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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.
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.