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Moving 65,000 Microsofties to DevOps with VSTS
Willy-Peter Schaub
Willy[-Peter] Schaub
Program Manager | Developer Ops Canada
willys@microsoft.com
@wpschaub
I work
here
I was born here
I grew up here
Truk Lagoon
Semiahmoo Bay
Protea Banks
Hawaii
Wondergat
Aliwal Shoal
Truk Lagoon
DevOps
Visual Studio
Application Insights
Any language, Any Platform
One Engineering System using VSTS
What is DevOps?
Increase flow of value Shorten cycle times Continuously Improve
Our Definition of Done
Customer Focused
STARTOF OUR JOURNEY
August 2010
Sprint 1
Extensions
Nov 2015
Sprint 931ES
June 2014
Sprint 67
GVFS
June 2016
Sprint 102
Ranger community
adopted VSTS
April 2011
VSTS
April 2014
Sprint 64
over night 
~destination! 
continuous innovation! 
Five habits we’ve learned so far
++
++
++
Five habits we’ve learned so far
Listen to our customers
Customer Focused
Collect data
broadly (but carefully)
But measure what’s important (KPI’s)
Customer Focused
• Original estimate
• Completed hours
• Lines of Code
• Team capacity
• Team burndown
• Team velocity
• # of bugs found
Things we don’t watch
• Acquisition
• Engagement
• Satisfaction
• Churn
• Feature Usage
Usage
• Time to Detect
• Time to Communicate
• Time to Mitigate
• Customer Impact
• Incident Prevention Items
• Aging Live Site Problems
• SLA per Customer
• Customer Support Metrics
Live Site Health
• Time to Build
• Time to Self Test
• Time to Deploy
• Time to Learn
Process Velocity
Maximize learning and influence value
Customer Focused
Validatedlearning
Deployment frequency
PROVEN DISPROVEN
VALIDATE
business
service
value
Feature Flags – fine tune user experience
Customer Focused
if ( flag )
else
Five habits we’ve learned so far
Live Site Incidents
Be Transparent
Production First Mindset
Alerting is the key to fast detection
Production First Mindset
Before
• Redundant alerts for same the issue
• Needed to set right thresholds and
tune often
• Stateless alerts contributed to
further noise
After
• Every alert must be actionable and
represent a real issue with the
system.
• Alerts should create a sense of
urgency – false alerts dilutes that
• Use alerts to auto-dial the DRIs.
Automate completely
Tracking Deployments to Production
Circuit Breakers
https://github.com/Netflix/Hystrix/wiki
Security Mindset
Production First Mindset
 Double blind test
 Full disclosure at or near end
vs.
 Share tactics & lessons learned
 Continued evolution
Assume Breach - Use War Games to the learn attacks and practice response
Five habits we’ve learned so far
Agile at Scale with Aligned Autonomy
Team Autonomy & Enterprise Alignment
Alignment
within the
business
Team
autonomy
“Let’s try to give our teams three things….
Autonomy, Mastery, Purpose”
Anarchy
Team Autonomy & Enterprise Alignment
Roles
Team Autonomy & Enterprise Alignment
Program Management Dev Test
Roles
Team Autonomy & Enterprise Alignment
Program Management Engineering
Yes, there are other roles…
Team Autonomy & Enterprise Alignment
Program Management Engineering Service DeliveryUX UE
Service Delivery is integrated
directly into our organization.
