Abstract:Powerful large language models have facilitated the development of writing assistants that promise to significantly improve the quality and efficiency of composition and communication. However, a barrier to effective assistance is the lack of personalization in LLM outputs to the author's communication style and specialized knowledge. In this paper, we address this challenge by proposing PEARL, a retrieval-augmented LLM writing assistant personalized with a generation-calibrated retriever. Our retriever is trained to select historic user-authored documents for prompt augmentation, such that they are likely to best personalize LLM generations for a user request. We propose two key novelties for training our retriever: 1) A training data selection method that identifies user requests likely to benefit from personalization and documents that provide that benefit; and 2) A scale-calibrating KL-divergence objective that ensures that our retriever closely tracks the benefit of a document for personalized generation. We demonstrate the effectiveness of PEARL in generating personalized workplace social media posts and Reddit comments. Finally, we showcase the potential of a generation-calibrated retriever to double as a performance predictor and further improve low-quality generations via LLM chaining.