Books I Read in 2020

This year's list focuses on leadership, management, startups, strategy, and job transitions.

It takes me time to read books. I treat them like textbooks and make notes by highlighting intriguing passages, capturing my thoughts in the margins, dog-earring pages, and capturing critical takeaways on the blank pages at the beginning of the books.

I find ways to apply the concepts contained in the pages to the context of my life, often pausing my reading until I’ve tested concepts in the real world.

When something produces a better outcome by simplifying my work, clarifying my thinking, or making the work more joyful, I weave it into my leadership and management practices as part of my learning process.

This year my reading focused on re-affirming and deepening existing strengths, living my values fully, exploring new areas of interest, and filling newly discovered gaps that were surfaced by taking on new and exciting challenges in 2019.

This Years First Time Reads

Die Empty: Unleash Your Best Work Every Day

Written by Todd Henry

Image for post
Image for post

I struggled with motivation this year and thought Die Empty, by one of my favorite authors, would help me spark the desire and curiosity to create, build, and explore my passions by combining hard work with intention.

The book's subject is central to my core leadership values of making and sharing, and I hoped Todd had some new tools, perspectives, and insights to help me live my values more deeply.

“Overtime we learn the art of compromise. The problem is we often compromise the most valuable thing: the fire that drives our best work.”
― Todd Henry, Die Empty: Unleash Your Best Work Every Day

The book delivered.

One of my favorite sections of the book is in Chapter 5: Be Furiously Creative. On pages 73 to 81, Todd walks through four areas that will help you define the shape of the problems getting in your way from unleashing your best work. I also enjoyed the 7 deadly sins of mediocrity which speaks to areas that prevent us from creating our best work.

Todd connected with me on an experiential level, re-affirming lessons I’ve learned from the mistakes I’ve made throughout my career.

“Make sure that you’re nurturing your process. It’s the only thing you can truly control, and it’s the thing you’ll always have regardless of where you end up.”
― Todd Henry, Die Empty: Unleash Your Best Work Every Day

At one point in my career, I had moved across the country to take on a new role. In this role, I was strongly discouraged from using my process, tools, and beliefs, which I had developed and refined over my career of leading and managing teams. Not only did I stop nurturing the process, but I removed it entirely. When I did this, the joy I found in my work, and the outcomes I was capable of producing suffered.

I highly recommend reading Die Empty and applying the tools Todd Henry provides if you want to lead a richer and more rewarding life, sustain your drive, re-kindle a passion, or you find yourself constantly overwhelmed by ideas.

I had many take-aways from the book, and I’m sure that I’ll be returning to this book as a reference many times over the coming years.

The Speed of Trust

Written by Stephen M. R. Covey

Image for post
Image for post

Transitioning to new teams, roles, or companies is one of the most challenging and stressful times in your career. Often the work, reputation, and trust you’ve built in your last role, team, or company get reset, and you need to re-establish trust in your character and competency.

I hoped this book would give me new tools, perspectives, and approaches to help me build trust when I join teams. Beyond helping myself, I was hoping it would give me a greater ability as a manager to help my teams build trust when new people join.

“Trust always affects two outcomes—speed and cost. When trust goes down, speed will also go down and costs will go up.”
― Stephen M.R. Covey, The SPEED of Trust: The One Thing that Changes Everything

This quote, from Stephens section on The Economics of Trust, is a simple model that makes clear the relationship between trust and business. It reminded me how much focus, care, and attention needs to be put into understanding the needs of teams, hiring the right people, and setting up successful onboarding practices to build and maintain a high-trust culture.

It is equally important for the existing leader and team to build trust with the new team member. Unfortunately, people who have tenure tend to view their time at the company as having already built trust in their reputation and skills and don’t need to re-establish trust when a single person joins their team.

From the perspective of the new team member; trust in peers, managers, and leaders has not been established. There is too much at stake for teams to approach trust-building in a single direction.

The process of grafting new people into a company, team, role, or discipline within the organization will accelerate or create friction in the trust-building process needed to establish and maintain high-performing teams.

Stephen covers a variety of concepts including his 13 trust behaviors that make it clear where you can build and improve trust. The 5 Waves of Trust will help you understand and explore how trust applies at multiple scales from individuals to societies—ideas that apply to every level in your leadership and management practices.

Some of the insights were also deeply personal, resonating with my past experiences and struggles.

