Twelve Books To Prepare You For The Future
A Reading List For Game-Changing Association Leaders
Summary
I am fairly new to associations. I spent most of my career in higher ed innovation, building and helping run new programs, initiatives, and colleges. When I first joined an association as chief learning officer ten years ago, I was happy to learn that my previous experience translated quite well. This is, in part, because there are concepts that apply across the sectors of nonprofit, government, associations, corporate, etc.
This is an article about books. I consume lots of content, but I especially love books and I love reading. This is, in part, because books help anchor me in the frenzy of modern daily life. The twelve books I recommend come from three broad areas: strategy, innovation, and member discovery. They are for leaders looking to prepare their associations for an innovative future.
I lead the product community, a product development learning community designed specifically for associations. Let’s compare ideas and build something great.
Why Books?
“To be remarkable, read books.”
Kevin Kelly
Of all the media I consume nowadays — podcasts, social media, journalism, newsletters, expert colleagues, mastermind groups — I’m still reading physical books. They offer something that nearly any other source does not. I’ve achieved some success, in part, because I steep myself in the world of ideas: reading, consuming, grappling, discussing, debating, etc.
Reading long-form forces me to focus, think, and reflect in a way that things like social media do not. Books are also still the best vehicle to relay in-depth frameworks to guide association leaders in the areas of strategy and innovation.
I strongly believe all professionals need to read outside the domain of their expertise. Yes, we need deep experts in finance, technology, events planning, and volunteer management, but we also need boundary-crossers fluent in collaboration, coalition-building, idea generation, product development, and strategic thinking. This is, in part, the reason that none of these books come from the association literature.
The Best Books For Association Leaders
"If you only read the books that everyone else is reading, you can only think what everyone else is thinking"
Haruki Murakami
The following books cover three overlapping topics: strategy, innovation, and member discovery. In leading the product community, I borrow heavily from concepts, frameworks, and models in the areas of psychology, human factors engineering, product development, user experience, software development, design thinking, and customer success.
Strategy: Books on making a set of focused choices that define a shared, compelling future. The common purpose of strategy is to develop a unique value proposition and to gain competitive advantage. In associations, building a focused strategy means sustainably delivering unique value. These four books are best-in-class examples of how to build a winning strategy.
Playing to Win: How Strategy Really Works. A.G. Lafley, Roger L. Martin. This book frames strategy as making specific choices to win in a particular market. It introduces a practical five-question framework for developing effective strategy: (a) what is your winning aspiration? (define success), where will you play? (choose markets, customers), how will you win? (create your advantage), what capabilities do you need? (build required skills), what management systems are necessary? (support your choices). The authors argue that strategic thinking isn't just for executives; it should permeate all levels of an organization. Why association leaders should read it: Most associations rely on traditional strategic planning. This book gets at the practice of building an integrated, succinct, yet deeply impactful strategy. It is a masterclass in making specific, yet compelling choices and setting boundaries and creating systems to effectively execute. Your strategic planning will never be the same.
Strategy That Works: How Winning Companies Close the Strategy-to-Execution. Paul Leinwand, Cesare R. Mainardi. This book tackles the common problem of how to implement an ambitious strategy. Based on research of high-performing orgs, the authors identify five key practices that help us successfully connect strategy with execution: (a) commit to a distinctive identity (know who you are), (b) translate strategic direction into everyday actions, (c) put your culture to work (rather than fighting it), (d) cut costs to grow stronger (focus resources on what matters), and (e) shape your future (don't just react to market changes). Why association leaders should read it: This book stretches us to think clearly about building coherence across our capabilities, offerings, and strategic positioning. It also stresses culture as a vital component to strategy building.
Good Strategy Bad Strategy: The Difference and Why It Matters. Richard Rumelt. Most strategies aren't strategies but vague aspirations, motivational statements, or financial goals. Good strategy has three essential components: a diagnosis of the challenge being faced, a guiding policy for dealing with the challenge, and a set of coherent actions to carry out the policy. This book contrasts meaningful strategy (which involves making tough choices and focusing resources) with bad strategy characterized by fluff, failure to address obstacles, mistaking goals for strategy, and poor strategic objectives. Rumelt provides numerous examples from business, politics, and military history to illustrate these principles. Why association leaders should read it: A classic! This book challenges our traditional conception of strategic planning (and why these plans often become obsolete “shelf documents”) while pushing us to make coherent actions to carry out our aspirations.
