So Many Questions Podcast: How to Move Fast When You Can’t Afford to Be Wrong With Guest Rawia Ashraf, Head of Product, CoCounsel Transactional & GCOs at Thomson Reuters
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What does it take to move quickly inside a business where a mistake carries real consequences? On this episode of So Many Questions, Rawia Ashraf, head of product, CoCounsel Transactional & GCOs at Thomson Reuters, talks with Moses Singer CEO Rebecca Goodman-Stephens about balancing speed and accuracy while building AI products for lawyers, accountants, and auditors.
Rawia walks through her career path, beginning as a lawyer at Simpson Thacher, before joining Thomson Reuters, where she now co-leads Thomson Reuters’ legal product portfolio, including Westlaw, Practical Law, and CoCounsel.
Rawia shares the two types of people she looks for when hiring, spreadsheet people and whiteboard people, and why you need both. She also digs into why law firms need to rethink the billable hour now that AI is changing what junior lawyers learn on the job, tells the story of how her team rebuilt CoCounsel as an agentic AI platform grounded in Westlaw and Practical Law, and explains why giving a team room to get things wrong, as long as they learn from it, ends up making for a stronger product.
In this episode
00:29 — Rebecca Goodman-Stephens welcomes her guest from Thomson Reuters.
04:26 — Why a 175-year-old content company now calls itself an AI company.
05:59 — Hiring for a mix of detail-driven executors and big-picture thinkers.
08:52 — The advice a Big Law partner gave during late-night deposition prep.
10:12 — How Liz Wiseman’s book “Multipliers” shaped a habit of asking questions instead of making statements.
12:12 — Why law firms should charge for outcomes rather than inputs.
17:35 — Advice to a younger self about not needing the path figured out.
19:59 — Inside the “brain transplant” that rebuilt CoCounsel on the Claude Agent SDK.
23:35 — What changes in an organization when women hold the leadership seats.
25:58 — Testing ideas fast while accuracy for lawyers stays non-negotiable.
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