Chase Seibert

Director of Engineering at Dropbox

Many tech companies have been working remote for most of the year due to COVID, expecting to return to the office sometime in 2021. I have recently learned that my company will not be returning to regular office work. This announcement marked a mind shift for me, where I need to stop just surviving remote work, and start thriving in remote work. Not only for my own sake, but also for the teams I lead.

I plan to document my learnings over the next couple of years in a dedicated series of blog posts.

Baby Steps

Like everyone else, I have already tried to incorporate some basic best practices for remote work. I have slowly created a comfortable and ergonomic home office. I’ve tried to be more intentional about getting out of the house, for both exercise and socialization. I’ve created more separation between work and home life, such as by taking work apps off my personal phone. These are all smaller, personal changes.

Preconceived Ideas & Questions

Coming into this, I have a number of half baked preconceived notions about how to do remote work well. First, I want to use this as an opportunity to brush up on basic hygiene stuff like meetings, and 1:1s. I want to have fewer meetings in general, move some meetings to be fully async, and more maker time for people on my team. I want to learn how to lead better remote first meetings.

I want to invest in documentation, next year. Especially for onboarding new people. How do we give them the best possible experience, on par with in-person onboarding? I’ve generally been strong in my career in written communication. How do I impart that to a team?

How do you keep people engaged with their teams remotely. When I look back at my career, so many of the memories involve getting together in person. Having a beer at a late planning session. How do we create natural work appropriate socialization when we’re all remote, without it feeling forced?

I expect this change will not be someone everyone wants to go through. I expect some existing employees to be turned off. But, I also expect new hires to be very engaged, because they self-selected in to a fully remote company. Still, there will be painful conversations about existing employee location changes, and compensation changes. I suspect that remote work, on balance, may be a better fit for more experienced hires, because they are generally more self-sufficient.

Getting Serious about Learning

What I have started doing is reading a lot. Here are the most helpful resources for remote work I’ve found, so far. I’ve compiled them, together with learnings, in a GitHub repo.

Best Reading

Learnings & Best Practices

Communication

  • Have ONE of each communication tool: synchronous, asynchronous, and long term storage, be explicit about what method to use when (S) (T) (C)
  • Be explicit about tone, ex: “I’m kidding”, if there is any tone confusion, up level to higher mode (video) (S) (T) (C) (H)
  • Communicate with repetition (I)
  • Ensure visibility of work (newsletters, boards, exec reports, demos) (I)
  • Conscious shift to async communication (C)
  • Default status to “On Track”, status updates only for when things are at risk of NOT being on track (H)

Meetings

  • Start and end rituals
  • Most meetings need to be recorded, and have transcripts
  • Meetings can be asynchronous, long form threaded conversations (B)
  • Don’t mix in-person and remote attendees; even local people should dial in if there is even one remote person (T)
  • High fidelity and async → make screen share recordings with voiceover easy (C)
  • Making meetings less abundant / more scarce, people make better use of the meeting time that does happen (C)
  • Reducing meeting time comes with increased time spent on written communication (H)

Brainstorming

  • Use an online whiteboard
  • Dedicated time for folks to show off/share one thing they are working on (I)

Timezones

  • Ask questions publicly, not privately (B)
  • Recommend 4 hours overlap (C)
  • People need to be able to find anything they need w/o asking or waiting for someone else, i.e. most work needs to be possible async (C)

Culture

  • There should be hundreds of Slack channels devoted to socializing/off-topic
  • Standing team interaction time (games, meditation, cooking) (I)
  • Remote can amplify existing cultural problems (I)
  • Foster 1:1 peer connections to combat loneliness (B)
  • Live video “work side by side” sessions (S)
  • Consider company sponsorship for interest groups (C)
  • Trust inside a team tied to 75% less stress, 50% higher productivity (H)
  • Transparency by default can aid in building trust with remote teams (H)

Hiring

  • Ideal traits: bias to action, can prioritize, good written communication, trustworthy
  • Written (not just verbal) communication is so critical that you should evaluate it in hiring — insist on and evaluate a cover letter (C) (H)
  • Retaining existing folks with org knowledge is even more important in remote first (C)
  • If you pay top-band rates to every hiring market, you get an unfair hiring and retention advantage (C)
  • Engineers: ask the candidate to do real work, and pay for it, versus a coding interview, see also contract to perm (C)
  • Fully remote companies hire people 33% faster, and have 25% lower attrition (H)
  • Best selling points for candidates: flexible schedule, work from anywhere, no commute (H)

Onboarding

  • Buddy system, check-in via Slack multiple times a week

Focus / Time Management / Productivity

  • People need long stretches of uninterrupted time to get work done (C)
  • Real risk that people work too much, long hours (C) (H)
  • Best review of available research is not conclusive re: remote productivity (H)

Technology

  • Separate work/home devices (laptop and phone) for better separation (C)

Cost savings

  • Remote saves about $13k/year per employee in tech hubs vs having a dedicated office (H)

What’s Next

Again, I have not incorporated these leanings yet into daily practice. I hope to put some of these in to action over time, and write about my experiences. I also hope to find answers to some of the questions rolling around in my head, here at the start of this journey. How will the productivity of engineering be effected? How often will we collaborate, in person? How does this change how we hire people? Will engineering compensation change?

Stay tuned!