May 21, 2019
Sometimes the most poignant lessons on how to improve as a sales leader come not from conference keynotes or costly coaching services—sometimes the best advice is right there at your fingertips. If you’re looking for your next great read, don’t go past these 9 books that should be on every sales leader’s bookshelf.
Hang on, books? Who needs books when you’ve got Google?
We live in a digital era of constant connectivity where access to near-infinite information is never more than an arm's reach away.
So, why bother with books if I can find everything I need to know online, right?
Well, sort of, but not quite.
It turns out there are myriad benefits to reading, which is why some of the most successful and influential people dedicate a significant portion of their time to books.
Proposify’s own CEO Kyle Racki is a shameless bookworm, and a big proponent of reading as an effective way to learn and grow as a leader (check out the nine books he recently read and recommends, plus one he wrote).
Research has shown that reading books increases vocabulary, general knowledge and verbal intelligence, makes you more empathetic, and increases theory of mind and your ability to understand others.
(As a bonus, if you need further convincing, reading may also protect against Alzheimer’s, reduces general cognitive decline, and even predicts a longer life.)
While these attributes transfer across many aspects of life and business, they are critical for sales professionals. What’s more, they’re essential qualities for those in or aspiring to management and leadership positions.
Reading plugs you directly into the mind of the author. There is no better way to learn from people who’ve been where we want to go and achieved what we want to achieve. Through reading, we learn from the mistakes and successes of those we wish to emulate.
As Warren Buffett says, the knowledge gained from books builds up like compound interest.
For sales leaders, industry-specific books represent the ultimate ROI when it comes to levelling-up your knowledge and expertise. Apply the principles detailed in the right book to your career, you’ll make your money back in a heartbeat.
In this article, we explore the core messages of some of the best sales management and leadership books available. We explain what makes them so good, how best to apply the wisdom they carry to your career as a sales leader, and why we consider them books every sales leader should read.
The 9 books on every top sales leader's bookshelf
Cracking the Sales Management Code
The Sales Development Playbook
Practice what you preach: actionable management advice
You know what it takes to sell, but can you instill that know-how and drive in your team? Management is all about getting individuals to work together as a cohesive unit, with each team member striving to contribute their best work every day.
If you’re a current or future sales leader, these three books better be on your list. They lay out the coaching strategies and techniques needed to get your team to close with devastating consistency.
Cracking the Sales Management Code
The Secrets to Measuring and Managing Sales Performance
By Jason Jordan & Michelle Vazzana
The modern sales machine is far more sophisticated than it used to be.
New technology, sales processes, and CRM systems have given us innumerable metrics with which to track the success of a sales team. As a new sales leader, selecting the right process is overwhelming, and can mean the difference between regularly going above and beyond or merely getting by.
To succeed in sales management, you must possess an intimate understanding of the factors that lead to success in this dynamic new era of selling.
Cracking the Sales Management Code outlines these factors with profound depth and clarity. And, unlike other books on leadership and general selling, it delivers specific, practical advice targeted directly at sales managers.
Based on in-depth research into the best practices of some of the top sales forces in the world, this book identifies and analyzes the metrics, management approaches, and methodologies used by those high-performing companies.
Why you should read it:
As they proceed to ‘crack the code’, Jordan and Vazzana articulate many truths concerning common pain points and bottlenecks of sales management; truths that too often otherwise go unsaid.
Sometimes the science of sales management gets obscured by the art of the sale. Selling itself is an artform, there’s no doubt about it, but that sentiment still tends to cloud the underlying analytical systems of a good sales process. This book puts the focus back on that science, offering practical advice on how best to measure progress and strive toward success.
Identifying relevant metrics—the ones that truly reflect the goals of your sales force—is a highly logical process. Cracking the Sales Management Code highlights the importance of thinking with critical, data-driven precision when it comes time to determine how to track the performance of sales activities and ensure long-term gains.
If you’re a sales leader who wants a better understanding of which metrics to implement and measure against based on the specific skills and goals of your team, this book is for you.
