Robert Keeling

Career

Robert Keeling, a Partner at Redgrave LLP, is widely recognized as a leading authority on eDiscovery, focusing on coordinating discovery for large, complex, and data-intensive matters. He represents clients in major regulatory enforcement actions, government investigations, and internal investigations, helping them navigate all phases of the discovery process.

Robert leads Redgrave’s Second Request practice, where he manages all aspects of discovery in connection with Hart-Scott-Rodino (HSR) “Second Requests” issued by the U.S. Department of Justice (DOJ) or Federal Trade Commission (FTC). He serves as lead discovery counsel for high-profile antitrust litigation against the government and plaintiffs’ attorneys and works alongside antitrust counsel to address the complexities of discovery compliance. Robert has been responsible for achieving substantial compliance with Second Requests in connection with transactions with a combined value of more than $230 billion.

Robert is widely recognized as a leading authority on eDiscovery, focusing on coordinating discovery for large, complex, and data-intensive matters. He represents clients in major regulatory enforcement actions, government investigations, and internal investigations, helping them navigate all phases of the discovery process. Chambers USA and Chambers Global have consistently ranked Robert as a top attorney for eDiscovery and Information Governance.

Robert leads Redgrave’s Second Request practice, where he manages all aspects of discovery in connection with Hart-Scott-Rodino (HSR) “Second Requests” issued by the U.S. Department of Justice (DOJ) or Federal Trade Commission (FTC). He serves as lead discovery counsel for high-profile antitrust litigation against the government and plaintiffs’ attorneys and works alongside antitrust counsel to address the complexities of discovery compliance. Robert has been responsible for achieving substantial compliance with Second Requests in connection with transactions with a combined value of more than $230 billion.

For over a decade, Robert has stood at the forefront of technology in litigation and government investigations. He applies a targeted combination of data analytics and machine learning to efficiently identify key evidence, reduce client costs, and synthesize information into compelling legal arguments. Robert is a leading thinker in the application of artificial intelligence (AI), including generative AI (GenAI) to eDiscovery challenges.

Robert helps clients across a broad range of industries with a variety of discovery and information governance needs, including: counseling on the effective management of eDiscovery costs and risks; navigating emerging eDiscovery issues, including implementing best practices for defensible eDiscovery policies and procedures, developing defensible strategies for the remediation and disposal of unneeded data; creating, updating, and improving records retention policies; and addressing records management and information governance issues.

Among eDiscovery practitioners, Robert is a leading author and has published nine law review articles, including articles with the Cornell Journal of Law and Public Policy and The Sedona Conference Journal. He is also a contributing author to four legal compilations — two compilations on predictive coding, The General Counsel’s Guide to Government Investigations, and The Complex Commercial Litigation Law Review.

Robert has published several technical research papers on applied machine learning that have received recognition outside the legal sphere, including an article selected for the annual Institute of Electrical and Electronics Engineers (IEEE) conference on machine learning. He also leads the drafting team for the Sedona Conference’s Commentary on Discovery Sanctions and is part of the drafting team for the Sedona Conference’s TAR Case Law Primer.

Robert is recognized as a preeminent speaker and thought leader on eDiscovery issues, and he is routinely invited to speak at conferences organized by the leading eDiscovery organizations, including The Sedona Conference®, the Electronic Discovery Institute (EDI), the Georgetown Advanced eDiscovery Institute (AEDI), Legalweek, and The Master’s Conference.

Robert is an Adjunct Professor at George Mason University Law School, where he teaches a course on eDiscovery. He has also lectured on eDiscovery and technology issues at the nation’s top law schools, including Harvard, Vanderbilt, Georgetown, Fordham, the University of Virginia, and American University.

Before joining Redgrave, Robert was a Partner at Sidley Austin LLP and was the founder and head of Sidley’s eDiscovery and Data Analytics group.

Professional Memberships

• Inaugural chair, EDRM Global Advisory Council

• Steering Committee Member, The Sedona Conference® Working Group on Electronic Document Retention and Production (WG1)

• Former co-chair, D.C. Bar eDiscovery Subcommittee

• Former chair, eDiscovery & Information Governance Retreat

Publications

Selected Publications

• “‘Like Little Novels’: Technology Made Privilege Logging Unwieldy. Can AI Fix It?” (New York Law Journal) (March 2024)

• “Replacing Attorney Review? Sidley's Experimental Assessment of GPT-4’s Performance in Document Review” (The American Lawyer) (December 2023)

• “The Case That Showed Me The Value Of E-Discovery Plans” (Law360) (June 2022)

• “The Burden of Privacy in Discovery” (Judicature Magazine) (2021)

• “CC’ed Emails and Attorney-Client Privilege” (ABA Pretrial Practice & Discovery) (May 2021)

• “Using Data De-Identification to Protect Companies” (Bloomberg Law) (May 2021)

• “Contract Law: Similarities and Differences in D.C. and Virginia Approaches” (Virginia Lawyer) (April 2021)

• “Handling Technology That Hides Privileged Correspondence” (Bloomberg Law) (April 2021)

• “Keyword Searches To Improve Your Privilege Doc Review” (Law360) (January 2021)

• “Humans Against the Machines: Reaffirming the Superiority of Human Attorneys in Legal Document Review and Examining the Limitations of Algorithmic Approaches to Discovery” (Richmond Journal of Law & Technology) (2020)

• “Document Review: You’re Doing It Wrong – Cognitive Psychology and The Attorney’s Mental Plate” (UA Little Rock Law Review, Vol 42) (2020)

• “Using Machine Learning on Legal Matters: Paying Attention to the Data Behind the Curtain” (Hastings Science and Technology Law Journal) (2020)

Recent Speaking Engagements

• Speaker, “Navigating the AI Revolution,” INBLF Washington, D.C. Chapter Meeting (May 2025)

• Panelist, “The Evolving Roles of AI Tech and Humans in Discovery,” The Sedona Conference Working Group 1 Midyear Meeting (April 2025)

• Panelist, “Generative AI in e-Discovery: How to Test, Trust, and Thrive in a New AI Era,” The Masters Conference (April 2025)

• Panelist, “Navigating the AI Revolution: Strategic Insights and Innovations,” Legalweek (March 2025)

• Guest, “AI Revolution in Legal Tech,” BDO Legal Tech Talk Podcast (March 2025)

• Presenter, “Modern Communications and Forensics: Using Data to Tell the Full Story in the Age of Cloud and AI,” Right Discovery (February 2025)

• Presenter, “The Litigator’s Toolkit: Streamlining Case Preparation with AI and Modern Technology,” EDRM (February 2025)

• Panelist, “Beyond the Hype: A Deep Dive into the Reality of Generative AI for eDiscovery,” Georgetown Advanced eDiscovery Institute (November 2024)

• Presenter, “How AI is Transforming the Law Firm Internally and Externally,” Disruption and Innovation in the Delivery of Legal Services Conference (October 2024)

• Moderator, “Voices from the Bench: The Judicial Perspective for 2024 and Beyond,” The Sedona Conference Working Group 1 Annual Meeting (October 2024)