Principles of Project Management Flow Part 1 and 2

Bad project management makes everything _10x worse_. Good project management makes everything _10x better_. This talk shows how anyone can go from bad to good by understanding a few core principles and following a simple structure.

Relevant to anyone who works in a team. It can be summarised as “How to Jira without losing your mind.”

## Part 1: Principles

What drives good (and bad) project management, and how do we reason about visibility? We cover principles around these questions:

1. How and what to track? 🔎
2. Todo lists. Yay 🙌🏼 or Nay 👎🏼
3. Unambiguous Priority. What does that mean?
4. The thin and important line between busywork and prep work
5. What to communicate, what to avoid

## Part 2: Practical Considerations

Principles only take us so far; we still must deal with Jira.

We will make sense of Epics, User Stories, Labels, Swimlanes, etc.

1. What if you already have a project that’s messed up?
2. What if you’re starting from scratch?

Transcript

1. Principles of Project Management Flow A Playbook for effective work management
2. h/t Donald G. Reinertsen
3. Swanand Pagnis • CTO at CoLearn (Surge 3, 2020) • Track record of working on things before they became cool (or hot): • AI, ML (RE/MAX, 4 years) 🏠 • Fintech (Deserve, 1 year) 💳 • Last Mile (DispatchTrack, 5 years) 🚚 • 15+ years of all flavors of remote teams
4. Part 1: Principles — Why Part 2: Practicals — How
5. Part 1: Principles — Why Part 2: Practicals — How
6. First, some questions.
8. Lawn mowing, of course
10. Jigsaw Puzzles 🧩
13. Tidying Up 😰
15. Grocery Shopping! 🛍
16. • Are you done? • How much is done?
17. Lawn Mowing Jigsaw Puzzles Tidying Up Grocery Shopping
18. • Writing a long-form blog post 🖊 • Hiring 5 members for your team 👯 • Fundraising 💰 • Writing a novel 📖 • Getting a Ph.D. 👩🏫
19. • Retarget users on WhatsApp 📣 • Craft a Trial + Paid events schedule 📆 • Increase Retention by X% 📈 • Mute bad words in uploaded videos 📹 • E-receipts system for PoS customers 🧾
20. • Are you done? • How much is done? • Collaboration needed
21. • Work is complex, with many to-dos
22. • Work is complex, with many to-dos • Different things take different times
23. • Work is complex, with many to-dos • Different things take different times • Multiple people need to do things in parallel
24. • Work is complex, with many to-dos • Different things take different times • Multiple people need to do things in parallel • Multiple people need to do things sequentially
25. Show of Hands 🤚
26. You felt like there were too many things on your mind.
27. Sometimes, you are in the "zone" and you work at 10x your normal.
28. You felt like you really need help on something.
29. • What are you working on? • When will this be done? • Where are we with this?
30. You have too many things to do, yet you struggle to pick one and roll with it.
31. You were working on something, but something else came up, and it has now occupied your headspace.
32. Have I missed something? I need an extra set of eyes.
33. You're not alone.
34. Solution?
35. Todo lists? 🗒 🤔
36. Two Problems • Single list, so less freedom, more restrictive structure.
37. Two Problems • Single list, so less freedom, more restrictive structure. • Tasks have only two states: pending and done
38. Enter Boards. 🐉
39. Why? • 🧠 Offload your brain • 📚 Batch your work • 🤝 Collaborate on tasks • 🔮 One look update • 👓 Clarity, looking ahead, and retrospective • 📥 Capture incoming work better • 👀 A second set of eyes
40. How? 🤔
41. Six Principles • 1⃣ Track all the work. All. Document every single task that needs to be done. 🌟 • This is important — your brain needs to develop belief in this system, and that can only happen if everything gets captured as a habit. • My favorite question about Jira boards is...
42. Six Principles • 1⃣ Track all the work. All. Document every single task that needs to be done. 🌟 • This is important — your brain needs to develop belief in this system, and that can only happen if everything gets captured as a habit. • Is the Jira board an accurate representation of all work?
43. Six Principles • 2⃣ Start with 4 simple lists • To Do ☑ • Doing 🧗 • Review 🕵 • Done 🏆
44. Six Principles • 3⃣ Work Right to Left, Top to Bottom • Right to left: • Always finish ongoing work first • Prioritize reviewing and unblocking • Top to bottom: Priority order
45. Six Principles • 4⃣ Divide the work into tasks of 1 or 2 days max • Anything larger: Split into smaller chunks • Engage in some upfront thinking • This helps with estimates and timelines
46. Six Principles • 5⃣ Why > What >> How • Start cards with "why" to provide context • Otherwise, we run the risk of becoming "JIRA card pushers"
