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Business Strategy

From Sun Tzu, the OODA loop and Wardley Maps to goals and measures, the creation of categories and the place of technology and AI, business strategy as told through the descriptions, contents and free samples of the Leanpub books about it.

Created from the free samples of 9 Leanpub books and the descriptions and tables of contents of 23 more books and courses, with every source cited.

Business strategy is the set of choices by which an organisation decides where it will compete and how it expects to succeed, and the craft of keeping those choices coherent as circumstances change. One book on this shelf borrows its definition from a military thinker: strategy is a pattern of changing intentions that harmonises and focuses effort towards an aim, in a world that unfolds in ways nobody foresaw, and its purpose is to improve the ability to shape events and to adapt to them.[1]

The books here are few and mostly recent, and they fall into three groups: those that teach a way of seeing the competitive landscape, chiefly by drawing maps of it; those about goals and the measures that accompany them; and those about strategy for products and for technology, which are now much occupied with artificial intelligence. They share a suspicion of strategy made by comparison with rivals. One author recalls two years and tens of millions spent bringing a product level with its competitors, feature by feature, while one of those competitors redefined what the product was for.[3]

This article follows the subject from the landscape and its maps through goals and measures, markets, categories and value, technology in strategy, AI as a question for boards, and strategy under uncertainty and in the smallest firms. The shelf is thin and many of its books offer no sample: the sources are the free samples of nine books and the descriptions and tables of contents of twenty-three more books and courses, listed at the end, and every claim that rests on a source is cited to it.

Where to start

A reader new to the subject can begin with THE ART OF STRATEGY (2026), thirteen short chapters that set an ancient treatise beside two modern thinkers,[1] or with Draw your company strategy (2024), a workbook on mapping that leaves space for the reader's own drawings.[2] A business leader without a technical background who wants to know what AI means for strategy has a mini-book, The AI Revolution: AI 101 for Business Leaders (2024).[24]

Managers who set goals can go to Little Book of OKRs & KPIs (2026), a short and still unfinished book on two kinds of measure and how they differ,[12] and to a short video course on product goals and visions, Long term Product Goals for creating superior products (2026).[14] Founders have What to Code (2026), on choosing what to build,[5] and Know Your Numbers (2026), on the arithmetic of a young business.[4]

The experienced reader will find Designing for Scale (2026), which is written for product leaders who already understand how a product finds its market,[3] Crossing the Chasm with Wardley Maps (2025), which assumes that the reader can already map,[10] and Wholehearted (2025), an advanced book on organisations that adapt.[28]

History

The word comes from the Greek for generalship, and the oldest text on the subject that managers still read is a Chinese treatise on war from about the fifth century BC. Business strategy as a field of study dates from the corporate planning of the 1960s, acquired its economics in the 1980s with the analysis of industries and competitive position, and has been challenged ever since by writers on emergence, disruption and agility, who doubt that a plan made at the top survives events.

The books draw on all of these layers. THE ART OF STRATEGY rewords the ancient treatise for business and sets beside each chapter passages from a twentieth-century theorist of air combat and from the inventor of a method of mapping.[1] The author of Draw your company strategy recalls surprise at finding that strategy had no body of standard practice of the kind that exists for managing projects or IT services, and the discovery of mapping in 2013; the workbook goes on to review the older schools, among them the analysis of competitive forces and the cascade of strategic choices.[2] The Operating System of Product (2026) opens with the planning habit those schools left behind, an annual roadmap drawn up over three weeks of executive meetings and overtaken by the market nine months later.[8]

