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Principles of Project Management Flow A Playbook for effective work management

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h/t Donald G. Reinertsen

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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

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Part 1: Principles — Why Part 2: Practicals — How

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Part 1: Principles — Why Part 2: Practicals — How

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First, some questions.

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Lawn mowing, of course

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Jigsaw Puzzles 🧩

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Tidying Up 😰

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Grocery Shopping! 🛍

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• Are you done? • How much is done?

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Lawn Mowing Jigsaw Puzzles Tidying Up Grocery Shopping

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• Writing a long-form blog post 🖊 • Hiring 5 members for your team 👯 • Fundraising 💰 • Writing a novel 📖 • Getting a Ph.D. 👩🏫

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• 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 🧾

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• Are you done? • How much is done? • Collaboration needed

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• Work is complex, with many to-dos

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• Work is complex, with many to-dos • Different things take different times

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• Work is complex, with many to-dos • Different things take different times • Multiple people need to do things in parallel

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• 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

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Show of Hands 🤚

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You felt like there were too many things on your mind.

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Sometimes, you are in the "zone" and you work at 10x your normal.

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You felt like you really need help on something.

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• What are you working on? • When will this be done? • Where are we with this?

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You have too many things to do, yet you struggle to pick one and roll with it.

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You were working on something, but something else came up, and it has now occupied your headspace.

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Have I missed something? I need an extra set of eyes.

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You're not alone.

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Solution?

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Todo lists? 🗒 🤔

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Two Problems • Single list, so less freedom, more restrictive structure.

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Two Problems • Single list, so less freedom, more restrictive structure. • Tasks have only two states: pending and done

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Enter Boards. 🐉

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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

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How? 🤔

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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...

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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?

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Six Principles • 2⃣ Start with 4 simple lists • To Do ☑ • Doing 🧗 • Review 🕵 • Done 🏆

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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

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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

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Six Principles • 5⃣ Why > What >> How • Start cards with "why" to provide context • Otherwise, we run the risk of becoming "JIRA card pushers"

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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.

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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.

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🧢 Recap Lawn Mowing Jigsaw Puzzles Tidying Up Grocery Shopping

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Questions?

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Part 1: Principles — Why Part 2: Practicals — How

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🤔

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✅ 🤦

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Tools of the Trade • Subtasks • Tasks • User Stories • Epics • Projects • Sprints • Statuses • Labels • Swimlanes

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Task • Work that needs to be tracked • Typically not user-facing • No more than a few days, 1 to 2 is best

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Task • Work that needs to be tracked • Typically not user-facing • No more than a few days, 1 to 2 is best

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Subtask • Work that doesn't need to be independently tracked • At the discretion of the task owner(s) • No more than 1 day

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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.

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🌟 User Story 🌟 • User facing work • Independently verifiable • The primary unit of work

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🌟 User Story 🌟 • User facing work • Independently verifiable • The primary unit of work

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🌟 User Story 🌟 • When in doubt about "Task" vs. "User Story," create a user story

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🌟 User Story 🌟 • When in doubt about "Task" vs. "User Story," create a user story • They bring user-centric thinking into work

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As a student, I want to get a reminder before a class, so that I will not miss the class.

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As a student, I want to get a reminder before a class, so that I will not miss the class.

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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.

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Send a reminder to students 5 minutes before a class.

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Epic • Larger body of work • Needs multiple user stories • Should have a start and end date

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Epic • Larger body of work • Needs multiple user stories • Should have a start and end date

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Project • Ongoing responsibility or initiative • A team level entity • Does not "end" 🤨

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🌟 Sprint 🌟 • Represents Cadence • An excellent planning tool • Has a start and end date • 1 to 2 weeks

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"Okay, but I already have a project, and it's a mess! 🤦"

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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

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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

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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.

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Labels! 🏷

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Labels are Powerful 🦾 • Flexible • Searchable • First-class support in all tools

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Horizontal and vertical categorization at the same time is only possible with labels.

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When it comes to information architecture, you're worse than you think you are.

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Swimlanes 🏊

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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

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Process 📐

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• Think in terms of the Roadmap

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• Think in terms of the Roadmap • Break it down into Epics

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• Think in terms of the Roadmap • Break it down into Epics • Break them down into User Stories

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• Think in terms of the Roadmap • Break it down into Epics • Break them down into User Stories • Use Sprints to drive cadence

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Sprints are a cadence mechanism, not a release mechanism. 💡

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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

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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.

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Thank you! 🙏

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Questions?