Eugene Soltes | Harvard | Managing the Gray Area - The Fine Line Between Puffery & Lying | Part 2

A CMO Confidential Interview with Dr. Eugene Soltes, Harvard Business School Professor and author of "Why They Do It - Inside the Mind of the White Collar Criminal". Eugene discusses how most crimes start out as small, often unnoticed decisions made by strategic people, how nearly everyone has a chance to step over the line, why many companies (Air BnB, Uber, AI) take regulatory risk, and how culture drives poor individual choices. Key topics include: when puffery gets murky; why it's dangerous to "convince yourself;" why it doesn't matter "who signed off;" and the "fraud triangle." Listen in to hear why humility and counterpoints are critical, what he learned about risk assessment from the Free Solo climber, the "difference between being an arms dealer and a transportation company," and how there are "a million ways to pay a bribe."

In Part 2 of our conversation with Harvard Business School professor and author of Why They Do It, Dr. Eugene Soltes, we dive even deeper into the ethical gray zones that surround today’s most ambitious companies. From social media firms that hide behind “just connecting people” to leaders who convince themselves their actions are justified, Eugene explains how culture, rationalization, and groupthink drive even the smartest executives into trouble.

You’ll learn why having a sign-off from Legal is never enough, why the “show me where it says I can’t” culture is so corrosive, and why CMOs must understand the difference between business risk and integrity risk. We also hear Eugene’s story of climbing (briefly) with Free Solo legend Alex Honnold and how that shaped his thinking around open-eyed risk—a model every marketing leader should understand.

Topics include:

• Why CMOs can’t hide behind Legal

• The “arms dealer” mindset in corporate marketing

• Risk culture vs. innovation culture

• How companies accidentally incentivize bad behavior

• Psychological safety vs. performative candor

• The million ways bribes get disguised

• The importance of personal humility—even in the C-Suite

📌 Sponsored by  @PublicisSapient  – AI marketing platforms for personalization

00:00 – Intro

01:00 – Welcome Back: Convincing Yourself It’s Okay

Mike and Eugene dive into self-deception and ethical gray zones in corporate decisions.

02:10 – Don’t Count on the Sign-Off

Why “someone else signed off” isn’t a defense, and the importance of owning your decisions.

03:30 – The Explain-to-Your-Spouse Test

Eugene’s replacement for the outdated “newspaper test” of ethical clarity.

04:45 – Know What You’re Signing Up For

Ignorance as a leadership failure and why it’s never an excuse.

06:00 – Taking Ethical Stands as a Marketer

What to do when legal says it’s okay but your gut says otherwise.

07:15 – Integrity vs. Strategic Risk

A key distinction for marketers: smart business risk vs. ethical risk.

08:20 – “A Million Ways to Pay a Bribe”

Creative examples of corruption and why culture enables them.

10:15 – The “Show Me Where It Says I Can’t” Culture

How policy loopholes can foster ethical erosion.

12:00 – The Role of Legal and Compliance

How to use counsel the right way—not just for CYA.

14:00 – The Fraud Triangle + Rationalization Risk

How pressure, opportunity, and rationalization lead to ethical drift.

15:45 – Everyone Has the Chance to Be the Bad Apple

The universal risk of stepping over the line—and why culture matters.

16:30 – Regulatory Arbitrage: Uber, AI, and the Gray Zone

Why innovation often requires pushing boundaries—and accepting consequences.

18:00 – Free Solo Climbing and Open-Eyed Risk

What Eugene learned about risk from Alex Honnold and what CMOs can take from it.

20:30 – Evaluating Risk from Multiple Angles

Why great leaders view risk with humility and diversity of perspective.

22:00 – Groupthink and the Myth of Momentum

The danger of unchecked optimism and lack of internal dissent.

23:30 – The Limits of Mandated Psychological Safety

Why culture change can’t be legislated—and how real safety is built.

24:30 – Final Question: Funny Story or Practical Advice

Eugene’s “most awkward moment” and his parting advice on cultivating humility.

27:00 – Wrap-Up and Upcoming Episodes

Mike closes out with highlights from other case-based episodes.

Eugene Soltes, Harvard Business School, white collar crime, C