Counterintuitive Questioning: The Key to Breaking Corporate Barriers for growth

More often than not, I noticed that the difficult part in corporate life is for executives to find the right questions to ask.

In the pursuit of success, businesses often ask those historically pre-coded questions, “How do we grow?” or “How do we improve customer experience?”While these are logical questions, they may not always yield transformative insights.

A counterintuitive approach—asking “How do we make a business fail?”—can expose blind spots, challenge assumptions, and drive strategic clarity.

The Power of Reverse Thinking

Humans are wired to seek solutions by thinking forward. But great breakthroughs often come from flipping the perspective. Instead of listing ways to win, consider ways to lose. If failure patterns can be identified, businesses can deliberately avoid them and, in turn, improve their odds of success.

For example, instead of asking:

? “How can we retain customers?” ask “What would drive customers away?”

? “How can we increase profits?” ask “What would drain our profitability?”

? “How do we create a strong brand?” ask “What would make our brand irrelevant?”

By defining failure, organizations gain a roadmap of pitfalls to sidestep.

Identifying unintended self-sabotage in business

Many companies fail not because of market forces but due to self-inflicted mistakes—complacency, poor decision-making, or resistance to change. A reverse-engineered approach helps uncover these risks.

Consider a retail company struggling with customer churn. Instead of brainstorming retention strategies, leaders should ask, “If we wanted to lose more customers, what would we do?” The answers—neglect customer complaints, delay service, overprice products—reveal areas needing immediate attention.

Similarly, if a startup wants to avoid stagnation, it can ask, “If we wanted to ensure no innovation happened, what would we do?” Answers like discouraging experimentation or punishing failure highlight toxic cultural norms that must be addressed.

The Danger of Complacency and Inertia

A major cause of corporate failure is clinging to outdated business models and practices while expecting to stay relevant and differentiated. Many legacy companies fail because they assume what worked in the past will continue working in the future.

Asking “If we wanted to become obsolete, what would we do?” often highlights reliance on aging systems, rigid hierarchies, or an aversion to digital transformation.

For example:

? Blockbuster assumed physical rentals would remain dominant, failing to adapt to streaming.

? Kodak invented digital photography but hesitated to embrace it, fearing it would cannibalize film sales.

? Nokia was once the leader in mobile phones but resisted shifting to smartphones, allowing competitors to take over.

By questioning inertia, businesses can identify when their own policies and traditions are keeping them from evolving.

Unmasking Dangerous Assumptions

Counterintuitive questioning also dismantles dangerous assumptions. Many businesses assume they are customer-centric, yet when asked “How would we frustrate customers?” they discover they are already doing some of those things—hidden in policies, pricing, or service design.

By answering the question, “How would we ensure our competitors outgrow us?” executives may realize, while listing the negative initiatives needed, they are doing exactly this: not investing in emerging trends, innovation, talent, or technology.

Applying the Framework

1. Define the Goal – Identify a key business challenge (e.g., improving revenue, enhancing CX).

2. Flip the Question – Instead of asking how to succeed, ask how to fail.

3. List Failure Tactics – Identify destructive behaviors, practices, or decisions.

4. Compare with Reality – Assess whether any failure behaviors are already present.

5. Develop a Success Strategy – Reverse the failure insights into positive actions.

Shift focus on what is actually happening and needs to be changed in priority

The key aim of counterintuitive thinking is to shift executive focus away from projecting an ideal future state. Instead, it forces them to compare their answers with what they are actually doing today—actions that may already be causing unintended problems and should be addressed urgently before any other incremental initiatives. This real-world grounding makes counterintuitive questioning a practical tool for uncovering blind spots and driving meaningful change.

Conclusion

By questioning success through the lens of failure, companies gain a sharper strategic edge. In a fast-changing world, understanding the inherent elements of failure may be just the key gate to success. Instead of asking, “How do we thrive?” The better question is, “How do we avoid becoming obsolete?”

Joe Ayoub- Brandcell consulting

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