Dual Transformation: How to Reposition Today’s Business While Creating the Future. Scott D. Anthony, Clark G. Gilbert, Mark W. Johnson. This book addresses how organizations can respond to disruptive change by pursuing two transformations simultaneously: Transformation A – Repositioning the core business to maximize its resilience and relevance and Transformation B – Creating a new growth business that could eventually replace the core. The dual approach allows orgs to leverage existing advantages while building the future. The authors emphasize that these transformations require different approaches but must be connected by capabilities that span both transformations. Why association leaders should read it: The main reason I recommend this book is that it helps us coherently balance our existing, legacy worlds with our bold futures. The bridge between these worlds is an investment in staff capabilities while providing the empathy needed to help us navigate change.
Innovation: Books on the strategic and practical implementation of ideas that result in new products, programming, or offerings. Associations have an enormous opportunity to innovate but I find that: (1) it’s rare, (2) it’s underfed, and (3) it’s almost always tactical in nature. Here are some resources that I use to help associations build cultures that help us get in the innovation game incrementally and meaningfully: through focus, via experimentation and trying new things, through iterative value creation, and by learning to manage our idea flow.
Ten Types of Innovation: The Discipline of Building Breakthroughs. Larry Keeley, Helen Walters, Ryan Pikkel, Brian Quinn. This book challenges the belief that innovation is mainly about creating new products. The authors present a comprehensive framework of ten distinct types of innovation that any org can leverage. These range from profit model innovations to customer engagement strategies. Most successful innovations combine multiple types, creating offerings that are hard for competitors to copy. The authors argue that innovation can be a structured, disciplined process rather than just random flashes of inspiration, and they provide practical tools for teams to systematically develop breakthrough ideas. Why association leaders should read it: This book is useful for embedding innovation in your association. I recommend it for its accessibility, practicality, and graphic-rich examples. Their framework provides ample flexibility for associations to test different types of innovation.
Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers. Alexander Osterwalder, Yves Pigneur. This handbook introduces the Business Model Canvas, a practical tool that helps people design, visualize, and reinvent their business models. The canvas breaks down a business model into nine essential building blocks, including customer segments, value propositions, revenue streams, and key partnerships. Rather than presenting business planning as a dense written document, the authors transform it into a collaborative, visual activity. The book is designed like a workbook, filled with examples, exercises, and illustrations to help readers apply these concepts to their own ventures or to revitalize existing businesses. Why association leaders should read it: All associations need a business model. They force us to think about our value proposition, customers, revenue, and cost structure in a succinct and powerful way.
The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses. Eric Ries. Ries introduces a methodology that challenges traditional development approaches by advocating for rapid experimentation instead of elaborate planning. The core idea is the build-measure-learn cycle, where entrepreneurs quickly create minimal viable products, test them with real customers, and use data to make informed decisions about whether to persevere or pivot. Rather than spending months or years developing a perfect product that customers might not want, Lean Startup emphasizes validated learning through experimentation. This approach helps orgs avoid wasting resources by determining what customers actually value before committing substantial resources. Why association leaders should read it: This book is a masterclass in lean product development. It recommends we invest in experimentation to test new ideas as opposed to investing enormous resources to build the next big thing. Serial experimentation is investment in our member communities.
Ideaflow: The Only Business Metric That Matters. Jeremy Utley and Perry Klebahn. The rate at which an organization generates ideas is the critical factor in determining innovation success. The authors, Stanford design thinking experts, present idea flow as a measurable metric that directly correlates with organizational performance. They outline practical techniques to dramatically increase the quantity and quality of ideas, including constraints-based thinking, radical collaboration, and systematic experimentation. The book challenges common barriers to creativity in businesses and provides frameworks for making innovation a consistent, reliable process rather than an unpredictable event that depends on rare creative genius. Why association leaders should read it: The well-worn cliche is true: we have too many ideas, we aren’t very good at evaluating and prioritizing them, and if a good idea emerges it is often hard to execute. This book helps us become both focused and idea-centric.
Member Discovery: These are books on learning about, gaining insight, and building relationships with members. They involve empathy-building and a longitudinal understanding of who we serve. We live in a vastly complex and ambiguous world. It’s imperative that we stay apprised of member wants, needs, pain points, and opportunities. This will sharpen our readiness and help us build indispensable communities.
