The Trusty Oak Blog

Recommended Reading List for Leaders and Entrepreneurs

Leadership development should be a continuous, ongoing process. As a leader, it is important to understand that you will always need to improve your skills. Whether you are a business owner, leader, entrepreneur or just wanting to learning something new, there is something on this list for you. Get ready to be inspired! 


  1. 9 Minutes on Monday – James Robbins – How to connect with your team and the importance of making room for relationships with the people in your office. It does not take much time each week and the effects of this habit are game changing. Increase productivity, retention of your team, and overall levels of satisfaction in the workplace.
  2. Crucial Conversations – Kerry Patterson – It is inevitable that hard conversations will come up. It does not matter what career or industry you are in, knowing how to handle the topics that make us uncomfortable and have those conversations in a structured way will help prevent the wrong outcomes from happening.  
  3. Drive – Daniel Pink – This is one of my favorite books as it explains why carrots and sticks are not the answer when trying to motivate a person. It also dives into the psychology around why a person will contribute countless hours contributing to an open source project for free and what the structure for that change looks like. 
  4. Extreme Ownership – Jocko Willink – This is a very intense book about leadership that takes you into the heart of the battlefield from the eyes of the most elite Navy Seals.  Each chapter is broken down into a combat situation, a leadership principle, and an application to corporate America. I could not put this book down as it was very intense and engaging.  
  5. Hard Things about Hard Things – Ben Horowitz – This book has been referenced by many CEOs I have worked with as being an influential book for how they run a company. The main focus of this book is how to deal with failure; layoffs, having to fire or let go of a long time friend, and what it looks like behind the scenes to keep companies going.  

Team Leadership

  1. 5 Dysfunctions of a Team – Patrick Lencioni – This is a top three must-read for any leader or anyone working in a team environment. Understanding the foundational elements of teams, how each one builds on one another, and how to take action within your team will help you achieve the culture and commitments from your teams. 
  2. Happiness Advantage – Shawn Achor – Our team is what makes our company successful and the attitudes that they bring to work are a force multiplier for efficiency. Do you know the impacts that having a friend in the office will do for your quality of life? This book dives into that and more in relation to happiness in the workplace.  
  3. Ideal Team Player – Patrick Lencioni – What type of people do you have on your team?  What type of leader are you? The Ideal Team Player dives into what traits of an individual help make a high performing team. What traits are toxic? This book also dives into how to sniff out the negative traits through process and interviewing.  
  4. No Gossip Zone – Sam Chapman – Toxic cultures are fed from gossip. The practice of talking behind a person’s back, negativity can turn a motivated team member to not in a matter of weeks. Look at how this practice takes shape and how to remediate it.  
  5. Death by Meeting – Patrick Lencioni – We all spend time in meetings but how many of those are unproductive or could be solved by an email? This book is not about eliminating meetings but making sure that the ones we do have are effective. 

Related: From the CEO’s Desk: Add These Books to Your 2020 List

Project Management

  1. The Lean Startup – Eric Ries – Thinking about and understanding your internal processes for products, development, or operation is important. Without it, it is hard to automate or find points of failure. This book talks about the Lean mindset and how to apply it to your business.  
  2. The Goal – Eliyahu M. Goldratt – The Goal is also a book that heavily focuses on your processes but from an area of efficiency. The example of how to march a troop of Boy Scouts in the woods drives home the message on how to align your processes.  
  3. Theory of Constraints – Eliyahu M. Goldratt – As with The Goal, Mr. Goldratt dives into the areas of process that hurts us the most… constraints. Having an awareness to the areas that can slow you down, risk mitigation, and how to think about end-to-end process will enable you to ask the right questions when in design phase or reevaluating workflows. 
  4. The Dip – Seth Godin –  When our projects or initiatives start to encounter adversity, when is the right time to keep pushing and when should we walk away? Over 90% of small businesses fail in the first five years. Understanding “The Dip” will help you look at challenges differently and give you insight into what to try next.  
  5. The Phoenix Project – Gene Kim – This book is focused on the Information Technology side of project management and for anyone whose product is software, this is a must read.  DEVOPS, CI/CD, LEAN, Kaizen area all focuses of this book and will change your perception on how you develop and release your products.  


