40 Articles and Books that will make you a Great Digital Strategist

Everything a digital strategist needs to know, from McLuhan to Russell Davis to Steve Blank. 

Updated May 29th, 2014

This is my attempt to recreate Noah Weiss’s wonderfully link-baitey listicle, 48 Articles and Books that will Make you a Great Product Manager, except for digital strategists. Noah did an incredible round-up of PM links, so be sure to check that out too. Thanks to Mike Arauz, Clay Parker Jones, Aaron Dignan, and Johanna Beyenbach for providing many of the sources.

Must Reads

• The Cluetrain Manifesto — Rick Levine. The first book you should read about the Internet.
• Understanding Media (1964)— Marshall McLuhan. As new channels emerge, OG McLuhan becomes even more relevant.
• Software is Eating the World — Marc Andreessen.
• Customer Development Manifesto, Part 2, Part 3, Part 4, Part 5 — Steve Blank. This is how clients should start thinking about product.
• Getting Real — 37 Signals. An incredible document that clarifies how small teams ship faster, better.

Level up your Client: Org Design and Operating Systems

• Scaling Agile @ Spotify — how Spotify organizes its 1,000 person product team to function like a startup (into squads, tribes, and guilds)
• The Operating Model that’s Eating the World and The Last Re-org You’ll ever do — Undercurrent’s (by Aaron Dignan) latest theory on how digital firms operate.
• The Innovator’s Dilemma — Clayton M. Christensen. Theory on why clients struggle with disruption.
• Stevey’s Google Platforms Rant — Steve Yegge. Building an org that is connected and platforms-focused.
• Inside Instagram—Mat Honan. On understanding scaling decisions and how small companies can build great things.
• The Uncanny Valley of the Functional Organization and Why Microsoft’s Reorgnization is a Bad Idea—Ben Thompson.
• Gabe Newell on Valve—this article is relatively new (Jan, 2014), but really distills how the next generation of companies will operate. Gabe is also a legend in the industry.

How Ideas Spread, Content Theory

• Transmedia Planning — Faris Yakob
• Thinking Allowed, Part 2, Part 3 — Russell Davies
• Permission Marketing — Seth Godin
• Buzzfeed’s Strategy — Jonah Peretti
• How to make something go viral (Gawker study)— Neetzan Zimmerman. Understand primary and secondary sources for content on the Internet.
• Distribution…Now — John Borthwick (Betaworks). One of the first articles to discuss the stream and its impact on sharing.
• Spreadable Media — Henry Jenkins
• Stock and Flow — Robin Sloan. One of the most important articles on how clients should approach small and big bets in content.
• Why Gawker is Moving Beyond the Blog — Nick Denton
• 10 Web Content Urban Legends — Ricky Van Veen
• On the Bubble—Rick Webb. One of my favorite articles on how brands think about digital and channels.

The Art of Strategy

Too often are a strategist’s recommendations fluffy bullshit. Here’s examples on how to write a strategy that directs an organization on exactly what to do.

• The 2012 UK Digital Strategy and Audit— the gold standard for an excellently written strategy with coherent actions. I believe Russell Davies was involved in the recommendations.
• The leaked NY Times Innovation Report —similar to the UK strategy, this is a thoughtfully written audit and strategy with crystal clear recommendations.
• Don’t Let Strategy Become Planning — By Roger Martin
• What is Strategy? (Michael Porter) and What is Strategy? (Mike Arauz)
• 1997 Letter to Shareholders — Jeff Bezos. This is what a long-term looks like — a nearly unchanged vision for the past decade and a half.
• Business Model Generation — Alexander Osterwalder
• Good Strategy, Bad Strategy—Richard Rumelt

Products and Solving Needs

• Product / Market Fit — Marc Andreessen.
• The Startup Pyramid — Sean Ellis. How to evaluate product/market fit.
• Why Wesabe Lost to Mint — Marc Hedlund. Why “better” features sometimes don’t matter.
• How Spotify Builds Products—Henrik Kniberg. Includes Spotify’s build process.
• What Hackers Should Know About Design Thinking—Interview with Gentry Underwood. What you need to know about design thinking/human-centered design.
• Social Software: The Other ‘Design for Social Impact’— Gentry Underwood. This distills some of the most important nuances to product design that involve human-to-human interaction, including the notion of “ethnography by prototype.”

Complex Systems

• If You Liked This, You’re Sure to Love That — Clive Thompson
• Emergence and Where do Good Ideas Come From — Steven Johnson
• The Fifth Discipline— Peter M. Senge

Communities and Collective Action

• Why I Love Bees: A Case Study in Collective Intelligence Gaming — Jane McGonigal
• Why Youth Heart Social Networks — danah boyd (bonus: Youth, Identity, and Digital Media).

Coming up with Good Ideas

• Startup = Growth, How to get good startup ideas — Paul Graham
• Bless the Tool Makers—Robin Sloan.

Bonus:

• Entrepreneurial Design 101, SVA — this is the syllabus from an SVA course on entrepreneurial design. It is brilliant.
• Peter Thiel’s CS183: Startup—Stanford, Spring 2012