28 - The Courage to Rethink: Why Strong Leaders Change Their Minds
- Jennifer Diamond
- Apr 30
- 5 min read
Updated: May 4
How Adaptability Strengthens Leadership, Not Weakens It
Introduction: The Fear of Changing Course
Leaders are often praised for being decisive, confident, and unwavering in their vision.
Employees look for leaders who provide clarity and direction.
Organizations want executives who can stand by tough decisions.
Stakeholders expect leaders to stay committed to a strategy once it’s set.
But what happens when new information proves that an original decision was flawed?
What if market conditions shift, and the strategy that once made sense no longer serves the organization?
What if a team raises concerns, and their insights reveal a better way forward?
What if the right leadership move isn’t pushing forward harder—but having the courage to change course?
Strong leaders aren’t the ones who never change their minds.
They’re the ones who know when to adjust, when to pivot, and when to rethink—without losing credibility or confidence.
Step 1: Rethinking Isn’t Weakness—It’s Leadership Strength
There’s a common misconception that changing direction is a sign of uncertainty or failure.
In reality, the strongest leaders are those who:
Recognize when new information calls for a shift.
Adapt to changing circumstances rather than staying locked into past decisions.
Prioritize the best path forward, even if it means adjusting their previous stance.
An executive leading a global expansion strategy was deeply invested in the original plan. The market research was strong. The team had spent months preparing. But early indicators suggested that customer demand wasn’t aligning with expectations.
At first, leadership resisted change, afraid of appearing indecisive. But over time, they realized:
Staying the course wasn’t a sign of conviction—it was a refusal to acknowledge reality.
Pivoting wasn’t abandoning the strategy—it was ensuring that the company didn’t waste resources on a flawed direction.
By openly reassessing the approach, leadership didn’t lose credibility—they strengthened trust by demonstrating practical decision-making over ego-driven attachment.
How to Shift Course Without Losing Leadership Credibility
Frame the change as learning, not failure. Leaders don’t backtrack—they evolve their strategy based on new insights.
Be transparent about the reasoning. People respect leaders who say, “Based on what we’ve learned, this is the better way forward.”
Keep conviction in the mission, even if tactics change. A shift in approach doesn’t mean a lack of vision—it means a commitment to getting it right.
Leadership Reflection:
Do I view adjusting direction as a weakness, or as a sign of smart leadership?
Am I making decisions based on what is best now, or what was best when the original choice was made?
Have I built a culture where teams feel safe to challenge past assumptions?
Step 2: Recognizing When It’s Time to Change Course
Leaders sometimes hold onto past decisions longer than they should.
Sometimes it’s because of sunk costs—so much time, money, and effort has already been invested.
Sometimes it’s because of pride—changing direction feels like admitting a mistake.
Sometimes it’s because of uncertainty—rethinking a strategy means stepping into the unknown again.
But strong leaders know that sticking with a plan simply because it was the original plan is not a good reason to continue.
A leadership team overseeing a major technology rollout found that implementation was slower than expected. Teams were struggling with the transition, and productivity was dropping.
At first, leadership resisted feedback. The plan was already in motion. The budget was set. The timeline was announced. Changing course felt impossible.
But when leaders finally stepped back, they saw the real issue:
The technology wasn’t flawed—the rollout strategy was.
Teams weren’t resisting change—they needed more training and phased implementation.
Doubling down on the original approach wasn’t commitment—it was stubbornness.
Once they adjusted the execution strategy, adoption increased, and the change was ultimately successful—not because they pushed forward harder, but because they recognized when to recalibrate.
Signs It’s Time to Rethink a Leadership Decision
The environment has changed, but the strategy hasn’t. Markets, teams, and industries evolve—what worked before may not work now.
The data doesn’t support the original assumptions. If execution isn’t producing expected results, it’s time to ask why.
Resistance isn’t just discomfort—it’s a signal of deeper issues. Some friction is normal, but if pushback is consistent, something might need to shift.
Leadership Reflection:
Am I holding onto a past decision because it’s truly right, or because I feel committed to it?
Have I encouraged my team to speak up when they see a need to pivot?
Do I regularly assess strategies to ensure they’re still the best path forward?
Step 3: Creating a Culture Where Rethinking Is Normalized, Not Penalized
If leaders want to retain the ability to adjust, they must create a culture where rethinking is seen as smart leadership—not a failure.
When leadership treats adaptability as a strength, teams feel safe challenging outdated thinking.
When organizations embrace learning over defensiveness, they become more innovative and resilient.
When leaders show that changing direction is about improvement, not weakness, they build credibility, not lose it.
A leadership team once faced a tough choice—a product launch was underperforming, and customers weren’t responding as expected. The team had two options:
Defend the original strategy and hope adjustments would improve adoption.
Step back, reassess the approach, and make a bold change.
Rather than doubling down, the team invited key stakeholders into a recalibration process.
They assessed what was working and what wasn’t.
They kept the elements that were effective but reworked the aspects that weren’t resonating.
They communicated the shift as an investment in getting it right, not an admission of failure.
Because of this approach, teams remained engaged, trust in leadership remained high, and the adjusted launch outperformed the original projections.
How to Build a Culture That Supports Smart Rethinking
Encourage curiosity over defensiveness. Leaders should ask, “What new insights might change how we approach this?”
Reward good decision-making, not just initial decisions. If a shift improves outcomes, it’s a success—not a failure.
Model the behavior. If senior leaders never adjust their thinking, teams won’t feel empowered to challenge their own assumptions.
Leadership Reflection:
Have I built an environment where rethinking is seen as intelligence, not indecision?
Do my teams feel safe to challenge outdated assumptions?
Am I personally willing to adjust course when better information is available?
Final Thought: The Strongest Leaders Know When to Hold Firm and When to Adjust
Great leadership isn’t about never changing your mind. It’s about knowing when to stay the course and when to pivot toward a better path.
Before your next major decision, ask yourself:
Am I holding onto this course of action because it’s right—or because it was the original choice?
Have I built the flexibility to adjust when new insights emerge?
Do I model rethinking as part of smart leadership?
Because the best leaders aren’t the ones who never change their minds. They’re the ones who know when rethinking is the smartest move they can make.
This post is part of Maypop Grove’s Leadership Evolution Series—a collection of in-depth reflections on leadership, influence, and strategy. Designed for leaders navigating complexity, this series explores how to drive change, build resilient teams, and lead with confidence.
©2025 Maypop Grove, LLC. All rights reserved.
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