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

Alexia Crawford has reinvented herself more times than most people get to try once. She moved to the U.S. at 19 with no work permit and started a jewelry business because it was the only option she had. That business eventually became a 55-location retail chain. Then came the bankruptcies, the burnout, and a single 11-hour seminar that changed everything. She is now CEO of 8westervelt, helping retail companies automate their operations, and she will tell you the 30 years of hard experience is the real product, not the technology.

Rebecca Goodman-Stephens, CEO of Moses Singer and host of “So Many Questions,” sat down with Alexia to talk through all of it, the chapters that were exciting, the ones that were brutal, and what she actually learned from each.

They get into what it felt like to scale faster than her systems could support, how a difficult earn-out year changed the way she receives feedback, and how she ended up in an AI seminar that sent her life in a completely different direction. Alexia talks honestly about burnout, what caused it, what it cost her, and why she thinks it carried important lessons she needed she needed. She also makes a case that starting fresh, without legacy systems and entrenched ways of doing things, is one of the biggest advantages a company can have right now.

If you have ever wondered what sustained reinvention actually feels like from the inside, this one is worth your time.

In This Episode

01:35 — From Australia to New York

02:21 — The Barney’s Lesson

04:21 — Building Laila Row

09:48 — When Growth Outpaces Structure

12:07 — Having a Boss For the First Time

18:51 — Burnout

20:11 — Rebuilding Through YPO

21:43 — Discovering AI

24:52 — Full Automation in Practice

26:16 — Leading Without Certainty

37:07 — The Efficiency-First framework

39:56 — Advice to Entrepreneurs

Guest Bio

Alexia Crawford is CEO of 8westervelt, an AI and automation company focused on retail operations. She spent more than three decades building businesses across jewelry manufacturing, wholesale, and retail before pivoting to AI. She is currently pursuing her MBA at NYU and has been a YPO member for 20 years.

Relevant Links

Moses Singer on LinkedIn

Connect with Rebecca Goodman-Stephens on LinkedIn

YPO

After 12 years helping HubSpot scale from 300 to 8,000 employees, Katie Burke joined Harvey with one clear conviction: the key ingredient for scaling any company is humility.

In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, sits down with Katie Burke, chief operating officer of Harvey, to talk about what strong leadership actually requires when a company is growing fast and constantly evolving.

Katie shares:

• Why humility and curiosity matter more than a proven playbook
• How Harvey’s hiring process is designed to talk candidates out of joining
• What transparency should and should not include inside a growing organization
• Why “Jobs Not Finished” is her favorite company value and what it looks like in practice
• Why people management is something leaders have to relearn constantly

If you lead a team in a fast-moving environment, this conversation is worth your time.

Connect with Rebecca Goodman-Stephens on LinkedIn

What separates leaders who inspire bold thinking from those who quietly kill it? In this episode of So Many Questions, Moses Singer CEO and host Rebecca Goodman-Stephens sits down with Daniel Curtis, Chief Strategy Officer of global events agency emc3, for a conversation about fearless leadership, psychological safety, and the culture-building decisions that shape high-performing organizations.

Daniel shares what it actually took to build a culture at emc3 where people feel safe taking risks and pushing creative boundaries. He talks about how four members of his leadership team publicly owned their biggest professional mistakes in front of the whole company, why he stepped out of his own role so a rising team member could take it, and what his move to New York signaled to the rest of the organization. He also walks through how emc3 built its values from the ground up, the non-negotiable behaviors baked into every onboarding, and why he believes culture without values is just background noise.

Relevant Links Moses Singer emc3 Connect with Rebecca Goodman-Stephens on LinkedIn

What if the key to becoming a stronger leader isn’t changing yourself, but trusting how you’re wired?

Kara Brothers, Founder of New Juice Studios, joins host Rebecca Goodman-Stephens to discuss building leadership confidence by understanding your natural style.

Kara shares why it’s normal to question your worth in demanding environments, and how experience helps you separate “I’m not good enough” from “this isn’t the right fit.” Together, they discuss perspective-taking, quiet leadership, and how leaders can bring out the best in teams with different working styles.

Links: www.mosessinger.com

Rebecca Goodman-Stephens on LinkedIn

Leadership today isn’t just about managing teams — it’s about designing how work gets done. Host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Cindy Machles, Co-founder and CEO of Glue Advertising and Public Relations, about leadership in the future of work. They discuss how leaders can design organizations for flexibility, why courage and self-trust matter when making career-defining decisions, and how skills-based teams and technology are reshaping professional services.

Links: Moses Singer: www.mosessinger.com Glue Advertising and Public Relations: glueadvertising.com Connect with host Rebecca Goodman-Stephens on LinkedIn