Best Business Books I Read in 2022: The Year of the Challenge

by | Perspectives

Welcome to the 2022 edition of my Best Business Books of the Year post. This is my fourth annual Best Business Books post, and the reading required to build it is more than just a tradition. It’s a means to creating a strategic business edge.

Selecting a particular book doesn’t happen by chance for me. It’s usually when I’m in pursuit of insight around a particular topic or concept. If you look through the titles of past lists (and I include them all at the end of the post), a theme typically emerges.

2022 was no different.

This year’s theme: Sales strategy

To develop our Digital Twin sales and marketing strategy — in which we use online content to create a Digital Twin of a company’s sales team — I knew our company had to learn more about sales.

We’re pretty well-versed on the marketing front and have obviously used sales to build our own business. But we wanted to go deeper and really learn more and more about tactics and strategies.

Far and away, the most significant books I read this year were The Challenger Sale and The Challenger Customer. I’ll begin with them, but be sure to read on because you’ll find plenty of other gems in the 2022 mix.

The list: Business books I read in 2022


The Challenger Sale: Taking Control of the Customer Conversation – Matthew Dixon and Brent Adamson


The Challenger Sale

“Surveys of customers consistently show that they put the highest value on salespeople who make them think, who bring new ideas, and who find creative and innovative ways to help the customer’s business.” – The Challenger Sale

I love The Challenger Sale for multiple reasons. Not only is it the book that reveals the most effective strategy for complex sales; it’s all backed by research. And the biggest surprise was discovering just how highly customers value business insights from a salesperson.

What really shocked (and delighted) me was how closely that and other aspects of The Challenger Sale aligned with basic tenets of content marketing. They also meshed beautifully with our Digital Twin strategy, and helped us redefine ourselves as a sales and marketing agency.

There are plenty of other eye-opening ideas in The Challenger Sale, and it will be an ongoing reference for Winbound.


The Challenger Customer: Selling to the Hidden Influencer Who Can Multiply Your ResultsBrent Adamson, Matthew Dixon, Pat Spenner and Nick Toman

The Challenger Customer

“The most important dynamic in B2B selling today: Finding a way to connect the diverse individuals that comprise a buying group around a higher-level vision than where they’re most likely to land on their own.” – The Challenger Customer

The Challenger Customer is an evolution of The Challenger Sale. It brings new data to light regarding the customers involved in a B2B. It really helped Winbound fine-tune our strategic thinking, especially in the field of manufacturing.

The book’s findings really blew away some conventional wisdom, including thinking that you need to create individual strategies and marketing content for all the customers involved in a complex sale. The data reveals how inefficient and potentially detrimental that approach can be.

What was even more revelatory was the idea expressed in the quote above — that redefining the problem, including how it impacts the customer on a larger scale, is critical to avoiding sales engagements based solely on price.


Traction: How Any Startup Can Achieve Explosive Customer Growth – Gabriel Weinberg and Justin Mares



“Poor distribution — not product — is the number one cause of failure. If you can get even a single distribution channel to work, you have a great business. If you try for several but don’t nail one, you’re finished.” – Traction

At Winbound, we like to think in terms of “distribution” when it comes to marketing our content. How do we distribute our content to the channel that will drive the greatest demand?

Written for start-ups, Traction provides a look at multiple methods of distribution — nineteen in all, ranging from publicity and SEO to offline ads and sales teams. The book shows how to use low-cost testing in each channel and how to find the one that truly moves the needle.

Some of these channels seem more resistant to low-cost testing than others, and the book doesn’t account for the value of frequency and keeping your message out there consistently.  But the book’s discussion of all the distribution methods is alone worth the price of purchase.


SPIN Selling – Neil Rackham


Spin Selling

“Closing techniques, like all forms of pressure, become less effective as decision size increases.” SPIN Selling

It’s hardly a coincidence that Neil Rackham wrote the introduction to The Challenger Sale. Much of that book was built on Rackham’s research-based approach, and he considered Challenger to be an evolution of the approach explained in SPIN Selling.

The essence of SPIN is that the traditional closing methods once championed by sales managers simply don’t apply to complex sales.

Instead, Rackham and his team found that uncovering Implied Needs and developing them into Explicit Needs is far more effective. The approach includes more nuances, but it’s based on asking the right questions.

There are aspects of the approach that seem dated in today’s digital age, but it definitely provides you with historical context for selling complex products.


Product-Led SEO: The Why Behind Building Your Organic Growth Strategy – Eli Schwartz


Product-Led SEO

“The goal was never to win on any specific keyword, but instead to win on many keywords, whatever they might be.” – Product-Led SEO

Building on Traction’s focus on distribution, Product-Led SEO focuses on a channel we’ve been using for years: search engine optimization (SEO).

