Thomson Reuters’ Head of Product of CoCounsel Transactional & GCOs, Rawia Ashraf, builds AI products for lawyers, accountants, and auditors, and moves fast without sacrificing accuracy. Rawia started her career as a lawyer at Simpson Thacher before moving into product management at Thomson Reuters.

On this episode of So Many Questions, Rawia tells host Rebecca Goodman-Stephens, CEO of Moses Singer, how a piece of advice from a Big Law partner, don’t let perfect be the enemy of good, shaped the way she runs product today. They discuss how Rawia and her team rebuilt CoCounsel as an agentic AI platform, why she looks to hire a mix of detail-oriented “spreadsheet people” and big-picture “whiteboard people,” and why she believes law firms need to rethink the billable hour as AI changes how junior lawyers learn.

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. 1

0:12 — 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.

Relevant Links:

• Moses Singer: www.mosessinger.com

• Thomson Reuters: https://www.thomsonreuters.com

• Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

• CoCounsel: https://www.thomsonreuters.com/en/cocounsel

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How does an optimistic leader avoid burning out the team around them?

Steven Lerche, President of Goldstar Jewellery, joins host Rebecca Goodman-Stephens, CEO of Moses Singer, to talk about leading a large, multigenerational business through pressure and constant change.

Steven explains how his instinct toward optimism shapes his leadership, and why he leans on methodical people to balance his big-picture thinking. Rebecca, who admits her own version can tip into toxic positivity, digs into the friction that shows up when a leader hands off tasks without explaining the reasoning behind them, and why a colleague who pushes back is usually trying to help an idea succeed, not block it.

The conversation moves into leading through real pressure: commodity swings, a 56% tariff that forced Goldstar to open a new factory within 90 days, and where AI is actually useful in the business. Steven also shares the fear he considers the biggest of his life.

In This Episode

01:14 – The scale of the business Steven leads 05:24 – Employee tenure and company culture 08:07 – Optimism as a leadership style 10:01 – Objections as a sign of investment 11:08 – Delegating without full context 14:28 – Responding to the tariff crisis 17:39 – A therapy concept for business crises 19:28 – Rethinking the interview process 22:45 – Balancing fatherhood and business 25:30 – The fear of the second generation

Relevant Links

• Moses Singer: www.mosessinger.com
• Goldstar Jewellery: www.goldstarjewellery.com
• Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

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What does it take to build trust with the people you lead, and make it last?

In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, talks with Michael Luongo, owner of Evolve Athletic Club, where he trains CEOs, entrepreneurs, and high-performing professionals. Michael shares how a simple first conversation can become the foundation of a real working relationship, how pushing past his discomfort with outreach changed the trajectory of his business, and what he's observed about the leaders who grow the fastest.

Relevant Links Moses Singer Evolve Athletic Club Connect with Rebecca Goodman-Stephens on LinkedIn