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Rule Your Roadmap ,[object Object],[object Object],David Etheridge Sr. Director, PMO Tiny Prints (Shutterfly)
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
About Me ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],Project & Program Management since 1992:
Why a Roadmap

Strategic Planning ,[object Object],[object Object],[object Object],[object Object]
Navigate Change ,[object Object],[object Object],[object Object]
ROADMAP NEW PROJECT “ TORPEDOS”
What Fails

My Roadmap Delusions ,[object Object],[object Object],[object Object],[object Object],[object Object]
What Works

Sprints  Work, 2 wks at a time ,[object Object],[object Object]
A Roadmap is a Sprint
 a really big one
Recipe ,[object Object],Excel Collaboration Confluence Projectors Serving >100 Projects in 2011
Garbage In, Garbage Out
First:  Put Your Roadmap In JIRA
Roadmap Pivot
Second:  Collaborate ,[object Object],[object Object],[object Object],[object Object]
Project A Project A SPRINTS DOERS JIRA ROADMAP Project B Project C Project A Project D EXECS JIRA MANAGERS  CONF USER STORIES
Third:  Off-The-Wall Meetings
ROADMAP PROJECTS SPRINTS
Why Collaborate? ,[object Object],[object Object],[object Object],[object Object]
Ecosystem of Artifacts ROADMAP UI Designs Backlogs Project Dashboards Release Notes Sprints Product Definition User Stories Resource Map Mtg Minutes
Torpedo Management
Change Permeates Ecosystem ROADMAP UI Designs Backlogs Project Dashboards Release Notes Sprints Product Definition User Stories Resource Map Mtg Minutes
Benefits ,[object Object],[object Object],[object Object],[object Object],[object Object]
Benefits (cont’d) ,[object Object],[object Object],[object Object]
Ignorance Wasn’t Bliss
 

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Rule Your Roadmap: Stay on track, no matter how much it moves

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  1. What I must stress is that, like any recipe, this one is subject to Garbage In, Garbage Out. This requires your organization has a handle on who’s-doing-what day-to-day, as well as roadmap objectives for the year. This method definitely highlights where either of these two are lacking. It really drove home the value of early Product Definition and scoping, which is now something my organization does out of habit.
  2. What I must stress is that, like any recipe, this one is subject to Garbage In, Garbage Out. This requires your organization has a handle on who’s-doing-what day-to-day, as well as roadmap objectives for the year. This method definitely highlights where either of these two are lacking. It really drove home the value of early Product Definition and scoping, which is now something my organization does out of habit.
  3. The purpose of a roadmap is to align thinking around strategic initiatives AND choose the most valuable projects in support of those initiatives that can be delivered with limited time and resources. It also allows for slotting projects to deliver at key times of the year to support market events. It’s the IMMUTABLE GRAND VISION for BLINDING SUCCESS Of course, the integrity of the IMMUTABLE GRAND VISION is SHORT-LIVED. Week-to-week IRRESISTABLE forces are INJECTING CHANGE: New project opportunities force project swap decisions Scope creep calls ROI into question and/or the question of cannibalizing existing projects – “Stick with it or Move On? Better keep track of all the changes so you have a basis for continuous improvement, but also because, six months later, execs will forget why their project got cut. To be useful, IMMUTABLE Roadmaps must accommodate CONTINUOUS CHANGE.
  4. We make customized personal stationery and greeting cards online.
  5. The purpose of a roadmap is to align thinking around strategic initiatives AND choose the most valuable projects in support of those initiatives that can be delivered with limited time and resources. It also allows for slotting projects to deliver at key times of the year to support market events. It’s the IMMUTABLE GRAND VISION for BLINDING SUCCESS
  6. Of course, the integrity of the IMMUTABLE GRAND VISION is SHORT-LIVED. Week-to-week IRRESISTABLE forces are INJECTING CHANGE: New project opportunities force TRADE OFF decisions Scope Creep calls ROI into question and/or the question of cannibalizing existing projects – “Stick with it or Move On? Track Decisions Made because its fascinating to review the life-cycle of a project. To be useful, IMMUTABLE Roadmaps must accommodate CONTINUOUS CHANGE.
  7. There’s no getting around it. To actually plan work the Roadmap must include Who, What, When, How Long for every project. But when scaled up to capture an entire organization for a whole year the amount of detail can’t withstand the tornado of the day-to-day change.
  8. Keeping up with the amount of change in a fully fleshed out roadmap is really, really hard. Two common means of doing so are: Oversimplify – Mythical Man Month with Fluid Capacity with Homogenous Skill Sets This approach can respond to tactical changes day-to-day but ignores dependencies: Skill Sets, Project to Project, Vacations
 Defend the IMMUTABLE VISION to the death with a GANTT chart fortified with every start-finish detail. Gantt Charts DO HAVE THE DETAIL to support all the decisions we need to make, but its too cumbersome to keep up with the tactical events week-to-week. When faced with imminent deadlines the priority will always be to ‘do the work’ versus ‘update the Gantt’. Images Crooked Road Flexibility GANTT Chart
  9. Sprints are capable of answering all these questions, but only two weeks at a time.
  10. How can you drive the same interactions you get in a sprint a the roadmap level?
  11. I’ve learned a trick I want to share with you. My goal here is to convey a very concrete means of keeping your roadmap in line with the daily work and the daily work aligned with your roadmap. No plugins, no xml. This is out of the box. Consider this the Martha Stuart recipe for Roadmaps. This is a simple trick. All you need is Jira and a reporting tool like Excel , and an organization that can tolerate transparency. Using this method you will not learn your roadmap was torpedoed after-the-fact, you will see the torpedo coming form some distance. I’ll take you through this step-by-step and provide a URL to this presentation so you’ll have a copy for your reference.
  12. Like any recipe - Garbage In. Garbage Out
  13. You DON’T ESTIMATE roadmap projects. You allocate time for them and estimate them later. “ Hey – you can’t share a roadmap with the doers they’ll mess it all up.” They already have – you just don’t know about it.
  14. HOUSE of CARDS – 2 nd Dellusion of Roadmaps.
  15. Share sprint data UP into the Dashboards and Roadmap Share roadmap date DOWN into the Dashboards & Sprints Same Data viewed in different ways across all verticals and levels of the org.
  16. All Wikis and Dashboards need to be shining on the wall when discussed in meetings so everyone sees the same thing, knows where they are, whats being updated in real-time. Meeting Minutes (very often people refine their assertions after reading what they’ve said – drives clarity into the discussion) Project Status Task Estimates Backlog Priority Bugs/Tasks 
 everything. Every artifact I mention here will be shining on the wall if it comes up in a meeting.
  17. We’ve all been in meetings where you feel like you’re talking to yourself. Why would Product Mgrs, Dev Mgrs, Engineers, QA and Stakeholders care to discuss the roadmap, much less really focus on it, question it, and therefore contribute to its upkeep? Its the focus of the meetings so its easy. Management Responds because Management is consuming the SAME INFO
  18. ECOSYSTEM of ARTIFACTS
  19. Customers want to buy more than 1 Mothers Day Card, Valentines Day Card, Fathers Day Card

  20. From the roadmap outward the proposed change cascades through the ecosystem of artifacts in a crude form. Doers refine Product Definition into User Stories and discover “we want to include the address verification roadmap feature since we have to test that flow anyway”. The PMO/Scrum Master adds that proposal to the project status. PMO confirms and updates the Roadmap. In the next Roadmap steering meeting Execs learn they’re getting a 2-fer and say THANK YOU.