From the book:
“This book makes one big step toward establishing a rigorous sales management discipline. Based on our research into how leading companies use metrics to manage their sales forces, we have developed a management system that will predictably link the activities in the war room to the battle on the field.
It will help sales managers floating in a sea of data to focus their attention on the few metrics that really matter. It will help sales executives to drive their sales forces with a clear set of operating instructions. It will provide a framework for improved sales performance reporting. It will finally crack the sales management code.”
– Jason Jordan & Michelle Vazzana
The Talent Code
Unlocking the Secret of Skill in Sports, Art, Music, Math, and Just About Everything Else
By Daniel Coyle
This book presents a blueprint for solving two of the hardest challenges in sales leadership.
First, how do you design effective training programs that help your reps master new skills quickly and reach their full potential?
Second, how do you ignite the commitment and drive within your team to put those skills to good use and strive for a collective goal?
Drawing on neuroscience, management theory, and first-hand research, The Talent Code outlines exactly what happens in our brains when we learn new skills. On top of that, it explains how to optimize skill acquisition through a process author Daniel Coyle terms ‘deep practice’, and offers a method to leverage deep practice in your training programs.
Certain things transcend disciplinary boundaries; skill acquisition is one of them. Once you understand this process, a little ingenuity is all that stands between you and a coaching program optimized to extract results from your sales team.
Why you should read it:
One of the hardest things to do in sales leadership is to get things done through your people. It’s not easy to get your team motivated to do what they’re supposed to do or develop their competencies in a way that drives results.
The Talent Code outlines a framework and provides the tools to do those things well. That’s an invaluable thing for a sales leader to have in their back pocket.
The advice in this book serves as a blueprint for implementing training programs designed to leverage the biological process every brain undertakes when encoding new skills. This wisdom will help you unleash the talent in your sales reps. What’s more, you can apply this advice to your own approach to learning as you refine what is takes to become a killer closer and even better leader.
From the book:
“Coaching is a long, intimate conversation, a series of signals and responses that move toward a shared goal. A coach’s true skill consists not in some universally applicable wisdom that he can communicate to all, but rather in the subtle ability to locate the sweet spot on the edge of each individual student’s ability, and to send the right signals to help the student reach toward the right goal, over and over.”
– Daniel Coyle
Sales Management. Simplified.
The Straight Truth About Getting Exceptional Results from Your Sales Team
By Mike Weinberg
There’s no two ways about it: sales leadership is a tough job. If your sales team isn’t performing, the whole company feels it.
Solidifying the sales process, culture, and proper management necessary for a team to thrive can take years of careful planning and implementation.
This book delivers a framework for building and managing a high-performance sales team and offers simple, relevant advice to ensure lasting success. It presents some painful truths about why modern sales teams underperform, and how the right management, leadership, and coaching can transform results from mediocre to exceptional.
Author Mike Weinberg—a highly experienced sales coach, consultant, and speaker—explores the characteristics of a vibrant and healthy sales culture and presents tips on how to emulate that energy and drive among your own people.
Why you should read it:
It’s easy to point out flaws, but it’s much more difficult to offer constructive advice on how to improve.
Weinberg forces even the most seasoned sales professionals to reflect on the effectiveness of their entrenched management processes, and suggests how to fix the parts that just aren’t working.
Part one of Sales Management. Simplified. calls out the blunt truth about why legacy processes needlessly produce costly mistakes. Part two rolls out a blueprint to address these pitfalls, eliminate the common diversions and distractions that plague sales leaders, and refocus on the components of the job that produce quality results.
This book challenges you to reassess the fundamental duties of the sales leader. More than that, it forces you to consider whether your management style is contributing to the underperformance of an otherwise solid sales force.
Sales Management. Simplified. radiates authenticity; written from the front lines of the selling field, it’s based on the first-hand experiences of someone who’s both led and consulted high-stakes sales teams.
There’s a good reason this book is considered mandatory reading among serious sales leaders. Countless books explain every facet of the mechanics of selling, but few thoroughly deconstruct what it takes to manage and lead a sales team effectively. Sales Management. Simplified. is one of those books.
