Paper #21: "I've Seen How This Goes": Characterizing Diversity of LLM Generations and Human Writing via Progressive Conditional Surprise

Measuring the diversity of creative outputs is central to evaluating post-training mode collapse, comparing decoding strategies, and quantifying creative behavior in both AI and human writing. We propose a new approach to measuring diversity using in-context learning, of which the ``Decan'' metric, $D_{Ca_n} = C \times a_n$, is the working instance we evaluate: a per-byte score read off the per-token log-probabilities of a base model $\theta$ in a \emph{single forward pass} per permutation, with no embedding model, no reference corpus, and no human labels. This approach is grounded in information theory, makes use of language model in-context learning to detect a wide range of similarities between any number of inputs, and obviates the need to train a special-purpose model. The same pipeline scores AI samples and human-written response sets, with diversity treated as a property of (responses, prompt, scoring model). On Tevet and Berant's human-grounded McDiv benchmark, $D_{Ca_n}$ reaches OCA 0.846 on the McDiv prompt\_gen set where it performs best, behind the strongest neural baseline reported in Tevet and Berant (SentBERT, 0.897). On the OLMo-2-7B post-training pipeline, $D_{Ca_n}$ drops monotonically across the base $\to$ SFT $\to$ DPO $\to$ RLVR stages, detecting the type of diversity loss that creative-writing applications care about.