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Digital Transformation

From the architect who rides between board room and engine room to cloud and platform strategy, product culture, data and the organisation's own beliefs, digital transformation as told through the free samples of the Leanpub books about it.

Created from the free samples of 11 Leanpub books and the descriptions and tables of contents of 29 more books and courses, with every source cited.

Digital transformation is the name given to the efforts of established organisations to change how they work and what they offer by means of software, data and networks. One book on this shelf insists on the order of the words: the thing is primarily a transformation, with the digital as its enabler. It divides companies into two kinds, the digital ones whose product is the technology itself and the traditional ones whose products thrived for decades without it, and it is the second kind, the bank and the retail chain learning to use technology to improve an existing business, that is being transformed.[1]

The books here see the subject mostly from inside the technology function of a large enterprise, through its architecture, its move to the cloud, its platforms, its products and its data, and the best of them warn against treating any of this as a purchase or a project. A book on cloud strategy tells its readers to prepare not for one more IT project but for a change of lifestyle, and adds that there is no copying and pasting a transformation.[3]

This article follows the subject from strategy and the role of the architect through cloud, platforms and legacy systems, product thinking, organisation and culture, data and AI, and the processes and systems that keep a business running. Its sources are the free samples of the Leanpub books and courses listed at the end, with the descriptions and tables of contents of those whose samples were not available or not read, and every claim that rests on a source is cited to it.

Where to start

The leader of a company, or of a transformation, can begin with Digital Transformation and Product Culture (2025), which defines the terms and approaches the subject through the management of digital products,[1] and with 37 Things One Architect Knows About IT Transformation (2024), short episodes on what an architect does in a large organisation that is changing its IT.[2] For artificial intelligence the plainest introduction is Generative AI in a Nutshell (2025), which is also offered as a course with exercises and video.[7] Someone who uses business systems and spreadsheets daily without being at ease with data has Getting Started with Data (2020).[33]

The practitioner planning a migration can go to Cloud Strategy (2024), which offers decision models in place of instructions,[3] and the one building an internal platform to Platform Strategy (2026), the most widely read book here, whose chapters each stand alone.[4] All Hands on Tech (2025) is written for the heads of technology organisations, with each chapter answering one practical question.[12]

The specialist has Lean Enterprise Architecture (2026) for enterprise architecture[10] and Elements of Data Strategy (2023) for the strategy of data.[31] Quintessence (2022) is the most abstract book on the shelf, for those who believe that the obstacle is the organisation's own assumptions.[5]

History

The phrase came into general use in the 2010s, but the thing is older. Mainframes automated clerical work from the 1960s; enterprise resource-planning systems and the re-engineering of business processes reshaped companies in the 1990s; the web obliged every business to meet its customers online; and cloud computing and the smartphone, from the late 2000s, changed both the tools and the competition. Since 2022 generative AI has been added to the list.

The books supply some markers. Digital Transformation and Product Culture takes its examples of traditional companies from a bank founded in 1924 and a retail chain founded in 1957, both now investing heavily in applications and an online presence.[1] Platform Strategy cites a report that seven of the ten most valuable companies of 2018 owed their success to a platform business model, where ten years earlier none had.[4] Deliver Value in the Data Economy (2022) observes that the trade in data is still taking its first steps and recalls that the comparable economy of programming interfaces took about a decade to succeed.[6] And Generative AI in a Nutshell dates the present wave to November 2022, when a chatbot built on a large language model gained a million users in five days and a hundred million within two months.[7]

Strategy and the architect

37 Things One Architect Knows About IT Transformation is a former chief architect's account of the role. Architects, it concedes, are thought by many to be overpaid residents of an ivory tower, and yet they are among the most sought-after people in IT as traditional enterprises try to change, while many of the most successful digital companies have excellent architecture and no architects at all. The book defines the role by what it is not, a firefighter, a senior developer, a project manager or a scientist, and proposes a test of an architect's value: whether the systems are still running and still able to absorb change five years on. Counting decisions would be the wrong measure, since avoiding a decision can be as much the architect's work as making one; architecture needs thought, which does not fit into half-hour slots between emergencies; and where a scientist tends to make things more complex, the architect's task is to make complex things easy to understand. Senior architects work at three levels, defining the IT strategy, which includes retiring old systems, governing the landscape of systems and delivering projects so as to stay grounded in reality. Its central image is the lift in a tall building. In a large organisation the people who hold the relevant knowledge are often not the people empowered to decide, and the architect is the one who rides between the board room and the engine room, explaining technology upstairs without losing the essence and translating the business strategy into technical decisions downstairs. Since the job is to move people, the book adds, an architect must be able to tell a story.[2]

