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From Chaos to Confidence: DevOps at LeanKit

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Jon Terry
Jon Terry

This document outlines LeanKit's product development operating model, which aims to transition the organization from chaos to confidence. Key elements of the model include using Kanban and cadences to visualize and limit work-in-progress, organizing teams into squads and guilds for autonomous delivery, and holding regular meetings like tribal councils and architecture committees. The model emphasizes continuous delivery of value through deploying increments every 5 days, measuring outcomes, and improving collaboratively.

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@leankitjon From Chaos to Confidence: LeanKit’s PD Model Jon Terry
@leankitjon
@leankitjon
@leankitjon
@leankitjon
@leankitjon
@leankitjon
@leankitjon
From Chaos to Confidence: DevOps at LeanKit
From Chaos to Confidence: DevOps at LeanKit
From Chaos to Confidence: DevOps at LeanKit
From Chaos to Confidence: DevOps at LeanKit
From Chaos to Confidence: DevOps at LeanKit
@leankitjon Values First & Non-negotiable
@leankitjon Lean: A virtuous cycle of continuous improvement
@leankitjon Kanban: See better to evolve together 1. Visualize the current workflow 2. Limit Work-in-Progress (WIP) 3. Manage for smooth flow 4. Make process policies explicit 5. Implement rapid feedback loops 6. Improve collaboratively using Kanban to implement Lean
@leankitjon
From Chaos to Confidence: DevOps at LeanKit
@leankitjon
@leankitjon Jidoka: Auto(nom)ating for Scale
@leankitjon Andon: Slow down to speed up • Trying to solve a critical issue alongside normal work, or worse ignoring it, helps nobody • Everyone has the right and responsibility to call out what they believe to be critical issues • False alarms are OK • A stop-the-line involves a least a whole squad as well as any squad with experts needed for the issue • Communicate resolution as soon as practical • Don’t resume normal work until the team has done a root cause analysis
@leankitjon Org Structures for Autonomy
Guilds and Squads “Direct reporting” org chart Hiring Training Standards Mentoring Squad “Dotted line” delivery groups Goal is 7 +/- 2 members Has skills for 80% of work Member can belong to only 1 squad Located together (physically or virtually) Work assigned to the squad not squad members Guild
Guilds and Squads Web 1 Web 2 Mobile Arch, Tools & Auto Analytics Platform Ops Business Enablement Product Management & UX Product Development Operations & Quality
@leankitjon (Craft) Guilds - Hiring, Training & Standards
@leankitjon Squads - Decoupled Planning & Delivery
@leankitjon Squads - Decoupled Planning & Delivery
@leankitjon Squad Rooms - In Between Open and Individual
@leankitjon Tribal Council WhatWho When Discuss Road Map Departmental Policies Tribal Leaders PD Execs Council Members Product Managers UX Leads Technical Managers in their role as Delivery Leads Mon - Wed Stand-up to surface delivery issues Thu Full meeting to resolve issues
@leankitjon WhatWho When Discuss Technical standards AT-AT Roadmap Develop A3’s for additional sustainability investments Chairmen CTO & CIO Members Technical Managers in their role as Architects Tue Working session Thu Report back to Tribal Council Architecture Committee
@leankitjon Product Roadmap
@leankitjon Roadmap Forecasting Goal Squad Last This Sweep Next 2 Out Later 1 Rollout & Measurement Executing Pull Plan A3 & Mockups A3 Theme 2 Rollout & Measurement Theme N Rollout & Measurement A3 & Mockups A3 ThemeA3 & Mockups A3 Executing Pull Plan Executing Pull Plan
Value created Value captured Key metrics Definition Value of modeling Usage metrics (e.g., time to perform tasks / jobs) Economic value of Leankit for all customers and partners Easy to test for, fewer assumptions, shorter lead time Key assumptions comparable across projects (opportunity cost of users’ time, capture rate) Operational metrics: # of seats, ARPU, costs, etc Leankit profit Translates better to actual money in the bank (as long as assumptions are correct) Exec team prioritizes through Cost of Delay
@leankitjon A3s: A conversation not a contract A3 • The main communication artifact from the product team • Customer and user-driven • A living document • Handwritten in pencil • Designed to… make conversations happen
@leankitjon A3: A business problem not technical spec What is this? Why should I care? How?Who will notice? Why? What else?
