Initiatives Planning

Hero image for Initiatives Planning

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 worked on, the owner – the team member proposing and entrusted to deliver the initiative – must research the problem it addresses, recommend a solution and estimate the effort required.

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 the team is trying to solve.
  • Solution → How will the team 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 the odds of successfully delivering the initiative.

Once all the information has been compiled, and the owner wants to share this initiative with the team, 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 Initiatives Planning board:

Initiatives Planning board on Notion


The Engineering Leadership team meets every two months – at the end of each eight-week cycle – for the pompously (because why not? 😉) named “Engineering Summit” session.

Before the session, every Engineering Lead must have:

  • Provided an update on the status of the initiatives they worked on in the current cycle.
  • Completed the pitch for the initiatives for their respective assigned roadmap objectives they plan to work on during the next cycle(s).
  • Selected the initiatives they want to work on for the next cycle.
  • Familiarized themselves with all the initiatives on the board.

During the session, only the initiatives on the Initiatives Planning Board can be discussed. All participants are invited to debate the value and solutions offered by each initiative.

Initiatives for the next cycle are prioritized by each Engineering Lead, i.e., each Engineering Lead must select the initiatives they want to work on for the next cycle. While the CTO provides guidance and can veto an initiative in some instances, each Engineering Lead is responsible for assessing the priority of the initiatives they plan to work on to deliver their assigned roadmap’s objectives.

The selection is finalized in two steps:

  1. Moving the initiative card from the “Ready To Pitch” column to the “To Do” column.
  2. Setting the cycle attribute to the next cycle number.

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

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.


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

  • Enlist and coordinate with contributors, if any, who will execute the actual work. The contributors can be any engineering team member, including Engineering Leads.
  • Define the estimated “Completion Date” field. The planned completion date must be within the current cycle

Information on an engineering initiative card

The owner is accountable to ensure:

  • All the deliverables are completed timely.
  • 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, Engineering Leads provide regular updates to the CTO during the bi-weekly retrospectives.