Slate Money Presents: Women in Charge

Episode Date: October 11, 2018
Host: Julia Turner (Editor in Chief, Slate)
Slate Money Panel: Felix Salmon, Emily Peck, Anna Szymanski
Guest: Sukhinder Singh Cassidy (President of StubHub; Founder, The Boardlist)

Overview

This special episode introduces Women in Charge, a podcast series hosted by Julia Turner that spotlights women in high-level leadership roles. The episode features an in-depth interview with Sukhinder Singh Cassidy, exploring her leadership philosophy, her experiences as a woman in tech and finance, and her efforts to diversify corporate boards through The Boardlist initiative. The conversation delves into practical management tactics, gender-related workplace stereotypes, and actionable approaches for increasing diversity in the business world.

Key Discussion Points and Insights

1. Debating the Framing: "Women in Charge"

• Introduction to the Podcast Series
  Julia Turner describes the genesis of her new show, aiming not to reinforce stereotypes but to genuinely examine leadership (01:00–03:54).
• Debunking Stereotypes

  “I have a real allergy to, you know, sort of gendered assumptions about anything… The reason to want more women in charge… is not about the fact that the true best type of human has been somehow disadvantaged through history. It’s that society at large has incredibly, stupidly thwarted the potential talents and contributions of huge chunks of society…” — Julia Turner (02:32)

• Focus is primarily on tactical and strategic leadership, not on “women’s” workplace issues like work-life balance.

  “This show is kind of a Trojan horse for me to just ask other women bosses, just about bossing, just about management tactics.” — Julia Turner (03:10)

[Memorable Moment, 05:44]

Emily Peck points out the show’s “stealth breaking down the stereotype” by not focusing on typical ‘women in charge’ topics.

2. CEO Interviews and Pushing Past Talking Points

• Julia Turner explains her approach to interviewing: focusing on granular, tactical management methods rather than high-level platitudes or gendered questions (09:15–10:28).
• She acknowledges it can take time for guests to move beyond rehearsed answers:

  “For each of them, there’s the first few minutes… you can hear the talking points and the stories they’ve told before. What I’ve been trying to do is get granular and get down to a level of insight and information that feels revealing and useful.” — Julia Turner (10:28)

3. Why Leadership Conversations Matter for Everyone

• Julia argues management skills are relevant beyond the C-suite:

  “Even if you’re not managing a company, you are constantly managing your own life. I find them psychologically fascinating.” — Julia Turner (11:30)

Featured Interview: Sukhinder Singh Cassidy

President, StubHub & Founder, The Boardlist
(13:29–52:18)

4. Leadership Philosophy: Progress Over Perfection & Authenticity

• Fan-First Mentality
  The need for decisions grounded in customer-centric thinking:

  “A good outcome looks like waking up and making decisions based on a fan first mentality. So driving customer centricity.” — Sukhinder Singh Cassidy (13:49)

• Progress Over Perfection
  Encourages her teams to move forward rather than get paralyzed seeking perfection:

  “My other job is to get people to value progress over perfection… I try to lead by example. I try and do that in large company events and I try and do it in small meetings where I’ll throw out a hypothesis and say, do I have it right?” — Sukhinder Singh Cassidy (14:58)

[Memorable Moment, 16:21]

• Julia reflects on the pressure underrepresented leaders face to be “twice as good,” and Sukhinder responds with the value of showing thoughtful imperfection.

5. Customer-Centricity in Practice

• Brings real customers into the building, has all staff listen to actual customer-service calls, and involves employees in direct customer feedback loops:

  “We bring a panel of customers into the building and have everybody from engineers to product managers… listen to what a fan or user has to say…” — Sukhinder Singh Cassidy (19:14)

6. Consistent Versus Tailored Management Styles

• Certain approaches persist across organizations (progress over perfection, authenticity, “operating range”), but scale requires transitioning from direct action to managing through others (22:25–24:32).
• Looks for managers who “manage me” — those who come with solutions, opinions, and initiative rather than just questions:

  “Your primary job is to surround yourself with people who manage you… you want people who walk into the room with solutions, not questions.” — Sukhinder Singh Cassidy (25:05)

7. Building Relationships Deep into the Organization

• Practical steps for assessing and empowering two or three layers of staff below the top team:

  “When I arrived at StubHub, I… told my leadership team, you cannot pitch these projects… I want the people who are doing the work to come in and pitch the projects…” — Sukhinder Singh Cassidy (29:11)

• Also runs open office hours via Slack for direct feedback from all employees.

8. Comparing Wall Street and Silicon Valley Experiences

• Sukhinder’s early finance career provided direct access to senior management and large projects, while Silicon Valley initially proved less welcoming, partly due to stereotypes about “aggressiveness” (31:59–34:29).