@leankitjon Cadences
@leankitjon Aligning Cadence to Calendar 1 2 3 4 65 Jan 4 All Hands Annual Kickoff Board Jan 27 Feb 15 May 9 June 20 All Hands Mid-Year Party Board Sep 29 Aug 1Mar 28 All Leaders Board Apr 22 7 Sep 12 All Leaders Board Oct 21 8 Oct 24 Long sweep to allow for holidays
Work Distribution Goals ● Problems and operational requests are inevitable. We must allow for unplannable work ● People close to the work understand risks & quick wins better than management. We must allow time for them to do the right thing. ● We need to ensure as steady a flow as possible of planned roadmap work ● We use cadence to give ourselves the best chance of hitting these goals
Work Distribution by Cadence Week 0 Week 1 Week 2 Week 3 Week 5Week 4 Pull Planning Hackathon or Squad Driven Work A3 A3 A3A3
Pull Planning Week Monday Tuesday Wednesday FridayThursday All day Team Time Travel & Emerging Leaders Training 12:30 - 2:30 Squad Kickoff 9:00 - 11:00 Company All-Hands 3:00 - 5:00 Squad Kickoff 12:30 - 1:30 Tribal Council Sweep Kickoff 9:00 - 11:00 Squad Kickoff 12:30 - 2:30 Squad Kickoff 3:00 - 5:00 Squad Kickoff 12:30 - 2:30 Squad Kickoff 9:00 - 11:00 Squad Kickoff 2:00 - 5:00 Team Time 3:00 - 5:00 Team Time & Travel Company Fun Company Fun Company Fun 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep
@leankitjon ❏ Squad ❏ Is everybody dedicated to this squad #1? ❏ Does any member of this squad have work on other boards or in other squads? ❏ Product Roadmap ❏ Does everybody understand the A3 goal of this sweep? ❏ Is the A3 broken into DIV’s? ❏ Do we feel comfortable that we can meet the roadmap? ❏ Any blockers or risks? ❏ Squad Driven Work ❏ Any reason not to keep the normal schedule? ❏ Will we be ready to transition to A3 work at the beginning of week 2? ❏ Any blockers or risks? Squad Kickoff Template ❏ Tribal Council / Architecture Committee ❏ Any new technology or changes to cross cutting technology? ❏ Demo DIV ❏ What are we going to show at each meeting? ❏ What are we going to measure? ❏ Deployments to Production ❏ Demo DIV ❏ Anything Else? ❏ Continuous Improvement ❏ Any opportunities this sweep? ❏ Any bucks for Speed? ❏ Meeting Cadences ❏ Retros? ❏ Standups? ❏ When is this team coming to town this quarter?