From the book:
“I love sales and helping salespeople excel at developing new business. But what I love even more is experiencing a high-performance, results-focused, winning sales team with solid leadership, smart talent management, a strong sales culture, and a sound sales process.
My two primary goals in writing Sales Management. Simplified. are to bluntly share the reasons so few sales organizations today exhibit these characteristics, and to offer a simple, actionable framework that sales managers and senior executives can adopt to create dramatic and lasting sales performance improvement.”
– Mike Weinberg
Killer process: sales strategies that close
Leading a sales team is equal parts knowing HOW to coach and manage, and knowing precisely WHAT to teach them.
Creating an effective sales strategy is a core component of a sales leader’s job. It’s up to you to decide which methodologies and sales tools to implement to keep the pipeline full.
An effective sales leader understands how to utilize each of their team members’ strengths, implement the right processes at the right time, and ensure the fundamentals of selling are solid throughout the team.
The three books in this section are some of the best books for sales leaders when it comes to developing strategy.
The Sales Development Playbook
Build Repeatable Pipeline and Accelerate Growth with Inside Sales
By Trish Bertuzzi
B2B selling and buying is changing fast.
Prospects are drowning in a sea of information and requests for time. Sales reps are up against an increasingly complex web of decision-makers.
The key to growth in a crowded market—according to author Trish Bertuzzi, a sales strategist and consultant with three decades of experience—lies in sales development.
In this book, Bertuzzi makes the case for the importance of a unit dedicated to owning the top-of-the-funnel activity, building a repeatable sales pipeline, and reaching and qualifying leads with breakneck speed and efficiency.
The Sales Development Playbook dissects the following six crucial elements for building a successful sales development team:
- Strategy
- Specialization
- Recruiting
- Retention
- Execution
- Leadership
Why you should read it:
The Sales Development Playbook lays out a method for how best to identify, pitch, and progress keen and qualified leads along the sales cycle.
It’s one of the rare sales books with relevant, actionable advice in every chapter. This book has helped us here at Proposify understand the sales development rep (SDR) role, divide labour appropriately, and run our sales team according to an optimal and predictable inside sales process.
Understanding market maturity is one of the most important takeaways. It’s helped us put together a compensation plan relevant to Proposify’s position in the market, and accelerated growth and drive in the SDR team. The Sales Development Playbook lays out a comprehensive framework for building an SDR team—from hiring, training, and coaching to how best compensate your reps for their hard work.
If you’re a sales leader serious about getting in front of more prospects, building a new pipeline, and accelerating revenue growth, this book lays out a plan to achieve it over and again.
From the book:
“Perhaps you’re already excelling at some of the six elements today. You can achieve lift-off if you execute one or two well. Good strategy and good recruiting, for instance, will deliver some return. You can even produce respectable results by excelling at three or four elements. But if you truly want to nail sales development—if you want to be a legend in building repeatable pipeline and leading a world-class team—all six elements need to be mastered.”
– Trish Bertuzzi
Predictable Revenue
Turn Your Business Into a Sales Machine with the $100 Million Best Practices of Salesforce
By Aaron Ross & Marylou Tyler
A favourite among sales leaders, this bestselling book has helped countless businesses generate predictable, repeatable, scalable revenue year after year.
Authors Aaron Ross and Marylou Tyler break down a comprehensive sales process and offer dozens of strategies to implement to help drive growth.
Primary among them include:
- The importance of specializing your sales team into roles with distinct and separate functions
- Short and sweet messaging tips to generate referrals to the decision-makers
- Being patient, taking baby steps: knowing how to build trust and close at the opportune moment
Predictable Revenue details the outbound process that redefined traditional cold calling and prospecting. Pick yourself up a copy of this book and learn from these two icons of the sales world.
Why you should read it:
The sales machine, even at smaller companies, is a highly complex mechanism. As sales leader, you are responsible for the seamless operation of dozens of moving parts. Predictable Revenue distills even the most intricate concepts that deal with maintaining those parts down to concise, cogent advice without diluting the content or cheapening the message.