The frameworks are several. Lean Enterprise Architecture presents enterprise architecture as a practice driven by value, in chapters that can be read separately,[10] and The Cybernetic Enterprise (2025), by one of the same authors, is an operating model for organisations that have adopted agile methods and still adapt slowly as a whole.[11] All Hands on Tech gathers current ideas about the structure of teams, domains, platforms and data into a guide for those who lead technology organisations.[12] Crossing the Chasm with Wardley Maps (2025) is about introducing one technique of strategic mapping to a team.[13] BizTech Evolution (2025) looks across the boundary of the firm, at the relation between organisations and the technology providers that serve them, and argues for moving from transactions to alliances.[14]

Cloud, platforms and legacy systems

Cloud Strategy warns its readers that they will finish with more questions than they began with, and counts that a benefit, since better questions lead to decisions that fit an organisation's own situation where a framework followed by numbers does not. Much of the material written about the cloud, it says, is centred on products or promises benefits without saying how they are obtained, which puts the technology cart before the enterprise horse. The swarm of fish on its cover, shaped like one large fish, is there to say that the sum of the parts has a shape and a dynamic of its own, as a complex architecture does. Its own starting point is that the role of IT in the enterprise is changing, that organisations which grew up with the cloud think and work differently from those migrating to it, and that adopting the cloud because everyone else does is no basis for a strategy: an organisation needs to know why it is moving and what success would look like, and to accept that there is no stable end point. Several chapters close with lists of things to do and to avoid.[3]

Platform Strategy, by the same author, begins from the observation that the word platform is overloaded, and sets out to say what distinguishes a platform from the frameworks and shared services that came before, when something deserves the name and how it brings benefit; cloud services, it notes, are platforms themselves, as are the internal platforms that speed up a company's developers, the data platforms on which it makes decisions and, beneath them all, the internet. Its cover carries a jellyfish, an animal of some complexity that is well coordinated without a central nervous system. Its parts are addressed to different readers, executives being invited to skip the technical ones. The author records that the book was written without generative AI.[4] Building Software Platforms (2022) is a guide to building internal platforms on one cloud provider's managed services, written for software companies that are moving to selling their products as services paid for by use. An internal platform helps, on its account, by offering developers curated building blocks that they can serve themselves, leaving them free to work on what customers value. Its introduction includes a lesson in timing: one provider's service for running code without managing servers, launched in 2008, failed because developers were not ready for it, and a rival's later one came to lead the market by meeting them where they were.[15]

Older systems are the harder part. Modern Applications Strategy (2025) is about choosing which applications to modernise and how, tying the choice to business goals and comparing strategies that begin from different technical foundations.[16] Modernizing Legacy Software with AI (2026) is a technical leader's playbook for doing such work with AI-assisted development,[17] and a course, Microservices Masterclass (2026), covers the design of systems as small independent services and its common traps.[18] Reimagine, Don't Retrofit (2026) states a rule for every such shift: organisations first bolt a new capability onto their existing processes, and the ones that thrive are those that stop bolting and start redesigning.[19]

Product thinking

Digital Transformation and Product Culture ties the transformation of a traditional company to the management of digital products. A digital company is one that could not exist without its technology, as a search company could not exist without its search software. In such a company, it says, product management sits at the centre and defines much of the strategy; in a traditional one the technology people are seen as enablers, usually gathered in what is called the digital team, and must earn their place by showing what technology can do for the business. It lists the benefits on offer as closer relations with customers, data from which to learn, innovation through rapid experiment, and faster and better processes through automation, and its examples come largely from the Brazilian market, where its author led the transformation of a property company.[1]

The rest of the product shelf fills in the craft. Product Management (2020) follows a digital product through its life from innovation to retirement. Its sample takes up a question that large organisations often get wrong, the difference between a product manager and the Product Owner of a Scrum team, and answers that they are two sides of one coin, the what and the how of a development team's work, since nobody can order a backlog without knowing the goals of the business and of the users. A company that has divided the roles between two people should not conclude that it has staff to spare, the author adds; more probably another role, such as product marketing, is missing.[20] Digital products leadership (2020) is about the head of product and the teams that role directs,[21] and Startup Guide (2020) is about creating a software product that pays its way.[22] API Product Management (2021) applies the same thinking to products offered through programming interfaces.[23]

