Relevance has become the most fragile asset in business.
Not scale.
Not market share.
Not even profitability.
Across industries, organizations that once appeared invincible have found themselves disrupted—not because they lacked resources, but because they failed to ask the right questions early enough.
History shows us a sobering pattern:
Most companies do not collapse suddenly. They fade gradually, while still appearing busy, successful, and confident.
In my work as a business strategist and leadership advisor, I’ve observed that organizations which stay relevant over decades do one thing exceptionally well:
They continuously question their assumptions.
Strategy, at its core, is not about forecasting the future with precision. It is about preparing the organization to adapt intelligently.
The following ten questions are not theoretical exercises. They are strategic lenses that help leaders re-examine their business models, leadership choices, and long-term direction. More importantly, they force uncomfortable—but necessary—conversations.
1. Where Is My Industry Truly Headed—not Just This Year, but Over the Next Decade?
Many leadership teams operate with short planning horizons. Quarterly performance, annual targets, and immediate competitive pressures dominate executive attention.
Yet relevance is shaped by long-term directional shifts, not short-term fluctuations.
Industries rarely disappear overnight. What changes is where value migrates.
Consider media, retail, banking, or education. None of these industries vanished—but the rules of value creation changed dramatically. Organizations that tracked only near-term indicators missed the deeper trajectory.
Strategic leaders distinguish between:
- Cyclical changes (temporary ups and downs)
- Structural shifts (permanent redefinitions of value)
The question leaders must ask is not, “How do we grow next year?”
It is, “If current trends continue, where will profit pools exist five years from now?”
Strategic implication:
Relevance requires horizon thinking. Leaders must allocate time for future-oriented dialogue, even when current performance appears stable.
2. What Is Fundamentally Changing in Customer Behavior?
Technology does not disrupt industries.
Behavior does.
E-commerce did not disrupt retail; changing expectations of convenience did.
Digital payments did not disrupt banking; impatience with friction did.
Many organizations track customer satisfaction metrics but fail to study behavioral shifts—how customers discover, evaluate, purchase, and use offerings differently than before.
In multiple consulting engagements, I’ve seen companies lose relevance while believing they were customer-centric—because they focused on improving existing touchpoints rather than rethinking the journey itself.
Customers today expect:
- Speed over perfection
- Personalization over standardization
- Transparency over persuasion
Strategic implication:
Leaders must invest in understanding how customers decide, not just what they buy. Behavioral insight has become a core strategic capability.
3. Which Assumptions About Our Business Are No Longer True?
Every organization is built on assumptions—about customers, competitors, cost structures, and capabilities.
The danger arises when assumptions become invisible truths.
What once made sense may no longer hold:
- Customers may no longer value scale
- Loyalty may no longer be guaranteed
- Entry barriers may no longer exist
A recurring pattern in declining firms is not lack of intelligence, but assumption inertia.
Strong leadership teams institutionalize assumption testing. They ask:
- What do we believe that might no longer be true?
- Which beliefs are we protecting because they made us successful?
Strategic implication:
Relevance requires intellectual humility. Leaders must be willing to unlearn before they can reinvent.
4. How Is Technology Reshaping Cost, Speed, and Access in Our Industry?
Technology discussions often focus on tools rather than consequences.
The strategic question is not whether a technology is advanced, but whether it:
- Reduces cost dramatically
- Increases speed exponentially
- Expands access to new players
Technologies such as AI, automation, platforms, and analytics are lowering barriers that once protected incumbents.
In several industries, startups with minimal infrastructure are outperforming established firms—not because they are smarter, but because their operating logic is different.
Strategic implication:
Leaders must evaluate technology not as an IT function, but as a strategic force reshaping competitive advantage.
5. If We Were Starting This Business Today, Would We Design It the Same Way?
This question often produces silence in boardrooms.
Legacy structures—processes, hierarchies, product lines—exist largely because of history, not strategic intent.
When leaders imagine designing their business from scratch today, many existing elements disappear:
- Complex approval systems
- Redundant layers
- Offerings created for outdated customer needs
This exercise reveals the cost of legacy thinking.
Strategic implication:
Relevance requires periodic reinvention. Leaders must distinguish between what is essential and what is inherited.
6. What New Forces of Competition Could Disrupt Us from Outside Our Industry?
Competition is no longer confined within industry boundaries.
New competitors emerge from:
- Adjacent industries
- Platforms
- Ecosystems
- Customers themselves
Traditional competitor analysis often misses these threats because it focuses on known rivals rather than alternative value creators.
The strategic question leaders must ask is:
“Who could solve our customer’s problem differently—and better—without looking like us?”
Strategic implication:
Leaders must expand their competitive lens beyond direct rivals to include substitutes, platforms, and nontraditional entrants.
7. Which of Our Core Strengths Is Becoming Less Valuable to Customers?
Strengths can quietly turn into liabilities.
Capabilities that once differentiated a firm—scale, efficiency, reach—may become commoditized as markets evolve.
I have seen organizations defend strengths long after customers stopped valuing them.
The critical shift is to view strengths from the customer’s perspective, not internal pride.
Strategic implication:
Leaders must continually reassess whether their advantages are still relevant—or merely familiar.
8. What Are Customers Expecting Today That We Are Not Yet Delivering?
Customer expectations evolve faster than organizational systems.
Often, dissatisfaction is not vocalized—it is expressed through disengagement.
Organizations that lose relevance often misinterpret silence as satisfaction.
Strategic leaders actively seek:
- Friction points
- Delays
- Moments of disappointment
They understand that customers compare experiences across industries, not within categories.
Strategic implication:
Relevance requires relentless attention to experience, not just product quality.
9. What Should We Stop Doing—Even If It Worked in the Past?
Strategy is as much about subtraction as it is about addition.
Peter Drucker famously observed that efficiency applied to irrelevance only accelerates decline.
Organizations accumulate activities, products, and processes that dilute focus and drain resources.
The discipline of stopping requires courage—especially when legacy initiatives carry emotional or political weight.
Strategic implication:
Leaders must free capacity by eliminating low-impact activities to create space for future growth.
10. What One Strategic Choice Could Make Us Unmistakably Distinct?
The ultimate goal of strategy is not to be better—but to be meaningfully different.
Organizations that remain relevant over time make clear choices:
- What they will do
- What they will not do
Distinctiveness often emerges from:
- Unique value propositions
- Bold positioning
- Experiences competitors cannot easily replicate
This question forces leaders to confront risk, courage, and commitment.
Strategic implication:
Relevance is built on deliberate choices, not incremental improvements.
These ten questions are not meant to be answered once.
They must be revisited continuously—because relevance is dynamic.
Organizations that endure are not those with perfect foresight, but those with adaptive intelligence.
In an era of disruption, uncertainty, and accelerated change, the greatest strategic risk is not experimentation.
It is complacency.
Ultimately, the future belongs to leaders who are willing to question deeply, decide deliberately, and act courageously—before relevance becomes an urgent problem rather than a strategic priority.