Initiatives Planning

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To deliver on the roadmap goals but also to tackle new emergent engineering needs, the Engineering leadership team must collaborate on defining, prioritizing, and executing numerous engineering initiatives.

The engineering planning process is loosely inspired by and adapted from the Shape Up methodology created by Ryan Singer at Basecamp.


Before diving into creating and delivering initiatives, it is critical to understand the planning cycle schedule.

The engineering leadership team plans and delivers initiatives in eight-week cycles:

  • Cycle #1 → January - February
  • Cycle #2 → March - April
  • Cycle #3 → May - June
  • Cycle #4 → July - August
  • Cycle #5 → September - October
  • Cycle #6 → November - December

Each cycle consists of six weeks dedicated to active work on initiatives and two weeks to cool down.

Six weeks is long enough to deliver on an initiative from start to finish and short enough that everyone can feel the deadline looming from the start. Therefore, everyone uses their time wisely and makes decisions with a specific time constraint.

Each initiative should be completed within one cycle. Strict time-boxing is needed to ensure the team has both focus and a sense of urgency. If it takes longer than one cycle, the best way is to adopt an iterative process by breaking it down into chunks that can be delivered in one cycle.

During the cool-down period, the engineering leadership team has the opportunity to review the output of completed initiatives, focus on non-engineering-leadership-related work (e.g., personal objectives, growth projects, etc.), plan/think of initiatives for the next cycle, and take a break 🏖️


Before an initiative can be executed upon, the owner/sponsor - basically the one bringing the idea to the table - must spend the time researching the problem it addresses, recommend a solution and estimate the effort required.

Once an idea is approved, the owner can be different from the one bringing the idea. In this case, the latter is called the sponsor and entrusts the owner to deliver the initiative from start to finish.

To create a new initiative, a new backlog item is added to the Engineering Initiatives board:

Engineering Initiatives board on Notion

The initiative content must be written using the “Engineering Initiative Template” :

Engineering Initiative Template on Notion

The template includes the following sections:

  • Problem → What is the issue we are trying to solve.
  • Solution → How will we fix the issue.
  • No Gos → What this initiative will not address.
  • Resources → What research elements can support this initiative.

The more detailed and convincing the information is, the better are the odds to prioritize the initiative in the next bi-monthly planning cycle.

Once all the information has been compiled, and the owner/sponsor wants to bring this initiative idea forward, the initiative card must be moved to the “Ready To Pitch” column.

"Ready To Pitch" column in the Engineering Initiative Template on Notion

All ready engineering initiatives are listed in the Pitching Board:

Pitching board on Notion


The Engineering Leadership team meets every two months - at the end of each eight-week cycle - on the last Thursday of the month - for the “Engineering - Bi-Monthly Planning” session.

During this session, only the initiatives on the Pitching Board are eligible to be prioritized. Every member must have completed their submissions on time and familiarized themselves with all the initiatives on the board.

During the session, both the owner/sponsor and participants are invited to debate the value and solutions offered by each initiative.

Initiatives are prioritized based on:

  • If a roadmap goal or objectives is fulfilled or at least being worked on. While there is space for non-roadmap-oriented initiatives, a higher priority is given to initiatives that are aligned with the yearly goals and objectives.
  • If an initiative has a well-defined problem and solution, thus guaranteeing a more robust path to completion. Incomplete or fuzzy initiatives are sent to be reworked. Important ideas come back.

The selected initiatives for the subsequent eight-week cycles are then moved to the “To Do” column to be worked on.

"To Do" column in the Engineering Initiative Template on Notion


Once an initiative has been prioritized to be worked on, the owner must ensure the following:

  • Enlist and brief the assignees who will execute the actual work. The assignees are usually software developers, but also Engineering Leads.
  • Define the estimated “Completion Date” field. The planned completion must be within the current cycle

Information on an engineering initiative card

The owner is accountable to ensure:

  • The delivery of the initiative from start to finish.
  • The standard product management, development, and code review processes are followed.
  • The status of the initiative is up-to-date on the Engineering Initiatives board e.g. when an initiative is being worked on and then completed, it must be moved from “To Do” to “In Progress” and then “In Review”.

Upon completion of the initiative, the CTO reviews the completed work, marks it as done or requests modifications if necessary. To avoid the latter case, the owner must keep the CTO in a short feedback loop.