This document discusses best practices for collaborating remotely based on scenarios where remote work failed. It recommends explicitly establishing deadlines, scopes of work, and action items with owners and due dates. It also suggests frequent communication, addressing issues immediately, dedicating time to employees, and setting clear expectations to avoid misunderstandings when working remotely.

1. Remote Control
collaborating in a remote environment

2. Zandy Ring
zandy@automattic.com
zandy.blog
@zandys
Elizabeth Urello
elizabeth@automattic.com
elizabeth.blog
@eurello

3. Deadlines are missed
Scenario 1

4. What went wrong?
• A deadline wasn’t established explicitly.
• The scope wasn’t defined and broken down into
steps that each had due dates.
• Everyone’s evaluation of the work to be done was
different.
• Check-ins were too infrequent, and there wasn’t
enough conversation happening.

5. A better way
Scenario 1

6. Takeaways
• When starting a project, always agree on a specific
deadline and scope. Make certain everyone involved
truly understands the deadline.
• Break the work into specific action items, and make
sure each one has an owner and a deadline.
• Put action items in writing and post them somewhere
everyone can view them at any time.
• Don’t wait for scheduled check in chats to
communicate obstacles.

7. Personality conflicts in a remote group
Scenario 2

8. What went wrong?
• The four volunteers didn’t get to know each other.
• The group never proactively discussed the sort of
culture they wanted.
• No one ever gave clear direct critical feedback.
• Everyone was aware there was a problem, but they
more or less ignored it.

9. A better way
Scenario 2

10. Takeaways
• Reach out to others regularly with small talk and with
both compliments and critical feedback, so that you
develop an ongoing relationship with each of them.
• Set expectations early on and agree to hold each other
accountable to them. Write the expectations down.
• When a problem arises with a colleague, deal with it
privately, immediately, and clearly.

11. Delivering critical feedback remotely
Scenario 3

12. What went wrong?
• Roz never took the time to fully understand what was
going wrong with Franz’s performance.
• She hadn’t been candid with him about his
performance, and what it means.
• She hadn’t considered his improvement as something
that she needed to work on with him, and something
that is an on-going project between the two of them.
• She also never given him the support he needed to
be successful in his role.

13. A better way
Scenario 3

14. Takeaways
• Dedicate time to your employees in order to work with
them on performance.
• Talk right away about issues, and if a problem
continues, step up your support.
• Acknowledge that performance issues are something
that you need to work on as a team, and address
them promptly.
• Try a variety of methods to communicate, like both
chat and video, and summarize both in writing after.

15. Meetings are getting in the way of remote work
Scenario 4

16. What went wrong?
• Dany knew there was an issue, but she didn’t make it
a priority to get to the bottom of it.
• The team knew that Jorah was getting left out of
conversations, but didn’t do a good job of including
remote workers.
• Jorah decided to just stop working from home,
instead of addressing the frustration he felt with Dany
and the other teams he works with.

17. A better way
Scenario 4

18. Takeaways
• Check in regularly about how things are going, and ask
about pain points.
• Be committed to helping remove roadblocks and make
necessary adjustments.
• Encourage your team to be willing to experiment to find a
solution, even if it means changing habits.
• Have a well-defined agenda ahead of meetings so that
remote worker(s) have time to come up with questions.
• Assign someone to keep the meeting on track and on
time.
• Make notes and action items available after the meeting.

19. Mismatch of expectations on the
work being done
Scenario 5

20. What went wrong?
• Bianca didn’t communicate her progress as she went
along, and Katherina didn’t ask.
• They acted as two separate individuals working on
different things, even though they were actually a
team collaborating on a shared project.

21. A better way
Scenario 5

22. Takeaways
• Assume nothing, and check in about everything.
• Share your work in progress frequently, and ask to
see your collaborators’ work.

23. Goal setting - how to get everyone to
accept the same goals and stay on
the same page
Scenario 6

24. What went wrong?
• Alvin, Simon, and Theodore agreed on a goal
(improve their support), but it wasn’t specific in any
way.
• They did not discuss what the expectations were for
each of them, in service to the goal.
• The three of them didn’t communicate with each other
at all.
• When things did not go as expected, they kept their
frustrations to themselves and just kept doing the
same thing.

25. A better way
Scenario 6

26. Takeaways
• Set goals that are very specific, and agree on a specific
timeframe for reaching those goals or reevaluating.
• Agree on a plan to meet the goals, and make sure each
participant understands their role.
• If work isn’t getting done as expected, don’t just let it go.
Talk about it together, and reevaluate the goals, come up
with a new plan, divide up tasks, assign participants, and
pick new deadlines.
• When working with a remote team, do not leave anything
up to guesswork.

27. Key Points
• Write down everything. Everything.
• Give all work specific goals, deadlines, and owners.
• Find a way to create the same ongoing conversations
you would have in real life while remote.
• Surface even minor problems or confusion early and
often. Don’t wait until it is too late.
• Don’t wait to share work until it’s completed.
• Have crucial conversations privately and in a format
that’s comfortable for both parties. Put the takeaways
in writing.
• When working with others remotely, do everything that
you would do in person, only moreso.