Seeing the landscape

THE ART OF STRATEGY reduces its sources to five factors that must all be mastered: purpose, which keeps people united through success and failure; landscape, the environment with its positions and obstacles; climate, the forces acting on that environment; doctrine, the ways of operating that apply whatever the landscape; and leadership, the choices made in the light of the other four. Strategy is assessed by asking of each side who has the more compelling purpose, the more skilled leadership, the better position and the better-trained people, and it is carried out by shaping how things appear to the competition: to seem unable when able and far when near, to engage where the other side is unprepared and to appear where it is not expected. Careful assessment, the treatise holds, shows who will succeed before any engagement begins. From the second of its sources the book takes the loop of observing, orienting, deciding and acting, with the remark that orientation is the most important part, since inherited habits, culture and experience shape what is observed and decided; the advantage goes to the side that passes through the loop less conspicuously and more quickly than its rival. The same source asks for a unifying vision attractive enough to draw in the uncommitted and to weaken an adversary's resolve. The book's own summary of the art is to succeed by securing harmony among stakeholders and keeping competitors off balance, and it asks readers to think of business as succeeding together with stakeholders and not as maximising value for shareholders, of agility as adapting to situations and influencing them more skilfully than the competition, which includes leaving a successful pattern in time, and of leadership as a service that anyone in the organisation may provide. Much of the text is quoted or adapted from its sources under an open licence.[1]

Draw your company strategy teaches the mapping method as a practice. Its chapters run from users and their needs through the evolution of components, the patterns of the wider climate and a table of doctrines, which it arranges in four phases, from stopping self-destructive behaviour through awareness of context and doing better for less to continuous evolution, to the moves a company can make in a market, defensive, attacking and through its ecosystem. A later chapter treats the building of a strategy as iterative and contrasts attitudes to it, the instructor's and the gardener's, the finite game and the infinite one; another shows maps used in managing projects, writing proposals and reviewing a business.[2]

Two shorter books assume the method. Crossing the Chasm with Wardley Maps is a framework for introducing mapping to a team, with roles and events of its own, which its author calls temporary.[10] Negotiation with Wardley Mapping (2024) applies maps to negotiation.[11]

Goals and measures

A strategy is usually handed on as goals. Little Book of OKRs & KPIs explains objectives with key results and key performance indicators, how they differ and how to use them together; it sorts indicators into three types, informal, targeted and monitoring, and warns against managing by numbers alone.[12] OKR, the right way (2026), written in Italian, starts from why objectives and key results so often fail and follows an invented company through writing, checking and carrying them out.[13] Long term Product Goals for creating superior products covers the goals of a product, its vision and the single guiding measure that some teams call a north star.[14]

Know Your Numbers argues that a founder needs arithmetic before spreadsheets, not to become a human calculator but to estimate, simplify and see what matters. Its example is a subscription priced at fifty a month that someone proposes to raise to sixty. With a thousand customers the rise is worth ten thousand a month before any are lost, and since eighty-four customers at the new price bring in what a hundred did at the old, sales could fall by about a sixth before revenue suffered. The sum does not say what will happen; it says what would have to happen for the change to fail, which turns a vague fear into a threshold that can be tested. A second example takes a shop that spends thirty to win an order of eighty at a margin of one half, and finds ten left before fixed costs. The questions the book wants asked quickly are how large an effect is, what must be true for a plan to work, where the real constraint lies and whether the answer is close enough to act on, and the habit it warns against is false precision, exact-looking figures computed from weak assumptions.[4]

Markets, categories and value

Designing for Scale holds that optimisation leads only to parity and to being treated as a commodity, and that leadership of a market comes from creating a category. Its opening story is of a team that shipped a dozen requested features, made its product faster and raised trial sign-ups, all by the book, and saw growth flatten, because a competitor had meanwhile offered a shared workspace where the incumbents sold a system of record. It divides the work into two phases with different strategies: from nothing to one, in which a product must solve a problem that is not obvious in a way that is its own, and from one to a hundred million users, in which the aims are defensibility, falling marginal cost and effects that grow with the network, and in which the evidence shifts from what early users say to measured share and cost. Three tasks run together throughout, developing the product, educating the market and designing the business model. The balance between them depends on the market: in emerging markets, the author writes from experience, most of the effort goes into education and sometimes into building missing infrastructure such as payments, while in mature markets it goes into a sharper product for a niche that others have overlooked. The fault it warns against is the roadmap built from a table of competitors' features, and the test it sets is whether the product is ten times better than the present alternative, which is often not a competitor at all but a spreadsheet or doing nothing. Its checklist for a launch ends with giving the new category a name.[3]

