Transformational Decision Making
Leading Through Transformative Decisions
By Robert K Ryan
“I am not a product of my circumstances. I am a product of my decisions.” Steven Covey
In business leadership, the most consequential decisions are rarely just strategic—they’re transformative. These are decisions that don’t simply shift direction or reallocate resources. They reshape how leaders think, what they value, and how they define success.
Unlike tactical or operational choices, transformative decisions introduce a unique challenge: you cannot fully know what you're choosing until after you’ve made the choice. Whether it’s launching a new business model, stepping down from a role, expanding globally, or reorienting a company’s mission, these decisions change both the business and the person leading it.
Rational Models Can Fall Short
Most executives rely on data, metrics, forecasts, and experience to make decisions. That works when the outcomes are measurable—market entry, product pricing, operational efficiency. But transformative decisions don’t fit into a spreadsheet. Why? Because they involve unknowns that can't be calculated: how the decision will change your values, goals, and sense of purpose.
You may think you're choosing a growth strategy—but you’re also choosing a new identity as a leader and a new culture for your company. These aren't variables you can model. They evolve only through experience.
Case in Point: The Limits of Metrics and Forecasting
Mayo Clinic’s decision to embrace a long-term strategy centered around virtual care, AI diagnostics, and platform-based healthcare delivery. In the mid-2010s, Mayo faced growing pressure: an aging population, rising costs, physician burnout, and mounting competition from both traditional systems and tech companies moving into health. Rather than doubling down on brick-and-mortar expansion, leadership chose a fundamentally different path.
Mayo invested heavily in Mayo Clinic Platform, a bold initiative to integrate data science, cloud infrastructure, and AI into the heart of its care model. They partnered with companies like Google and nference to build tools for predictive diagnostics, remote monitoring, and scalable digital therapeutics.
This wasn’t a tactical play—it was a transformative bet on the future of medicine. There was no reliable data model to forecast exactly how these innovations would affect revenue, reputation, or patient outcomes. The tools themselves were evolving. But Mayo’s leadership understood that the transformation wasn’t just technological—it was cultural. It would change how patients engage, how physicians work, and how the institution defines itself.
Such decisions don’t fit traditional business logic. They require long-term vision, a deep understanding of the organization's mission, and the willingness to lead into uncertainty.
Moving Beyond Calculation
Strategic tools are valuable—but they’re not enough. The most important decisions require something more: discernment. This is not about pro/con lists. It's about asking deeper questions:
What kind of leader do I want to become?
What do I want this company to stand for in 10 years?
Am I making this decision based on who I am now—or who I hope to become?
Luke Burgis, an entrepreneurship professor, puts it well: we need more meditative thinking in leadership—reflecting on purpose, not just outcomes. Strategic thinking can clarify options. But only reflection helps you recognize which path aligns with your deeper values.
Trusted Counsel and Lived Wisdom
High-stakes decisions shouldn’t be made alone. Leaders need perspective from people who know them well and who’ve faced similar moments. Whether it’s a mentor, board member, spouse, or peer, others can often see where a decision is leading—especially when our own vision is clouded by pressure or emotion.
Tradition and precedent also matter. Sometimes there’s wisdom in doing what has worked across generations: building with integrity, prioritizing people over scale, aligning work with family and values. If you don’t yet understand why these things matter, listen to those who do.
Anchoring in Values
Transformative decisions require a stable core. Values—whether moral, religious, or philosophical—give clarity when metrics don’t. They help you distinguish between short-term gain and long-term good. A strong value foundation allows leaders to adapt without losing direction.
As one executive put it, “You can pivot your strategy without pivoting your soul.” That’s the essence of integrity in leadership.
Courage, Uncertainty, and Faith
No transformative decision is made without risk. But courage isn't the absence of uncertainty—it's the willingness to move forward despite it.
For many leaders, what sustains that courage is faith. Faith in a bigger purpose, in providence, or in the belief that the work they’re doing matters beyond the balance sheet. It’s what allows leaders to grow through change—and help others grow with them.
Executive Takeaways
Recognize transformative decisions: These aren't just strategic—they reshape your leadership and your company’s identity.
Don’t rely solely on data: Use strategy tools, but know their limits. Transformation requires vision, not just analysis.
Take time to reflect: Ask who you want to become, not just what you want to achieve.
Seek out wise counsel: Trusted relationships can help you see clearly when the stakes are highest.
Lead with values: When outcomes are uncertain, values offer clarity and consistency.
Accept the unknown: The most meaningful decisions can’t be guaranteed—but they can be guided by purpose and courage.
“The measure of a man is what he does with power.” Plato