editione1.0.3
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.
Typically, the first 30 days are about learning, the next 30 are about contributing, and the final 30 are about reaching independence (or leading, depending on the role). An effective written plan states concrete goals for each time phase, and ends with the final goals of the position (which essentially will be to independently execute their job description).
As a manager, you will have a corresponding document with your own goals to support the new hire: for example, finding an appropriate project for them to own at the 30-day mark, or delegating a significant responsibility at the 60-day mark. In a remote context, it’s important for both sides to have a clear expectation of the job, and of what success looks like.
HubSpot has excellent templates for 30-60-90 day plans, for both new hires and their managers.
Brené Brown’s work and research in Dare To Lead shows that organizations that have clear expectations also foster higher levels of vulnerability, trust, and connection. The motto “clear is kind” is one of the most important things a manager of remote workers can remember. When Brown mentions “clear,” she speaks of a highly descriptive activity—“painting done”:*
“Painting done means not just assigning a task, but explaining the reason—clarifying how the end product will be used.
Providing color and context—the purpose, not just the mechanics.
Sharing the reason for a task helps uncover stealth expectations and stealth intentions, cultivates commitment and contribution, and facilitates growth and learning.”
Remote workers, like all workers, will fail if they don’t have the clarity and context they need to execute a task and succeed in their role. This is true of all roles, but in a remote setting where context is more easily lost, it’s a particular risk. A short-term investment in thorough onboarding can make a major difference in how productive a new remote worker is as a long-term teammate.
The second major challenge with successfully onboarding a remote team member is integrating them into the culture. Culture gets shared in casual and social interactions, so co-located teams will find it easier to maintain a certain culture (whether that culture is “good” or not is unrelated—in-office and remote teams can both be healthy or toxic). New hires in a remote team will have fewer interactions to observe, and so the signals they’re collecting to understand expected cultural behaviors are more limited. Additionally, in a growing team, new people may band together, viewing the fellow new hire as the safest person to ask a potentially “dumb” question, rather than their teammate or manager. This risks sub-cultures developing as new hires onboard, further fragmenting the culture away from the overall company’s direction.
When people say that “maintaining culture when you hire remotely” is hard, this is what they mean. The default is a forking, branching culture, with each “generation” of new hires developing their own ethos; maintaining one common shared culture takes continued, focused work. David Loftesness, who has worked at Twitter and Eero, suggests a few tactics for dealing with changing culture as people onboard:
Fostering an understanding of what each team does, what their challenges are, the basic act of putting names to faces after a meaningful interaction, is a great way to sidestep factions down the road … Get new hires in a room with your veteran employees, for example, to maintain a thread to your earliest days. Encourage them to share stories, both difficult failures and energizing successes. This can give the new folks some perspective of what the old-timers went through to get the company to where it is today.*