Strategies for remote-work success: Set clear start and end times, check in on people, have patience

Ward Vuillemot, CTO/CPO at Seattle-based RealSelf, working from his home in Central Washington. (Photo courtesy of Ward Vuillemot)

Guest Post: If you’re working in technology you’re likely working remotely, whether you want to or not.

Working remotely is not new; for years people have embraced its many advantages. But with COVID-19 forcing entire industries to adopt remote work, many people, myself included, theorized remote-work was here to stay. Why is it then, when so many of us are working remotely, and companies such as Dropbox are transforming their office spaces into collaboration spaces, that we find people unsatisfied with what was supposed to be a utopian vision of our future?

The answer is simple: remote work was never meant for everyone. Now, entire companies are forced to adopt whether they, their managers, or their organizations are ready. I wanted to share best practices I’ve learned over more than five years of working 100% remotely as a technology executive — practices that could make you a world-class remote worker. 

Before I do, though, it’s critical we acknowledge that this year is unlike any year in recent memory. The stresses of 2020 cannot be overstated. As stressful as our work is with houses stuffed to overflowing with families with nowhere to go, these challenges pale in comparison to folks who must work in offices or stores, or worse for those who are still struggling to find work at all. Perspective is important.

Let me repeat and emphasize: remote work is no panacea. While it’s a viable option for many companies, it’s naive to apply it to an entire industry. More so, 2020 is very different than any other year: 1) entire families are home at the same time; and 2) we’ve lost our second or third-places such as cafes or libraries to work to decompress. This is not how any of us would work from home in other years.  

Suffice it to say, when things get back to normal, remote work, just like working in person, will have its own distinct set of benefits and drawbacks. The skills learned from in-person collaboration don’t always translate well to remote work; we require new skills to be successful. While it’s beyond the scope of this article to go into all the nuance and detail, what follows are high-level strategies I believe everyone should consider adopting.

Space and time: Creating structure for yourself to be the most effective version of yourself.

  1. Dedicated space: Establish a place in your home that is dedicated to work. This may mean removing distractions such as TV or games. Now that you’re saving on commute costs, invest in comfortable office furniture.
  2. Structured time: Use a calendar to schedule “think time” to ensure you have time to reflect and plan out conversations and next steps.  
  3. Work-life separation: Create clear start and end times for yourself. Consider leaving your house to take a 5-minute walk before “going to work” and then repeat at the end of the day. Don’t forget to make time for exercise, shopping, and friends. It’s easy to not be thoughtful about these things, especially as everything can start to blur together.

Meeting people over meetings: The vast majority of interactions are now through planned meetings, whether as a group or one-on-one.

  1. Make time to connect: Absent now are coffee breaks, lunches, and hallway chats to keep us connected. Meetings, and I do mean every meeting, requires we connect with each other as human beings before getting down to business. The same can be said for things such as Slack: make it a point to check in on people, especially after a weekend.
  2. Video mostly always on — make eye contact, face the camera: Whenever possible have your camera on when in a meeting to help establish rapport. Face directly toward the camera: not making eye contact can signal disinterest or aloofness that is rarely well received. That said, it’s equally important to turn it off when you just need to be alone. 
  3. Reach out and talk: While it can be tempting to communicate entirely via text, some conversations are better done live. Don’t try to resolve disagreements by text; talk it out over video. 

One-on-ones for the wins: It’s more important than ever to create space for each other on a more personal level.

  1. Keep it regular: With random encounters gone, it’s important to keep sacred frequent one-on-ones. As a leader, have these every week with your directs. I recommend every other week with your skips. Also set up one-on-ones with people throughout your organization.
  2. Agenda for two: Create a shared document for both of you to add notes to help each prepare ahead of time.
  3. Leave room for more: While some structure is good, remember to also use this time to get to know each other. Ask about life outside of work. Be inquisitive about each other as human beings.

Keeping it real: Let’s not forget our shared humanity.

  1. Be vulnerable: Too often we don’t let our colleagues into our heads and hearts in an attempt to create a facade of having it “all together.” Let’s be real: none of us have it all together, especially this year. Help each other by reminding everyone we’re not alone.
  2. Be authentic: It’s also important to remember to be ourselves, our whole self. Remember to laugh. Allow ourselves to cry, if appropriate. Remember to share quiet moments. You be you, and give space for your colleagues to do the same.
  3. Be patient: We all have good days, so-so days, and days to forget. Don’t just be patient with others, also be patient with yourself.

Working remotely requires the qualities of self-discipline, self-awareness, and superior organizational and communication skills. Those most successful are those with a deep ethos and culture founded in trust, collaboration, and psychological safety. While remote work may not be ideal for everyone, it’s certainly something we can all become adept at through practice, patience, and effort.

Want to learn more? Check out my articles on leading remotely and creating culture from afar.

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