My Inspirations

Now as a Director of Engineering at Docker, I’ve been doing some type of engineering leadership for the last decade.

I have learned from the best over the years, and many resources have shaped who I am and philosophies for how I lead.

These are the resources that come to mind that may help other engineering managers, staff engineers, or other leaders in their journey.

Discord Chat

First, I’ll pitch a new Discord channel where you can discuss and promote additional resources that have helped shape you.

Join Practically Leading on Discord!

Books

While many business books are full of fluff, are dry, and at times hard-to-read, there are many gems that have left an impact lasting years.

I’ve summarized some of the key takeaways I’ve had.

Leaders Eat Last by Simon Sinek

Building high-performance teams considering neuroscience, psychological safety, and empathy

Start With Why by Simon Sinek

Lead with context and carrots, beginning with purpose, cause, and beliefs. Why is more of the motivation and direction behind behavior, not How or What.
“There are only two ways to influence human behavior: you can manipulate it or you can inspire it.”
See Simon’s TED Talk here.

Drive by Daniel Pink

People will be happier and work harder if you share context and opportunities for Autonomy, Purpose, Mastery

It’s Your Ship by Captain D. Michael Abrashoff

Lead with purpose, vision, and create a team of leaders.
Listen “aggressively”, build up your people into leaders, and expect the best.

The Happiness Advantage by Shawn Achor

“When we are positive, our brains become more engaged, creative, motivated, energetic, resilient, and productive.”
Work can be fun, and there are good reasons to strive for it.

Team Topologies by Matthew Skelton and Manuel Pais

Minimizing Cognitive Load on teams
Split teams with "fracture planes"
Stream-aligned team: aligned to a flow of work from (usually) a segment of the business domain
Enabling team: helps a Stream-aligned team to overcome obstacles. Also detects missing capabilities.
Complicated Subsystem team: where significant mathematics/calculation/technical expertise is needed.
Platform team: a grouping of other team types that provide a compelling internal product to accelerate delivery by Stream-aligned teams

The Culture Code by Daniel Coyle

Psychological Safety is conducive to strong group work.
Vulnerability gives people a signal to speak up and cooperate.
Sharing values and close bonds leads to higher performance than companies that focus on the best talent or specific skillsets.
Some people are “Super-Cooperators”, putting teams first, giving signals that bond and direct a group.

The Culture Map by Erin Meyer

Cultures vary widely in how they give feedback, perceive hierarchy, make decisions based on relationships or mutual tasks, and concepts of time.
What may work in your culture may be understood wildly differently in other cultural settings.

No Rules Rules by Reed Hastings and Erin Meyer

Mediocre performance can drag down a team, lowering performance of the high performers, even setting a negative tone in the environment.
Netflix leads with freedom, responsibility, and low red tape.
Employees are empowered to make bottom-up decisions.

Working Backwards by Bill Carr and Colin Bryar

Narrative-driven documents work well for facilitating in-depth discussion, even for executive presentations.
Hiring should focus on raising the bar, and can include shadowing or other practices like Bar Raisers.
Single-threaded leaders help with efficiency and cohesiveness over projects or domains.
Use PR/FAQs to start with the end in mind, predicting success or failures of the final product and responding to concerns within the planning process.
Focus on inputs, not outputs. Look at and measure what levers can be pulled, not the indirect outcome.

Thinking in Systems by Donella Meadows

Most multi-part organization can be thought of in systems.
Systems include stocks and flows, and feedback loops.
Feedback loop types vary; some have goals of an equillibrium outcome, others amplify into a virtuous cycle.

Staff Engineer: Leadership Beyond the Management Track by Will Larson

Staff Engineer titles vary in responsibility betwee companies.
4 archetypes are most commonly seen.
Staff Engineers most often take on leadership aspects, such as team leadership, complex subsystem leadership, cross-architecture leadership, or being a technical voice counterpart to managers.

High Output Management by Andrew Grove

Information gathering, decision making, and nudging others
Utilizing meetings, KPIs effectively
Leading through Objectives and Key Results (OKRs)
Organizational and management leverage

Never Split the Difference by Chris Voss

Unconventional, highly practical approaches to negotiations and difficult discussions
Mirroring, labeling, and reframing questions helps disarm and engage in active listening

Atomic Habits

Making 1% improvements each day
Creating habits that build off each other and are maintainable

Getting Things Done by David Allen

Getting work onto paper lowers stress
Regularly review your todos, curate

Crucial Conversations by Kerry Patterson

Succeed in conversations through self-reflection, creating shared meaning, candor, psychological safety, expression, and persuasion

Team of Teams by General Stanley McChrystal

Modern organizational systems can be complex and hard to map out, organic in design, versus complicated.
With complex systems, teams must be more adaptable to change, resilient, lower command and control.
Complex system design can look more like joined spiderwebs (teams) with little hierarchy: a team of teams.
Team leadership requires high transparency, decentralized decision-making to make these systems work well.

Work Rules! by Laszlo Bock

Employees should act as founders
“Culture Eats Strategy for Breakfast”
Smart generalists can be superior than experts. People clever and curious, able to solve change and problems unknown at time of hire.
Hiring managers and employees should be part of the hiring process, including sourcing.
Be objective about hiring. Scorecards, good note-taking.
Be data-driven.
Nudges are powerful as a leader, and are ways of avoiding micromanagement while having impact.

Deep Work by Cal Newport

All roles require some level of deep thinking, a lost art.
Deep work requires blocking off uninterrupted time, whether on a calendar or your own will.
Proper environment, inspiration, boredom, and time to think helps facilitate deep work.

The Manager’s Path by Camille Fournier