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Top 5 must-read leadership books to level-up in your role

Top 5 must-read leadership books to level-up in your role Blog Feature

Tom DiScipio

VP of Product, Speaker, 8+ Years Sales & Client Success Expertise

May 22nd, 2020 min read

It was my favorite time of the year. 

I was huddled up with the rest of the IMPACT leadership team for three days in a conference room for our annual retreat and planning session, this year in Las Vegas.

All eyes were on the TV at the front of the conference room. 

We were reviewing a spreadsheet that included a list of the current and future departments at IMPACT on the left and a list of empty cells where we were to input the name of the person that would run (or “own”) the department on the right.

At the bottom of the spreadsheet was an entirely new department for IMPACT: “Client Advocacy.” 

In the empty cell just to the right… my name.

It was an emotionally perplexing moment.

I had the desire and the drive to do this. I wanted it.

At the same time, however, the little voice in the back of my mind said things like, “Tom, you’ve never built a department from scratch before.” and “Are you sure you’re the best person for this role? The company is trusting YOU to make this successful...” 

I didn’t want to let anyone down, and I knew I had to level-up quickly. 

5 books (and skills) to level-up every leader and manager

As I frequently do, I turned to books to prepare and grow in several areas I hoped to level-up in as I went into my new role.

Over the last 12 months, I’ve been lucky enough to be exposed to several books that aligned tightly with them.

In this article, I’ll share each of those books and how they impacted my professional (and personal) development.

Please note: What’s shared below is simply a glimpse into what I found most valuable within each book specific to my growth as a leader.

So, don’t let these brief summaries stop you from taking advantage of the countless other lessons, tools, and stories that each of these books has to offer, and learning how they might shape your leadership and management journey.

1. The Five Dysfunctions of a Team by Patrick Lencioni

Who it’s for:

  • Leaders building a new or growing an existing team
  • Leaders needing to address a poorly performing team

If you’re building or repairing a team, read this book first.

The Five Dysfunctions of a Team explores the reasons (or dysfunctions) why even the most talented teams fail, and stories out how a leader can overcome those dysfunctions to build a high-performing team.

The five dysfunctions (in order of importance) are:

  1. Absence of Trust
  2. Fear of Conflict
  3. Lack of Commitment
  4. Fear of Accountability
  5. Inattention to results

What’s unique about this book is that it’s written as a fable. For me, this made the concepts and material within so much more accessible and memorable.

Throughout the book, you meet characters that likely perfectly personify coworkers you’ve led or teamed up with throughout your career. This makes it much easier to see how the insights can be adapted to real life.

Main leadership lesson(s): The importance of trust in leading a team

Trust is the foundational building block of all relationships (personal and professional). Simply put, teams that have it succeed, and teams that don’t, struggle (or fail entirely).

Showing vulnerability or weakness as a leader isn’t just a good thing, it’s table stakes for building a trusting, cohesive, and high-performing team.

There are many ways to build trust with team mates. Fulfilling a promise by doing what you say you’ll do or sharing a story are just a couple examples.

But, as detailed in the book, the deepest levels of trust are built upon teammates who can safely express their own weaknesses, shortcomings, failures, or emotions with one another, free of judgement from others on the team. 

This is what it means to be vulnerable.

Vulnerability is contagious, but it always has to start with the leader.

Throughout our lives we’re conditioned to see leaders as winners — never failing, never succumbing to weakness, and always stoic in their emotion.

So for many leaders (including myself), being vulnerable for the first time can be incredibly uncomfortable.

That’s why, in order for a team to practice vulnerability, the leader has to take the first step. 

In the book, Catherine Peterson, the newly appointed CEO shares a story of a past failure, humanizing her as a leader, and bringing down the walls of her executive team.

Being a vulnerable leader is a small, but powerful tool to fostering unwavering trust with your team.

2. Extreme Ownership by Jocko Willink & Leif Babin

Who it’s for:

  • Leaders who need to improve their personal accountability

Extreme Ownership is intense.