@leankitjon ● Valuable small product ideas that are not on roadmap ● Requires squad consensus ● Does not require A3 or roadmap approval ● Can be: ○ Sustainability ○ UX improvements ○ Research for A3 submissions ● Executed by squads, but multi-squad collaboration projects are allowed Squad Driven Work
Week 1 - Squad Driven Work* Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Test / Deploy Deploy / Wrap- up *Unless A3 is date driven. Defer to week 5. 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 3:00 - 5:00 Guild Training
Week 2 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep 10:00 - 11:00 Company Trg
Week 3 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Company All Hands 3:00 - 5:00 Guild Training
Week 4 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep 10:00 - 11:00 Company Trg
Week 5 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dep All Hands 9:00 - 10:00 PD Execs
@leankitjon Demoing DIVs Purposeful Metrics
From business problem to working softwareTheme: Aligned with company strategy. Not always executed contiguously ≥ quarter A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task
@leankitjon How we’ll get value to users: • Release plans (i.e., how we get it to prod) • Rollout plans (i.e., how we enable it, editions, communication, etc) • Measurement plans What you’ll be demoing: • Reiterate the Theme • Explain what the A3 means for users • Explain the DIV in terms of A3 progress What? Name of A3 & DIV Why you’re demoing it: • Explain who will use it (i. e., target user) • Explain why it’s important (i.e., cost of delay or primary use case) So what? What now? This is in prod, either enabled for all or ready to be enabled This is in dogfood, we are planning to push to prod soon This is still in dev, not QA certified yet, still changing Value in hand of customer (pick one)
Deployments this Sweep - Ex
@leankitjon Hackathons
@leankitjon Hackathons ● 1st week of every 4th sweep ● Participants can be remote ● Self-organizing teams (recommended 7 max) ● No need for cost of delay analysis ● Appropriate things to hack on: ○ Experiments ○ Low hanging fruit ○ Research ● NOT for starting big projects ● When the week ends so does hackathon
@leankitjon Week 1 Hackathon Variant Monday 3/28 Tuesday 3/29 Wednesday 3/30 Friday 4/01 Thursday 3/31 Hacking 10:00 - 11:00 Hackathon Kickoff Hacking Hacking 10:00 - 11:00 Hackathon Judging Wrap-Up Hack Projects Transition to A3 Work
From Chaos to Confidence: DevOps at LeanKit
@leankitjon Most Likely to Succeed A feature, improvement, or technical debt reduction that has a very real chance of becoming a part of the LeanKit product.
@leankitjon Most Likely to Win a Nobel Prize Groundbreaking research, learning, or experiment that pertains to how we build LeanKit.
@leankitjon Best Personality A surprise hit that we couldn’t predict before Hackathon.
@leankitjon Results
@leankitjon Results ● Eight months of hitting roadmap with speed still increasing ● Higher product quality, less rework ● Significantly better morale in product development and relationship with revenue teams ● Sweep cycle becoming automatic, allowing time for kaizen ● More executive time for strategy instead of peacemaking
From Chaos to Confidence: DevOps at LeanKit
@leankitjon From Chaos to Confidence PD’s Operating Model

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From Chaos to Confidence: DevOps at LeanKit

  • 1. @leankitjon From Chaos to Confidence: LeanKit’s PD Model Jon Terry
  • 14. @leankitjon Values First & Non-negotiable
  • 15. @leankitjon Lean: A virtuous cycle of continuous improvement
  • 16. @leankitjon Kanban: See better to evolve together 1. Visualize the current workflow 2. Limit Work-in-Progress (WIP) 3. Manage for smooth flow 4. Make process policies explicit 5. Implement rapid feedback loops 6. Improve collaboratively using Kanban to implement Lean
  • 21. @leankitjon Andon: Slow down to speed up • Trying to solve a critical issue alongside normal work, or worse ignoring it, helps nobody • Everyone has the right and responsibility to call out what they believe to be critical issues • False alarms are OK • A stop-the-line involves a least a whole squad as well as any squad with experts needed for the issue • Communicate resolution as soon as practical • Don’t resume normal work until the team has done a root cause analysis
  • 23. Guilds and Squads “Direct reporting” org chart Hiring Training Standards Mentoring Squad “Dotted line” delivery groups Goal is 7 +/- 2 members Has skills for 80% of work Member can belong to only 1 squad Located together (physically or virtually) Work assigned to the squad not squad members Guild