“The moment there is suspicion about a person’s motives, everything he does becomes tainted. — MAHATMA GANDHI”
― Stephen M.R. Covey, The SPEED of Trust: The One Thing that Changes Everything

This quote reminded me of how important it is for leaders to clearly articulate what they value, what they believe, and make sure what they preach shows up in their actions and behaviors in their day-to-day interactions.

I’ve joined teams where the relationship between the team and the leader was filled with distrust, anxiety, frustration, and fear on both sides. These teams lack transparency, ownership, and candor. Joining this environment was the worst experience of my 10+ years leading and managing teams.

Whether the team believes the leader's intent is positive or not, the leader's ability to find and address the inconsistencies between what they say and how they act makes the difference between re-establishing trust or deepening the dysfunction.

I recommend leaders focus on consistently doing four things to build a high-trust culture.

  1. Be transparent by communicating and reinforcing your intentions, values, beliefs, and expectations and align people on how these show up in practice.
  2. Create a safe environment for conversation and dialog by fostering what Kim Scott calls, Radical Candor.
  3. Take ownership of being the model for others to follow. Encourage your team to hold you accountable and give you immediate feedback when you don’t live up to the ideals you’ve set for yourself and others.
  4. Address the feedback you receive in a timely manner. Follow-up with the person who gave it and letting them know what you’ve done to address it. If the feedback is unclear or vague, be curious, ask questions, and find the root cause of concerns being surfaced.

I highly recommend this book to anyone who wants to build strong teams capable of working effectively together, who want to change an existing team's culture, or who wants to improve a toxic culture.

The Vision Driven Leader

Written by Michael Hyatt

Image for post
Image for post

There are many different leadership types, each with its own pros and cons, and each with an appropriate context to apply each to. My default leadership style helps energize the people around me by clarifying our team's purpose and aligning that purpose with the work we do every day. By helping people see how they, as unique people, help the team fulfill our purpose. At the root of my leadership practice is vision—working to transform the current state into a more idealistic future state.

This is the style of leadership I’m most passionate about. It’s great when you need to improve team engagement, create leverage across a team or organization, or help people see they are capable of achieving more than they thought possible.

I picked this book because I wanted to deepen my skills in my favorite style of leadership.

“From that vision comes this year’s annual plan. What will you do this coming year to make progress on your vision? What projects will you undertake that will bring you closer? What initiatives will you start or stop? What products will you create or retire? The clearer your Vision Script, the more apparent the answers to these questions will be.”
― Michael Hyatt, The Vision Driven Leader: 10 Questions to Focus Your Efforts, Energize Your Team, and Scale Your Business

Vision is a great way to deal with ambiguity as a leader. Working with your team to create a clear vision will help everyone picture a similar version of what the future looks like. It will let you and others identify what’s in or out of alignment with that version of the future. It will help people at all levels in your organization map a shared vision onto their respective roles and responsibilities—vision enables cohesive decision making at scale while maintaining individual autonomy and ownership of the individual and teams.

Combined with good strategy, I recommend reading Good Strategy, Bad Strategy, vision creates leverage, align teams, set everyone up for greater success.

The Vision Driven Leader also points out things to pay attention to as you become more future-thinking as a leader.

“Leaders who refuse to listen will eventually be surrounded by people who have nothing significant to say.”
― Michael Hyatt, The Vision Driven Leader: 10 Questions to Focus Your Efforts, Energize Your Team, and Scale Your Business

I’ve seen leaders who espouse open-door policies where nobody wants to walk through the door, and they think everything is fine because nobody shows up—which is often a sign something is deeply wrong. I’ve seen leaders complain they aren’t getting feedback from their teams when they neither seek nor address feedback from their teams.

What’s more troubling is when leaders or managers put targets on the backs of people who surface constructive but negatively perceived feedback. This harmful practice by people in positions of authority, whether conscious or not, suppresses a culture that fosters meaningful feedback.

In the worst cases, people become afraid to speak up for fear of losing their jobs. This leads to bad leaders taking hold because the people in their charge learn to stay quiet to survive. The organization never becomes aware of critical problems, which can have high costs for the company, the team, and the individual, the severity of which compounds over longer periods of time.

If you’re a leader and find that you aren’t getting candid, honest, and timely feedback from your teams, I highly recommend you start solving the problem by looking inward at the culture you’ve created and how your actions might be in or out of alignment with your words and beliefs.

