Make Agile awesome for executives and senior managers

Make Agile awesome for executives and senior managers

A fleet needs an admiral

Executives, directors, and managers of managers need a way to provide meaningful oversight and strategic input, without getting bogged down in minutiae. This challenge is not particular to Agile. But every methodology has its particular challenges. A fleet of empowered, self-organizing project teams needs an admiral to provide high-level coordination and direction. In theory, Agile frameworks like Scrum can scale. In practice, when you’re explaining, you’re losing. For anyone who didn’t begin their career in software development, hierarchies of backlogs and adaptations of frameworks like SAFe involve a crushing amount of explanation. Backlogs and sprint plans are great for implementation teams, but include a prohibitive level of detail for upper management to interact with. Milestone maps make it easy for executives and senior managers to get the right level of information and give the right level of input.

Scrum’s principles for process controls in complex and unpredictable circumstances apply at all levels, even where Scrum’s tools and events do not. Milestone maps apply the same concepts of transparency, inspection, and adaptation at a higher level, that is, to teams over weeks and quarters, rather than individuals over days and sprints. They make a team’s progress visible for themselves and everyone who depends on them (transparency). They make it easy to drill down to see how reported progress is being measured: against what particular targets, and based on what actual work products (inspection). And when any team’s work is not going as expected, this information circulates quickly and efficiently, so people have the opportunity to adjust (adaptation).

Here’s how milestone maps work:

  • Milestone maps visualize work moving through time, like a GPS visualizes a boat moving through the water. A milestone map is made in a spreadsheet. Work toward a major milestone or sequence of milestones is represented in a row. A one-page milestone map can easily visualize 20-30 work streams or projects (rows).
  • Expected future work is gray. As work moves forward from left to right, gray cells turn green, yellow, or red, to indicate if the work toward the next milestone is on track, behind, or at risk, as seen in Figure 1. Transparency.
  • Deadlines for milestones are indicated by dark gray cells with the letter “M.” Each “M” has a comment listing a few specific, achievable, measurable outcomes or outputs articulated as yes/no statements with checkboxes. When the deadline arrives, the cell will be turned green if all the boxes can be checked, yellow if only some can be checked, or red if critical deliverables were missed. This is not a substitute for project management software like Jira, Asana, MS Project, etc. It’s just enough detail to take subjectivity out of the green/yellow/red evaluation. If further detail is desired, people can drill down into specific implementation plans linked under Plans & Tasks, as seen in Figure 2. Inspection.
  • When a work stream turns yellow, it’s not going as expected, but there’s still a viable path to the next milestone, this prompts the question: How will we know when we’re back in the green? Do we need to adjust anyones plans or expectations? When a work stream turns red, the team has come to the conclusion that it can’t hit the milestone without adjusting the scope, budget, or timeline, this prompts the question: Are any of these things adjustable? Who can make this call? If they can’t be adjusted, are we better off spending our resources elsewhere? These conversations may lead to adjustments in timelines, priorities, and resource allocations. Surfacing and visualizing these adjustments, as seen as in Figure 3. Adaptation, makes it much easier to maintain alignment as plans evolve.

Figure 1. Transparency

Expected future work is gray. As work moves forward from left to right, gray cells turn green, yellow, or red, to indicate if the work toward the next milestone is on track, behind, or at risk.

Figure 2. Inspection

Figure 3. Adaptation

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From a practical, tactical standpoint, here are common ways to use milestone maps:

  • People who oversee or coordinate the work of implementers (e.g. project managers, product owners, service managers, experience owners) update and discuss green/yellow/red status for their teams at weekly “Scrum of Scrum” (SoS) meetings.
  • Leadership groups or executive steering committees use milestone maps to get a quick view of trends, to identify hotspots, or to efficiently identify where drilling into detail is a good use of someone’s time. Milestone maps also give these groups early visibility into places where circumstances are changing and plans may need to evolve.

  1. Communication is clearest when each row has one point person or owner, responsible for delivering on the next milestone and providing status updates. When outcomes require work from multiple teams, these can be represented in multiple rows with the outcome described in a shared heading. This makes it visually clear how outputs from different teams (potentially different departments or organizations) relate to desired outcomes.


This is post 2 of 5 in a series on #Agile and #MilestoneMapping for #GovernmentTechnology projects here:

  1. Government organizations that practice Agile with milestone maps are 3 times more likely to deliver successful outcomes
  2. Make Agile awesome for executives and senior managers
  3. Prevent people from starting projects destined to fail
  4. Empirical feedback on where to invest
  5. Improve transparency so adjustments are smaller, faster, and less costly

If you’d like to try making a milestone map or bringing this approach into your organization check out the info here.

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