Teams
Team Autonomy & Enterprise Alignment
Program Management is responsible for:
WHAT we’re building, and
WHY we’re building it
Engineering is responsible for
HOW we’re building it, and that
we’re building it with QUALITY
Teams
 Physical team rooms
 Cross discipline
 10-12 people
 Self managing
 Clear charter and goals
 Intact for 12-18 months
 Own features in production
 Own deployment of features
Instead of Horizontal…
Team Autonomy & Enterprise Alignment
UI
API
Data
We strive for Vertical
Team Autonomy & Enterprise Alignment
UI
API
Data
Employee choice, not
manager driven
Typically <20%
change, but 100% get
to make a choice
Cross-pollinate talent
and micro-culture
Sticky Note Exercise - Self Forming Teams
Sprint
3 weeks
confident
1
Plan
3 sprints
thoughtful
3
Season
6 months
hopeful
6
Planning
Team Autonomy & Enterprise Alignment
Scenario
18 months
asprirational
Teams are responsible for the detail
Leadership is responsible
for driving the big picture
Planning
Team Autonomy & Enterprise Alignment
Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
18 month scenario
6 month plan
Planning
Team Autonomy & Enterprise Alignment
Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
18 month scenario
6 month plan
Planning
Team Autonomy & Enterprise Alignment
Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
18 month scenario
6 month plan
Planning
Team Autonomy & Enterprise Alignment
Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
18 month scenario
6 month plan
Traditional Planning
Team Autonomy & Enterprise Alignment
TIME
VALUE
Plan, Deliver, and Learn
Team Autonomy & Enterprise Alignment
TIME
VALUE
Let’s Compare
Team Autonomy & Enterprise Alignment
What we accomplished
3 week sprints
Team Autonomy & Enterprise Aligmen
Progressive
Deployment
Week 1 Week 2 Week 3
Week 1 Week 2 Week 3Week 2 Week 3
Sprint 98Sprint 97 Sprint 99
The sprint plan
930!
Sprint mails
Team Chats
Team Autonomy & Enterprise Alignment
SpringFallSpring Fall
3 sprints
Direct. No “lost in translation”.
Team Autonomy & Enterprise Alignment
Experience Reviews
Team Autonomy & Enterprise Alignment
SpringFallSpring Fall
Benefits
Team Autonomy & Enterprise Alignment
Five habits we’ve learned so far
engineers on
your team#
Bug Cap
Shift Left Quality
5 ?x =
Bug Cap
Shift Left Quality
Rule: If your bug count exceeds your bug cap… stop working
on new features until you’re back under the cap.
5 50x =10
Code Test & Stabilize Code Test & Stabilize
Code
Complete
Planning
Before – Debt Cycle
Shift Left Quality
After
Shift Left Quality
• Tests that anyone can run anywhere (inc production)
• Shifted to unit tests from automated functional tests
• Core tests run before pull request
• Fast and 100% reliable build and test is critical
• Rolling tests run after commit
Test Portfolio - Shift Left from Integration to Unit
Pull Requests 
Release Flow Branching Structure
Shift Left Quality
LSI
Five habits we’ve learned so far
Customer Focused
Production First Mindset
Team Autonomy + Enterprise Alignment
Shift Left Quality
Infrastructure as Flexible Resource
From Labs to VM’s to DevTest Labs
Multiple Data Centers with incremental roll out
Shared Platform Services (SPS)
North Central
TFS SU1
North Central
AT
AT
AT
JA
JA
JA
Blob
TFS SU7
Australia
TFS SU0
West Central
Containerized Services
Architecture Modernization
•
•
•
•
•
• If you are starting out today and cloud native, consider
PaaS, Service Fabric + Azure Functions
• We need to ship same code to on-prem & cloud
DevOps isn’t magic
Our DevOps Transformation – the story so far
After
• 3-week sprints
• Vertical teams
• Team rooms
• Continual Planning & Learning
• PM & Engineering
• Continual customer engagement
• Everyone in master
• 8-12 person teams
• Publicly shared roadmap
• Zero debt
• Mockups in PPT
• Inner source
• Flattened organization hierarchy
• User satisfaction determines success
• Features shipped every sprint
Before
• 4-6 month milestones
• Horizontal teams
• Personal offices
• Long planning cycles
• PM, Dev, Test
• Yearly customer engagement
• Feature branches
• 20+ person teams
• Secret roadmap
• Bug debt
• 100 page spec documents
• Private repositories
• Deep organizational hierarchy
• Success is a measure of install numbers
• Features shipped once a year
Lastly the DevOps Ranger Transformation
DevOps even works for a part-time open source community 
After
• 2-5 person teams
• 0.25 program managers
• Automated CI
• Automated CD
• 3-5 sprints cadence
• 3-week sprints
• Proactive telemetry
• Minutes to days to resolve issues
• Minutes to build
• Minutes to release
Before
• 10-15 person teams
• 2 program managers
• Manual and error prone builds
• Manual and error probe releases
• 6-12 sprint cadence
• 1 month sprints
• Issues detected by users
• Days to weeks to resolve issues
• Hours to build
• Days to release
Quick Reference Posters – ping me if you’re interested in a digital copy!
