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Updated March 23, 2023You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
This section was written by Juan Pablo Buriticá.
For collaboration to work well in a remote organization, not only is healthy, intentional communication required, but a distributed team must clearly understand the direction they’re heading together: they need goals. Teams also need to determine a predictable rhythm to work towards those goals, giving space and autonomy to individuals to focus on their work. Goal alignment and autonomy thrive in a trusting environment supported by explicit working agreements that eliminate assumptions about how to work at a distance.
Getting teams to collaborate effectively takes effort, time, patience, and practice to refine the skills that support effective collaboration and coordination. Consider the concepts in this section as a set of capabilities that your team can strive to understand, try out, and adjust to their localized contexts. Every team is unique, and objectively defining what success looks like for your team is not something we can achieve in this guide. We hope that as you build these capabilities, you share what you learn with us and others so we can continue moving remote work forward.
Before teams can collaborate, they need an end goal. Most often, teams employ some kind of strategic planning to set goals; this is not unique to remote work. Commonly used frameworks, like objectives and key results (OKRs) or SMART goals, can help teams create strategies and goals over specific periods of time that fit their business needs. For small teams, a roadmap may be more than enough, or minimum viable products (MVPs) can also align startup teams to quickly bring a product to market.
Whichever you choose, all goals for remote teams can benefit from these universal guidelines:
Clarity. Every member of the team understands the goals’ importance and the reason for setting them.
Written down. Writing goals down translates to an 80% higher chance of achieving them. Effective goals are accessible to everyone; consider using a knowledge base, project management tool, or specialized goal-setting tool. Basecamp uses their own tool to publish and announce theirs.
Time-constrained. It’s best to set an explicit time period for your strategy, so you can evaluate its success or failure, continue improving on it, or change it completely. This will also be the basis for your team’s cadence.
Measurable. Understanding whether a goal will be met or not requires that you are able to monitor its progress. Imagine the goal of “Becoming an iconic company.” How does your team know if they’re on track to achieve this goal or not? How are they supposed to understand or measure what “iconic” is? Achieving 100M in annual recurring revenue is a clearer redefinition of the goal, or perhaps getting 10M subscribers. By making goals measurable, teams can share an understanding of what success looks like, monitor their progress, and evaluate whether they continue to be on track or not.
Limited in number. It’s critical to limit the number of objectives to maximize your team’s focus. When everything is important, nothing is.
Specific and account for context. Factors like the size of the team, the size of the company, the stage of the company, and whether the team is growing or not are factors to consider when you set goals.
To run strategic planning with a remote team, you must increase each participant’s individual responsibility for preparing and working outside the meeting. It’s the only way to get through planning within the time during which people can effectively engage online.Elise Keith, co-founder and CEO, Lucid*
Most co-located companies approach setting goals by getting small planning groups together in person, often for multi-day sessions. This is potentially infeasible for remote teams, so it’s helpful to think about how you can facilitate planning and setting goals remotely. Lucid has a fairly comprehensive guide to strategic planning for remote teams, but you will note that it details a specific goal-setting process that may or may not be appropriate for your company—it’s likely to be too heavyweight for a startup or small company. It does offer a few useful suggestions for how to run remote planning sessions, which draw from key remote practices around asynchronous documentation. These practices recommend:
Kicking off asynchronously. Prepare background material for team members to review individually before the meeting(s).
Keeping it short. You can’t keep people’s attention via video call for nearly as long as you can in person. As a result, it’s wise to constrain any synchronous planning meetings to 2 hours or less.
Brainstorming individually. For any idea generation or brainstorming activities, it’s best to have people do so on their own, documenting their ideas in writing to share with the group when they meet.
Being flexible. You won’t want to constrain the process to a predetermined set of tools. Instead, look at experimenting with and using a mix of options for sharing ideas and collaborative editing.
Finishing asynchronously. Documenting and sharing a final draft can happen after the in-person work is done.
importantIf any goals change, it’s important for leadership and managers to broadcast changes using multiple communication channels so everyone on the team can remain consistent. This includes updating all the company artifacts that contain goals.
story “The first time we used OKRs at Splice, our CEO Steve and I brainstormed for an entire afternoon and left convinced we had done excellent planning. Little did we know that it would take us the next six quarters, and full time staff and allocated time to actually come up with objectives that were ambitious yet achievable, along with key results that allowed us to fulfill those objectives. We also got to see our teams understand their capacity much better over time, leading to an overall increase in our organizational performance. Spending tens and possibly hundreds of hours every quarter coming up with quarterly plans was painful, but eventually worth it.” —Juan Pablo Buriticá, VP of Engineering, Splice
Learning how to plan is a skill in itself. Planning takes time and effort, and requires more coordination than execution. It will also take time to learn and iterate on a planning process that allows your team to decide what to work on and why.
Almost anyone who has worked in a corporate environment is familiar with the litany of methods for communicating about progress and status. Status reports, burn-down charts, sync meetings, and weekly or even daily updates—they all presume that everyone needs to dedicate significant time updating everyone else. Remote work is an opportunity to re-evaluate this set of cultural assumptions. Establishing a set of conventions about collaboration can eliminate assumptions about status, and give a clear set of expectations for everyone in a distributed team.
The first convention for your team to consider is making its default state be “on track.” This means everyone assumes the team is able to accomplish its goals, giving individuals the autonomy to finish their tasks, release their products, or reach their sales milestones—unless someone explicitly says otherwise. This helps everyone reclaim time otherwise spent confirming whether they’re on track or not, and use it to focus on their work.