The book builds on an evolution we’ve experienced with our own SEO work, in which we’re focused less on the almighty keyword and more on user search intent. Schwartz takes this premise to a whole new level.

With all the changes in Google’s algorithm and an increasingly competitive landscape, your content needs to address what the customer wants, and it may not always be the keywords you think. In fact, it might not even be your product or service keywords at all.

Schwarz isn’t just espousing a theory either. With the examples he provides, you get a vivid sense of how trying to game Google is folly. The real prize lies in meeting the content needs of your customers, whatever those may be.


The Effective Executive – Peter Drucker


The Effective Executive

“Pick the future as against the past; Focus on opportunity rather than on problem; Choose your own direction — rather than climb on the bandwagon; and Aim high, aim for something that will make a difference, rather than for something that is ‘safe’ and easy to do.” – The Effective Executive

How the heck have I been reading business books for years, yet I’m just finally getting to Peter Drucker? He’s one of the business world’s most influential thinkers, and The Effective Executive is loaded with insights on decision making, time management, and the role of knowledge workers.

The historical reflections on some of the titans of industry (and war) are fascinating. But the thing that has really stuck with me is Drucker’s insistence that we focus on the strengths of our people, not on their weaknesses.

That means abandoning the idea that you can fix an employee’s problems. Drucker asserts it’s inefficient and highly ineffective. On the other hand, lean into what makes a person truly effective and you and your personnel will soar.


Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success – Gary Vaynerchuk


Twelve and a Half

“The black and white is still important. But to me, it’s a distant second to mastering soft skills.” – Twelve and a Half

This was definitely a revelatory year for me on the “soft skills” front. Soft skills are defined as the personal skills that allow you to interact successfully with other people. Yet they are basically given lip service by most people (particularly men).

Vaynerchuk digs deep into these soft skills and emotional intelligence, and isolates his 12.5 ingredients that he feels are critical for business success. When you read the book and his examples, you’ll find it’s hard to dispute his claim.

I’ve been working on these skills in a big way this past year, and I’d have to say it’s really had a life-changing impact on my relationships at work and at home. I’ve definitely been in a better headspace.

A special thanks to Spencer X. Smith for giving me the book in the first place, and to my son Sam, who also read the book. Sam told me that Vaynerchuk believes emotional intelligence will be one of the defining characteristics for success. Thanks guys — you showed me the light!


CEO: Customer Engagement Officer – Mark Hillary


CEO: Customer Engagement Officer

“You can prepare the words and feed the lines to your CEO, but when the Q&A begins, there is no prepared script; they need to know their own business.” – CEO

I’ve noticed an uptick in the social media and blogging presence of CEOs, and so I thought I’d dig into the subject a bit more. This book helped me redefine the title “Chief Executive Officer” to “Chief Engagement Officer.”

Why? Because who else should be the ultimate Digital Twin for the company? Who else should be accessible to the customer, and understand what they think about an organization and what they want in terms of products and services?

The CEO should be on the front lines, setting the tone for the company and reading the room on a macro-level. Hillary’s book shows you how CEOs can engage by sharing thought-leadership content and sparking engagement.


Relentless: From Good to Great to Unstoppable – Tim S. Grover


Relentless: From Good to Great to Unstoppable

“The greatest battles you will ever fight are with yourself, and you must always be your toughest opponent.” – Relentless

One of Gary Vaynerchuk’s soft skills in Twelve and a Half is tenacity. Tim S. Grover’s book Relentless takes tenacity to a whole new level, literally and figuratively.

Grover trained basketball legends Michael Jordan, Kobe Bryant, and Dwayne Wade, and he shares much about their indefatigable drive to win. Their journeys were filled with loneliness, endless battles, and many setbacks, but they were relentless in their pursuit of success.

He refers to people who are relentless as “Cleaners,” and shares the nuances that differentiate them from the rest. For example, while some will admit defeat, others will work harder. “The Cleaner strategizes for a different outcome.”

Thanks to Edwin Ojeda for this one!


Family Business Abundance: A Management System for Family Businesses – Bradley G. Fisher


Family Business Abundance

“The challenge is not to force growth but to unlock it.” – Family Business Abundance

You may not have heard of Brad Fisher, and you may not be part of a family business, but that shouldn’t stop you from reading this book. The business wisdom in these pages comes from a guy who’s been there, grown that — and it will help anyone who runs a business.

Fisher digs deep into concepts that are near and dear to my own heart, including the need for clarity and defining a purpose for your business. He’s also given me plenty to think about as a business owner with a family, including involving them more with the operation.

Ultimately, I see value in thinking about all the people who work for you as part of your family.  They rely on you each and every day to help them put food on the table. This book is a great tool to help ensure you never let them down.