This is a great book for managers who want to learn more about the differences between leadership and management and want to lead with a sense of purpose, to motivate themselves and their team, and create a highly energized culture that tackles big and challenging problems.

Zero to One

Written by Peter Thiel

Image for post
Image for post

I’ve been diving deeper into the differences between leading and managing teams in service and product companies. Zero to One made my list this year because for these reasons, but I’m also interested in becoming more entrepreneurial at this point in my life.

This book is considered by many to be a must-read for anyone entering the world of startups and product-based development.

“Even in engineering-driven Silicon Valley, the buzzwords of the moment call for building a “lean startup” that can “adapt” and “evolve” to an ever-changing environment. Would-be entrepreneurs are told that nothing can be known in advance: we’re supposed to listen to what customers say they want, make nothing more than a “minimum viable product,” and iterate our way to success. But leanness is a methodology, not a goal. Making small changes to things that already exist might lead you to a local maximum, but it won’t help you find the global maximum. You could build the best version of an app that lets people order toilet paper from their iPhone. But iteration without a bold plan won’t take you from 0 to 1. A company is the strangest place of all for an indefinite optimist: why should you expect your own business to succeed without a plan to make it happen? Darwinism may be a fine theory in other contexts, but in startups, intelligent design works best.”
― Peter Thiel, Zero to One: Notes on Startups, or How to Build the Future

This is one of my favorite quotes in the book that talks about finding a balance between micro and macro perspectives and the importance of finding global maxims, or principles, that are durable and lead to greater success over time and scale.

Peter also brings up the concept of working from first principles. Something Elon Musk does very well.

“the single most powerful pattern I have noticed is that successful people find value in unexpected places, and they do this by thinking about business from first principles instead of formulas.”
― Peter Thiel, Zero to One: Notes on Start Ups, or How to Build the Future

Peter also identifies some subtle concepts that, for me, distinguish between new managers and leaders and people with more seasoned perspectives and experience.

“Those who succumb to measurement mania obsess about weekly active user statistics, monthly revenue targets, and quarterly earnings reports. However, you can hit those numbers and still overlook deeper, harder-to-measure problems that threaten the durability of your business.”
― Peter Thiel, Zero to One: Notes on Start Ups, or How to Build the Future

So many managers are focused on measuring the bottom-line impact on shipping velocity and revenue. They are so focused on these measurements that they over-look hard to quantify measurements like team engagement, burn-out, job satisfaction, alignment with vision and values, and employee growth.

This book will give you a wealth of value and will be a book you continually reference when you dive headlong into entrepreneurship, building products, or want to demystify the dogma found in startup culture.

The First 90 Days

Written by Michael D. Watkins

Image for post
Image for post

Moving into a new role is one of the most challenging and stressful times in your life. It requires a different set of skills than you need to do the job you were hired for and you can’t rely on a company or team onboarding you so that you can successfully make the transition.

When done well, onboarding takes place at multiple levels within the organization, from general company onboarding and subsequently to department, team, role, and area of specialization.

Unfortunately, you won’t be able to rely on consistently great onboarding experiences. Some may be fun, get you inspired, but rarely do they get you up and running quickly, especially when you are coming in at a leadership or management level.

I’m not a job hopper and spent 14 years, the majority of my career, in two roles. After starting a new management position after 8 years in a leadership role, I felt the full effect of this gap in my career experience.

I hoped Michael’s book would give me new models, tools, and insights that would help me and the people I hire to become successful in their roles in a significantly shorter period of time.

My biggest takeaway was a model I can use to classify the business, department, or team situation when I arrive in a new position. The S.T.A.R.S model covering five different organizational situations, which starts on page 71, will give you a new way to analyze and prioritize the work you’ll need to focus on to be successful and avoid the unique perils of each situation.

“The situational diagnosis conversation. In this conversation, you seek to understand how your new boss sees the STARS portfolio you have inherited. Are there elements of start-up, turnaround, accelerated growth, realignment, and sustaining success? How did the organization reach this point? What factors — both soft and hard — make this situation a challenge? What resources within the organization can you draw on? Your view may differ from your boss’s, but it is essential to grasp how she sees the situation.

This model allowed me to think about how to approach challenges I would face in the future and a lens to look through when I reflect on my past.

This book also contained many insights and wisdom that I’ve had to learn the hard way, through setbacks and failure.

