An elegant puzzle

Systems of Engineering Management

Harry Cheslaw
3 min readFeb 5


By Will Larson

A brief overview

Will Larson has led tech teams at many hyper growth companies such as Stripe, Uber & now the app Calm. The book is a practical manual on how to grow and manage teams, balancing an human approach with strategic principles.

Will continues to make the point that there are no principles that apply to all cases, however, holding certain principles in mind can provide a framework to address all puzzles.

Team Sizes

Will argues that a true team cannot exist if below 4 individuals as they do not provide the benefits of a team. Below this number, the teams are “sufficiently leaky abstractions that they function indistinguishable from individuals”. A single person leaving or going on holiday can be hugely destructive in teams under 4 making them difficult to manage and plan.

Keep innovation and maintenance together

Instead of having one team which innovates and another which performs maintenance, Will proposes innovating within existing teams.

Team Sizes

Will argues that:

  • Team should be six to eight people normally
  • To grow a new team, grow an existing team to eight to ten and then bud into two teams of four or five
  • Never create empty teams
  • Never leave a manager supporting more than 8 people

Technical Debt Snowball

Will mentions the “debt-repayment snowball” in which: “each piece of debt you repay leads to more time to repay more debt”.

Systems Thinking

Will argues that the most effective managers use system thinking to make effective decisions. He recommends reading Systems: A Primer by Donella H. Meadows for a deep-dive into the topic.

The fundamental observation of systems thinking is that the links between event are often more subtle then they appear. We want to describe events causally but few events occur in a vacuum.

Thinking in systems is made up of diagrams comprised of:

  • Stocks: Stocks are entities that can accumulate or be depleted, such as a bathtub, which fills with water from a faucet
  • Flows:Flows, on the other hand, are entities that make stocks increase or decrease, like a faucet or drain affects the level of water in a bathtub.

Solution Validation

Will argues that before dedicating significant resources to a project, one should perform an explicit solution validation phase.

It’s far more reliable to get good at cheap validation that it is to get great at consistently picking the right solution. Even if you’re brilliant, you are almost always missing essential information when you begin desisning.

This phase could include:

  • Write a customer letter: write the launch announcement which you want to publish post launch
  • Identify prior art: how are other people solving this problem in the industry?
  • Find reference users: can you find users who state that they want to use what you are building?
  • Find the path more quickly travelled: find the cheapest way to validate what you are building vs building the entire solution while hoping you are right.

Presenting to senior leadership

When presenting to senior leaders, Will recommend to:

  1. Start with the conclusion
  2. Frame why the topic matters
  3. Use a narrative

People over process

A few years back, one of the leaders I worked with told me, “With the right people, any process works, and with the wrong people, no process works”. I’ve found this to be pretty accurate. Process is a tool to make it easy to collaborate, and the process that the team enjoys is usually the right process. If your process if failing somehow, it’s worth really digging into how it’s failing before you start looking for another process to replace it…. My experience is that a different process probably isn’t the solution you’re looking for.

Company culture and freedoms

When thinking about company culture and the freedoms is should or shouldn’t enable, Will starts by discussing the difference between positive and negative freedoms.

  • Positive freedoms: the freedom to do: to vote, to own arms etc.
  • Negative freedom: the freedom from things such as being forced to go into battle

Each positive freedom allowed will reduce negative freedoms and vice versa — the paradox of Liberty.