The Art of Distributed Work
Harnessing strengths & mitigating weaknesses
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Gonçalo 🇵🇹
@goncalossilva
Gonçalo 🇵🇹
@goncalossilva
15y of distwork
Freelance, contract, bootstrap
11y at Doist
Freelancer, IC, team leader, CXO
6y as CTO
Doist 🌐
doist.com
Doist 🌐
Bootstrapped
Fully distributed
Creators of Todoist & Twist
109 Doisters across 34 countries
Structure
Learning from history
Learning from Doist
Learning from history
Learning from Doist
Harnessing strengths and mitigating weaknessses
Learning from
History
Part 1
Old and ubiquitous
Distributed work
33–today
Catholic church
Fully distributed
Asynchronous work
Emissaries, books, letters
A-s-y-n-c-h-r-o-n-o-u-s
Insights
Extensive documentation
Catholic church
Insights
Thorough documentation
Clear roles
Catholic church
Insights
Thorough documentation
Clear responsibilities
(Dis)ambiguity
Catholic church
Insights
Thorough documentation
Clear responsibilities
Consolidation & flexibility
Old and ubiquitous
Telecommuting
500–1400
Middle ages
Working from home
Clear goal
Uninterrupted
Insights
Uninterrupted time
Middle ages
Insights
Uninterrupted time
Deep focus
Clear goals
Middle ages
Insights
Uninterrupted time
Deep focus
Clear goals
1300-1600
Renaissance
Build & sell
Insights
Renaissance
Insights
Uninterrupted time
Deep focus
Clear goals
Deliberate context switching
1670-today
Hudson's Bay Company
1670-today
Hudson's Bay Company
Research on dynamics, problems, and potential of distributed work
Distributed Work
Insights
Clear roles
HBC
Insights
Clear roles
Explicit information
HBC
Insights
Clear roles
Explicit information
Internal branding
HBC
Insights
Clear roles
Explicit information
Internal branding
Detailed record keeping
HBC
Insights
Clear roles
Explicit vision
Internal branding
Detailed record keeping
Trust and control
HBC
Insights
Clear roles
Explicit vision
Internal branding
Detailed record keeping
Trust but verify (and correct)
1991-today
Linux kernel
30 years of distributed development
25M+ lines of code
15K+ of individual contributors
1.5K+ active maintainers
Insights
Linux
Insights
Clear vision
Clear roles
Clear responsibilities
Good tools
Linux
Insights
Clear vision
Clear roles
Clear responsibilities
Good tools
Peer reviews
Linux
Insights
Clear vision
Clear roles
Clear responsibilities
Good tools
Peer reviews
Learning from
History
History
Insights
Thorough documentation
Clear vision and goals
Clear roles and responsibilities
Consolidated, but flexible
Autonomy, but peer reviewed
Deep focus, minimal interruptions and context switching
Internal branding
Good tools
Learning from
Doist
Part 2
Skin in the game
Freelancers?
Skin in the game
Freelancers
Skin in the game
Employement & benefits
Skin in the game
Hybrid
It's hard
Hybrid
Documentation
Documentation, documentation, documentation
Handbook
Documentation
Handbook
Documentation
Handbook
Documentation
Handbook
Documentation
Handbook
Documentation
Handbook
Documentation
Handbook
Documentation
Long-form text
Documentation
Long-form text
Documentation
Meetings
Documentation
Meeting
Documentation
Everything, all the time
Documentation
Internal branding
Core values
Internal branding
12 core values
Internal branding
12 5 core values
Internal branding
5 4 core values
Internal branding
Core values when hiring
Internal branding
Core values when onboarding
Internal branding
Autonomy & trust
Internal branding
High performance
Balance is timing, not intensity.
It is not doing multiple tasks at 80%, but developing the skill of turning it on and turning it off.
Sleep fully, then work intensely. Focus deeply, then relax completely. Give each phase your full attention.
Balance is “when to” not “how to.”
— James Clear
Intensity and competency
High performance
Clear expectations
High performance
Consistent delivery
High performance
High performance
Ownership with feedback
DRI
Ownership with feedback
Peer reviews
Ownership with feedback
Ownership with feedback
Manufactured serendipity
Retreats
Manufactured serendipity
Company retreat
Manufactured serendipity
Team retreat
Manufactured serendipity
Casual hangouts
Manufactured serendipity
Interest-based channels
Manufactured serendipity
Deliberate empathy
Manufactured serendipity
Deliberate empathy
Manufactured serendipity
Manufactured serendipity
Doist
Lessons
Skin in the game
Documentation
Internal branding
High performance
Ownership with feedback
Manufactured serendipity
Mitigating weaknesses
Harnessing strengths
Part 3
Deep work
Deep work
Flexibility
Deep work
Flexibility
Autonomy
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Silos
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Silos Documentation and transparency
Lack of mentoring
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Documentation and transparency
Lack of mentoring Peer reviews and collaboration
Lack of serendipity
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Documentation and transparency
Peer reviews and collaboration
Manufactured serendipity
Bonus
Explicit intent
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Documentation and transparency
Peer reviews and collaboration
Manufactured serendipity
Explicit intent
Mitigating weaknesses
Harnessing strengths
Deep work
Flexibility
Autonomy
Outcomes > outputs > inputs
Documentation and transparency
Peer reviews and collaboration
Manufactured serendipity
Explicit intent