Forget your morning coffee. Read a few chapters of this early in the day, and you’ll be hyped for hours.

I say this because the leadership principles within this book are exposed through the narration of Jacko and Leif’s boots-on-the-ground stories of serving as Navy SEALs during the war in Iraq.

What’s most powerful about this book is its ability to break down their principles of leadership into no uncertain terms, and align them around one, core mantra:

“Extreme Ownership. Leaders must own everything in their world. There is no one else to blame.” 

The stories create a 360º view of every aspect of ownership, beyond just taking the blame.

It extends from accepting responsibility for the mistakes of your team to the responsibility of clearly communicating with your superiors — or, “leading up” as it’s referred to in the book.

Main leadership lesson(s): Taking ownership

Ownership: Ownership means accepting complete responsibility for the actions and outcomes of my actions, my team’s actions, and even the organization as a whole. No excuses.

“There are no bad teams, only bad leaders.” - Jocko Willink

Again, in no uncertain terms, the performance of my team is directly reflective of my performance as a leader.

My name was written in that box as the “owner” of our “Customer Advocacy” department, no one else's. 

Great leaders acknowledge and accept the mistakes and failures of their teams as their own, and figure out a way to overcome them, despite the performance of individual team members.

Great leaders prevent poor performance from becoming the standard on a team by not tolerating their own mediocrity, or pushing off personal accountability.

3. Thanks for the Feedback: The Science & Art of Receiving Feedback Well by Douglas Stone & Sheila Heen

Who it’s for:

  • Leaders looking for strategies to navigate difficult conversations
  • Leaders looking to become better coaches
  • Any individual or team member that wants to deliver or receive feedback in a better way

Oftentimes, some of the most difficult conversations in business center around having to share feedback with another team member.

This inherent difficulty stems from two things:

  • The giver’s delivery method of specific feedback
  • The receivers interpretation of the feedback being delivered

The book describes this as, “the intersection of two realities” — the opportunity we see for our peer’s development, and the story they tell themselves in hearing such feedback, typically, “I’m not good enough the way that I am.” 

The book outlines the mindset, concepts, and strategies necessary to bridge that gap.

What makes this book so special is that it’s written primarily in the context of the receiver of feedback, as opposed to the giver. 

Leaders, managers, and those on their team should all read it in an effort to align around how to receive and deliver feedback in a meaningful, non-defensive way.  

Only when we understand how to receive feedback effectively, can we then effectively deliver it to others. 

Main Leadership Lesson(s): Feedback is a gift

Feedback is the single greatest mechanism for personal and professional growth. But it has to be both received and delivered in the right way to be effective.

As a giver or receiver of feedback: The time in which feedback is received or delivered is as important as the type of feedback.

Prior to reading Thanks for the Feedback, my knowledge of how to receive or deliver feedback stopped at what I had learned in One Minute Manager — If a person does something poorly or well, immediately reprimand or praise them accordingly.

I always thought there was one type of feedback for any purpose and one time to give it: good or bad, and immediately.

This book revealed that I’d been doing it wrong for a long time.

It goes on to describe the three different types of feedback:

  1. Appreciation (relationship building and encouragement)
  2. Coaching (personal or professional growth)
  3. Evaluation (assessment of performance)

The key here is meeting your team member where they want to be met.

Is that team member looking to be appreciated at this moment? Or, are they actually looking to be compared against their peers so they can know where they stand and improve their performance?

But as important as the “where” is the “when.” 

As it turns out, delivering evaluative feedback directly after someone had a rough day at home, can dramatically hinder the receiver from even acknowledging the feedback being received.

Therefore, I learned to give myself the space necessary to think about the type of feedback I want to receive in a given moment and similarly, the type of feedback my team member may want to receive, and when is the appropriate time to do so.

4. Scaling Up: How a Few Companies Make It...and Why the Rest Don't, Rockefeller Habits 2.0 by Verne Harnish

Who it’s for:

  • Business leaders / executives looking for a framework to operate the business
  • Team leaders who need to reduce waste, improve efficiencies and create scale

It isn’t too often you come across a book that can bridge the gap between high-level strategic concepts and the tactics and tools like Scaling Up can.

