Reading List. Here are a few worthy books to help you become a better leader.

The journey from an individual contributor to a manager is relatively quick if we aim to settle down quickly thinking, “I arrived”. However, the journey to becoming a true leader (with or without a formal rank or title) is long, and to be honest, it never ends. Books are the best way to expand our horizons and expose ourselves to different concepts and thinking that we can incorporate into our own lives. It’s a path of learning and self-improvement planted with lessons on every corner, if that’s how we decide to see things.

“People who don’t read have no advantage over those who cannot read.”

I want to share with you a list of a few most important books I read that helped to shape and improve my personal and work life. I’m sure you saw some of these titles in the past. However, I hope you will find a few new that might be particularly interesting and help you on your journey. Harry Truman famously said that not all readers are leaders, but all leaders are readers — they have to be. Keep that in mind.

On importance of taking notes from books.

I realised that every book provides so much content that it is simply impossible to remember it all. So we need to create hooks in our memory for the most important bits. Notes are the most accessible form, and I tend to make Keep notes with a book title and a long list of things worth remembering.

Of course, taking notes is not enough, and for knowledge to stick, we have to review it once in a while. I come back to mine once a month and review most of them each time, and currently, it takes me over 2 hours! Interestingly, every time I do it, something new and meaningful pop out that I have already forgotten about. Occasionally I will pick the book where these notes are coming from and read a little bit. It really helps ground the knowledge and incorporate new information into my life.

The list

None of these books has been written explicitly for “software engineers”, which actually makes them a great source of learning. A different perspective is what you need, and I will explain why I’m recommending each of them.

Extreme Ownership — Jacko Willink

Extreme Ownership — Jocko Willink

I found this book quite late, but it gave me words to describe and expand on things I was already doing. The title drew me, as I always believed that an effective team is one where each member takes full ownership beyond expectations. The book is an exciting mix of battlefield stories explained and analysed from the point of leadership, ownership and mistakes. Excellent read and I would strongly suggest starting here.

Top notes from the book:

  • There are only two types of leaders. Effective and ineffective.
  • Leadership is the greatest single factor in a team’s performance.
  • The true test of a good brief/plan is not whether the senior executives are impressed. It’s whether or not the people in the team understands it.
  • The goal of all leaders should be to work themselves out of a job.
CAptivate — Vanessa van edwards

Captivate — Vanessa van Edwards

This book was crucial to better understanding The Big Five personality traits (also called OCEAN) and gave me good insights into peoples’ values and appreciation language. New topics to explore led me to content from Jordan Peterson, whose lectures filled the gaps. Something I wasn’t expecting is that all my learnings from here will allow me to develop a better hiring process. It shaped my interview conversations to find the best candidates possible with much success.

Top notes from the book:

  • The first impression’s power is not what we say but how we say it. Hand gestures, eye contact and posture, are the three most significant elements.
  • If you give somebody a positive label, they will aim to achieve that.
  • When you introduce somebody, make sure you do it the most exciting way, don’t waste an opportunity to give a positive label.
  • If you want to go fast, go alone. If you want to go far, go together.
Deep Work — Cal Newport

Deep Work — Cal Newport

Understanding the importance of deep work and uninterrupted focus is crucial to implementing these ideas at your workplace. Unfortunately, software engineering (especially after covid) became a very distracted environment, and it is not uncommon to find people writing code less than 2hrs per day. Read the book, understand the impact and try to make some changes. In my case, I permanently blocked calendar time slots for my team and me — twice a day, 1.5hrs “No meeting zone”, plus one more early in the morning, but changes did not end up here.

Top notes from the book:

  • Bimodal philosophy of deep work. When we dedicate a chunk of our time to do deep work only and then another piece to focus on shallow tasks.
  • Trying to squeeze a little more work out of your evenings might reduce your effectiveness the next day enough to get less done.
  • Social media replaced value with a shallow collective.
  • Plan your day, and don’t let it run on autopilot. You will waste much more time than you think on doing non-important stuff.
Quiet — Susan Cain

Quiet — Susan Cain

This particular book has a special place on this list as I consider it the first important book that actually changed my life and started the transformation many years ago. I’ve learnt from it that there are more weird people like me, and our weirdness even has a name — introvertism! This gave me a better perspective on many aspects of my life and the people around me. It also opened me up (I actually started giving a shit) about other people’s personalities and ways of thinking.

Top notes from the book:

  • Openspace office creates more disruptions and makes people less creative and more stressed. Introverts and creative minds need to be alone.
  • There is no such thing as multitasking. People are 50% less creative and perform worse when they need to jump between different tasks.
  • People are afraid of judgment in public. They will perform better on their own rather when somebody is looking at them.