“Joining a new company is akin to an organ transplant — and you’re the new organ. If you’re not thoughtful in adapting to the new situation, you could end up being attacked by the organizational immune system and rejected.”
― Michael D. Watkins, The First 90 Days, Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter

If a company truly believes in diversity and the benefits that diversity of experience, background, approach, and perspective brings, then it will be easier for companies to bring people into the fold; however, if your company or team is hyper-focused on velocity and efficiency, then you’ll struggle if you have a different way of approaching problems, exploring solutions, and leading teams.

“recruiting is like romance, and employment is like marriage.”
― Michael D. Watkins, The First 90 Days, Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter

After experience being both the hiring manager and the person being hired, it’s become clear that the most difficult challenge on both sides of the table is learning about the not-so-nice things you will deal with the hiring is done. This book has helped me learn new approaches that will help me create a more accurate and realistic picture of what I’ll be walking into.

I would recommend this book to anyone who is changing roles, teams, or companies. It is also amazing if you are leading a team because it will give you a bunch of insight into the challenges people you hire will encounter. You can proactively address items in your onboarding programs, early communication, expectation setting, and alignment that will help guide early growth planning for new hires. This will help you set yourself, the team, and the new hire for the greatest chance of success.

Books I’ve Read Before

Some books are relevant beyond a single situation or moment in time. These books, or sections within the book, become more relevant throughout your life and career.

When I re-read a book, I’ll purchase the audiobook format and listen to it while I go for a run or take a drive in the car at 1.5x speed. I’ll also review my notes, which I keep in the first few blank pages of the book, and skim sections that I’ve dog-eared or the notes I’ve scribbled in the margins.

My notes from Todd Henry’s book Die Empty.

The 80/20 Manager

Written by Richard Koch

Image for post
Image for post

I keep returning to this book to see how I’m progressing and growing as a manager. It helps me identify my gaps, measure my growth, and re-affirms my strengths.

Reviewing the management approaches reminds me that there are many ways to become a great manager. It helps me recognize different management styles, appreciate how others manage differently than myself, and helps me coach and mentor people who have different approaches than myself.

It also helps identify and promote more people who are well suited for management who share a greater diversity of skills, perspectives, and approaches.

For new managers, this will help you find a style that feels effortless and show you how to lean into it, and help you develop an appreciation and respect for the diversity of styles that show up in different people.

As you mature throughout your career, you can use this book as a reference to pick a new style to lean into and improve, masting several and being able to apply more leverage and insight to the work you and your teams do every day.

As you begin managing managers or promoting individual contributors into management positions, this book will help you understand what to look for in people who might be well suited to the specific management situation you need to fill on your team.

I recommend this book to anyone in a leadership or management role—it’s essential reading and a primer on effective management. If you’re looking for a generic how to be a manager book, this isn’t for you.

Good Strategy, Bad Strategy

Written by Richard P. Rummelt

Image for post
Image for post

The word strategy has become a meaningless buzzword that gets thrown around in companies and teams. This book breaks down how to recognize what good and bad strategy looks like and what goes into developing a good strategy.

“Bad strategy is long on goals and short on policy or action. It assumes that goals are all you need. It puts forward strategic objectives that are incoherent and, sometimes, totally impracticable. It uses high-sounding words and phrases to hide these failings.”
― Richard Rumelt, Good Strategy Bad Strategy: The Difference and Why It Matters

As a leader and manager, a large portion of your work is strategic. Any challenge, goal, problem, initiative, process, or outcome you hope to achieve will have a strategy you set in motion—good or bad, with intention or without. It makes clear what effective strategy requires.

“The kernel of a strategy contains three elements: a diagnosis, a guiding policy, and coherent action.”
― Richard Rumelt, Good Strategy/Bad Strategy: The Difference and Why It Matters

I come from a design and user-experience background building digital products, applications, and experiences. This book resonated with me because, as a designer, solving user experience challenges or designing an application or user-flow is a strategic endeavor.

The book helped me connect my specific knowledge in design and UX with an abstracted model to apply to how I lead and manage teams, develop effective processes within businesses, and achieve more with less anxiety and stress.

I recommend this book to anyone who wants to overcome challenges or obstacles they face in their work or life.

Reading in 2021

This year, I plan to learn more about content marketing, developing and selling products, and starting and running a product company while continuing my obsession with leadership.

If you have any great books, newsletters, articles, or authors that come to mind, I’d love to know what I should add to my reading list.

I help businesses build, lead, and manage design teams.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store