In the past few months I’ve spoken at several events about remote work – one online at the Remote Future Summit about “Tracking Hours or Results?” at the Middle Market Forum in Palo Alto, and to ESADE MBA students at Santa Clara University. At each of these events I touched on the type of person who will thrive in a remote organization, and will amplify the work you’re doing as a manager and ultimately your organization.

Remote work can accommodate multiple management styles as well as different types of workers, but you’ll really see the multiplier effect in a distributed company when you can build and grow an organization made up of self-starters.

What is a self-starter? I’ve been guilty of using self-starter as a catch-all for a type of person who will thrive in a remote/distributed organization, and I wanted to break down that specific term a bit further.

Formally, a self-starter could be defined as:
a person who begins work or undertakes a project on his or her own initiative, without needing to be told or encouraged to do so.

But there are a lot of dimensions to appreciating and defining a self-starter, and I picked 3 Cs I’ve found as particularly standout qualities in exemplary remote workers during my 9 years working remotely, which are: Communication, Commitment, and Curiosity.

Communication

Can there really ever be too much communication? In a remote setting, it’s unlikely. Communication needs to be proactive, frequent, and predictable.

There was a saying in my former company, Automattic, that “communication is oxygen” and I would go as far to say that “Communication is your organization’s heartbeat” – When healthy, it’s a steady and predictable pulse of activity bringing new ideas, updates, and information with regularity.

Every person has their own communication pulse and rhythm, but once you get to know them, you’ll know what to expect from the cadence, depth, and timeliness of their communication.

Working with a remote or distributed workforce means you won’t have as many of those casual touchpoints and opportunities to check in with folks that a physical presence and office might provide, and as a remote manager you’ll need to be more deliberate, explicit, and intentional with your time as well as how often you check in with your team.

An excellent self-starter will help fill in any communication gaps for you – they’ll reach out regularly and they’ll update you with progress without prompting or reminders, and they will always be the first to tell you when they’re having trouble moving forward, are blocked, have too much work, or need help with prioritization or deadlines.

A lack of proactive communication leads to a lot of extra work on your part as a manager – chasing down updates, wondering about particular status or blockers, and in general not having the certainty about priorities and progress that consistent communication can bring.

For further reading, this HBR article talks about cadence in communication for remote workers (while aimed at making friendships while remote, it’s about that expectation of consistent-for-you communication).

Commitment

Beyond being committed to the job itself, where a good self-starter excels in terms of commitment is being proactive about requesting or confirming commitment from you as a manager in terms of prioritization as well as deadlines.

Some of the first questions out of their mouth when asked for something are “What’s the timing on this? When do you need this? What else depends on this?” with a small reminder of any existing priorities they may already have on their plate from you. Their dedication to clarifying their own commitment is one of their key assets.

As a manager your position provides you with a clearer view of the business’ needs and how your team’s work fits back into those organization’s overall goals, but you want to be wary of overloading your team with too many requests or too much work. Your team and managers are closer to the ground and know which priorities are being pushed forward in parallel and how much can be accomplished in a given time period, and should be able to remind you when there’s a risk of being overcommitted, distracted, or off-timeline.

Some of the most common questions I get when talking about remote working are “How do you measure productivity?” and “How do you know if someone is working?”

It’s actually shockingly easy to understand if someone is not working in a remote environment because the lack of physical visibility is directly replaced with the visibility of the results of their work. If there are no results to be seen, no work has been done. A poor self-starter won’t seek out commitment clarity because they may be afraid of actually locking themselves into getting work done, they won’t update on upcoming or at-risk deadlines, and their priorities won’t move off of their to-do list. The work doesn’t get done.

Curiosity

One of the hardest skills to teach, curiosity is a frame of mind which leads people to look beyond “what is” and delve further into “what might be.”

A practical example is looking beyond the actual question or request that is made regarding their work to be done (“what is”) to make sure they understand how their specific responsibility fits into the larger picture, if we’ve looked at all the information surrounding it, and in general thinking of what we’re not considering or what additional context, research, or resources could enrich the work (“what might be”).

At Automattic it was rare to have work that was purely tactical or execution; almost everyone had some element of strategy and hands-on / tactical work in their work. Those changed from project to team to time period, but the flexibility and ability to tackle them was key.

A self-starter who is curious considers going beyond the actual ask, at least in terms of evaluation and comprehension, to be a critical part of doing their job and understanding expectations.

If you manage remote workers, do you agree with my Cs? How do you define a self-starter?

You might want to read 10 More (Leadership!) Lessons from 10 Years Working in a Fully-Distributed and Remote Company about making a distributed team work in the long-term with deliberate planning and thoughtfulness about your culture, leadership, strategic planning, and team-building.