This book is DENSE. 

In the words of our CEO, Bob Ruffolo, “Every single line has something of importance in it. Best to read each section multiple times.”

Consider it the manifesto, handbook, and tool shed for installing a new operating system into your business.

Scaling Up’s framework centers around the four foundational areas companies must address in order to achieve scalable and sustainable growth:

  1. Attracting and retaining the right talent (people)
  2. Creating a differentiated business strategy
  3. Precise execution of that strategy
  4. Generating cash for preservation and growth

Main leadership lesson(s): The ability to scale is a mark of success

Scale: Successful teams and departments with the right processes and systems can operate at-scale, in a cost-effective and efficient way. Unsuccessful teams create wasted time and effort.

All too often, there exists a severed link between the specific objectives the company needs to achieve over a certain period of time, the daily activities of the employees on your team, AND the performance benchmarks they’re measured against.

In other words, there’s complete misalignment up and down the ranks, and employees are wasting time and effort on initiatives that aren’t tied to what the company defines as success.

Alignment creates clarity and accountability.

Amidst the treasure trove of information within this book, Verne, in so many words, poses a single question that can solve the alignment question for good — “How do your employees know they’re having a good day, week, or month?”

Here’s what this question is really asking: “Are the things your employees are responsible for and held accountable to executing on a daily, weekly, or monthly basis directly influencing the company achieving its quarterly and annual plans?”

As part of the Scaling Up framework, leaders and managers are responsible for cascading the company priorities down to their teams and aligning them around common, supporting objectives.

Leaders that are able to align their employees with the greater mission will create more productive work environment where they’ll know that the work they’re held accountable to is meaningful to the organization, while at the same time, having complete clarity on what to (or not to) prioritize on a daily basis. 

5. 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works by Dan Harris

Who it’s for:

  • Leaders who believe mental health is as important as any other aspect of leadership development
  • Any leader or individual who wants better control over their ego / reactivity in all situations

As leaders, we can often overlook the importance of mindfulness, or, being able to recognize what’s happening in the moment, in our minds right now.

Mindfulness is a leadership skill that must be developed like any of the skills mentioned above.

In 10% Happier, Dan Harris, an ABC News correspondent, brings us on his journey to quell his ego-driven stress and personally destructive behaviors by exploring the scientific benefits of mindfulness and meditation.

On his journey, he meets several influencers that rationally reshape his initial skepticisms regarding the power of meditation, turning him from radical skeptic to diligent practitioner, giving him the mental tools to navigate his challenging and stressful career.

This book makes the fundamentals of mindfulness and meditation accessible to all. 

Main leadership lesson(s): Mindful leaders are happy leaders

Mindfulness is an underlying element to achieving success in any of the above areas. It’s giving oneself the space to accept ownership, embrace feedback, and make good decisions, ultimately building trust with others.

During his journey, Dan is introduced to the concept of RAIN, a systematized application of mindfulness for any situation and acronym for the following:

Recognize:  acknowledgement of what you’re feeling at that moment.

Allow: accepting your feelings as they are.

Investigate: analyzing theconnection between your feelings and how they’re affecting your body.

Non-identification: remembering that what you felt in that moment does not represent you as a person.

This system is a great way for leaders or managers to create the mental space to think clearly - to respond instead of react - in any situation, but especially high-stress or high-stakes situations.

If they can master mindfulness, it will make sharpening the other skills on this list much easier.

Be deliberate with your growth as a leader

Over the years, my experience in previous roles has been an invaluable teacher for me.

But when tasked with the responsibility of building a new department and leading a new team, it’s not enough to simply lean on those past experiences.

My personal and professional growth as a leader had to be deliberate.

Discovering and reading the above books has armed me with a toolset necessary to step into and succeed in this new role.

The lessons learned allowed me to quiet the voice in my head, and instilled a newfound level of confidence in myself and my team and regardless of what the next step is in your career, I hope you fill find they do the same for you. 

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