Real-world demo




 
/* THANK YOU*/
WILLY SCHAUB
willys@microsoft.com
@wpschaub
aka.ms/devops
aka.ms/devopsassessment
aka.ms/vsarpublications
@VSTS
http://www.devconf.co.za/

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Devconf - Moving 65000 Microsofties to DevOps with Visual Studio Team Services

  • 1. Moving 65,000 Microsofties to DevOps with VSTS Willy-Peter Schaub
  • 2. Willy[-Peter] Schaub Program Manager | Developer Ops Canada willys@microsoft.com @wpschaub
  • 3. I work here I was born here I grew up here
  • 4. Truk Lagoon Semiahmoo Bay Protea Banks Hawaii Wondergat Aliwal Shoal Truk Lagoon
  • 7. What is DevOps? Increase flow of value Shorten cycle times Continuously Improve
  • 8. Our Definition of Done Customer Focused
  • 9. STARTOF OUR JOURNEY August 2010 Sprint 1 Extensions Nov 2015 Sprint 931ES June 2014 Sprint 67 GVFS June 2016 Sprint 102 Ranger community adopted VSTS April 2011 VSTS April 2014 Sprint 64 over night  ~destination!  continuous innovation! 
  • 10. Five habits we’ve learned so far ++ ++ ++
  • 11. Five habits we’ve learned so far
  • 12. Listen to our customers Customer Focused
  • 14. But measure what’s important (KPI’s) Customer Focused • Original estimate • Completed hours • Lines of Code • Team capacity • Team burndown • Team velocity • # of bugs found Things we don’t watch • Acquisition • Engagement • Satisfaction • Churn • Feature Usage Usage • Time to Detect • Time to Communicate • Time to Mitigate • Customer Impact • Incident Prevention Items • Aging Live Site Problems • SLA per Customer • Customer Support Metrics Live Site Health • Time to Build • Time to Self Test • Time to Deploy • Time to Learn Process Velocity
  • 15. Maximize learning and influence value Customer Focused Validatedlearning Deployment frequency PROVEN DISPROVEN VALIDATE business service value
  • 16. Feature Flags – fine tune user experience Customer Focused if ( flag ) else
  • 17. Five habits we’ve learned so far
  • 20. Alerting is the key to fast detection Production First Mindset Before • Redundant alerts for same the issue • Needed to set right thresholds and tune often • Stateless alerts contributed to further noise After • Every alert must be actionable and represent a real issue with the system. • Alerts should create a sense of urgency – false alerts dilutes that • Use alerts to auto-dial the DRIs.
  • 24. Security Mindset Production First Mindset  Double blind test  Full disclosure at or near end vs.  Share tactics & lessons learned  Continued evolution Assume Breach - Use War Games to the learn attacks and practice response
  • 25. Five habits we’ve learned so far
  • 26. Agile at Scale with Aligned Autonomy Team Autonomy & Enterprise Alignment Alignment within the business Team autonomy “Let’s try to give our teams three things…. Autonomy, Mastery, Purpose” Anarchy
  • 27.
  • 28. Team Autonomy & Enterprise Alignment
  • 29. Roles Team Autonomy & Enterprise Alignment Program Management Dev Test
  • 30. Roles Team Autonomy & Enterprise Alignment Program Management Engineering
  • 31. Yes, there are other roles… Team Autonomy & Enterprise Alignment Program Management Engineering Service DeliveryUX UE Service Delivery is integrated directly into our organization.