  “My first job in the Valley…my boss told me I was scaring the secretaries… by month six, I’d quit my first job because…something was off and I was constantly getting more junior assignments and being told I was 'the rookie' on the team while I saw a more volatile male colleague being constantly rewarded for his behavior.” — Sukhinder Singh Cassidy (32:47)

9. The Boardlist: Fixing the Pipeline Problem

• The Boardlist crowdsources nominations from CEOs/executives and offers a curated, transparent roster of qualified women for board positions (37:10–38:06).

  “The Boardlist is a curated platform… Think of it as a LinkedIn for boards where CEOs and senior executives with board experience nominate great women they know for board opportunities…” — Sukhinder Singh Cassidy (37:11)

• Aims to end excuses about the lack of qualified female candidates:

  “It… seeks to solve the problem…by making available outstanding, curated a diverse talent for boards in an easily accessible place by crowdsourcing it.” — Sukhinder Singh Cassidy (37:50)

10. Board Diversity & Corporate Effectiveness

• Boards need fresh, diverse, relevant perspectives for technological, demographic, and workforce changes (39:53–42:06).

  “If you think about employee base, demographic based technology change, the reality is you need new perspectives even to be able to take advantage of those three things.” — Sukhinder Singh Cassidy (41:11)

11. Status of Women in Tech: Glass Half-Full?

• Some Progress:
  • More women starting companies, new sources of capital, successful female-led “unicorns.”
  • Increased flexibility and resourcefulness in supporting mid-career female talent.
• Ongoing Challenges:
  • Engineering remains a pipeline problem with slow progress.
  • Shaming and public accountability drive some improvement in diversity, along with the competitive “greed” for talent (42:57–50:08).

  “Shame honestly has a big part to bear in this…one of the things that is true about the Valley and tech is it is like a huge consumer of talent...the appetite for talent in the Valley is ridiculous…if you want to get access to it, you better get more flexible…Otherwise you’re literally not going to be able to get all your jobs done.” — Sukhinder Singh Cassidy (48:05–50:08)

12. Spotting and Nurturing Talent

• Key traits Sukhinder looks for in employees:
  • Histories of both success and failure.
  • Experience in both large organizations and startups.
  • Doing more than their formal job requires.
  • Ownership mentality; willingness to step outside their defined roles (50:26–52:14).

  “If you want to know where you've got a successful employee, look at the person whose job title is X and who's doing job X, job Y and part of job Z, and you will have found yourself a star in some ways or not.” — Sukhinder Singh Cassidy (51:32)

Notable Quotes and Timestamps

• “Society at large has incredibly, stupidly thwarted the potential talents and contributions of huge chunks of society by suggesting that only a small chunk...can contribute.”
  — Julia Turner (02:32)
• “My job is to show up imperfectly, but with people knowing I care deeply and I’m committed to transparency.”
  — Sukhinder Singh Cassidy (22:29)
• “You want people who walk into the room with solutions, not questions.”
  — Sukhinder Singh Cassidy (25:10)
• "It turns out at least half the world's talent is female. And if you want to get access to it, you better get more flexible about what it takes…”
  — Sukhinder Singh Cassidy (49:43)
• "Those are the things I look for." (on spotting talent) — Sukhinder Singh Cassidy (52:02)

Timestamps for Major Segments

• Introduction & Podcast Rationale: 00:12–03:54
• CEO Interview Strategies: 09:05–11:30
• Sukhinder Singh Cassidy Interview Starts: 13:29
  • Leadership Style & Fan-Centric Approach: 13:35–19:14
  • Practical Management in Large Orgs: 22:07–29:11
  • Boardlist & Board Diversity: 34:29–39:53
  • State of Women in Tech: 42:38–50:08
  • Talent Spotting & Takeaways: 50:08–52:18

Language and Tone

The conversation is candid and energetic, balancing strategic insights with a sense of humor and personal vulnerability. Julia Turner and Sukhinder Singh Cassidy both avoid corporate jargon in favor of relatable, practical advice and stories.

Summary

Women in Charge draws back the curtain on what it means to be a woman in a position of power—focusing less on “lady boss” stereotypes and more on practical leadership, management tactics, and systemic change. Sukhinder Singh Cassidy offers firsthand insights on authentic leadership, breaking the perfection barrier, and broadening the candidate pool for influential board positions—advocating for diversity not as an end in itself, but as a key to better business and richer talent utilization for all.

For listeners seeking actionable leadership advice and a deeper understanding of women’s evolving position in business, this episode delivers thoughtful, evidence-based perspectives and compelling stories.