One of the most revealing interview questions a CEO can ask a Chief Customer Officer candidate is simple, yet often terrifying:
“Tell me about a time you disagreed with the CEO.”
It’s revealing because it exposes an important trait in an executive: the ability to balance and advocate for the needs of the customer against the short-term pressure of the business.
The strongest answers don't describe a stylistic difference or a minor debate over slide deck formatting. They describe a genuine conflict where revenue pressure, company vision, or leadership narrative collided with reality.
These are the high-stakes moments that test judgment and courage:
The Product Launch: Shipping or announcing products on a fixed timeline despite knowing the organization isn't ready to support them.
The "Bad Revenue" Deal: Closing a large, misaligned enterprise deal that comes with massive roadmap commits and guaranteed future churn.
The Budget Cut: Reducing investments in Support or Success to hit an EBITDA target, despite knowing it creates a retention cliff.
The Risky M&A: Pursuing an acquisition where forced migration or unrealistic cross-sell assumptions threaten long-term value.
The Art of the Pushback
The issue itself matters less than how the CCO handled it. A CCO who cannot challenge leadership in these moments cannot fully protect the customer or the business.
Effective executives handle these disagreements with a specific playbook:
1. Data vs. Anecdotes
They prove their points with numbers, not feelings. They attack the problem with evidence without attacking the person, avoiding interpersonal friction.
2. Alternatives vs. "No"
A hard "no" rarely works in the C-Suite. Great leaders bring alternatives. They propose specific, alternate paths that help the CEO achieve their goal (or a close approximation of it) without sacrificing the customer experience.
3. Decision Quality vs. "Winning"
The outcome isn’t about winning the argument. Sometimes the CEO changes direction; sometimes they don’t. The best result is that the friction improves the decision.
Ultimately, this question reveals whether a candidate has the backbone to disagree, the communication skills to navigate power dynamics, and the ability to earn the CEO's trust.
A note for everyone:
This doesn't just apply to the C-Suite. The same question applies to VP, Director, and Manager levels.
Do you have the courage to disagree when it matters most?
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