  • 32. Teams Team Autonomy & Enterprise Alignment Program Management is responsible for: WHAT we’re building, and WHY we’re building it Engineering is responsible for HOW we’re building it, and that we’re building it with QUALITY
  • 33. Teams  Physical team rooms  Cross discipline  10-12 people  Self managing  Clear charter and goals  Intact for 12-18 months  Own features in production  Own deployment of features
  • 34. Instead of Horizontal… Team Autonomy & Enterprise Alignment UI API Data
  • 35. We strive for Vertical Team Autonomy & Enterprise Alignment UI API Data
  • 36. Employee choice, not manager driven Typically <20% change, but 100% get to make a choice Cross-pollinate talent and micro-culture Sticky Note Exercise - Self Forming Teams
  • 37. Sprint 3 weeks confident 1 Plan 3 sprints thoughtful 3 Season 6 months hopeful 6 Planning Team Autonomy & Enterprise Alignment Scenario 18 months asprirational Teams are responsible for the detail Leadership is responsible for driving the big picture
  • 38. Planning Team Autonomy & Enterprise Alignment Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 18 month scenario 6 month plan
  • 39. Planning Team Autonomy & Enterprise Alignment Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 18 month scenario 6 month plan
  • 40. Planning Team Autonomy & Enterprise Alignment Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 18 month scenario 6 month plan
  • 41. Planning Team Autonomy & Enterprise Alignment Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 18 month scenario 6 month plan
  • 42. Traditional Planning Team Autonomy & Enterprise Alignment TIME VALUE
  • 43. Plan, Deliver, and Learn Team Autonomy & Enterprise Alignment TIME VALUE
  • 44. Let’s Compare Team Autonomy & Enterprise Alignment
  • 45. What we accomplished 3 week sprints Team Autonomy & Enterprise Aligmen Progressive Deployment Week 1 Week 2 Week 3 Week 1 Week 2 Week 3Week 2 Week 3 Sprint 98Sprint 97 Sprint 99 The sprint plan 930!
  • 47. Team Chats Team Autonomy & Enterprise Alignment SpringFallSpring Fall 3 sprints
  • 48. Direct. No “lost in translation”. Team Autonomy & Enterprise Alignment
  • 49. Experience Reviews Team Autonomy & Enterprise Alignment SpringFallSpring Fall
  • 50. Benefits Team Autonomy & Enterprise Alignment
  • 51. Five habits we’ve learned so far
  • 52. engineers on your team# Bug Cap Shift Left Quality 5 ?x =
  • 53. Bug Cap Shift Left Quality Rule: If your bug count exceeds your bug cap… stop working on new features until you’re back under the cap. 5 50x =10
  • 54. Code Test & Stabilize Code Test & Stabilize Code Complete Planning Before – Debt Cycle Shift Left Quality
  • 56. • Tests that anyone can run anywhere (inc production) • Shifted to unit tests from automated functional tests • Core tests run before pull request • Fast and 100% reliable build and test is critical • Rolling tests run after commit Test Portfolio - Shift Left from Integration to Unit
  • 58. Release Flow Branching Structure Shift Left Quality LSI
  • 59. Five habits we’ve learned so far Customer Focused Production First Mindset Team Autonomy + Enterprise Alignment Shift Left Quality Infrastructure as Flexible Resource
  • 60. From Labs to VM’s to DevTest Labs
  • 61. Multiple Data Centers with incremental roll out Shared Platform Services (SPS) North Central TFS SU1 North Central AT AT AT JA JA JA Blob TFS SU7 Australia TFS SU0 West Central Containerized Services
  • 62. Architecture Modernization • • • • • • If you are starting out today and cloud native, consider PaaS, Service Fabric + Azure Functions • We need to ship same code to on-prem & cloud
  • 64. Our DevOps Transformation – the story so far After • 3-week sprints • Vertical teams • Team rooms • Continual Planning & Learning • PM & Engineering • Continual customer engagement • Everyone in master • 8-12 person teams • Publicly shared roadmap • Zero debt • Mockups in PPT • Inner source • Flattened organization hierarchy • User satisfaction determines success • Features shipped every sprint Before • 4-6 month milestones • Horizontal teams • Personal offices • Long planning cycles • PM, Dev, Test • Yearly customer engagement • Feature branches • 20+ person teams • Secret roadmap • Bug debt • 100 page spec documents • Private repositories • Deep organizational hierarchy • Success is a measure of install numbers • Features shipped once a year
  • 65. Lastly the DevOps Ranger Transformation DevOps even works for a part-time open source community  After • 2-5 person teams • 0.25 program managers • Automated CI • Automated CD • 3-5 sprints cadence • 3-week sprints • Proactive telemetry • Minutes to days to resolve issues • Minutes to build • Minutes to release Before • 10-15 person teams • 2 program managers • Manual and error prone builds • Manual and error probe releases • 6-12 sprint cadence • 1 month sprints • Issues detected by users • Days to weeks to resolve issues • Hours to build • Days to release
  • 66. Quick Reference Posters – ping me if you’re interested in a digital copy!
  • 69. /* THANK YOU*/ WILLY SCHAUB willys@microsoft.com @wpschaub aka.ms/devops aka.ms/devopsassessment aka.ms/vsarpublications @VSTS http://www.devconf.co.za/