I remember exactly where I was when my certainty blinded me.
I was in a corner conference room that was brimming with the morning light that shone through its large, floor-to-ceiling windows. The tables and chairs were placed in a large u-shape and were scattered with printed agendas and half-empty coffee cups. I walked to the front of the room and faced over twenty five central office administrators and staff as their new executive director and began briefing them on what I described confidently as a straightforward fix to the current curriculum issues. The problem, as I saw it, was clear: the school district invested too many resources into the internally developed curriculum to simply discard it for an off-the-shelf product. The solution, I insisted, was equally clear: implement a tightly structured review process based on research-based standards in order to identify and address deficiencies. I had data, I had slides, and I had examples from other school districts, including the one I had just left. Most importantly, I had conviction. I remember telling myself, This is what leadership looks like. People need clarity, direction, and someone who knows what’s going on.
As an executive director of curriculum and instruction—new to the district, but not new to leadership—I believed this was the moment to show I could take control of a messy situation. In many respects, the district was unstable. The superintendent had just departed under controversial circumstances two weeks before I arrived. I was the third executive director of curriculum and instruction in four years. The curriculum had been revised repeatedly over the same period of time, and test scores refused to cooperate with anyone’s plan of improvement. To make matters worse, I joined mid-year as an outsider, and I knew it.
Friends and colleagues had warned me before I took the role. “Are you sure this is the right move?” they asked. Some tried to tell me about the district’s internal politics, long-standing racial tensions, and the weariness of teachers and administrators who had seen too many reforms come and go. I listened politely, and, then, I ignored much of it.
Part of me framed their concern as caution. Another part, if I’m honest, read it as doubt on their part. The doubt, I believed, was something I already had outgrown. I had earned a doctorate, successfully led district-wide initiatives before, including curriculum development, and had proved myself in three other school systems. What I didn’t yet understand was how thin the line is between confidence and blindness.
The plan passed. The initiative launched, and, then, quietly at first, it began to unravel. Increasingly the politics clouded our focus, which turned some my team members against me and led others to outright undermine or sabotage my decisions. Revisions took longer than expected, and I quickly became the perfect scapegoat for everything that wasn’t right. What I had framed as a clear solution was being framed as complicated, unclear, and unnecessary. What I had seen as structure felt, to them, like another bureaucratic obstacle.
No one stood up in a meeting and supported me when the pressure and accusations started flowing. Essentially, it was the beginning of the end for me, but, for a while, I was in denial, thinking things were not as bad as they seemed. That gap, between how sure I felt internally and what was happening externally, was the beginning of a reckoning.
What I Now Recognize as Overconfidence
Looking back, the pattern is embarrassingly clear. I projected more certainty than my evidence warranted. I underestimated the complexity of the system, leadership instability and character, internal politics, institutional history, and culture. And, I confused being articulate and knowledgeable with being right. In education leadership, those errors are easy to make and hard to detect. The feedback loops are long, and the outcomes are ambiguous.
By the time you know whether a decision helped or harmed, the context will have changed already. This is what psychologists call a noisy environment: one where cause and effect are delayed, obscured, or contradicted?. The field of education is full of noisy environments which make calibration, the relationship between how confident you say you are and how often you are actually correct, difficult. For example, if I say I’m 80% confident, I should be right about eight times out of ten. In practice, most of us aren’t. Classic studies show that when people report being 90% certain, they’re often right closer to 70–75% of the time. Even worse, when people claim near-absolute certainty, accuracy can drop to little better than chance. I didn’t know those statistics at the time, but I lived them. What made me especially vulnerable was the social reward structure around confidence. As an administrator and leader, I was subtly, and sometimes explicitly, rewarded for sounding sure. Clear answers were praised, hesitation was read as weakness, and ambiguity made people uncomfortable. So, I learned, without realizing it, to compress uncertainty into confident language.
The Human Costs of Being Too Sure
The impact of being overconfident don’t just derail projects, they can also negatively affect the team dynamics and culture. For my team, my certainty translated into rigidity. Procedures designed to “help” became blunt instruments. Struggle was interpreted too quickly as lack of competence and effort. Team members’ voices were narrowed to fit the initiative, not challenge it. I see now how confidence can silence nuance, not by shouting it down, but by leaving no room for it to surface. I thought I was inviting collaboration. In reality, I was often inviting agreement. For me, the emotional toll was real. When the initiative faltered, I felt embarrassment first, then defensiveness. The temptation to double down was strong; after all, reversing course would mean admitting that my confidence had outpaced my understanding. That gap, between my identity as a reflective educator and my behavior as a leader, was painful to confront.
How I Calibrate Confidence Now
I don’t try to eliminate confidence, as that would be both unrealistic and irresponsible. Confident leadership is still necessary for decisive action, but calibration is required to ensure sound decisions are made. So, to calibrate, I work to make my uncertainty explicit. I say things like, “I’m about 60–70% confident this will work, and here are the assumptions I’m making.” That language does something important: it models that uncertainty is not incompetence, it’s honesty. I also focus on improving feedback loops. Before launching initiatives, I now ask, What would tell us early that this isn’t working? I commit, in advance, to revisiting decisions if specific indicators don’t improve within a certain time frame. That makes revision a feature, not a failure.
Another key to my calibration is seeking structured dissent from my team or colleagues. Sometimes I pay attention to the skeptic in the room to see what captures their attention. Or, I listen longer to the quiet, outlier perspectives in the room, who I used to brush aside because they complicated my narrative. The biggest feature of my calibration is reflecting on my optimism. This is an informal but intentional action to notice how often I am overly optimistic about timelines, resistance, or my ability to explain change into existence. The more I reflect, the more patterns emerge if honest with myself. These practices have changed how I lead meetings, design programs, advise team members, and respond to students. I speak more slowly, ask more questions, and revise more publicly.
Returning to the Conference Room
Experiences like this, which I used to try move on from because I saw them as failures, I now embrace fully to improve my leadership style One improvement is that I have shifted from projecting certainty to hosting uncertainty responsibly. If I were back in that conference room today, I would still act with confidence, but differently. I would ask what I didn’t yet understand. I would test assumptions before enforcing structure. I would create space for doubt before insisting on clarity. The posture I now aspire to model for students, my team, colleagues, and myself, is simple but demanding: be confident enough to act, humble enough to revise, and honest enough to say, I don’t know yet.
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A couple of leadership lessons learned over the years include not marrying your decisions as the divorce will be messy and will occur much to late to produce any positive outcome. The second is the more complex the issues and project, the right decision requires everything to be right for a successful outcome. Without the right people, the right team environment, the right resources all being applied at exactly the right time for all the right reasons; the chances of achieving the right outcome decrease. So it’s not as much confidence in our decisions that get us in trouble, it our confidence that we can overcome the known obstacles, even when history suggests otherwise