  • 24. Guilds and Squads Web 1 Web 2 Mobile Arch, Tools & Auto Analytics Platform Ops Business Enablement Product Management & UX Product Development Operations & Quality
  • 25. @leankitjon (Craft) Guilds - Hiring, Training & Standards
  • 26. @leankitjon Squads - Decoupled Planning & Delivery
  • 27. @leankitjon Squads - Decoupled Planning & Delivery
  • 28. @leankitjon Squad Rooms - In Between Open and Individual
  • 29. @leankitjon Tribal Council WhatWho When Discuss Road Map Departmental Policies Tribal Leaders PD Execs Council Members Product Managers UX Leads Technical Managers in their role as Delivery Leads Mon - Wed Stand-up to surface delivery issues Thu Full meeting to resolve issues
  • 30. @leankitjon WhatWho When Discuss Technical standards AT-AT Roadmap Develop A3’s for additional sustainability investments Chairmen CTO & CIO Members Technical Managers in their role as Architects Tue Working session Thu Report back to Tribal Council Architecture Committee
  • 32. @leankitjon Roadmap Forecasting Goal Squad Last This Sweep Next 2 Out Later 1 Rollout & Measurement Executing Pull Plan A3 & Mockups A3 Theme 2 Rollout & Measurement Theme N Rollout & Measurement A3 & Mockups A3 ThemeA3 & Mockups A3 Executing Pull Plan Executing Pull Plan
  • 33. Value created Value captured Key metrics Definition Value of modeling Usage metrics (e.g., time to perform tasks / jobs) Economic value of Leankit for all customers and partners Easy to test for, fewer assumptions, shorter lead time Key assumptions comparable across projects (opportunity cost of users’ time, capture rate) Operational metrics: # of seats, ARPU, costs, etc Leankit profit Translates better to actual money in the bank (as long as assumptions are correct) Exec team prioritizes through Cost of Delay
  • 34. @leankitjon A3s: A conversation not a contract A3 • The main communication artifact from the product team • Customer and user-driven • A living document • Handwritten in pencil • Designed to… make conversations happen
  • 35. @leankitjon A3: A business problem not technical spec What is this? Why should I care? How?Who will notice? Why? What else?
  • 37. @leankitjon Aligning Cadence to Calendar 1 2 3 4 65 Jan 4 All Hands Annual Kickoff Board Jan 27 Feb 15 May 9 June 20 All Hands Mid-Year Party Board Sep 29 Aug 1Mar 28 All Leaders Board Apr 22 7 Sep 12 All Leaders Board Oct 21 8 Oct 24 Long sweep to allow for holidays
  • 38. Work Distribution Goals ● Problems and operational requests are inevitable. We must allow for unplannable work ● People close to the work understand risks & quick wins better than management. We must allow time for them to do the right thing. ● We need to ensure as steady a flow as possible of planned roadmap work ● We use cadence to give ourselves the best chance of hitting these goals
  • 39. Work Distribution by Cadence Week 0 Week 1 Week 2 Week 3 Week 5Week 4 Pull Planning Hackathon or Squad Driven Work A3 A3 A3A3
  • 40. Pull Planning Week Monday Tuesday Wednesday FridayThursday All day Team Time Travel & Emerging Leaders Training 12:30 - 2:30 Squad Kickoff 9:00 - 11:00 Company All-Hands 3:00 - 5:00 Squad Kickoff 12:30 - 1:30 Tribal Council Sweep Kickoff 9:00 - 11:00 Squad Kickoff 12:30 - 2:30 Squad Kickoff 3:00 - 5:00 Squad Kickoff 12:30 - 2:30 Squad Kickoff 9:00 - 11:00 Squad Kickoff 2:00 - 5:00 Team Time 3:00 - 5:00 Team Time & Travel Company Fun Company Fun Company Fun 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep
  • 41. @leankitjon ❏ Squad ❏ Is everybody dedicated to this squad #1? ❏ Does any member of this squad have work on other boards or in other squads? ❏ Product Roadmap ❏ Does everybody understand the A3 goal of this sweep? ❏ Is the A3 broken into DIV’s? ❏ Do we feel comfortable that we can meet the roadmap? ❏ Any blockers or risks? ❏ Squad Driven Work ❏ Any reason not to keep the normal schedule? ❏ Will we be ready to transition to A3 work at the beginning of week 2? ❏ Any blockers or risks? Squad Kickoff Template ❏ Tribal Council / Architecture Committee ❏ Any new technology or changes to cross cutting technology? ❏ Demo DIV ❏ What are we going to show at each meeting? ❏ What are we going to measure? ❏ Deployments to Production ❏ Demo DIV ❏ Anything Else? ❏ Continuous Improvement ❏ Any opportunities this sweep? ❏ Any bucks for Speed? ❏ Meeting Cadences ❏ Retros? ❏ Standups? ❏ When is this team coming to town this quarter?
