Tag: AI and content strategy

Human Judgment vs. AI Insight: Rethinking Strategy in an Automated World

Human Judgment vs. AI Insight: Rethinking Strategy in an Automated World

Debra W Kahn (@debrawk.bsky.social)

Visionaries have given us products that disrupted markets, but they have always had a strategy to back up the vision. Steve Jobs gave us a cellular phone (the iPhone) with a touchscreen keyboard because he hated mechanical keyboards. It also played music like Apple’s popular iPod and offered a world of apps you could download from Apple itself.

When Herb Kelleher took Southwest Airlines nationwide, he had a vision for making air travel affordable for all: he would model it after Greyhound bus lines. For better or worse, that led Southwest to implement its less expensive point-to-point flight patterns, distinct from the other airlines’ hub-and-spoke patterns.

The vision drove the strategy, and, no doubt, many project managers and communications professionals made it work.

In recent months, I have heard a subtle but important shift in how professionals talk about strategy. Increasingly, teams are not just using AI to support execution; they are asking it to suggest direction. Prompts such as “What should our strategy be?” or “What is the best approach?” crop up more and more in both project environments and content strategy discussions.

This shift raises an important question: Are we improving strategic thinking, or are we outsourcing it?

This post explores the following:

  • What Strategy Really Is
  • Features of Experience-Based Strategy
  • Features of AI-Influenced Strategy
  • Comparison of the Two Approaches
  • The Blended Approach—And Its Risks
  • Caveat: HITL Is Not a Panacea
  • Conditions for Effective Blending
  • Structuring Strategy in an AI Environment: A Model
  • Practical Applications
  • Strategy Still Requires Human Ownership
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Designing Content for AI Summaries: A Practical Guide for Communicators

Designing Content for AI Summaries: A Practical Guide for Communicators

Debra W Kahn (@debrawk.bsky.social)

There’s a certain irony in admitting this, but I recently struggled to write the introduction to one of my blog posts, “Agent vs Agency in GenAI Adoption: Framing Ethical Governance.” I wanted to frame the topic with a reflection on evolving terminology, a nod to Hamlet, and a meditation on AI’s “nature.” On top of that, I introduced the idea of the “ghost in the machine” only a few paragraphs later. In hindsight, I had written two introductions to the same post without meaning to.

At the time, the ideas felt connected. But when I later ran those paragraphs through an AI summarizer, the summary focused almost entirely on Hamlet’s moral dilemma and the mind–body problem—interesting concepts, certainly, but hardly the point of the post. The AI confidently reported that the blog was “about comparing the adoption of GenAI to Hamlet’s struggle with death.”

Not exactly the message I intended.

To be fair here, the most recent version of Google’s Gemini gave me a much more comprehensive summary. That summary mentions, as I did, “the tensions inherent in adopting Generative AI” and my proposed “governance framework.”

But looking back, I realize I had made two classic mistakes in writing that introduction—mistakes that human readers can forgive with patience but AI summarizers absolutely cannot. First, I opened with a metaphor instead of a clear point. Second, I layered multiple conceptual frameworks (terminology, nature vs. nurture, Hamlet, Koestler, agency) before stating my purpose. I know better. Many of us do. But as I’ve written elsewhere, expertise doesn’t exempt us from the structural pitfalls that now matter more than ever.

That experience became the seed of this post.

If our writing can be so easily misinterpreted by a summarizer—and thus by downstream readers who rely on that summary—then it’s worth rethinking what it means to write clearly and responsibly in an AI-influenced world. Good writing has always been about serving our readers. Now, increasingly, it must also serve the machine readers that bridge the gap between our content and those readers.

In this post, I explore why AI summarizers can distort meaning, how machines “read” what we write, and how we can design content that preserves accuracy, nuance, and intent—even after it’s digested by AI. (Note: Some content in this blog post was generated by ChatGPT.)

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