Omar Shaikh


2025

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SynthesizeMe! Inducing Persona-Guided Prompts for Personalized Reward Models in LLMs
Michael J Ryan | Omar Shaikh | Aditri Bhagirath | Daniel Frees | William Barr Held | Diyi Yang
Proceedings of the 63rd Annual Meeting of the Association for Computational Linguistics (Volume 1: Long Papers)

Recent calls for pluralistic alignment of Large Language Models (LLMs) encourage adapting models to diverse user preferences. However, most prior work on personalized reward models heavily rely on additional identity information, such as demographic details or a predefined set of preference categories. To this end, we introduce SynthesizeMe, an approach to inducing synthetic user personas from user interactions for personalized reward modeling. SynthesizeMe first generates and verifies reasoning to explain user preferences, then induces synthetic user personas from that reasoning, and finally filters to informative prior user interactions in order to build personalized prompts for a particular user. We show that using SynthesizeMe induced prompts improves personalized LLM-as-a-judge accuracy by 4.4% on Chatbot Arena. Combining SynthesizeMe derived prompts with a reward model achieves top performance on PersonalRewardBench: a new curation of user-stratified interactions with chatbots collected from 854 users of Chatbot Arena and PRISM.

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Navigating Rifts in Human-LLM Grounding: Study and Benchmark
Omar Shaikh | Hussein Mozannar | Gagan Bansal | Adam Fourney | Eric Horvitz
Proceedings of the 63rd Annual Meeting of the Association for Computational Linguistics (Volume 1: Long Papers)

Language models excel at following instructions but often struggle with the collaborative aspects of conversation that humans naturally employ. This limitation in grounding—the process by which conversation participants establish mutual understanding—can lead to outcomes ranging from frustrated users to serious consequences in high-stakes scenarios. To systematically study grounding challenges in human-LLM interactions, we analyze logs from three human-assistant datasets: WildChat, MultiWOZ, and Bing Chat. We develop a taxonomy of grounding acts and build models to annotate and forecast grounding behavior. Our findings reveal significant differences in human-human and human-LLM grounding: LLMs were three times less likely to initiate clarification and sixteen times less likely to provide follow-up requests than humans. Additionally, we find that early grounding failures predict later interaction breakdowns. Building on these insights, we introduce Rifts, a benchmark derived from publicly available LLM interaction data containing situations where LLMs fail to initiate grounding. We note that current frontier models perform poorly on Rifts, highlighting the need to reconsider how we train and prompt LLMs for human interaction. To this end, we develop a preliminary intervention aimed at mitigating grounding failures.

2024

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Can Large Language Models Transform Computational Social Science?
Caleb Ziems | William Held | Omar Shaikh | Jiaao Chen | Zhehao Zhang | Diyi Yang
Computational Linguistics, Volume 50, Issue 1 - March 2024

Large language models (LLMs) are capable of successfully performing many language processing tasks zero-shot (without training data). If zero-shot LLMs can also reliably classify and explain social phenomena like persuasiveness and political ideology, then LLMs could augment the computational social science (CSS) pipeline in important ways. This work provides a road map for using LLMs as CSS tools. Towards this end, we contribute a set of prompting best practices and an extensive evaluation pipeline to measure the zero-shot performance of 13 language models on 25 representative English CSS benchmarks. On taxonomic labeling tasks (classification), LLMs fail to outperform the best fine-tuned models but still achieve fair levels of agreement with humans. On free-form coding tasks (generation), LLMs produce explanations that often exceed the quality of crowdworkers’ gold references. We conclude that the performance of today’s LLMs can augment the CSS research pipeline in two ways: (1) serving as zero-shot data annotators on human annotation teams, and (2) bootstrapping challenging creative generation tasks (e.g., explaining the underlying attributes of a text). In summary, LLMs are posed to meaningfully participate in social science analysis in partnership with humans.