Organisation and culture

Quintessence argues that an organisation's effectiveness depends not on its structure or its processes but on the assumptions and beliefs its people hold in common, which most would call its culture. The book is a map of an ideal software development organisation drawn in beliefs instead of methods. Its account of why change is hard is that such beliefs interlock: to challenge one is to make the others tighten their grip, so that only coordinated intervention at several points at once can displace the set. The values it proposes for the ideal organisation are three: to attend to people's needs, to nurture an environment in which good relationships can form, and to make nonviolence an institution. The author, writing from some forty years in the field and from running a software house, is candid that a book is unlikely to do more than arouse curiosity, since a change of perspective rarely comes from the experience of others.[5]

Other books work at the level of structure. The Modern (IT) Organisation (2018) describes an enterprise that is agile from corporate strategy to the release of software.[24] Organisational Plasticity (2021) defines its subject as the ability to change an organisation's structures and processes quickly and without much trauma,[25] Dynamic Reteaming (2019) treats the changing membership of teams as something to be done on purpose,[26] and User Needs Mapping (2025) offers a visual method for aligning teams around the needs of those they serve.[27] Living Complexity (2022) is a catalogue of practices for teams whose problems do not yield to linear methods,[28] and Problem? What Problem? (2020) is about the obstacles that slow teams down, within the team and beyond it.[8]

Two satires stand as a warning. Scaled Agile DevOps Maturity Framework (2026) is the mock manual of an invented framework which, unlike other transformation frameworks, does not ask the organisation to change,[29] and The Incredible Story of Deft (2nd ed.) (2025) is a novel about improvement methods sold as cures for everything.[30]

Data and AI

Deliver Value in the Data Economy is written for the business side. Data, it says, is ceasing to be a by-product and becoming an article of trade, a product or a service, and value is created less inside single organisations than in networks that cross industries. It treats the opening of public data as a force that enlarges the market and turns data into a commodity, interchangeable and traded like grain, gold or oil, and the programming interface as the means by which data and services are offered to outsiders.[6] Elements of Data Strategy defines the work of the data strategist in three phases, due diligence, design and delivery,[31] and How to do things with data (2025) asks what data does in an organisation and how a business becomes one that is driven by it.[32] Getting Started with Data is the primer for everyone else.[33]

On artificial intelligence Generative AI in a Nutshell begins with definitions. AI is not new, since the recommendation of a video and the approval of a card payment are both its work; generative AI produces new content where the older kind found or classified what existed; and a large language model is generative AI that communicates in ordinary language, which is why anyone could use it without being a programmer. The architecture behind such models was introduced in a research paper of 2017, and because the products built on them keep overtaking one another, the book refers to them all by one collective term instead of naming a favourite.[7] Reliable Generative AI (2026) is concerned with making such work repeatable and safe, through the design of prompts, retrieval, evaluation and governance.[34]

Processes, systems and sectors

Beneath the strategy lies the running of the business. Business Process Modeling, Management, and Mining (2021) is a set of illustrated lecture notes on modelling processes, mining them from data, improving and automating them.[35] IT Asset Management (2025) argues that the management of IT assets, which many technical executives think a dull and low-grade task, is a concern for senior management.[36] Microsoft Dynamics 365 Business Central Field Guide (2026) is a field guide for customers implementing one vendor's cloud system for accounts and operations, a kind of software that has traditionally been sold and installed through partners.[37] Building SharePoint Online Intranets (2025) does the same for an intranet,[38] and On Defining Quality Engineering (2022) proposes quality engineering as the discipline that lets software be delivered fast without losing quality.[39]

Two books look at particular sectors. A Guide To The Future Of Hospitals (2026) considers how hospitals may be designed and run as digital health moves routine care outside their walls,[40] and Rethinking Capital Project Delivery (2026) argues that the delivery of refineries, power plants and other capital projects should become iterative; one of its forewords recalls engineers objecting that a project is not a conveyor belt, and the reply that the teams passing through it are.[9]