47. Six Principles • 6⃣ Describe the finish line, not the route. • "Done" is essential. What do we mean by done? • There is a lovely term called "acceptance criteria." Use it well. • Don't write "how to do this" on the card.
48. Six Principles 1. Track all the work. All. 2. Start with four lists: Todo, Doing, Review, and Done. 3. Work from Right to Left, Top to Bottom. 4. Divide work into 1 or 2-day chunks 5. Focus on Why and Context. 6. Describe the finish line, not the route.
49. 🧢 Recap Lawn Mowing Jigsaw Puzzles Tidying Up Grocery Shopping
50. Questions?
51. Part 1: Principles — Why Part 2: Practicals — How
52. 🤔
53. ✅ 🤦
54. Tools of the Trade • Subtasks • Tasks • User Stories • Epics • Projects • Sprints • Statuses • Labels • Swimlanes
55. Task • Work that needs to be tracked • Typically not user-facing • No more than a few days, 1 to 2 is best
56. Task • Work that needs to be tracked • Typically not user-facing • No more than a few days, 1 to 2 is best
57. Subtask • Work that doesn't need to be independently tracked • At the discretion of the task owner(s) • No more than 1 day
58. Six Principles 1. Track all the work. All. 2. Start with four lists: Todo, Doing, Review, and Done. 3. Work from Right to Left, Top to Bottom. 4. Divide work into 1 or 2-day chunks 5. Focus on Why and Context. 6. Describe the finish line, not the route.
59. 🌟 User Story 🌟 • User facing work • Independently verifiable • The primary unit of work
60. 🌟 User Story 🌟 • User facing work • Independently verifiable • The primary unit of work
61. 🌟 User Story 🌟 • When in doubt about "Task" vs. "User Story," create a user story
62. 🌟 User Story 🌟 • When in doubt about "Task" vs. "User Story," create a user story • They bring user-centric thinking into work
63. As a student, I want to get a reminder before a class, so that I will not miss the class.
64. As a student, I want to get a reminder before a class, so that I will not miss the class.
65. Six Principles 1. Track all the work. All. 2. Start with four lists: Todo, Doing, Review, and Done. 3. Work from Right to Left, Top to Bottom. 4. Divide work into 1 or 2-day chunks 5. Focus on Why and Context. 6. Describe the finish line, not the route.
66. Send a reminder to students 5 minutes before a class.
67. Epic • Larger body of work • Needs multiple user stories • Should have a start and end date
68. Epic • Larger body of work • Needs multiple user stories • Should have a start and end date
69. Project • Ongoing responsibility or initiative • A team level entity • Does not "end" 🤨
70. 🌟 Sprint 🌟 • Represents Cadence • An excellent planning tool • Has a start and end date • 1 to 2 weeks
71. "Okay, but I already have a project, and it's a mess! 🤦"
72. If you already have a project • Capture all work that hasn't been captured • Create Epics with tentative date — categorize all your WIP finishable pieces of work into these • Have 3 upcoming sprints filled up with the work categorized above
73. If starting from scratch • Capture all work that hasn't been captured. • Create Epics with tentative date — categorize all your WIP finishable pieces of work into these • Have 3 upcoming sprints filled up with the work categorized above
74. Six Principles 1. Track all the work. All. 2. Start with four lists: Todo, Doing, Review, and Done. 3. Work from Right to Left, Top to Bottom. 4. Divide work into 1 or 2-day chunks 5. Focus on Why and Context. 6. Describe the finish line, not the route.
75. Labels! 🏷
76. Labels are Powerful 🦾 • Flexible • Searchable • First-class support in all tools
77. Horizontal and vertical categorization at the same time is only possible with labels.
78. When it comes to information architecture, you're worse than you think you are.
79. Swimlanes 🏊
80. Swimlanes are a review tool • Vertically group and divide the work. e.g. One swim lane per Product Manager • A tool for leadership — you must get good at swimlanes • Review board weekly through various swimlanes: by Assignee, by Epic, by Label
81. Process 📐
82. • Think in terms of the Roadmap
83. • Think in terms of the Roadmap • Break it down into Epics
84. • Think in terms of the Roadmap • Break it down into Epics • Break them down into User Stories
85. • Think in terms of the Roadmap • Break it down into Epics • Break them down into User Stories • Use Sprints to drive cadence
86. Sprints are a cadence mechanism, not a release mechanism. 💡
87. Everyday Operations • Optimize for left-to-right movement of cards • Too big a card won't move fast • Too many small cards overwhelm with volume • Priority must be visually clear • Keep the "TODO" column sorted by priority • Revisit the Backlog once a month
88. Six Principles 1. Track all the work. All. 2. Start with four lists: Todo, Doing, Review, and Done. 3. Work from Right to Left, Top to Bottom. 4. Divide work into 1 or 2-day chunks 5. Focus on Why and Context. 6. Describe the finish line, not the route.
89. Thank you! 🙏
90. Questions?