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Grounding Gaps in Language Model Generations
Omar Shaikh | Kristina Gligoric | Ashna Khetan | Matthias Gerstgrasser | Diyi Yang | Dan Jurafsky
Proceedings of the 2024 Conference of the North American Chapter of the Association for Computational Linguistics: Human Language Technologies (Volume 1: Long Papers)

Effective conversation requires common ground: a shared understanding between the participants. Common ground, however, does not emerge spontaneously in conversation. Speakers and listeners work together to both identify and construct a shared basis while avoiding misunderstanding. To accomplish grounding, humans rely on a range of dialogue acts, like clarification (What do you mean?) and acknowledgment (I understand.). However, it is unclear whether large language models (LLMs) generate text that reflects human grounding. To this end, we curate a set of grounding acts and propose corresponding metrics that quantify attempted grounding. We study whether LLM generations contain grounding acts, simulating turn-taking from several dialogue datasets and comparing results to humans. We find that—compared to humans—LLMs generate language with less conversational grounding, instead generating text that appears to simply presume common ground. To understand the roots of the identified grounding gap, we examine the role of instruction tuning and preference optimization, finding that training on contemporary preference data leads to a reduction in generated grounding acts. Altogether, we highlight the need for more research investigating conversational grounding in human-AI interaction.

2023

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On Second Thought, Let’s Not Think Step by Step! Bias and Toxicity in Zero-Shot Reasoning
Omar Shaikh | Hongxin Zhang | William Held | Michael Bernstein | Diyi Yang
Proceedings of the 61st Annual Meeting of the Association for Computational Linguistics (Volume 1: Long Papers)

Generating a Chain of Thought (CoT) has been shown to consistently improve large language model (LLM) performance on a wide range of NLP tasks. However, prior work has mainly focused on logical reasoning tasks (e.g. arithmetic, commonsense QA); it remains unclear whether improvements hold for more diverse types of reasoning, especially in socially situated contexts. Concretely, we perform a controlled evaluation of zero-shot CoT across two socially sensitive domains: harmful questions and stereotype benchmarks. We find that zero-shot CoT reasoning in sensitive domains significantly increases a model’s likelihood to produce harmful or undesirable output, with trends holding across different prompt formats and model variants. Furthermore, we show that harmful CoTs increase with model size, but decrease with improved instruction following. Our work suggests that zero-shot CoT should be used with caution on socially important tasks, especially when marginalized groups or sensitive topics are involved.

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Modeling Cross-Cultural Pragmatic Inference with Codenames Duet
Omar Shaikh | Caleb Ziems | William Held | Aryan Pariani | Fred Morstatter | Diyi Yang
Findings of the Association for Computational Linguistics: ACL 2023

Pragmatic reference enables efficient interpersonal communication. Prior work uses simple reference games to test models of pragmatic reasoning, often with unidentified speakers and listeners. In practice, however, speakers’ sociocultural background shapes their pragmatic assumptions. For example, readers of this paper assume NLP refers to Natural Language Processing, and not “Neuro-linguistic Programming.” This work introduces the Cultural Codes dataset, which operationalizes sociocultural pragmatic inference in a simple word reference game. Cultural Codes is based on the multi-turn collaborative two-player game, Codenames Duet. Our dataset consists of 794 games with 7,703 turns, distributed across 153 unique players. Alongside gameplay, we collect information about players’ personalities, values, and demographics. Utilizing theories of communication and pragmatics, we predict each player’s actions via joint modeling of their sociocultural priors and the game context. Our experiments show that accounting for background characteristics significantly improves model performance for tasks related to both clue-giving and guessing, indicating that sociocultural priors play a vital role in gameplay decisions.

2020

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Examining the Ordering of Rhetorical Strategies in Persuasive Requests
Omar Shaikh | Jiaao Chen | Jon Saad-Falcon | Polo Chau | Diyi Yang
Findings of the Association for Computational Linguistics: EMNLP 2020

Interpreting how persuasive language influences audiences has implications across many domains like advertising, argumentation, and propaganda. Persuasion relies on more than a message’s content. Arranging the order of the message itself (i.e., ordering specific rhetorical strategies) also plays an important role. To examine how strategy orderings contribute to persuasiveness, we first utilize a Variational Autoencoder model to disentangle content and rhetorical strategies in textual requests from a large-scale loan request corpus. We then visualize interplay between content and strategy through an attentional LSTM that predicts the success of textual requests. We find that specific (orderings of) strategies interact uniquely with a request’s content to impact success rate, and thus the persuasiveness of a request.