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.
    Digital Transformation and Product Culture, Joaquim Torres (Joca): How to put technology at the center of your company's strategy Free sample: the section on types of company. 2025. Free sample: PDF · EPUB
  2. 2.
    37 Things One Architect Knows About IT Transformation, Gregor Hohpe: A Chief Architect's Journey Free sample: the chapters on what architects are and on the architect elevator. 2024. Free sample: PDF · EPUB
  3. 3.
    Cloud Strategy, Gregor Hohpe: A Decision-Based Approach to Successful Cloud Migration Free sample: the introduction and the opening of the first part. 2024. Free sample: PDF · EPUB
  4. 4.
    Platform Strategy, Gregor Hohpe: Innovation Through Harmonization Free sample: the introduction and the opening of the first part. 2026. Free sample: PDF · EPUB
  5. 5.
    Quintessence, Bob Marshall: An acme for software development organisations Free sample: the chapter about the book and the nature of the challenge. 2022. Free sample: PDF · EPUB
  6. 6.
    Deliver Value in the Data Economy, Jarkko Moilanen, PhD, Toni Luhti, D.Sc., Jussi Niilahti: Data monetization explained so that everyone understands it! Free sample: the sections on data as a commodity and on platforms and interfaces. 2022. Free sample: PDF
  7. 7.
    Generative AI in a Nutshell, Henrik Kniberg: How to Survive and Thrive in the Age of AI Free sample: the section on terminology. Also offered as a course under the same name. 2025. Free sample: PDF · EPUB
  8. 8.
    Problem? What Problem?, Ben Linders: Dealing Effectively with Impediments using Agile Thinking with Problem-solving Practices Free sample: the acknowledgements and the introduction. 2020. Free sample: PDF · EPUB
  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.
    Lean Enterprise Architecture, Romano Roth, Dietmar Wettach: A Practical Guide to Value-Driven Enterprise Architecture No sample: from the description and table of contents. 2026.
  11. 11.
    The Cybernetic Enterprise, Romano Roth: How to Build a Future-Ready Organization No sample: from the description and table of contents. 2025.
  12. 12.
    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.
  13. 13.
    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
  14. 14.
    BizTech Evolution, Ivan Krnic: From Transactional Services to Strategic Alliances From the description and table of contents. 2025. Free sample: PDF
  15. 15.
    Building Software Platforms, Pablo Bermejo Free sample: part of the introduction, on timing and on who the book is for. 2022. Free sample: PDF · EPUB
  16. 16.
    Modern Applications Strategy, Jaime Nagase: Connecting Business to Architecture Decisions No sample: from the description and table of contents. 2025.
  17. 17.
    Modernizing Legacy Software with AI, Nils Boeffel: A Technical Leader's Guide to AI-Driven Transformation No sample: from the description and table of contents. 2026.
  18. 18.
    Microservices MasterclassCourse, David Farley, CourseAI A course; no sample: from the description and lesson titles. 2026.
  19. 19.
    Reimagine, Don't Retrofit, Ricardo Gonzalez Vargas: A Leadership Guide to AI-Driven Software Development No sample: from the description and table of contents. 2026.
  20. 20.
    Product Management, Joaquim Torres (Joca): How to increase the chances of success of your digital product Free sample: the section on product managers and Product Owners. 2020. Free sample: PDF · EPUB
  21. 21.
    Digital products leadership, Joaquim Torres (Joca): The science and art of managing product teams No sample: from the description and table of contents. 2020.
  22. 22.
    Startup Guide, Joaquim Torres (Joca): How startups and established companies can create profitable digital products From the description and table of contents. 2020. Free sample: PDF · EPUB
  23. 23.
    API Product Management, Andrea Zulian, Amancio Bouza: Product Strategy and Execution for the Digital Economy No sample: from the description and table of contents. 2021.
  24. 24.
    The Modern (IT) Organisation, Sandro Quaranta: Be agile from top to bottom From the description and table of contents. 2018. Free sample: PDF
  25. 25.
    Organisational Plasticity, Manoel Pimentel: unlocking flexibility and responsiveness in your company No sample: from the description and table of contents. 2021.
  26. 26.
    Dynamic Reteaming, Heidi Helfand: The Art and Wisdom of Changing Teams, First Edition No sample: from the description and table of contents. 2019.
  27. 27.
    User Needs Mapping, Rich Allen: Aligning Teams Around What Matters No sample: from the description alone. 2025.
  28. 28.
    Living Complexity, Luca Minudel: Practical applications of Human Complexity in software and digital products development From the description and table of contents. 2022. Free sample: PDF · EPUB
  29. 29.
    Scaled Agile DevOps Maturity Framework, SADMF Documentation, Operations, and Governance Management Authority : The SADMF Accredited Facilitator's Guide to Organizational Transformation No sample: from the description and table of contents. 2026.
  30. 30.
    The Incredible Story of Deft (2nd ed.), Isaak Tsalicoglou: Buzzwords, Blunders, and Better-Work Myths (Lean, Agile, etc.) From the description. 2025. Free sample: PDF · EPUB
  31. 31.
    Elements of Data Strategy, Boyan Angelov: A Framework for Data and AI-Driven Transformation No sample: from the description and table of contents. 2023.
  32. 32.
    How to do things with data, Richard Veryard: Setting off towards the data-driven business No sample: from the description and table of contents. 2025.
  33. 33.
    Getting Started with Data, Simbiose Ventures Team: The first book you should read to successfully get along with data. From the description and table of contents. 2020. Free sample: PDF · EPUB
  34. 34.
    Reliable Generative AI, George Tome: A Practical Guide to Prompt Design, RAG, Agents, and Safer AI Workflows No sample: from the description and table of contents. 2026.
  35. 35.
    Business Process Modeling, Management, and Mining, Cesare Pautasso: visual lecture notes No sample: from the description and table of contents. 2021.
  36. 36.
    IT Asset Management, Thejendra Sreenivas: A Practical Guide for Technical and Business Executives No sample: from the description alone. 2025.
  37. 37.
    Microsoft Dynamics 365 Business Central Field Guide, Erik Hougaard: Your companion to a successful implementation. Tips to get ahead as you venture into the cloud No sample: from the description and table of contents. 2026.
  38. 38.
    Building SharePoint Online Intranets, Steve Knutson: Practical Advice for building Intranets with SharePoint Online No sample: from the description and table of contents. 2025.
  39. 39.
    On Defining Quality Engineering, Antoine Craske, Rémi Dewitte: Thrive your business with Quality at Speed software No sample: from the description and table of contents. 2022.
  40. 40.
    A Guide To The Future Of Hospitals, Dr. Bertalan Mesko: Learn how hospitals of the future will be designed, and what technologies will be used in hospitals to change the healthcare experience for all. 60-day Money-back guarantee: If you're not satisfied, simply return the book and you get a full refund From the description. 2026. Free sample: PDF