The clear analyses of even the most complex sales processes is what makes this book so approachable for all sales professionals looking to grow revenue.
Many of the best sales leadership books contain pearls of wisdom. But not all authors of such books can claim the success Aaron Ross and Marylou Tyler have had by putting their words into action.
After implementing the sales process outlined in this book at Salesforce, Ross raised their ARR from $5m to $100m.
With 30 years of sales experience under her belt, Tyler is currently the CEO of Strategic Pipeline, a consulting company that advises titans like Apple, Bose, and Mastercard.
From the book:
“Of course you want more revenue, but what good is it if it isn't predictable? One-time revenue spikes that aren't repeatable won't help you achieve consistent year-after-year growth. You want growth that doesn’t require guessing, hope, and frantic last-minute deals hustling every quarter- and year-end.”
– Aaron Ross & Marylou Tyler
Pitch Anything
An Innovative Method for Presenting, Persuading, and Winning the Deal
By Oren Klaff
This book will change the way you think about pitching.
Author Oren Klaff is an investment banker who pitches deals for a living. Pitch Anything presents a thorough deconstruction of the pitching process, relying on a combination of first-hand experience and research into neuroeconomics (a field at the intersection of biology, neuroscience, and behavioural economics).
With credentials like that, you can bet his book is a treasure trove of insight for anyone looking to close more deals.
Klaff explains the structure of the brain and why that matters as we process financial decisions. He highlights the importance of appealing to what he calls the croc brain.
In a nutshell, our brain is structured in three basic layers:
- Neocortex — the part of the brain responsible for complex problem solving, language, and logical thought. It’s the highest and most recently evolved part of our brain
- Midbrain — the part responsible for social interaction and relationships
- Crocodile Brain — or the reptilian brain, it’s the oldest part of our brain and is responsible for survival; as such, it processes information in a binary, high-contrast fashion
Contrary to what we may think, when we pitch, we’re talking to our prospect’s croc brain. Armed with this realization, Klaff details how exactly to effectively communicate with our reptilian audience.
Why you should read it:
Pitch Anything presents strategies to dominate the pitching process. You’ll learn how to present a concise, jargon-free pitch, capture and hold your prospect’s attention by harnessing the power of narrative, and close with finality and confidence.
The strategies in Pitch Anything are bold, unconventional, and audacious, but you don’t need to be aggressive or contentious to put them into action. Have fun. Crack a joke here or there. Assert your status with a wink and a smile.
Most importantly, you need to believe deep down that you are the prize to be won and be willing to walk away if the client disagrees.
Pitch Anything fundamentally changed everything we thought we knew about sales pitches and presentations, and flies in the face of virtually every classic sales technique we’ve been taught.
From the book:
“There is a fundamental disconnect between the way we pitch anything and the way it is received by our audience. As a result, at the crucial moment, when it is most important to be convincing, nine out of ten times we are not. Our most important messages have a surprisingly low chance of getting through.
“You need to understand why this disconnect occurs in order to overcome it, succeed, and profit. This book tells you how.”
– Oren Klaff
From the front: unleash your inner leader
The best leaders don’t just lead by example, they also set precedents and put systems in place to support and empower their team to accomplish their goals.
The foundational principles of leadership are universal. They are equally applicable in business, on the sports field, battlefield, or in life. The three books in this section come from authors who’ve studied these principles with meticulous dedication and dominated their respective arenas.
Understanding how to earn the confidence and respect of your coworkers and team members is paramount to your success as a sales leader. These books outline some of the philosophies that drive leaders from all walks of life.
The Psychology of Winning
Ten Qualities of a Total Winner
By Denis Waitley
The classics are classics for a reason, and this book is among the heavyweights of motivational literature.
An oldie but a goodie, there’s a high likelihood the rest of the books on this list were influenced by Dr. Denis Waitley’s 1978 classic, The Psychology of Winning. Not only is it a pioneer of the motivation genre, but it’s also one of the first ever audiobooks, back when audiobooks still resided in cassette tapes.