  • 42. @leankitjon ● Valuable small product ideas that are not on roadmap ● Requires squad consensus ● Does not require A3 or roadmap approval ● Can be: ○ Sustainability ○ UX improvements ○ Research for A3 submissions ● Executed by squads, but multi-squad collaboration projects are allowed Squad Driven Work
  • 43. Week 1 - Squad Driven Work* Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Test / Deploy Deploy / Wrap- up *Unless A3 is date driven. Defer to week 5. 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 3:00 - 5:00 Guild Training
  • 44. Week 2 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep 10:00 - 11:00 Company Trg
  • 45. Week 3 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Company All Hands 3:00 - 5:00 Guild Training
  • 46. Week 4 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 9:00 - 10:00 PD Execs 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dem Div 9:00 - 10:00 Preso Prep 10:00 - 11:00 Company Trg
  • 47. Week 5 - Roadmap A3 Work Monday Tuesday Wednesday FridayThursday Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy Dev / Test / Deploy 10:00 - 11:00 Tribal Council 1:00 - 2:00 Arch. Comm. 10:00 - 11:00 Dep All Hands 9:00 - 10:00 PD Execs
  • 49. From business problem to working softwareTheme: Aligned with company strategy. Not always executed contiguously ≥ quarter A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task A3: Value reaches users inside a sweep. ≤ 4 weeks DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task DIV: Deployed. Iterative. Value. ≤ 5 days Task Task
  • 50. @leankitjon How we’ll get value to users: • Release plans (i.e., how we get it to prod) • Rollout plans (i.e., how we enable it, editions, communication, etc) • Measurement plans What you’ll be demoing: • Reiterate the Theme • Explain what the A3 means for users • Explain the DIV in terms of A3 progress What? Name of A3 & DIV Why you’re demoing it: • Explain who will use it (i. e., target user) • Explain why it’s important (i.e., cost of delay or primary use case) So what? What now? This is in prod, either enabled for all or ready to be enabled This is in dogfood, we are planning to push to prod soon This is still in dev, not QA certified yet, still changing Value in hand of customer (pick one)
  • 53. @leankitjon Hackathons ● 1st week of every 4th sweep ● Participants can be remote ● Self-organizing teams (recommended 7 max) ● No need for cost of delay analysis ● Appropriate things to hack on: ○ Experiments ○ Low hanging fruit ○ Research ● NOT for starting big projects ● When the week ends so does hackathon
  • 54. @leankitjon Week 1 Hackathon Variant Monday 3/28 Tuesday 3/29 Wednesday 3/30 Friday 4/01 Thursday 3/31 Hacking 10:00 - 11:00 Hackathon Kickoff Hacking Hacking 10:00 - 11:00 Hackathon Judging Wrap-Up Hack Projects Transition to A3 Work
  • 56. @leankitjon Most Likely to Succeed A feature, improvement, or technical debt reduction that has a very real chance of becoming a part of the LeanKit product.
  • 57. @leankitjon Most Likely to Win a Nobel Prize Groundbreaking research, learning, or experiment that pertains to how we build LeanKit.
  • 58. @leankitjon Best Personality A surprise hit that we couldn’t predict before Hackathon.
  • 60. @leankitjon Results ● Eight months of hitting roadmap with speed still increasing ● Higher product quality, less rework ● Significantly better morale in product development and relationship with revenue teams ● Sweep cycle becoming automatic, allowing time for kaizen ● More executive time for strategy instead of peacemaking
  • 62. @leankitjon From Chaos to Confidence PD’s Operating Model