The most dangerous phase of leadership is often not early struggle, but sustained success when assumptions become leadership blind spots.
Leadership blind spots arise because success is reassuring. It tells leaders that their judgment is sound, their instincts are reliable, and their approach works.
But at senior levels, past success can quietly become a liability.
Many of the leaders I work with are accomplished, capable, and respected. They have succeeded beyond what they once imagined. Yet they find themselves surprised when results start to stall, resistance increases, or decisions don’t land the way they expect.
Leadership blind spots are a surprisingly easy trap to fall into. Once something works, it’s tempting to assume it will keep working—even as conditions change. Later, when markets shift but your thinking doesn’t, the same decision returns a different—and far worse—result.
That’s how early success turns into leadership blind spots—and how learning quietly slows just as complexity increases.
Key Takeaways → Leadership Blind Spots
- Past success can reduce testing and curiosity
- Early wins can create leadership blind spots
- Complexity exposes limits in senior leadership judgment
- Sustained leadership effectiveness depends on continual learning
When Success Becomes a Liability
Early success builds confidence, credibility, and momentum. It also creates expectations — from others and from leaders themselves.
When leaders have been right many times before, it becomes easier to trust instinct and harder to pause. Decisions are made faster. Assumptions go untested. Input that complicates the picture can feel unnecessary.
None of this is reckless. It’s efficient. And in stable environments, it often works.
The problem is that leadership environments rarely stay stable. Markets change. Competition edges in. Disruption is inevitable. Doing what made you successful at this point stops working and actually often harms results.
The Misleading Comfort of Past Success in Leadership
Over time, organizations grow, markets shift, and teams become more complex. At that point, leadership decision making requires more testing, not less.
Yet this is precisely when leaders are most tempted to rely on what has worked before. But at this point assumptions, which may feel like lived experience and knowledge, become a liability.
Jon Katzenbach, in The Discipline of Teams, describes how early success at Enron created a sense of infallibility among its leaders. Having exceeded every expectation, they believed deeply in their own judgment. Decisions were driven by confidence and not reality-tested. The organization stopped serving a market and started trying to make outcomes happen.
Unfortunately, their assumptions stopped matching the current business landscape. They panicked when results failed and tried to cover up the problems. Eventually, the company collapsed under its own weight, taking the savings of thousands of investors and employees down with them.
This pattern shows up in far more ordinary circumstances. It even happened to me. For too long, I based my decisions on experiences from my early success phase, instead of testing how markets had changed. I paid dearly for that. Ultimately, I was lucky to survive. Many companies don’t —because the cost of outdated judgment compounds faster than leaders expect.
Leadership blind spots appear wherever early wins are interpreted as proof that judgment no longer needs to be questioned.
How Early Wins Create Leadership Blind Spots
Leadership blind spots rarely form because leaders stop caring. They form because leaders stop listening carefully.
When success accumulates:
- Assumptions are reused instead of tested
- Dissent feels inefficient and is sometimes punished harshly
- Speed is mistaken for clarity
- Agreement is mistaken for alignment
Over time, these patterns narrow perspective and weaken senior leadership judgment.
This is why the most dangerous phase of leadership is often not early struggle, but sustained success.
Why Reality Testing Stops as Confidence Grows
In technology, the phrase “fail fast, fail early” emerged for a reason. Early failure forces humility, listening, reality testing, and learning.
Early success can do the opposite. It rewards decisiveness, reinforces existing beliefs, and discourages questioning.
As confidence grows, leaders may unconsciously shift from asking What’s working? to asking How do we make this work?
That shift reduces learning just as stakes increase.
What Sustains Senior Leadership Judgment Over Time
Strong senior leadership judgment is not about doubting every decision. It is about maintaining habits that keep judgment accurate.
Leaders who sustain effectiveness over time tend to:
- Treat confidence as provisional, not permanent
- Test assumptions deliberately against real-time data
- Make small trials for proof-of-concept before launching large projects
- Make space for dissent and alternative views
- Listen for weak signals, not just clear agreement
These are not personality traits. They are leadership skills — and they can be learned.
Keep Learning
- Read why leadership stops working as responsibility grows
- Learn how leadership friction creates hidden costs
- Explore how feedback signals leaders miss shape outcomes
If you want to strengthen leadership decision making as complexity grows, the Leadership Skills Audit highlights where judgment, trust, and influence may need to evolve.
FAQs
Why can past success hurt leadership effectiveness?
Because it can reduce curiosity and reality testing just as complexity increases.
Are leadership blind spots inevitable?
They are common, but not inevitable. Awareness and skill-building can reduce them.
How can senior leaders maintain good judgment over time?
By continuing to test assumptions against reality, invite dissent, and treat learning as ongoing.
