Influential Books

The following are a few of the books which I’ve found impactful in my day-to-day thinking, work and career development since graduating from university.

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs

Takeaways:

• OKRs are incredibly valuable in their ability to focus an organization or team, but poorly constructed OKRs can do more damage than good.
• Clear goals and measurable results are a focus mechanism that help an organization scale out.
• Use OKRs as an opportunity to set stretch goals and aspirational targets instead of sticking with the status quo.
• OKRs are an opportunity to communicate the why alongside the what.

The DevOps Handbook: How to Create World-Class Agility, Reliability, and Security in Technology Organizations

Of all the books in this list, The DevOps Handbook is the single most influential book and has been a guiding hand in how I attempt to organize engineering processes and teams.

Takeaways:

• Optimize delivery for rapid and small releases to make it easier to debug issues.
• Structure your teams such that they own and maintain the code you ship to production.
• You don’t “hand off to ops” after you’ve built the feature.
• Closely follow and optimize for cycle time and lead time.
• DevOps is a culture not a job title.

An Elegant Puzzle: Systems of Engineering Management

This is a quick read full of useful learnings over Will Larson’s career.

I would recommend it for new managers.

Takeaways:

• Always be recruiting and have a hiring funnel.
• Inbound recruiting can be difficult without a strong company brand.
• You should build up referral networks over the course of your career.
• Learn to manage and present upwards.
• Finish fully staffing one team before attempting to build a second half staffed team.

Powerful: Building a Culture of Freedom and Responsibility

I genuinely love this book and revisit it often to get an idea for how Patty McCord helped recruit, retain and motivate talent at Netflix.

• “A business leader’s job is to create great teams that do amazing work on time. That’s it. That’s the job of management”.
• You need to be great at hiring to also be great at letting people go.
• Employees are always looking for challenging opportunities and interesting problems to solve.
• Like the above, people want to learn. Don’t optimize for office perks.
• Challenge your team(s).
• Everyone should understand the business.
• Be as transparent as possible about the success and failures of the business.
• Annual performance bonuses won’t necessarily make people work harder.
• Whenever possible remove structure, policies, and process to move the authority to the team. This is very similar to the advice in Turn the Ship Around.

The Phoenix Project

A fun quick read.

Takeaways:

• Interpersonal communication skills are as important as coding.
• Small changes can snowball across an organization, so chaining together a lot of small wins using a bottom-up approach can be very effective.

Turn the Ship Around! A True Story of Turning Followers Into Leaders

Another quick read with parallels to engineering leadership or leadership more generally.

Takeaways:

• To grant authority to mid-organization teams you need to provide them with clarity and competence.
• Speak with intent instead of asking for permission.
• Move from a leader-follower model to a leader-leader model.

Inspired

A good reference when you are asking yourself what to do as new product owner.

Takeaways:

• Product roadmaps are not necessarily the most effective way of communicating product strategy or long-term needs.

The Hard Thing about Hard Things

One of the earliest books that I read when first promoted to CTO.

Ben’s new book What You Do Is Who You Are: How to Create Your Business Culture is also very good.

Takeaways:

• Peacetime CEO vs Wartime CEO
• Building tech companies is not as romanticized as it’s made out to be.