So Many Questions
Wish you could get in the head of an effective business leader? Host Rebecca Goodman Stephens, a law firm CEO who trained in clinical and organizational psychology, does just that on her podcast. Each episode, she interviews leaders across industries who share real stories of success. So Many Questions features authentic, fun, and insightful conversations that reveal what it really takes to lead in business.
Episodes
As managing director of business development at Oaklins DeSilva+Phillips, Marci Weisler works mostly with founder-led media and technology companies. Her superpower comes in two parts: a deep curiosity and a knack for connecting people who should know one another.
She tells host Rebecca Goodman-Stephens how a winding career commercializing emerging technology brought her to M&A, and why today's leaders can't afford to sta...
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...
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. Rebe...
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 w...
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 operat...
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 evolvi...
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 t...
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”...
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 h...
Moses Singer CEO Rebecca Goodman-Stephens speaks with Oxygen co-CEO Ashley Fina about what it truly takes to develop strong leaders, and the systems today’s managers need to perform at their best.
In this Discussion 00:29 – Guest introduction 01:53 – Becoming CEO at 25 06:36 – Coaching and leadership development 08:33 – The leadership skills gap 12:55 – Coachability ...
Lindsi Shine, CEO of INsider NYC, discusses what it means to lead with vulnerability. Her and host Rebecca Goodman-Stephens explore how balancing strength with openness shapes leadership, builds trust, and creates resilient workplace cultures.
Key Timecodes: 00:28 – Guest Introduction 01:00 – The Heart of Lifestyle Management 03:16 – Valuing Vendors Like Family 09:13 – Showing Up With What You’ve Got 1...
In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Shireen Hilal, CEO of Maior Consultants, about culture and leadership in professional services. They explore how empowering people, building trust, and shaping authentic culture drives firm performance and client success.
Key Timecodes00:28 – Guest Introduction 01:18 – Career Journey: From Law to Consulting 07:06 &ndas...
In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Jacqueline Newman, Managing Partner of Berkman Bottger Newman & Schein, LLP, about women leading change in law and the power of building impact beyond the practice. They explore her journey as a leader in a male-dominated industry, the creation of the 2181 Group to accelerate gender parity in law, and her philanthropic project...
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