Direction Setting with Roadmaps

A clear path aligns everyone to work toward the same goals.

With direction, it’s easier to work together, know what to focus on, and make meaningful progress. Roadmaps are a critical tool for shaping this direction.

Time-based milestones give planning and execution a regular rhythm. Examples include monthly, quarterly, and annual roadmaps.

Reviewing company metrics such as sign-up, activation, retention, and revenue is also essential.

Shorter milestones are easier to plan and encourage you to scope down projects so they fit within them. Success means realizing most of the projects.

Goal-oriented milestones tie work to specific outcomes.

Success means completing enough projects to ship or meet the goal.

Thematic milestones define a focus that narrows down the list of tasks. When using thematic landmarks, adding a time or number limit is helpful to keep the list of projects manageable.

Success means an impact that you can see or measure.

The projects you choose to work on make concrete progress in some way. They may create new functionality, launch a campaign or improve an existing product area.

Work on several smaller projects after shipping a more prominent feature to avoid burnout. You should work on as few projects as a team and as individuals.

Ship existing projects before starting new ones.

Focus produces higher quality work, and shipping builds execution into a habit. Order projects so new work builds on top of previous projects, which will make changes feel organic and can have compounding effects.

Create a routine around reviewing the roadmap and evaluating progress toward projects.

Include a roadmap review in weekly team meetings and communicate a weekly update to document the project’s progress over time.

Create an environment that encourages project leads to share and ask for help, not report a status or expected completion date. A great plan is only helpful if you’re following through on it, and you will know how well you’re doing that with regular reviews.

The roadmap should feel much and be possible. A balanced roadmap leaves up to a third of the total work hours spent on bugs, fixes, and backlog items.

Do your best to estimate projects and expect them to take longer than you think–it always does.

It’s also better to be ambitious and avoid adding too many tasks to the roadmap.

A couple more projects than practical will motivate the team to ship. More studies can lead you into a trap of working at the speed of the schedule, slowing down momentum.

Face your difficulties and think. Solve your problems yourself. Suffering and difficulties provide opportunities to become better.

Success is never giving up.

We need more time to work, but we pack our days with endless meetings.

We need the necessary information but are buried in emails, documents, and data.

We want speed and innovation, but we run from risk and inhibit our best people. We claim to work in teams but don’t trust one another. We know how we work isn’t working, but we can’t imagine an alternative.

We long for change but need to figure out how to get it.

People can be trusted and will trust one another to use judgment and do the right thing.

We are addicted to the idea that the world can be predicted and controlled — that our stoplights are the only way to keep things in check. But when you view the world that way, today’s uncertainty and volatility trigger retreating to what has worked in the past.

We need to hire more capable leaders. We need to squeeze out more efficiency and growth. We need to reorganize.

[¹]: Brave New Work: Are You Ready to Reinvent Your Organization?