When a compelling vision becomes a leadership blind spot
Several years into an executive leadership role, I became convinced that our organization needed to broaden the way we served our community.
Our existing programs were strong, our teams were effective, and our staff had built meaningful relationships throughout the community. But I saw an opportunity to add something different. Rather than develop the expertise internally, I looked outside the organization and formed a partnership with the founder and executive director of a small nonprofit organization whose work seemed to complement our mission.
On paper, it looked like a great fit.
It wasn’t.
We brought the leader into our organization, provided resources and staffing support, and created space for the new initiative to grow. Some elements of the work were successful, but over time a significant disconnect emerged between what I believed the partnership would accomplish and what the other leader actually wanted to build.
I envisioned a highly accessible community program that would connect with new participants, collaborate with existing teams, develop partnerships, and contribute to the fundraising necessary to sustain the work.
The other leader had a very different vision.
For three years, we worked around that difference rather than confronting it.
Eventually, the initiative ended with a financial deficit, the loss of employees, damaged relationships, and the closure of the program.
Looking back, the most important lesson is not that the initiative failed.
It is understanding how my own judgment contributed to the failure.
When past success becomes a poor predictor
Finkelstein, Whitehead, and Campbell (2008) describe how leaders can be influenced by misleading experiences, drawing connections between a new situation and previous experiences that appear similar but contain important differences.
That is exactly what I did.
I had strong leaders overseeing other areas of our organization. They were highly engaged in the community, collaborated well with external partners, supported organizational priorities, and willingly participated in activities that helped sustain their programs.
Without consciously realizing it, I assumed the new leader would operate in much the same way.
I connected two situations that looked similar on the surface but were fundamentally different.
I saw what could be based on what had worked before.
I failed to spend enough time understanding what actually was.
The other leader did not share the same assumptions about community engagement, organizational integration, or program development that I did. Those differences were visible relatively early, but I continued interpreting the situation through the lens of my previous experience.
Past success had become a filter through which I evaluated the present.
The assumptions we forget are assumptions
I also made what Finkelstein et al. (2008) describe as misleading prejudgments.
Both organizations were nonprofit.
We were both committed to serving people.
We both needed financial sustainability.
So, I assumed we would share similar attitudes toward fundraising, partnership development, and organizational responsibility.
We didn’t.
I believed that someone leading a nonprofit initiative would naturally see fundraising as part of sustaining the mission. The other leader viewed their primary responsibility much more narrowly and resisted participating in fundraising activities or donor conversations.
That difference became increasingly problematic.
What makes this part of the story particularly uncomfortable is that someone on my team saw the problem and raised it with me.
I dismissed the concern.
Not explicitly, perhaps, but effectively.
I had already developed an explanation that protected my original decision:
They just need more time.
That sentence allowed me to postpone confronting evidence that did not fit the story I wanted to believe.
When vision turns into attachment
There was another factor at work.
I was emotionally attached to the idea.
Finkelstein et al. (2008) identify inappropriate attachments as another condition that can distort executive judgment. In my case, my desire to see the initiative succeed became stronger than my willingness to critically examine whether the partnership itself was working.
I loved the vision.
And because I loved the vision, I became increasingly willing to explain away the warning signs.
I also failed to sufficiently involve other members of the organization in evaluating what was happening. Davenport (2013) emphasizes the importance of bringing appropriate knowledge and perspectives into decision processes. Instead, I relied too heavily on my own judgment.
I believed I understood what the organization needed.
I believed I had found the right person.
I believed the challenges could be worked through.
That confidence gradually became a blind spot.
What I thought was an integrated organizational initiative was, in reality, operating much more like an independent organization being provided with our space, resources, and salary support.
The evidence was there.
I simply wasn’t interpreting it clearly.
Good leaders can make bad decisions
Perhaps the most useful lesson from this experience is that poor decisions are not always caused by carelessness, incompetence, or lack of commitment.
Sometimes they emerge from exactly the opposite.
We care deeply.
We believe strongly.
We recognize an exciting opportunity.
We draw on experiences that have served us well before.
And then, almost imperceptibly, our confidence in the idea begins to influence how we interpret the evidence.
My decision-making process became distorted by three forces identified by Finkelstein et al. (2008):
- Misleading experiences: I assumed success in one leadership context would predict success in another.
- Misleading prejudgments: I assumed shared organizational characteristics meant shared beliefs and behaviours.
- Inappropriate attachment: I became invested enough in the vision that I resisted evidence suggesting the model was not working.
The result was not simply a program failure. It created financial consequences, organizational tension, staffing losses, and considerable leadership distraction.
The question I ask differently now
Today, when an opportunity feels like the perfect fit, I become a little more curious.
That feeling may be telling me something important.
But it may also be telling me that I have already started writing the story before all the evidence is in.
Executive leadership requires vision. Organizations rarely move forward without leaders who can imagine possibilities that do not yet exist.
But vision needs a companion.
Reflective curiosity.
Before committing to an exciting opportunity, we need to be willing to ask:
What am I assuming?
Which previous experience am I using to interpret this situation?
What is genuinely similar, and what is fundamentally different?
Whose perspective am I not hearing?
What evidence would cause me to reconsider my current judgment?
And perhaps the hardest question of all:
Have I fallen in love with the opportunity, or have I actually tested it?
Sometimes the most dangerous leadership blind spots are not hiding in the things we dislike.
They are hiding in the ideas we desperately want to succeed.
References:
Davenport, T. H. (2013). Make better decisions. In HBR’s 10 Must Reads: On Making Smart Decisions (pp. 133–143). Harvard Business School Publishing.
Finkelstein, S., Whitehead, J., & Campbell, A. (2008). Think Again: Why Good Leaders Make Bad Decisions and How to Keep It From Happening to You. Harvard Business School Publishing.