This book teaches you how to approach work, personal life, and leading a team with a winning mindset. And not winning in the literal coming-in-first-place sense, but adopting winning habits and a focus on a positivity that resonates in all you do.
Dr. Waitley spent years observing and documenting the habits of hyper-successful people—from Olympians to champion salespeople to top executives—determining what set them apart. The results are laid out in this book, distilled into ten recurring winning qualities shared by all those who reached the highest levels in their chosen fields.
The Psychology of Winning outlines the power of positive reinforcement; adopting a mindset of self-worth and self-trust in every aspect of your life, personal or business.
A word to the wise: while this book is packed with wisdom, it was written in the seventies, so expect some of the language and references to be somewhat…dated.
Why you should read it:
In today’s digital age it’s easy to get caught using technology as a crutch. Classics like The Psychology of Winning remind us that while technology has changed, people haven’t.
Despite massive innovation since this book was published, our fundamental psychology has remained the same. Dr. Waitley explains how the key to success in business and life lies in understanding how to tap into your innate mental potential.
When you get out in the world, you’ve got to sell yourself. Sales is a constant. Reading The Psychology of Winning early in his career helped Proposify’s COO Kevin Springer better understand people, and it taught him the importance of staying positive and staying confident as a salesperson and later as an entrepreneur.
There’s much more to sales than just the mechanics of the sale. This book teaches you how to get motivated, stay positive, accept a compliment, and apply that positive reinforcement, both in sales and in life.
As Dr. Waitley says, “It’s not what you are that holds you back, it’s what you think you are not.” We hesitate. This book teaches you not to hesitate, but to just go for it. What’s the worst thing that could happen?
From the book:
“You are either the captive or the captain of your thoughts. You can resign yourself to mediocrity or you can dare to dream of conquering outer space, inspiring the youth of our nation, discovering a cure for a dread disease, helping the less fortunate, creating a masterpiece of art or music, or even changing history .”
– Denis Waitley
Extreme Ownership
How U.S. Navy SEALs Lead and Win
By Jocko Willink & Leif Babin
While the context may change, the core principles of leadership remain the same.
Extreme Ownership articulates these principles with forthright, unbridled honesty, from two people who put them into action under the most extreme circumstances imaginable.
Jocko Willink and Leif Babin, both retired US Navy SEALs who served together in the most highly decorated Special Operations unit in the Iraq War, have taken their hard-earned wisdom from the battlefield and put it in this book.
Extreme ownership is the philosophy that drives their message. Leaders must own everything in their world; there is no one else to blame.
Only through acknowledging mistakes and admitting failure can a leader chart a true course to success. That and that alone, they argue, is the sole determining factor of an effective leader.
Why you should read it:
Leadership is about setting an example as much as it is about motivating and coaching those you lead. Extreme Ownership explains the importance of embodying the principles you wish to instill in your team.
Perhaps the ultimate virtue of a great leader is empathy; the capacity to put yourself in the shoes of another and understand and share what they’re experiencing. This book is a masterclass in empathy.
Very few of us will experience the horror of war firsthand. Yet, with an empathetic mindset, we can all take the lessons learnt by those who have and apply those principles in our own lives with the confidence that they stand up in the most wretched and dire of circumstances.
Owning your failures and mistakes takes courage and humility. If you expect to lead a team, you need to be well versed in each. Forgoing either trait jeopardizes the integrity and foundational trust essential to every high-achieving team.
This book dispenses invaluable wisdom to individuals involved in companies large and small. It’s is one of the best books for sales leaders looking to lead a high-performance team.
From the book:
“The only meaningful measure for a leader is whether the team succeeds or fails. For all the definitions, descriptions, and characterizations of leaders, there are only two that matter: effective and ineffective. Effective leaders lead successful teams that accomplish their mission and win. Ineffective leaders do not. The principles and concepts described in this book, when properly understood and implemented, enable any leader to become effective and dominate his or her own battlefield.”