Several books offer tools for the same questions. The Value Mix (2021) is a framework for understanding what customers value and defining what to offer them,[15] The Opportunity Lenses (2022) is about where business opportunities come from and how to frame them so that they can be compared,[16] and The Only Marketing Guide You’ll Ever Need (2024) builds a marketing strategy for a small business from its own figures, from where it stands to where it wants to be.[17] API as a Product (2022) collects articles on one modern business model, the programming interface sold as a product, with its ways of charging.[18]

Two books of 2026 argue that AI has moved the point of advantage. What to Code says that when a working application can be generated in seconds, knowing how to build is no longer what distinguishes a builder, and that the valuable skill is deciding what deserves to exist. Its questions are those that used to come before the coding and now decide the outcome: which problem is worth solving, for whom and why now, what should be automated and what left to people, and what the builder is placed to understand, sell or sustain better than others; most builders, it observes, still overvalue being able to build and undervalue being able to choose.[5] Taste makes the same case more broadly. Productivity, it says, is the least interesting way to describe the change; AI shortens the distance between a thought and a finished thing, so the scarce ability becomes judgement about what should exist and what to cut, which it defines as judgement where there is too much possibility, and which it admits is worth little without execution, knowledge of the field and speed.[6]

Technology in strategy

The Case for Connection (2026) argues that the organisations which do best are not those with the best technology but those in which the business and its technology are most closely joined. It gathers the work of thirty-six writers into twelve practices, and its sample assembles the evidence of failure from consultancies' surveys of transformations that fall short, features that go unused and AI investments without return; the figures are the book's. Technology does not fail companies, it says; the relationship between those who decide and those who deliver does. Its practices come down to a set of preferences: trust over control, results over output, shared ownership over hand-offs, small steps with visible feedback over large bets, and learning over adherence to a plan. AI in this account is a mirror before it is a multiplier, enlarging an organisation's strengths and its dysfunctions alike.[7]

The Operating System of Product names the opposite condition the roadmap factory, an organisation that counts features shipped instead of results. Its example is a mobile wallet whose team delivered a complex invoicing feature exactly on schedule while a competitor turned to simple payments between individuals, which was what the users had come to need. Its costs are slow feedback, reluctance to cancel work that is nearly finished and prioritisation by the loudest voice, and the author proposes that the accumulated cost of building the wrong things faster be measured as a debt, as technical debt is. If AI can write the code and draft the specifications, the book concludes, the product manager's value lies in the why and the when, in designing outcomes and no longer in managing tickets.[8]

Others address the people who hold technical office. All Hands on Tech (2025) is a guide to building and changing large software organisations,[19] Modern Applications Strategy (2025) ties the modernising of old applications to business goals,[20] and Startup Phases For CTOs describes how technical decisions should change through seven stages of a new company, from the idea to profitability.[21] Engineering as a Leadership System (2026) holds that what an engineering organisation produces is set by its operating model, its rights of decision and its measures,[22] and Surviving Strategy & Architecture (2025) is about bearing the emotional weight of such roles.[23]

AI as a question for boards

Four books treat AI as a matter of strategy and oversight. The AI Revolution: AI 101 for Business Leaders introduces the technology and its uses to executives who must plan its adoption.[24] Mind the AI Gap (2026) tells the story of a chief architect at an invented company and names seven gaps, any one of which, it says, can kill an initiative.[25] What Your AI Cannot Prove (2026) is written for the boards, executives and risk officers who decide whether an AI system is built, approved and defended.[26] And The Palantir Enigma (2026) is a case study of a single data-analytics company, its history, platforms, business model, finances and controversies.[27]