Further reading

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

  • Scrum Master, Joe Justice: The Agile Training Seminar for Business Performance A Scrum Master training seminar in book form, with a business case for agile methods and practices for hardware. 2023. Free sample: PDF
  • Standing on Bits, Steve Tendon: Agile Software Engineering Management at Scale with the Theory of Constraints Agile methods combined with the Theory of Constraints for software engineering at scale. 2022.
  • Ready, Luniel de Beer, Max Guernsey, III: Why Most Software Projects Fail and How to Fix It A method for maturing requirements before and while software teams build them. 2026. Free sample: PDF · EPUB
  • Succeeding with OKRs in Agile (2nd edition), Allan Kelly: How to create & deliver Objectives Key Results for teams Writing and delivering objectives and key results in agile teams. 2026. Free sample: PDF · EPUB
  • Better Estimates, Ines Garcia: Supercharge your forecasting (Agile Projects) A short booklet of methods for forecasting when work is unpredictable. 2021.
  • An Agile Playbook for Technical Communicators, Luke Pivac: A Guide for Technical Communicators Working with Agile Teams How writers of documentation fit their work into sprints. 2025.
  • How to Understand Almost Anything, Markus Voelter: A Practitioner's (updated) Guide to Domain Analysis A practitioner's guide to analysing a domain well enough to define a model or language for it. 2024.
  • Visual Collaboration Tools, João Rosa, Kenny Baas-Schwegler, Nick Tune, Mathias Verraes, Stefan Hofer, Henning Schwentner, Cédric Pontet, Trond Hjorteland, Pim Smeets, Krisztina Hirth, Gojko Adzic, Zsofia Herendi, Julius Gamanyi, Paul de Raaij, Michael Plöd, Dawn Ahukanna, Gayathri Thiyagarajan, Steve Pereira, Devon Burriss, Nancy Beers, Rich Allen, Matthew Skelton: for teams building software A community-written book on preparing and running visual modelling sessions for software teams. 2023.
  • 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 A short guide to recognising complex problems and acting on the difference. 2025. Free sample: PDF · EPUB
  • Snappy Data Management, Colin Conrad: Hands-on Data Management and Artificial Intelligence Lessons for Business and Social Science Students A hands-on introduction to data management and AI for students of business and social science. 2023.
  • 4th Industrial Revolution, Ahmad Manzoor A short booklet introducing the technologies grouped under the fourth industrial revolution. 2020. Free sample: PDF
  • Blockchain Beyond Bitcoin, Ahmad Manzoor: Blockchain is not about Bitcoin, This is far from that. An introduction to blockchain technology and its uses outside finance. 2020. Free sample: PDF

This is an article created from the free samples of 11 Leanpub books and the descriptions and tables of contents of 29 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: 370 books · 5 courses in the Digital Transformation category · also filed under Business and IT Alignment, IT Service Management, ISO27001

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