How Strong Leaders Make Decisions When There’s No Obvious “Right” Answer
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Posted by Jon Vaughn
- Last updated 1/07/26
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At some point in nearly every leadership journey, you face a decision that can’t be solved with a simple pros-and-cons list.
Both options are good.
The risks are real.
The outcomes are uncertain.
Recently, I was asked for counsel by a mid-career leader wrestling with a potential role change. The opportunity offered broader responsibility and long-term leadership growth—but also came with discomfort, a steep learning curve, and the fear of letting people down.
What struck me wasn’t the specifics of the role.
It was how familiar the dilemma felt.
Many capable leaders quietly wrestle with questions like:
- Should I stay where I’m effective—or stretch into something new?
- Am I being prudent… or just playing it safe?
- How do I honor the people I lead while still stewarding my own growth?
When I find myself in these moments, I often return to a book that has deeply shaped how I think about leadership, work, and life: How Will You Measure Your Life? by Clayton Christensen.
I lean on this book because it’s not abstract or theoretical. It offers practical decision-making frameworks that apply equally to business and life—grounded in a worldview that treats leadership as stewardship, not just advancement.
One question from that book, in particular, is incredibly helpful when the right path forward isn’t obvious.
The Question That Changes the Decision
Instead of asking, “Should I take this role?” Christensen suggests asking: What would need to be true for this to be a successful move?
It’s a simple question—but a powerful one. Why? Because fear thrives in ambiguity. Clarity weakens it. This question doesn’t eliminate risk. It names the assumptions hidden beneath the anxiety.
Turning Fear Into Testable Assumptions
When leaders ask “What would need to be true?”, they often surface assumptions like:
- Success in the role would need to be clearly defined in the first 6–12 months
- There would need to be support and air cover during the learning curve
- The role would need to emphasize leadership and outcomes, not just historical expertise
- The added responsibility would need to be sustainable, not all-consuming
Suddenly, the decision is no longer “safe” or “risky.” It becomes conditional. And that opens the door to a much better follow-up question.
Which Assumptions Can Be Tested Before You Decide?
Christensen believed that wise leaders don’t avoid risk — they design around it.
Once assumptions are visible, the next step is asking: Which of these need to be validated before I say yes?
That might mean:
- clarifying expectations with a manager
- asking how success will actually be measured
- understanding what support exists during the transition
- defining what the role is not responsible for
This transforms a career decision from a leap of faith into a discernment process.
A Word About People, Loyalty, and Growth
Often, the hardest part of leadership decisions isn’t the role itself — it’s the people.
Strong leaders care deeply. They don’t want to disappoint their teams or disrupt what’s working.
But there’s a hard truth worth sitting with: Leadership growth sometimes requires disappointing expectations in the short term in order to steward your gifts more fully in the long term.
Caring for people doesn’t always mean staying. Sometimes it means trusting that others can grow, step up, and be supported.
Why This Question Scales Beyond Career Decisions
While this framework surfaced in the context of a career conversation, it’s worth noting:
this is how senior leaders make business decisions, too.
The same “What would need to be true?” question applies when leaders are considering:
- launching a new product
- entering a new market
- investing in a new platform or capability
- restructuring a team or organization
Experienced leaders don’t ask, “Will this work?” Instead, they ask:
- What assumptions are we making?
- Which ones are riskiest?
- Which can we validate before committing resources?
That’s not just good strategy — it’s good leadership judgment. Leaders who learn to think this way about their own decisions are often surprised by how naturally it transfers to enterprise-level choices.
Two Good Options Is Still a Decision
In the situation that prompted this reflection, there was no “bad” choice. There were two good ones. When that’s the case, the real question becomes: Who am I being shaped into by this decision?
That’s not a career question. That’s a leadership one.
Why This Matters for Emerging Leaders
Mid-career leaders often feel this tension most acutely:
- They’re trusted
- They’re capable
- They’re being invited into broader influence
But few have been taught how to decide when the stakes are real and the answers aren’t obvious.
That’s one reason we built the Emerging Leaders Program — not to tell people what decisions to make, but to help them develop the judgment, frameworks, and confidence to make good ones consistently.
Leadership isn’t just about execution. It’s about discernment. And the earlier leaders learn how to decide, the better those decisions tend to be — for their organizations, their people, and their lives.
If you’re facing a decision where the next step isn’t obvious, you’re not alone. The goal isn’t certainty — it’s clarity about what truly matters.
Learn More About Quest’s Emerging Leaders Program
If this way of thinking resonates with you, you may be closer to senior leadership readiness than you realize. Strong leaders aren’t defined by having all the answers — they’re defined by how they think when the answers aren’t clear. These are exactly the kinds of moments the Emerging Leaders Program is designed to support.
Over the next few months, we’re hosting several upcoming information sessions where you can learn more about the program, hear how other leaders have navigated similar crossroads, and decide whether this experience is the right fit for you. These sessions are low-commitment, highly informative, and a great way to explore how building better judgment and decision-making frameworks can shape your leadership journey. We invite you to register for an upcoming info session and take the next step with intention and clarity.
