to give every team member:

  •  Shared baseline concepts and vocabulary to talk with each other about how we work.
  •  Insights into each other’s behaviors.
  •  Recognition of how we can work most effectively as a team.

Over the past year, we have invested time and resources in Birkman, including in-person sessions led by a professional Birkman coach. But the instrument is much less important than the process. There are lots of other options out there (CliftonStrengths, Enneagram, and DiSC, to name a few). My advice to any remote team is just to pick one and lean into it - it takes hard work to understand each other, but the benefits can be truly profound. 


Since the pandemic started, much has been made of the loss of chance encounters due to remote work, as well as the loss of company culture when there is no water cooler to gather around. In my opinion, these claims highly overestimate the value of most of these spontaneous in-person interactions, while also failing to acknowledge their harms - I don’t mourn them at all. 

But there is no doubt that magic can happen when a strong team comes together in the same place, so we decided last year to gather each quarter for a few days at a time. We did important work at our offsites with great participation by every team member. But we also made sure to plan time to just be together - dining, walking in the city, hiking, even learning to make ramen. These are the moments I think of when I think about our team - made even more special because I don’t see them every day.


These strategies really aren’t limited to remote work (nor are the challenges, for that matter!). They can help cultivate good work on any team. Most in-person organizations haven’t actually figured out how to optimize their practices for team productivity - they just hope that requiring workers to be physically present will ensure the best ROI. But hope is not a strategy. Now that I have worked remotely for almost three years, I am a firm believer that for knowledge workers, the best ROI can be achieved by being thoughtful and intentional about how the team functions and investing in designing systems to support their success as a team - regardless of whether they are in-person, hybrid, or remote.


Stay tuned for more thoughts on operations and data, and please send me your questions any time at!

Let's connect.

Sign up to receive community updates.
Sign Up