Maigret and the Headless Corpse – Georges Simenon


Maigret and the Headless Corpse

“It was becoming easy. It was no longer a question of asking questions haphazardly — fishing, as they called it at headquarters.” – Maigret and the Headless Corpse

Ok, why in the world am I including a mystery novel in my list of business books?

First of all, if you’re looking for a great read and a study in human behavior, read Georges Simenon’s series on Inspector Maigret. I’m not a big mystery reader, but I do love the lean writing of Dashiell Hammet. He never gets in the way of a story. Simenon is cut from the same cloth.

But I include this book simply because of the excerpt above.

Marketing is a lot like detective work. You ask a lot of people a lot of questions. You propose theories, run into dead-ends, and wind up frustrated and stumped. A lot.

But if you keep at it, suddenly, you’ll start connecting the dots. Then, like Maigret, it will become easy, and those questions will no longer be haphazard. Your fishing days will result in a big catch.


They Named You Right – Rock LaManna


They Named You Right

“Take what you learn and find a way to teach it to the next generation. Help them cross the ocean (real or metaphorical), build something amazing, then wrap their own version of the suit in paper and pass it along.” – They Named You Right

Ok, full disclosure on Rock LaManna’s memoir: I had the pleasure of ghostwriting it for him.

I say this not to pat myself on the back or sell more books (I don’t get paid royalties), but to share with you LaManna’s amazing story, and the life / business lessons he has to share.

The excerpt above refers to the LaManna family migration from Italy to the US. As the men would arrive, they would take off the suit they traveled in, wrap it in paper, then send it back to the mother country for the next family member.

Rock, like all the authors on this list, has passed their knowledge and insights on to future generations. To each author, I thank you for sharing your life-changing thoughts, and I deeply appreciate all you’ve done for me and for the community at large. We are in your debt.

Ok — those are my business reads from 2022. Here are some of the books from past years.

Best Business Books 2021

Think Like Google: Use SEO and Empathy to Rank, Convert and Profit No Matter How Much They Change the Rules – Tom Gerencer

The Road Less Stupid – Keith Cunningham

Limitless: Upgrade Your Brain, Learn Anything Faster and Unlock Your Exceptional Life – Jim Kwik

The Win Without Pitching Manifesto – Blair Enns

Building a StoryBrand: Clarify Your Message So Customers Will Listen – Donald Miller

New Sales. Simplified.: The Essential Handbook for Prospecting and New Business Development – Mike Weinberg

Every Book is a Startup – Todd Sattersten

Uncopyable: How to Create an Unfair Advantage Over Your Competition – Steve Miller

Content-Based Networking: How to Instantly Connect with Anyone You Want to Know – James Carbary

Think Again: The Power of Knowing What You Don’t Know – Adam Grant

ABM is B2B: Why B2B Marketing and Sales is Broken and How to Fix It – Sangram Vajre and Eric Spett

The Book on Account Based Marketing: Practical Tips for Exponential Revenue Growth – Bassem Hamdy

Best Business Books 2020

Web Analytics 2.0: The Art of Online Accountability and Science of Customer Centricity – Avinash Kaushik

Content Chemistry – Andy Crestodina

Faster, Better, Cheaper in the History of Manufacturing: From the Stone Age to Lean Manufacturing and Beyond – Christoph Roser

The Fourth Industrial Revolution – Klaus Schwab

Ditch the Act: Reveal the Surprising Power of the Real You for Greater Success – Leonard Kim and Ryan Foland

Stop Being the Best-Kept Secret: Manufacturing eCommerce Strategies – Curt Anderson

Best Business Books 2019

Live in a Better Way: Reflections of Truth, Love and Happiness – the Dalai Lama

The Six Secrets of Change: What the Best Leaders Do to Help Their Organizations Survive and Thrive – Michael Fullan

Hit Makers: The Science of Popularity in the Age of Distraction – Derek Thompson

Everybody Writes:  Your Go-To Guide for Creating Ridiculously Good Content – Ann Handley

Uncertainty: Turning Fear and Doubt into Fuel for Brilliance – Jonathan Fields

The Marketing Rebellion: The Most Human Company Wins – Mark Schaefer

Business Adventures: Twelve Class Tales from the World of Wall StreetJohn Brooks

The Big Data Driven Business: How to Use Big Data to Win Customers, Beat Competitors, and Boost Profits – Russell Glass, Sean Callahan

The Content Trap: A Strategist’s Guide to Digital Change – Bharat Anand

This is Marketing: You Can’t Be Seen Until You Learn to See – Seth Godin

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Greg Mischio

Greg Mischio

Greg Mischio has been a content marketing zealot for many moons. He is the Owner and Founder of Winbound, a marketing agency that provides content marketing for small marketing departments with a focus on manufacturing and industrial verticals.

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