Defining this convention is an opportunity for you and your team to evaluate whether you understand your goals and each other’s role in achieving them. This depends on your context. A sales team, a customer-experience team, a people-operations team, and a product-engineering team will all have very different definitions for what being “on track” means to them.
importantChoosing to be “on track” doesn’t mean you are always implicitly meeting objectives. Instead, by choosing a default, you open yourselves to examining the obstacles in your path with increased awareness. Now that you know what your normal state should look like, you can define how much risk you will tolerate before considering a change of state.
For example, a customer experience team can agree that when a customer satisfaction metric dips by a few points, they’re no longer on track. This also means they have to monitor this state so they can understand if, when, and how it changes.
importantThis strategy also requires a foundation of psychological safety on teams in order for a generative culture to develop. That means individuals aren’t blamed when something goes wrong, and raising a status change to “off track” leads to supportive inquiry to help get back on track. By choosing to be on track by default, distributed teams build an environment where they can come together to solve the challenges that lie ahead.
When remote teams default to on track, collaboration and coordination are enhanced in a few ways. First, and most importantly, the uncertainty of whether or not objectives will be met is gone. Operating from the mindset that the team is on track reduces unnecessary team effort: there’s less of a need for status meetings, emails, and syncs. Second, the team becomes highly in tune with this state; when a change of state happens, it doesn’t go without notice. Being off track is a big deal—it’s communicated clearly, and the group must focus any available efforts to getting back on track, whether it’s by reprioritizing, cutting scope, moving dates, or creating any other solutions that may be available.
Pause for a moment and consider which collaborative practices your team has built around the necessity to report its state to others. How would your team members respond if you asked them what being “on track” means? What would happen if you stopped putting so much energy towards informing people of the state, and instead chose a default? Do you have enough trust in your team to do so?
If I had to pick the one thing to get right about any collaborative effort, I would choose trust. Yes, trust. More than incentives, technology, roles, missions, or structures, it is trust that makes collaboration really work. There can be collaboration without it, but it won’t be very productive or sustainable in the long run.Larry Prusak, Senior Advisor and Faculty, Columbia University, author, Working Knowledge*
importantTrust is critical for healthy collaboration in remote teams. It’s also important for many other aspects of successful remote companies. For that reason, we’ve written an entire section on it, which we strongly recommend visiting in order to learn practical ideas for fostering trust in remote teams.
An organization’s cadence is the rhythm created by defining periods of planning and periods of execution.
Developing a work cadence—one that is specific to a team, and that uses explicitly defined work practices—is important in enabling distributed teams to make work more predictable. When teams define a rhythm, the next beat is known, and everyone can play on-tempo.
What cadence you choose is highly dependent on the context of the team, and arriving at the right one will take some experimentation. Below are a few things to keep in mind as you choose what works for your company or team.
Organizations usually define and revise their strategy over longer periods of time than those in which they execute their chosen strategy. Your communication approach may also vary during different periods. For instance, planning periods typically require more synchronous conversations to align everyone.
Distinct time periods for planning vs. execution are valuable because they help teams and individuals organize themselves around the pending work. There’s a planning period, a focused working period, and a subsequent conclusion that can be used for self-reflection to continuously improve as a team.
importantConsider using longer periods of time for strategic planning—perhaps yearly objectives that are broken into either halves or quarters, so that the plan doesn’t change too quickly. If you choose a period that is too short, your team may lack the necessary time to focus on getting work done. And if it’s too long, the company’s ability to act on strategic or market changes will be impacted. Execution best happens over shorter time periods to allow for focused work to get done.
GitLab has documented their entire cadence, from a 30-year strategy down to annual and quarterly planning, and how execution happens daily.
You can consider aligning your company or departments all to a similar cadence, depending on their size. Keeping track of two or three is much easier than ten, and too many teams operating at different rhythms leads to a feeling of uncertainty regarding whether you’re really on track—past a certain group size, you can’t really know who started what when. Teams don’t even need to use the exact same periods, as long as there is some alignment. For example, all teams can have their planning period on Mondays, but some can use one week as a cycle, and others, two weeks. This allows everyone to know “what time it is” for any given team, instead of wondering when a plan needs to be revised, or when the last planning period’s conclusions will be drawn.
These cadence periods, or iterations, derive from agile software development practices, which were developed by software teams for the purpose of adapting more rapidly to new information as they released new software or features to customers. Teams outside of software have found success using similar methodologies, even if their work is less planning intensive. Instead of planning, teams with longer cadences (like product teams) can replace these with team syncs where members know they’ll have the opportunity to have discussions and conversations about how work is progressing. For example, Basecamp teams work in six-week cycles.
Teams that are responsible for customer support or other high-touch activities may find that their work can’t even be planned a week in advance. For these cases, teams can use methodologies like kanban that allow them to quickly reprioritize and handle the influx of work, while still establishing a longer time period to reflect, spend some time together at the beginning and end, and monitor their progress.
Whatever cadence you or your teams choose, make sure it is documented, so everyone is aware of their goals and how they are expected to work towards them.
This section was written by Juan Pablo Buriticá.
When co-workers or managers aren’t readily available, it may take more time to get help from others. To mitigate this, remote teams and workers need to develop practices that bridge information pockets.
An information pocket occurs when individual members of the same team have access to differing levels of information. Individuals could have access to more or less information depending on social relationships with peers or managers, their time zone overlap, their ability to ask for help, or whether they come to an office or not. Access to the outcome of decisions, or how to do administrative tasks like getting expenses approved, are examples of information that could form in pockets if it’s not broadcasted adequately. Confidential information, or other information that should be shared on a need-to-know basis, doesn’t count as information pockets.