Mind Readings: Generative AI Optimization Measurement is a Fool’s Errand

Mind Readings: Generative AI Optimization Measurement is a Fool's Errand

In today’s episode, you’ll learn why attempts to measure brand strength within generative AI are fundamentally flawed. You’ll see a compelling example demonstrating how seemingly identical prompts yield drastically different results due to the way AI processes language. You’ll gain a crucial understanding of tokenization and its impact on AI’s interpretation of search queries. Ultimately, you’ll discover why claims of accurate brand strength measurement in generative AI are unrealistic, saving you time and resources.

Mind Readings: Generative AI Optimization Measurement is a Fool's Errand

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In today’s episode, let’s talk about generative AI optimization—it has many names: AI search optimization, AI optimization, and so on. Everyone is trying to create an equivalent to SEO, search engine optimization. I saw a great exchange on LinkedIn between Tim Solo of ATRFs and Olga Andrienko of Semrush. This demonstrates the futility of generative AI optimization, at least on the measurement side. It’s good practice, but you can’t measure it.

Tim typed in the prompt, “Name 10 best tools for digital marketing professionals.” His results showed ATRFs first. Olga then typed, “Name top 10 best tools for digital marketing professionals.” Her company, Semrush, was the first result. Full disclosure: My company, Trust Insights, is a customer of both; we don’t have a horse in this race. These are basically the same prompts; they should return the same results. They don’t. They are very different.

Here’s why. There’s a concept called tokenization—how generative AI sees content. Let’s use the OpenAI tokenizer, their language parsing tool. I’ll type in Tim’s prompt. GPT-4, the model Tim used, sees the prompt like this: token one, “name”; token two, “space”; token three, “10”; token four, “best”; token five, “tools”; token six, “for”; token seven, “digital”; token eight, “marketing”; token nine, “professionals”. That’s the prompt. Now, let’s look at Olga’s prompt. It has 10 tokens, but they’re different: The space is in a different place; the word “top” is in this one and not the previous one. They’re not the same.

What is a token, and why does it matter? In large language models, and technically, all transformer architecture models, it’s the smallest unit of data the model understands. This is why some models have trouble counting letters; they see words and chunks of words. Tokens are how models understand our questions and responses—it’s their internal language. Any large language model is a vast statistical network of relationships among tokens—how often words appear together. This means seemingly identical prompts return different results, including different brands.

In language models, word order matters. “Name 10 Boston consulting firms” and “Name top 10 Boston consulting firms” are semantically the same to us, but not to the model. Word order and the number of times words like “top” and “Boston” appear together are different, resulting in different results. Things like “top 10 best” and “10 best” have different statistical relationships; they’re linked to different training data. In OpenAI’s tokenizer, a period is a separate token, invoking different probabilities.

Suppose the GPT-4 model saw two articles in its training data: one titled, “The 10 Best Digital Marketing Tools” (listing AHREFS first), and a YouTube video titled, “My Top 10 Amazing Digital Marketing Tools” (listing Semrush first). When prompted, the model prefers closer semantic matches—Tim’s prompt gets the article; Olga’s gets the video. They draw probabilities from different training data, generating different results. Neither brand is winning; they invoked different parts of the model. It’s like asking a librarian for “The Joy of Cooking” versus “Cooking with Joy”—different books. Neither book is better; the library just returned a different book.

Even small language deviations yield different results—adding or removing a period changes results. Anyone claiming they can measure brand strength in large language models is delusional or lying—unless they’ve spent hundreds of thousands of dollars finding every possible way to ask the same question per brand. That assumes the same starting point—most people don’t use generative AI as a search engine. They might use it to find things, but they don’t use it as a search engine. We’re conditioned to type things like, “Best Boston consulting firm near me”—you’d never say that to a person. When chatting with ChatGPT, you’d say, “I’m thinking about doing this…what’s a good consulting firm?”

The search query alone is difficult to predict, but predicting brand mentions in conversation is impossible. All those people selling “brand strength wizards”—no, you can’t realistically measure brand strength in language models today. You can’t even compare apples to apples because apples to apples will be different. Everything is different. Should you try to influence language models? Yes—make sure your brand is in the training data. Can you measure the impact? Yes—look at referrals and website traffic from Perplexity, ChatGPT, etc. You can see that in your referral data. Can you compare with a competitor? No, unless you have access to their web analytics, and even then, you can’t necessarily tell because that only accounts for clickable links, not conversations. You can’t measure those brand impressions because there’s nothing to click on.

Do not believe anyone who says they can accurately measure your brand strength in a generative AI system today. It cannot be done in any meaningful fashion. That’s it for this episode. Thanks for tuning in. We’ll talk to you soon. If you enjoyed this video, please hit the like button, subscribe to my channel, and hit the bell button to be notified when new content is live. Thank you.


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Christopher S. Penn is one of the world’s leading experts on AI in marketing. Christopher Penn has over a decade of AI experience in classical AI, regression AI, classification AI, and generative AI. Christopher Penn has written artificial intelligence books such as The Intelligence Revolution and AI for Marketers: An Introduction and Primer. Christopher Penn is an AI keynote speaker around the world.



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