– Jocko Willink & Leif Babin
Radical Candor
Be a Kickass Boss Without Losing Your Humanity
By Kim Scott
We’ve all been stuck in the unenviable position of deciding how to let a buddy know his fly is down. When one finds oneself in such a predicament, there are a few courses of action toward addressing this unfortunate situation:
- Say nothing at all out of an unwillingness to embarrass your exposed friend
- “Dude, your fly is down.” Upfront, yes. Direct, sure. But did you have to point it out, loudly and theatrically, so the whole room hears it, too?
- Ignore it and say nothing to save yourself from embarrassment, who cares about him?
- Let him know, discreetly and with minimal theatrics, out of a genuine desire to help.
Each of these choices reflects a quadrant in Kim Scott’s Radical Candor framework, a guide that represents the relationship between directly challenging and personally caring at work:
- Ruinous Empathy: kind, but not helpful and potentially damaging in the long run
- Obnoxious Aggression: direct, but insincere and often unkind
- Manipulative Insincerity: the worst place to be, lacking both personal care and authentic criticism
- Radical Candor: say what needs to be said with genuine care and compassion
Yes, the fly-is-down example is over-the-top. But, as a leader, you need to carefully navigate complex scenarios like this every single day. How you choose to act may indeed have resounding effects among your team, your company, and your career.
In Radical Candor, Kim Scott has distilled the wisdom from a career spent advising and coaching managers, directors, and CEOs at some of the biggest companies in the world on how to be a kick-ass boss without losing humanity.
Scott’s experience extends beyond consulting. She’s put rubber to the road in management positions at Google, developed and taught leadership seminars at Apple, and co-founded three different companies—one of which ultimately failed due to her ruinous empathy, a story she shares in her book.
She’s the real deal; a true authority on business leadership and the antithesis of an armchair advisor.
Why you should read it:
Radical Candor makes the case for the importance of direct, honest, and genuine criticism and praise in the workplace. For a leader, it offers a foundation upon which to build a team driven by values of trust, reciprocation, and integrity.
This book is a powerful reminder of the importance of giving and receiving earnest praise and honest criticism. It speaks to the importance of remaining direct, clear, and sincere when tough situations inevitably arise.
Assume positive intent. Come into these conversations with the belief that those involved mean well. This attitude is the key to a meaningful connection with your colleagues, and the most direct path to productive professional growth.
The best bosses are more concerned about getting to the right answer than being right. We succeed only as a team; Radical Candor provides a framework for crafting a culture of open communication where open debate is encouraged, conflict is addressed and embraced, and egos are checked at the door.
The underlying principle of a radically candid attitude is a real desire for your colleagues to succeed. It’s a mindset we’ve adopted here at Proposify to significant effect.
From the book:
“Even in Silicon Valley, relationships don’t scale. Larry Page can’t have a real relationship with more than a handful of people any more than you can. But the relationships you have with the handful of people who report directly to you will have an enormous impact on the results your team achieves. If you lead a big organisation, you can’t have a relationship with everybody. But the relationships you have with your direct reports will impact the relationships they have with their direct reports. The ripple effect will go a long way toward creating—or destroying—a positive culture. Relationships may not scale, but culture does.”
— Kim Scott
Conclusion
There is a good reason habitual reading is a common trait among the highly successful.
Those at the pinnacle of their fields are constantly learning, always challenging themselves with new scenarios, incessantly striving to see things from as many perspectives as possible.
Books are the vehicle that makes those things possible.
The best books on sales, leadership, and management are direct conduits into the intimate, considered, and extended thoughts of people at the forefront of business.
Many sales authors speak at events that cost thousands to attend. More still offer consulting or coaching services that cost far more than that. Reading books written by some of the brightest minds in your industry grants you access to their ideas and insights at a fraction of the cost.
Making time to read some of these books will not only give you intimate access to remarkable people with seriously big brains, it will have a marked effect on your career, present or future, as a sales leader.
In case you missed it…
We gave away an entire set of these books to three lucky winners!
They’re sharpening their management skills, refining their sales strategy, and learning ways to more effectively lead their teams with some of the best sales books you can get your hands on.
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