  1. 4 Hour Work Week – Tim Ferris – This book changed the way I look at business as well as how to gain efficiency in everyday tasks. From lifestyle design, how much is enough, automating your life, and all of the tips and tricks along the way, this book is a must read.  
  2. E-Myth Revisited – Michael E. Gerber – We all have goals when it comes to our companies but do we have the strategy and thought process to handle the growth that comes with success? This book looks at identifying single points of failure with growth and how to approach common struggles that businesses have as they take shape. 
  3. Small Giants – Bo Burlingham – There are many stories of the “successful” companies that grow, disrupt an industry, went public, but what about the companies that choose to be small? This book goes into how bigger is not always better and that “success” comes in many forms.  
  4. Good to Great – Jim Collins – Many of us have worked for “good” companies but “great” companies are few and far between. Having the right people on the bus and the flywheel concepts are just a few of the nuggets of information to help transform your organization
  5. The Tipping Point – Malcom Gladwell – One of my favorite authors, Malcolm Gladwell talks about when the drops in the bucket, finally make it tip and your ideas or product “spreads like wildfire.” He also talks about Broken Window Theory and how those seemingly small things can evolve over time into big problems.  

Personal Growth

  1. Boundaries – Cloud & Townsend – If you are someone that feels exhausted, like people are taking advantage of you, or have struggling relationships with parents and co-workers, this could be a great book for you. This talks about different areas of our lives and why it is important to have lines that we should not allow others to cross.  
  2. 80/20 Principle – Richard Koch – Understanding the concept of 80/20 helps break down problems and efforts to a value/effort proposition. This principle is all around us in wealth distribution, our customer base breakdown, and even how we wear the clothes in our closet. This book is about gaining efficiency. 
  3. Power of Less – Leo Baubatua – We are surrounded by messages by product companies telling us that we need more and more and more. This book is about having less and how simplifying your life will have positive impacts on your well being.  
  4. The Alchemist – Paul Coelho – This is the book I read every year without fail. It is a short story about a shepherd who is looking for his personal treasure. It talks about risk, dreams, and belief and an interesting perception on life. 
  5. The Four Agreements – Don Miguel Ruiz – This is a very simple book with some simple messages around how to live life based on old Toltec wisdom. Being impeccable with your word and how to not take anything personally are just a few of the lessons in this book.  
  6. Outliers – Malcolm Gladwell – This is one of my favorite books as it opens up your eyes to things we see everyday and how to think about them differently. What do experts and 10,000 hours have in common, why are so many NHL Players born in the first part of the year and what it really takes in a plane crash are all very interesting parts of this book.  
  7. Ego is the Enemy – Ryan Holliday – There are many motivation drivers that leaders have, ego is one of them and the most toxic and problematic. This book breaks down the ego and discusses ways to curb what destruction it can cause in our lives.  
  8. Stillness is Key – Ryan Holliday – How to be quiet, still, patient, and not overreact are a few discussion points in this book. With the rat race of life, this book is a good reminder that there is a more stoic way to approach life vs getting out of bed and running with the pack each day.  
  9. The Motive – Patrick Lencioni – Why do leaders become leaders and what is your “motive” to be a leader in your company? The Motive breaks down in typical Lencioni fashion what the role of the CEO is in a company as well as what traits make them successful. 
  10. Gifts of Imperfection – Brene Brown – The TED talks around Shame and Vulnerability is what Dr. Brown is most famous for, however, her books are also fantastic as they dive deeper into these two emotions. Learning that “I am enough” is a valuable lesson when we are surrounded by marketing companies that are constantly telling us that we aren’t.

Continually investing in yourself is essential for any leader. Learning something new or developing your existing skills can open up opportunities and help you reach your desired goals faster. What’s on your reading list?

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