Introduction
An initiative is a critical tool for implementing the direction of your organization. By creating initiatives and mapping them out in a timeline, you make the mission more practical and how to build towards it more clear for everyone. This timeline combined with setting clear priority defines the path of execution for the near future, right in front of you, and should ideally be a bit out of reach. Anyone in your company can look at the timeline to quickly understand what the most important work is, why it matters, and how it is progressing.
They also solve the executive prioritization problem. Leadership cannot effectively prioritize 60 individual projects across a company without descending into chaotic horse-trading. To prevent initiatives from degenerating into bloated mega-projects, you must enforce a hard constraint: never have more than three initiatives at the same time, with only one being an opportunity. It should never go beyond three. It does not matter if one is just being planned (or pre-planned) and another two are almost done, we only have three at a maximum. By grouping by initiatives, and introducing the constraint of a maximum of three, it will finally be possible to effectively prioritize a few initiatives instead of an unmanageable bloated list of a hundred projects you never finish.
Types of initiatives
The ideal way to balance the two types of initiatives is mostly about removing bottlenecks to promote and improve output, while having one opportunity with your best people on it.
Most companies make the fatal error of assigning their highest achievers to fix chronic fires, broken legacy systems, or failing projects. Instead you should feed the opportunities, eliminate bottlenecks, and starve problems.
This is also a case of prioritization, where you should do first things first, and second things not at all. When an organization splinters its top performers across multiple initiatives, it guarantees mediocrity. No one remains effective while tackling more than two tasks at a time, and the most effective concentrate on exactly one.
Opportunities
Should have your highest achievers on them, and should be the only priority number 1. The people working on the opportunity should be dedicated 100% to it.
Since the opportunities are time bound, you should be able to remove all other tasks from the people working on your biggest opportunity.
Bottlenecks
The bottleneck is the rate-limiting factor of the entire machine. Solving them is not passive maintenance, it is an aggressive offensive act. A bottleneck initiative at the strategic level is simply an opportunity enabler and competition defender.
- If you cannot scale customer onboarding past 100 users a week because KYC is manual, fixing KYC isn't "maintenance"—it unlocks a $10M ARR vector.
- I would say if your warehouse can only pick 100 lines per hour due to both organizational and technological reasons, focusing on solving that bottleneck is the most important part.
This is the elon musk framework, look at which bottlenecks are halting progress the most, and only work focus on that until it gets resolved. This is also a place to put your top performers.
Can both be enablers and blockers. Anything that might decrease velocity.
| What it is | What it is not |
|---|---|
| A warehouse capped at 100 lines per hour, might be influenced by how shifts are scheduled, how inventory is slotted physically on shelves, how pickers are incentivized, and how the handheld scanners communicate with the database. | Internal tooling complaints (new project management thingy, slow build pipelines) |
Amazon’s Fulfillment Collapse (1999–2002)
In 1999 Amazon nearly died from its own success—then Bezos put his best people on the warehouse bottleneck, and Prime became possible.
Components of an initiative
An initiative requires documentation not for bureaucratic compliance, but to enforce fiscal and strategic discipline before capital is deployed. This includes:
- A clear problem statement
- A clear solution statement
- Objectives they support, objectives they introduce and associated metrics.
- Clear start dates and deadlines
- Effort estimates that describe deliveries and effort involved in each
All together, these become the lean business case. This is the declaration of war on either the bottleneck or opportunity. The contents of it needs to be scrutinized. Because the projects will be delivered.
These might sound like and can often become a set of bureaucratic steps one just "has to do", but these should be tools for understanding the complexities.
The goal is absolutely not to get perfect information, it has to be started with imperfect information and directional signals.
Projects and Programs
Primarily a way to effectively allocate resources: humans and capital. If for budget process reasons you need to group them, they become programs. But if you can fund the initiative fully, do it through that.
Read more about projects and programs
Objectives, milestones, and metrics
The strategic alignment mechanism that demands directional focus. Objectives and their metrics define the measurable outcome.
Read more about objectives and milestones
Features
The deliverables shipped by product teams in their cycles. Features provide the functional capabilities that end users touch, validating the initiative's assumptions against reality.
Read more about features