17 Leadership Books Recommended by Plato Mentors

Poya Osgouei
Engineering Leadership Blog
6 min readDec 3, 2018
Photo by Daria Nepriakhina on Unsplash

If you pop “Leadership Management Books” into Google Search, you’ll get a significant number of results, but how do you decide the best ones to add to your reading list?

We decided to ask our Plato Mentors which books have been impactful in their career, and which books they often suggest to new managers and team members. Here’s the list:

The Manager’s Path — this is the definitive guide on the modern career path for engineers, tech leads, and eng managers. It has a bunch of great things to think about, especially as you first become a Tech Lead (TL) or Engineering Manager (EM).

Switch by Daniel Pink — Often times, especially in the early stages of career growth, one has very little control and influence. Switch goes into what motivates people, how to influence others when you have no leverage, and into what motivates people, and how to change things when change is hard.

Crucial Conversations — I virtually never require my managers to read books, but Crucial Conversations is the one exception. It does an excellent job at bringing awareness and provide tactics to handle the critical human-to-human interactions that are necessary on a day-to-day basis to be an effective manager. This book does a great job at providing practical, memorable approaches to navigating your day-to-day managing people. Side-benefit: it can make improve your relationships outside of work as well!

It’s Your Ship by D. Michael Abrashoff — This is the book that completely capsized (ha!) my view of how a real leader operates. I was a Sr. Lead Engineer back then, coming from a painful history of working for what today we’d call micromanagers, and those experiences alone led me to have no interest whatsoever in taking over one of the first people leadership roles that became available at that gig, despite I was (unknowingly to me) the top internal candidate. That was until I was recommended this read from the local VP of Engineering when I initially expressed hesitation as he offered me that spot in a 1-on-1. This book introduced me to what empowering others really means, and how putting your reports in the driving seat initiates a virtuous chain reaction where trust is the starting point and the foundation on top of which to build strong ownership, growth opportunities and higher job satisfaction. I can still recall the sound of my mind being blown by this concept entirely new to me. The advises Abrashoff gives in the book all checked out right off the bat during my first year as a freshly minted leader supporting an incredibly talented team. I keep recommending this to all the ICs thinking of jumping on the leadership joyride as a foundational read.

Safe Enough to Soar — Some organizations pay a great deal of attention to ensuring the physical safety of their team members, but do the team members feel safe enough to speak up and raise tough concerns or share bold and still-in-formation ideas? In this book, bestselling authors and inclusion experts Frederick A. Miller and Judith H. Katz introduce the concept of “interaction safety” and demonstrate how it can help create a work environment of trust, inclusion, and collaboration.

It’s Okay to Manage Your Boss — a novel approach to managing up, It’s an invaluable resource for employees who want to work more effectively with their managers.

  • Vamsee Krishna, Director of Engineering Operations, Securly

Essentialism — This is the book that has really helped me prioritize my viewpoint and how I should be incredibly focused on prioritizing the most important thing each day.

  • Archana, Engineering Manager, Adobe

The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever — this book is a great intro to coaching, or a level-up for those experienced with coaching. It is a combination of profound insight, anecdotes, and practical tools that are a mainstay in my day-to-day.

  • Henry Hsu, Senior Engineering Manager, Zendesk

Accelerate — this book describes the necessary ingredients for a successful engineering team. What makes it unique, very valuable and credible is that it is to the point and based on data from an extensive multi-year study, written by stars like Jez Humble.

Decisive: How to Make Better Choices in Life and Work — the book gives a simple yet effective blueprint to decision making which is a constant activity a leader is engaged in. If you feel you are trigger-happy with decisions or slow to indecisive at times, this book is for you! The blueprint laid out by this book helps create consistency in one’s decision making.

Managing Humans — really just a collection of stories, but it’s real vs. theoretical. And it fits well with how mentoring in general is structured around gathering individual experiences, stories, and different perspectives vs. a binary right/wrong.

The Leadership Pipeline — sketches the path from IC to CEO of a Conglomerate, with profiles and sets of skills needed at every managerial step along the way (Manager, Director, VP, etc.). It’s also agnostic of industry, and provides good perspective on how these roles transcend domains.

The first 90 days — this book was recommended reading for all new managers who joined Stripe! I thought this book was great especially for anyone either transitioning into a new leadership role within the org or outside. It had very actionable advice about what to do and even more importantly what not to do when you join a new team as a manager.

High Output Management — Grove started his career as an engineer and his management concepts derive from the type of systems thinking that developers naturally align towards. In addition to being the “Father of OKRs”, Andy Grove founded many theories that bring clarification to complex human organizations and abstractions to optimize efficiencies in growing organizations. I return to this book often to help find the inputs, outputs, levers, force multipliers, limiting steps, quality controls, and variables in creating better management solutions.

Radical Candor — Radical Candor is a simple idea: to be a good boss, you have to Care Personally at the same time that you Challenge Directly. When you challenge without caring it’s obnoxious aggression; when you care without challenging it’s ruinous empathy. When you do neither it’s manipulative insincerity. This simple framework can help you build better relationships at work, and fulfill your three key responsibilities as a leader: creating a culture of feedback (praise and criticism), building a cohesive team, and achieving results you’re all proud of.

The One Thing — very powerful book that explains how to be more productive, how to achieve more without necessary doing more. Great to prioritize goals at work and in personal life, how to eliminate distractions. I am learning to focus on what really matters to have the most impact.

Start With Why — it’s inspiring and motivating, and helps you find your purpose in what you do.

Never heard of Plato, and you made it all the way to the bottom of the article?! Congrats. You can check us out here. But if you need the TL;DR, here’s a bit more about us:

Plato is on a mission to help engineering + product leaders develop soft skills and build better teams. Plato does this through a powerful mentoring platform, where new leaders connect with seasoned professionals for 1–1 sessions, AMAs, and a comprehensive knowledge base.

Plato Mentors have extensive experience in management, and come from top tech companies like Google, Facebook, Lyft, Slack, Netflix, and Spotify — among others.

Founded in 2017 by two French entrepreneurs, Quang Hoang, and Jean-Baptiste Coger who met while attending the prestigious ISAE-Supaero school of engineering, Plato is one of the fastest growing engineering + product mentoring platforms in the world.

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