Why Great Founders Struggle to Become Great CEOs | Steve Schloss
Leadership is often discussed as a competitive advantage, but what if it's actually one of the earliest indicators of enterprise value?
In this episode of People Multiple, Gia Ganesh sits down with Steve Schloss, former Chief People Officer, executive coach, and Operating Partner at Edison Partners, to explore how investors evaluate leadership long before financial results reveal the outcome. Drawing on decades of experience leading people functions and coaching CEOs inside growth-stage portfolio companies, Steve shares what separates companies that scale successfully from those that stall.
The conversation explores how private equity firms are evolving beyond financial engineering to recognize talent as a value creation lever, why coachability matters more than confidence during diligence, and how founder CEOs must transform their leadership as organizations grow. Steve also explains how leadership team health, organizational design, and executive behavior quietly shape business performance long before they appear in revenue, retention, or exit multiples.
Learn More About Steve Schloss:
- LinkedIn: https://www.linkedin.com/in/steve-schloss-0b2a7b2/
- Website: listenforwardllc.com
Timestamps:
01:12 — Small rituals that create calm and focus
03:14 — HR’s shift from operations to business value
06:18 — Talent as a value creation lever in PE
08:19 — Edison Partners’ leadership coaching model
12:10 — How founder and team readiness is assessed
16:58 — Leadership behind growth and execution issues
22:23 — Authentic vs. performative leadership
27:01 — From hustler mode to CEO mode
28:44 — Why playbooks fall short in growth PE
32:49 — The danger of moving too fast on transformation
36:24 — Assessing current vs. future capabilities
40:42 — Self-awareness, feedback, and behavioral change
45:58 — What predicts an outperforming leadership team
52:09 — Why deals go sideways
53:36 — A COVID-era talent decision with major impact
55:44 — Closing thoughts on leadership and multiples
Key Takeaways…
Leadership quality is one of the earliest predictors of enterprise value.
Leadership quality is one of the earliest predictors of enterprise value.
- Private equity firms are placing greater emphasis on talent during due diligence.
- Coachability is a critical trait for founders and CEOs.
- The leadership skills that build a startup are not always the skills that scale a business.
- Healthy leadership teams disagree before they align.
- Transformation succeeds when organizations are ready for change, not simply because leaders announce it.
- Executive coaching creates measurable business value in growth-stage companies.
- People strategy becomes a competitive advantage when CEOs view HR as a value creation partner.
- Leadership assessments should evaluate future scalability, not just current performance.
- Companies that consistently outperform expectations invest in leadership long before problems appear in the numbers.
The discussion also tackles questions....:
- How do private equity firms evaluate leadership during due diligence?
- What makes a founder CEO coachable, and why does it matter to investors?
- How can you tell if a leadership team will scale with the business?
- What leadership behaviors become liabilities as companies grow?
- What separates founder mode from CEO mode?
- Why do some leadership teams outperform expectations while others fall behind?
- How should CEOs prepare for life after receiving private equity investment?
- What are the earliest people signals that predict business performance?
- Why do some transformation initiatives fail before they begin?
- How can organizations create healthy urgency instead of constant firefighting?
- What role should HR play in creating enterprise value?
- How can executive coaching improve outcomes in PE-backed companies?
- Why is disagreement inside leadership teams often a sign of organizational health?
- How do investors distinguish authentic leadership from performative leadership?
- What leadership risks can prevent an investment from moving forward?
Similar episodes:
- Inside the Talent Strategies of Twitter, Mozilla, Intel, and NerdWallet | Lynee Luque: https://youtu.be/yXB7-GS0ahE?si=lb7AeuavsdXdqjLh
- Why Retention Is a Business Strategy, Not an HR Metric | Drew Harden: https://youtu.be/C_H2V9BaeF8?si=OGYGFG1Wm4LypwUb
- The CEO Mistake That Drives Away Top Talent | Patrick Lyons: https://youtu.be/TojvnJLD24s?si=Ao2x6VV65qpJHolJ
Production
Produced by: The AGN Group
Host: Gia Ganesh
Producer: Katie Hart
Websites: https://peoplemultiple.com/
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If you are interested in being a guest on the podcast, email us at gia@peoplemultiple.com