Continuous Discovery Habits. Teresa Torres. This book helps us discover member needs to inform our offerings. Torres introduces a framework where teams engage with customers weekly, use opportunity maps to organize customer needs, and conduct small, focused experiments to test solutions. Instead of relying on big research projects or gut instinct, she advocates for making discovery a regular habit — like brushing your teeth — that creates a steady flow of customer insights. The approach emphasizes cross-functional understanding with all team members participating in customer interviews and decision-making to build better products, programs, and offerings. Why association leaders should read it: We need to move beyond member surveys and event evaluations. Continuous discovery is an investment in multi-modal data collection, insight patterns, relationships, empathy, and community.
The Mom Test: How to talk to customers & learn if your business is a good idea when everyone is lying to you. Rob Fitzpatrick. Fitzpatrick explains why people tend to lie (often unintentionally) during customer interviews and how to get honest feedback instead. The Mom Test is a barometer in truth-telling: even your mom would lie to you about your business idea because she wants to be supportive. The book provides practical techniques for asking questions that reveal genuine customer needs rather than biased reassurance. Key principles include: learning about customer lives instead of your idea, asking about specific past behaviors rather than hypothetical futures, and focusing on concrete facts rather than opinions. Why association leaders should read it:. By following these guidelines, we can move beyond guesswork to gain truthful insights to validate our programming ideas before building them.
Mapping Experiences: A Complete Guide to Customer Alignment Through Journeys, Blueprints, and Diagrams. James Kalbach. This is a comprehensive guide to creating visual maps of customer experiences. Kalbach explains how to develop various mapping tools – including customer journey maps, service blueprints, and experience diagrams – to align organizations around customer needs. These visual representations help businesses identify pain points and opportunities in their current offerings. The book covers the entire mapping process: planning research, collecting data, creating the diagrams, and using them to drive strategic change. While technical in parts, it emphasizes that the ultimate goal isn't pretty diagrams but organizational alignment and customer-centered innovation. Why association leaders should read it: Our actions are often driven by short-term revenue, the next event, or board mandate. I believe we need to think creatively about engaging our members on longitudinal journeys and this book is an excellent guide to get started.
Health Design Thinking: Creating Products and Services for Better Health. Bon Ku, Ellen Lupton. This book applies design thinking to healthcare challenges. Ku (a physician) and Lupton (a design expert) show how creative problem-solving approaches can improve patient experiences, clinical outcomes, and healthcare systems. The book presents case studies of successful health design projects alongside practical methods for understanding healthcare stakeholders' needs, generating innovative solutions, and implementing meaningful change. It covers techniques for empathizing with patients, healthcare providers, and other stakeholders; visualizing complex healthcare data; prototyping solutions quickly; and testing ideas in real healthcare settings. Health Design Thinking bridges the gap between medical expertise and design innovation, offering a human-centered approach to addressing healthcare's most pressing problems. Why association leaders should read it: Although this book focuses on health care, it is an excellent primer on design thinking in search of human-centered solutions to hard problems. The graphical format and storytelling make the concept accessible and applicable.
These twelve books will help position your association for innovation and durable impact. Though I rely on books for my strategy practice, reading books is only part of the story. Becoming proficient at strategy, innovation, and member discovery takes consistent practice. This is why all twelve of these books are not read once and put on the bookshelf type books. They are vital to my ongoing learning journey.
What Are You Reading?
"In my whole life, I have known no wise people (over a broad subject matter area) who didn't read all the time -- none, zero. You'd be amazed at how much Warren reads--and at how much I read. My children laugh at me. They think I'm a book with a couple of legs sticking out."
Charlie Munger
In future articles, I will recommend additional books in areas relevant to the product community: marketing, positioning, community design, and value creation. Please reach out if you’d like to suggest a book or engage in a conversation.
I lead the product community; we are a learning community because we believe great relationships help us create the value our members want. Remember, product-led growth fuels connection. Join the product community and flip your destiny.
About the Author
James Young is founder and chief learning officer of the product community®. Jim is an engaging trainer and leading thinker in the worlds of associations, learning communities, and product development. Prior to starting the product community®, Jim served as Chief Learning Officer at both the American College of Chest Physicians and the Society of College and University Planning. Please contact me for a conversation: james@productcommunity.us