Plan on a Page Checklist

A brief mission statement and vision for your team. What does your team do? What is your mission? What gets you up in the morning—eager to help our customers, company, and community? What is your high-level focus area?
Short diagnosis statement. Imagine someone walking in and saying, “OK, what is the deal with X right now? What is going well? What isn’t?” The diagnosis statement is a well-crafted, crystal-clear diagnosis of the situation that leaves out all the frills. It can describe the “key problem” or the primary leverage point.
Two single-sentence focus statements in the 3m and 12m time ranges. Answer the “at the end of the day” focus question. At the end of the day, what do you want to accomplish in the next 3m and 12m? The best way to approach this is to imagine it is 3m from now (or 12m), and you are looking back on the time between then and now. You are kicking yourself, asking, “why didn’t I REALLY focus on X?”
A list of the key “workstreams”. Workstreams sit above projects and specific bets. They represent key levers, themes, personas, or other categories of works. Workstreams describe the Why, Who, and What (potentially), but not the How. Workstreams should have metrics/measures. Another word for workstream is “focus area”. Some work streams are problem-focused, and some are more opportunity-focused. Detail appropriately. A good rule of thumb is that if you can only think of one way to nudge a workstream goal, then it is probably too specific and solution-focused.
A suitably detailed 12-month initiative roadmap. It is dangerous to converge on decisions too early. We want to make decisions at the last responsible moment. That said, it is essential to “paint the picture” of the next 12 months—more detail in the near-term and broad strokes in the longer term. A roadmap is NOT a commitment (unless you indicate the work is committed). A roadmap paints a picture of your tactics and bets. You don’t need to be exhaustive. It is OK to have open-ended initiatives that are more opportunity-focused.
Upcoming key milestones. For work that is “committed” you will likely have key milestones in the coming days/weeks/months. These milestones represent key events in an initiative timeline. They may be delivery oriented, or they may be pivot/proceed points, learning goal-oriented, etc. Ideally, this doesn’t stretch out more than the next 3-6 months to avoid prematurely committing to work.
Key dependencies and partners. No work exists on an island. We sometimes “push” our work onto other teams (we need their help), and we sometimes need their help (“pull”). It is crucial to call this out.
A list of non-goals. What are you intentionally deprioritizing? Here we are trying to draw the box around our work and focus and set guardrails.
A list of key assumptions. Every plan is created based on some assumptions. You operate under these assumptions. It is helpful to list these assumptions so that other people have context on how you made your decisions. You can also periodically revisit these assumptions to see if your confidence levels have increased or decreased. How will you convert your assumptions into facts (with fast/cheap experiments)?
A list of key risks you are managing. Identify and address the key risks associated with your focus area. What is top of mind? What are you attempting to mitigate? Has anything changed?

The Beautiful Mess

Plan on a Page Checklist