Brief — Joseph McCormack

I actually ended up with a very long list of notes. Easy to read content focused on communication efficiency in different forms helped me re-work how I communicate, especially in emails. It also highlighted many small mistakes I was making during important conversations. Being brief is crucial, and we often forget about it. This book is a gentle reminder, and it will surely expand on your knowledge and help challenge some of your assumptions.

Top notes from the book:

  • Successful people demand brevity and don’t tolerate it when it’s missing.
  • If people see you don’t respect their time, they won’t respect you.
  • Storytelling trumps persuasion. Telling your audience a well researched and well-structured story is more effective than just selling your point of view.

Never Split the Difference — Chris Voss

Negotiations in any serious leadership role are our daily routine. We do it all the time, whether with other leaders in the company or people in our teams. Understanding the power of open questions and communication techniques helps in challenging situations, arguments, and everyday life. Excellent source of knowledge, but it’s not easy to incorporate it in real-life. I find it extremely difficult to re-adjust my communication techniques to focus more on other people’s needs when stakes are high. Must read book if your goal is to become the best self you can be.

Top notes from the book:

  • We have learned that “No” is the anti-” Yes” and therefore a word to be avoided at all costs. But it really often just means “Wait” or “I’m not comfortable with that.” Learn how to hear it calmly. “No” is not the end of the negotiation but the beginning.
  • Don’t commit to assumptions, but test them rigorously instead.
  • Negotiation is not a battle. It’s a process of discovery.
  • Never split the difference and compromise. No deal is better than a bad deal, and comprises quite often are bad deals for both sides.
Ego is the enemy — Ryan Holiday

Ego is the Enemy — Ryan Holiday

This book is an excellent introduction to the destructive effect of our EGO, and from my experience, the world of software engineering is full of it. It’s hard to navigate it, but getting exposure to what “big ego” means helps us see it and deal with it more efficiently. Ryan’s book is also a good step into Stoicism which he covered in his other book — Stillness is the Key. That led me finally to read Meditations by Marcus Aurelius.

Top notes from the book:

  • Ego — an unhealthy belief in our own importance. If ego is often a nasty side effect of great success, it can be fatal during failure.
  • If you are thinking you are better than others, it is still pride.
  • Don’t be deceived by the recognition you have gotten or the amount of money in your bank account.
  • The paradox of bitterness and hate. It accomplishes almost exactly the opposite of what we hope it does.

Thinking fast and slow — Daniel Kahneman

Daniel’s books are not an easy read as they are full of scientific language, and some people will simply not enjoy them. In this particular case, he unpacks how the brain’s systems work — the first, automatic and unconscious, which is fed by experience and habits. The second is purposeful and analytical, which require significant effort to use. This book is not about leadership but is relevant to working with people, and that’s what leading really means.

Top notes from the book:

  • Intuition cannot be trusted in the absence of stable regularities in the environment. That’s why the stock market experts are no better than random individuals.
  • Never do things for others, which they can do themselves. They will never take responsibility and feel comfortable and not feel independent.
  • People are less confident in their choice when they are asked to produce more arguments to support it.
  • Simplifying as much as possible is the key to success.

The Coaching Effect — Bill Eckstrom, Sarah Wirth

Fascinating book about leadership, which focuses on the importance of coaching over ‘just’ managing and holding leaders accountable for the growth and improvement of their team. Interestingly, it is written from the sales perspective and translates well into software engineering and other areas. Great insights and explanation of why balance is vital in every high-performing environment.

Top notes from the book:

  • Order is just one step from stagnation, leading to moving backwards. Being in a state of discomfort is the only way a person can grow.
  • Hold leaders accountable for implementing and improving their coaching skills.
  • The term ‘manager’ is an archaic term describing a role that, by definition, limits growth and performance.
Leaders Eat Last — Simon Sinek

Leaders Eat Last — Simon Sinek

I’m sure you heard about this one, and you are probably not surprised to find it on this list. A good book from Simon covering aspects of “servant leadership” which I found important many years ago. We, leaders, are there for our team, not the other way around. Being a leader is a responsibility and sacrifice, yet many don’t take it seriously.

Top notes from the book:

  • Leadership is the choice to serve others with or without any formal rank.
  • Leaders are the ones who are willing to give up something of their own for us.
  • The goal of a leader is to give no orders. Leaders are to provide direction and intent and allow others to figure out what to do and how to get there.

Anything I’ve missed?

I believe this selection should keep you busy for a while. If you have some other good suggestions on what I should read, please let me know. I will be happy to add more books to my current TO-READ list, which has 30+ titles already. At the speed of around 12–15 books a year, this will take me a whole to get through.

Now… Go and keep reading!

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Andrew Winnicki

Andrew Winnicki

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Software Engineering Changemaker. Driving digital transformation and sharing experiences and thoughts from my journey. 20 years and counting…