ktheoryAaron Suggs’s blog

March 14, 2021 — Tags: management

The Glossier Tech team wrapped up our annual roadmap exercise earlier this year. It takes a lot of time and attention from the team, especially managers.

I wanted to share some tips I’ve gleand to make reviews easy and productive. They’re organized into ‘filters’, or questions to ask about each project in a roadmap.

If product and engineering managers can speak to each of these filters, they’ll likely have a smooth review with no surprises.

Virtually all the questions and feedback that came up in our roadmap reviews fall into one of the filters below; and each one is a hard-learned lesson from watching my projects or teams stumble.

1. Sufficiently detailed

The appropriate level of detail increases during the roadmap process. In general, sufficient detail means that project outcomes and requirements are defined, and that key decisions and risks are highlighted and investigated. A 6-month project may not have a clear approach at the beginning of the road mapping process, but by the end it would likely have specific, realistic outcomes for each 2-week sprint.

Having documented examples of projects plans with the appropriate detail is helpful here (see Will Larson’s Discouraging Perfection). Some people take roadmapping too seriously, going into so much detail that the precision of their plan exceeds it’s accuracy. They get frustrated when they need to adapt to the unexpected. Others can be too casual or hedge so much that it’s difficult for others to depend on them. The key is the psychological safety to acknowledge that plans are imperfect and will inevitably change. The point is sufficient detail to reduce risks, not complete and rigid precision.

2. Aligned with business goals

Are these projects sufficient to meet the team’s mission and biz goals? If not, change up the projects, or set more realistic goals. For example, if a goal is to increase a conversion rate by X% this year, but the projects to improve conversion ship at the end of the year, they likely won’t have a significant impact on the conversion rate and there’s little time to respond.

3. Comprehensive of all work

Does this roadmap account for all the work the team will have to do? If a team spends 20% of their time responding to bugs filed by the customer support team, that should be accounted for in the resource planning. We call this Keep The Lights On (KTLO) work.

4. Sequenced effectively

Which projects have strict deadlines? Do Team A’s projects depend on one of Team B’s projects? Does Project X become easier or more valuable if we do Project Y first? A group roadmap review is one of the more obvious places to suss this out.

5. Resourced for success

Does the team have appropriate people and skills to deliver each project? What skill gaps or “bus factors” are there? What’s the plan to get those skills (hire, train, or borrow)?

6. Iterative milestones

Can you frontload more business value? I.e. be more agile and less waterfall. Are there narrow customer segments or journeys that you could support early on while you develop the rest of the project? Are there milestones that de-risk the project and enable real feedback as soon as possible?

Having presented and reviewed several roadmaps, I’ve found these filters to be a helpful linting tools to make more useful roadmaps. Or at least they allow me to learn new ways to fail rather than repeat my previous mistakes.