An interview with Scott Dawson on The Art of Working Remotely
Scott has been working remotely longer than anyone I know. When he started working from home over two decades ago there were hardly any resources available. Distributed work wasn’t really a thing yet, co-working spaces were far and wide in between, and today’s communities around location independent jobs did not exist. But Scott knew what he wanted - so he had to figure out a way to make it work.
His website Art of Working Remotely has long since been an inspiration for the remote community. Full of practical advice, his articles can make a difference when you are trying to do this remote thing well. If websites are not your thing, you are in luck: Scott is about to publish his combined knowledge in an inspiring and practical book.
I was lucky enough to get a pre-release of the book, and I loved it! Whether you are already working remote, or whether you are considering starting in a distributed company - this book will make you more productive and ensure that you don’t lose your personal life in the process. And if you lead (or plan to lead) a remote team, the book can help you to level up your team - you might even consider it required reading for every new hire.
Let’s get Scott to chime in himself
Question: Leading a remote team requires a lot more structured communication to make up for the missing lunch break/watercooler moments. How do you create trust between the people on the teams without being too rigid? What can the lead/manager do and what should the team member keep in mind?
The very first thing I thought of when I read this question was Maslow's hierarchy of needs. Though Maslow’s model is about physiological needs, I think any work environment can be described using a similar hierarchy.
Trust is certainly one of the higher levels of the hierarchy. As is the case with any structure, stability depends on the strength of the lowest levels. A remote manager must first and foremost ensure that the team is in a position to thrive:
Are the goals articulated well?
Does the team have the proper tools and knowledge?
Is adequate time allotted to meeting the goals?
Is the team operating in a culture of fear or mutual respect? Respect, I hope.
As a remote leader, generating trust among your team boils down to effective communication. You have to communicate at a team level and at an individual level. Now that everyone’s on the same page, let’s build some trust.
There are a few easy ways to build trust in the context of a team, whether on-site or remote. You can see that most of these apply to both managers and team members.
Keep your promises. Once you make a commitment, follow through on it. If you can’t, let people know the reason why, and what your new commitment will be. Communication is key. No matter what tool you use to persist data and communicate status, it’s most important that everyone use it, and use it well.
Be understanding and forgiving. People make mistakes. It’s unrealistic to expect them not to. When mistakes happen, learn from them and move on. Don’t shame or humiliate anyone, ever.
Be supportive. Your teammates will need you from time to time, and you’ll need them. Support each other. Lend a hand (or an ear) when needed. Graciously accept help when it’s offered.
Trust takes time. It takes repetition. Once destroyed, it can take a long time to rebuild. That said, it’s probably one of the top traits of highly effective teams, so it’s a wise investment.
Question: One of the secrets to being successful in a distributed role seems to be a knack for planning/organization - as if treating your own life as a project that you are managing. Is this something innate, or can that be learned? If the latter, how would you teach this skill to a new person on your team?
I think that’s true for a lot of people, yes! There are some in my weekly #remotechat on Twitter, though, that would tell you otherwise. They thrive on entropy and an organizational system that looks more like chaos to other observers. Everyone seems to have their own secret to planning and organization, different variations on the same theme. Like any skill, I believe that we all have a certain degree of innate organizational capability. I’m also a firm believer in the value of adopting a growth mindset, so I know this kind of thing can be learned.
If I had to teach it in the context of a team, I’d start a conversation around the specific tools the team uses. Why do we use them? How do we use them? What happens if we don’t use them? Tools are the framework around which conversations happen and decisions get made. They’re so much more important in the context of a distributed team, since knowledge can’t be shared over shoulders or while you wait for your coffee in the pantry. New teammates will thrive if they understand how tools contribute to the team’s overall efficiency.
Question: Is there such a thing as being too open and too transparent with your work (and your life) when working remotely?
Absolutely! It can be a real challenge to know how open and transparent you can (or should) be. Like many things in life, the degree to which you should share will vary based on the culture of your workplace and who you’re working with. We’re all sensitive to different extremes of communication. We all know people who are garrulous, secretive, extroverted, or shy. Some need to be asked a pointed question to share, and some can’t read a situation and keep talking anyway. It can be much more difficult when you’re limited to phone calls and videoconferences, too.
I tend to follow the group’s lead when I think about sharing personal details with colleagues or friends. If we’re waiting for a virtual meeting to start and colleagues start talking about their kids, I’ll share something about my kids. If I’m 1:1 with someone and they candidly share about how they’re feeling about work, I’ll add my two cents. If I feel that the person I’m talking to will be receptive to a sensitive topic I want to know more about, I’ll ask.
Conversely, there are times when you should be tight-lipped. For lack of a better term, it means employing some political savvy. It’s helpful to know more about who you’re talking to — what are their beliefs, fears, agendas, hopes, and biases? By knowing more in advance, you can tailor the degree to which you share details through the course of the conversation.
As a general rule, I err on the side of under-sharing until I know more about who I’m talking to. When you get to know someone better, you can take steps together to increase your openness. It can deepen your relationship, build empathy, and help you work more efficiently together. That said, it takes a willing partner to generate that familiarity.
Scott Dawson lives in Trumansburg, New York. He has worked remotely for 21 years and moderates a weekly Twitter chat (#remotechat) for remote workers. His recently-published book, The Art of Working Remotely, is available at artofworkingremotely.com/book.
Twitter: @scottpdawson
LinkedIn: linkedin.com/in/scottpdawson
Web Site: scottpdawson.com
Book: artofworkingremotely.com/book