Uncertainty, and the smallest firms

Some books doubt that strategy can be planned at all in the usual sense. Wholehearted treats strategising as one activity of an organisation built to adapt, on a model of viable systems,[28] Succeed over difficult problems by embracing Complexity-Thinking (2025) is a short guide to recognising problems that ordered methods will not solve,[29] and The forgotten new philosophy of work, management & leadership (2025) explains from the science of complexity why demanding projects resist estimate and control.[30] Rethinking Capital Project Delivery (2026) carries the argument into heavy industry, where it finds planning made up front and approved in stages to be the cause of overruns.[9]

At the other end of the scale are books for a business of one. The Austrian Side Business (2026) applies the economics of subjective value and opportunity cost to a small service business run beside a job,[31] and AI Money Systems (2026) sets out eight ways for an individual to earn with AI, each described as a repeatable system with its own pricing; the arithmetic is the book's.[32]

Sources

Every source is a Leanpub book or course. The note after each says which part of it was read; where no sample was available, only the public description and table of contents were used.

  1. 1.
    THE ART OF STRATEGY, Erik Schön: Steps Towards Business Agility. On Situational Awareness, OODA "Loops" and Wardley Mapping. Free sample: the reader's guide and the first chapter, on assessments. 2026. Free sample: PDF · EPUB
  2. 2.
    Draw your company strategy, Joaquín Peña Fernández: A practical workbook for mapping business strategy using Wardley Maps Free sample: the contents and the foreword. 2024. Free sample: PDF
  3. 3.
    Designing for Scale, Arinze Onugha Free sample: the opening of the first chapter, on creating a category. 2026. Free sample: PDF
  4. 4.
    Know Your Numbers, Finxter: Become a Financially Literate Founder by Mastering CAC, Conversion, Gross Margin, Churn, Payback, and Cash Burn Free sample: part of the introduction, with its worked examples. 2026. Free sample: PDF
  5. 5.
    What to Code, Finxter: The Indie Hacker's Guide to Finding Profitable Micro-SaaS Ideas in the Vibe Coding Era Free sample: part of the introduction. 2026. Free sample: PDF
  6. 6.
    Taste, Finxter: Turning Vibe into Assets in the AI Age Free sample: part of the first chapter. 2026. Free sample: PDF
  7. 7.
    The Case for Connection, Dave Clack: Why Connected Organizations Win: Twelve Practices for the AI Era Free sample: the summary and the opening of the case. 2026. Free sample: PDF · EPUB
  8. 8.
    The Operating System of Product, Arinze Onugha Free sample: the opening of the first chapter, on the roadmap factory. 2026. Free sample: PDF
  9. 9.
    Rethinking Capital Project Delivery, Edward Abramowich: The Owner's Guide to Al-Native Delivery Free sample: the two forewords. 2026. Free sample: PDF
  10. 10.
    Crossing the Chasm with Wardley Maps, Joaquín Peña Fernández: A temporary framework for mappers From the description and table of contents. 2025. Free sample: PDF
  11. 11.
    Negotiation with Wardley Mapping, Manish Andankar No sample: from the description alone. 2024.
  12. 12.
    Little Book of OKRs & KPIs, Allan Kelly: Managing with goals, numbers and purpose No sample: from the description and table of contents, which marks several chapters as unwritten. 2026.
  13. 13.
    OKR, the right way, Francesco Fullone: Allineare persone e strategia senza perdere il senso No sample: from the description and table of contents; in Italian. 2026.
  14. 14.
    Long term Product Goals for creating superior productsCourse, Allan Kelly: How to create and use product goals, product vision, north stars and true norths to deliver winning products A course; no sample: from the description and lesson titles. 2026.
  15. 15.
    The Value Mix, Guerric de Ternay: The Framework to Create Meaningful Products and Services for Your Audience From the description and table of contents. 2021. Free sample: PDF
  16. 16.
    The Opportunity Lenses, Guerric de Ternay: How to Spot Your Next Big Business Opportunities No sample: from the description alone. 2022.
  17. 17.
    The Only Marketing Guide You’ll Ever Need, Ivan Tesolkin: A Practical System for Finding the Real Problems and Fixing What Matters From the description. 2024. Free sample: PDF
  18. 18.
    API as a Product, Nordic APIs: Tips for Running an API-centric SaaS Business No sample: from the description and table of contents. 2022.
  19. 19.
    All Hands on Tech, Sophie Seiwald-Hojer, Matthias Patzak: Your How-To Guide for Building Great Tech Organizations at Scale No sample: from the description and table of contents. 2025.
  20. 20.
    Modern Applications Strategy, Jaime Nagase: Connecting Business to Architecture Decisions No sample: from the description and table of contents. 2025.
  21. 21.
    Startup Phases For CTOs, Stephan Schmidt: Growth, Scale, Exit: A Practical CTO's Progression Guide No sample: from the description and table of contents.
  22. 22.
    Engineering as a Leadership System, Martin Hinshelwood: Why engineering excellence fails systemically despite modern practices No sample: from the description and table of contents. 2026.
  23. 23.
    Surviving Strategy & Architecture, Michael D Stark: Getting Out of Your Own Way to Survive and Thrive in Strategy and Architecture No sample: from the description alone. 2025.
  24. 24.
    The AI Revolution: AI 101 for Business Leaders, Dr Tyrone Grandison From the description and table of contents. 2024. Free sample: PDF
  25. 25.
    Mind the AI Gap, Antoine Craske: The Chief AI Architect's Guide from Ambition to Reality No sample: from the description and table of contents. 2026.
  26. 26.
    What Your AI Cannot Prove, KnowlytiX: Governing AI in Regulated Industries No sample: from the description. 2026.
  27. 27.
    The Palantir Enigma, Daniel Paredes: Forging Operational Sovereignty in a Data-Driven World (Oct'26 Edition) No sample: from the description and table of contents. 2026.
  28. 28.
    Wholehearted, Mike Burrows: Engaging with Complexity in the Deliberately Adaptive Organisation No sample: from the description and table of contents. 2025.
  29. 29.
    Succeed over difficult problems by embracing Complexity-Thinking, Luca Minudel: Micro-guide to thriving in everyday complexity by breaking free from ordered and linear approaches From the description and table of contents. 2025. Free sample: PDF · EPUB
  30. 30.
    The forgotten new philosophy of work, management & leadership, Luca Minudel From the description and table of contents. 2025. Free sample: PDF · EPUB
  31. 31.
    The Austrian Side Business, Finxter: Use Austrian Economics to Build a Profitable, AI-Assisted Business Without Quitting Your Job From the description. 2026. Free sample: PDF
  32. 32.
    AI Money Systems, Finxter: The Finxter Playbook for AI-Driven Wealth From the description. 2026. Free sample: PDF

Further reading

Other books in the library on neighbouring ground, not cited above.

  • Stop Implementing AI, Cliff Robbins: The No-BS Playbook for AI That Works A method of planning, phased implementation and testing for moving AI-assisted engineering out of stalled pilots. 2025.
  • Leading Engineering Teams in the AI Era, CAIO INCAU: The manager's playbook for AI-native engineering organizations A playbook for engineering managers whose teams work with AI coding agents. 2026.
  • First Principles in Scrum: Advanced Strategies and Reflections, Jeff Sutherland Essays that take questions about Scrum back to first principles, with chapters on strategy and leadership. 2026.
  • e-Business, Robert P. Batzinger: A computer developer's perspective of doing business online A textbook for an undergraduate course on e-business, from business basics to online stores and customer systems. 2019. Free sample: PDF · EPUB
  • Amazon KDP for Introverts, Finxter Building a small self-publishing business on one retailer's platform. 2026. Free sample: PDF

This is an article created from the free samples of 9 Leanpub books and the descriptions and tables of contents of 23 more books and courses. We're building these articles to provide you, the Leanpub reader, with a good jumping-off point to discover more Leanpub books that are interesting and relevant to you. We never use material which is paid-only when building these articles: we only use material which is already free on Leanpub. However, Leanpub authors can opt out from inclusion in articles from their book settings page.

Updated November 2026.

In the Leanpub store: 158 books · 4 courses in the Strategy category · also filed under Business Strategy, Modular Business Models, Business, Communications, Property Branding

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