THE MYTH OF A GOOD FIT

Why school districts should stop hiring people who think alike

“Whatever you do in life, surround yourself with smart people who'll argue with you.” — John Wooden

John Wooden knew a thing or two about assembling successful teams. Ten national championships at UCLA suggest he was pretty good at it. But his advice about surrounding yourself with people willing to argue with you might not go over so well in the executive offices of some school districts.

Particularly those looking for a new superintendent, principal, or cabinet member who will be a good fit.

Ah, the elusive good fit. Two words that have probably ended more promising leadership candidacies than a lack of qualifications ever did. At least that's my suspicion after spending much of my professional life on both sides of the hiring table. I first wrote about this phenomenon in 2021, when school districts were confronting the chaos of pandemic schooling and facing enormous pressure to reinvent themselves. At the time, I argued that hiring for cultural compatibility was a questionable strategy for organizations seeking transformational change.

Five years later, I'm even more convinced.

The problem isn't that organizational culture doesn't matter. It matters enormously. Nor am I suggesting that school boards and superintendents should deliberately hire people who are difficult to work with. Nobody needs another contrarian whose primary contribution to a meeting is making it longer.

The problem is that good fit is often a euphemism for someone like us. And organizations that consistently hire people who think like the people already there shouldn't be surprised when they keep getting more of the same.

The Science Behind the Suspicion

There's empirical evidence supporting what many of us have observed over the years. In a 2024 study published in Work, Employment and Society, sociologist Gerbrand Tholen examined how recruitment consultants assess organizational fit. Drawing upon interviews with 47 recruiters, he found that loosely defined fit criteria can allow subjective preferences and social biases to influence hiring decisions.

The danger, of course, is that familiarity begins to masquerade as merit. It feels comfortable. And comfort is an awfully poor substitute for sound judgment.

Two concepts from organizational psychology help explain why. Psychologist Irving Janis introduced groupthink in his 1972 book, Victims of Groupthink, to describe how the desire for consensus can undermine critical judgment. Around the same time, management thinker Jerry B. Harvey introduced the Abilene Paradox in his 1974 article, The Abilene Paradox: The Management of Agreement, illustrating how groups sometimes agree to decisions that nobody actually wants.

The distinction is fascinating. In groupthink, people suppress doubts to preserve consensus. In the Abilene Paradox, people go along because they mistakenly believe everyone else wants something they themselves oppose.

Different routes. Same unfortunate destination.

Both demonstrate the dangers of organizations that fail to manage agreement. And hiring people principally because they fit the existing culture can make that problem worse.

Most experienced leaders will tell you that managing conflict is an essential part of their job. And it is. But how often do we consider the consequences of poorly managed agreement? Sometimes the most damaging organizational decisions occur not because people disagree, but because nobody is willing to disagree openly.

Worse yet, leaders can spend years trying to change an organization's culture only to wake up one day and realize that the very system they're trying to change is one they've helped create. Imagine a superintendent assembling a cabinet of highly capable administrators who share similar professional backgrounds, leadership philosophies, and assumptions about how schools should operate. Meetings are cordial. Decisions come quickly. Nobody seems particularly troubled by the direction of the organization.

Sounds like a high-functioning team, doesn't it? Maybe. Or perhaps it's a collection of intelligent people agreeing with one another because nobody has the inclination, or feels sufficiently safe, to challenge the prevailing wisdom. How would you know the difference?

The Case for Constructive Disagreement

Here's where contemporary research adds an important dimension to Wooden's advice.

In a 2024 meta-analysis published in Human Resource Management Review, Pierre-Marc Leblanc, Jean-François Harvey, and Vincent Rousseau examined team reflexivity, the process through which teams collectively examine their objectives, strategies, and performance.

Their findings support the value of deliberate team reflection while emphasizing the importance of leadership practices that encourage participation and create psychological safety. In other words, team members must believe they can question assumptions and contribute ideas without suffering interpersonal consequences.

Assembling smart people who disagree isn't enough. They must be willing to express their disagreement, and the person in charge must be willing to hear it. That last part is more difficult than it sounds. I've worked with plenty of highly capable educational leaders who genuinely believed they welcomed dissent. Until someone actually dissented.

Suddenly, the spirited exchange of ideas became a question of loyalty, teamwork, or whether the individual was a good fit. There's that phrase again. And there's the paradox. Leaders say they want independent thinkers but sometimes interpret independent thinking as insubordination.

To be fair, diversity of perspective doesn't automatically produce better decisions. In another 2024 meta-analysis published in Organizational Psychology Review, Allison Traylor and her colleagues examined relationships between demographic diversity and team processes across 38,304 teams.

Their findings complicate the conventional assumption that more diverse teams necessarily engage in more productive exchanges of information. They found no significant overall relationship between demographic diversity and information elaboration, while identifying associations with certain social categorization processes that can complicate teamwork.

Demographic diversity and diversity of thought aren't interchangeable, of course. But the findings reinforce an important principle: Differences among team members don't automatically translate into better collaboration or decision-making.

A team of people who disagree about everything isn't necessarily any better than a team that agrees about everything. The objective isn't conflict for its own sake. It's creating the conditions where assumptions can be questioned, evidence can be challenged, and people can change their minds without losing face. That's a leadership skill. And an organizational responsibility.

Hire for What the Organization Needs to Become

The implications for leadership recruitment are significant. Here's a finding that ought to concern school boards and superintendents. In the 2020 book, Taking Stock of Principal Pipelines, Gates, S.M., at el. found that approximately 40% of responding officials from districts enrolling at least 10,000 students identified school fit among their criteria for selecting principals. Only about 18% identified performance tasks.

Think about that. Fit was mentioned more than twice as frequently as performance-based assessments.

The study doesn't establish that districts selected unqualified candidates or that school fit was their overriding consideration. But it does raise a legitimate question about what we're actually measuring when we select educational leaders. More recently, Melissa Kay Diliberti, Heather L. Schwartz, and Samantha E. DiNicola examined principal preparation and development practices in 156 districts in their 2024 RAND report, How School Districts Prepare and Develop Principals. Their findings revealed substantial differences in the extent to which districts use systematic approaches to selecting, developing, and supporting school leaders.

The issue isn't simply hypothetical. A 2025 systematic review by Robert Hannan, Niamh Lafferty, and Patricia Mannix-McNamara, examining 25 empirical studies of principal promotion, identified persistent gender and racial biases in school leadership selection processes. Taken together, the research suggests that good intentions and professional judgment aren't enough. We need selection practices that make qualifications, demonstrated competencies, and organizational needs more explicit, and subjective impressions less influential.

Consider two finalists for an assistant superintendent position. Both have impressive credentials, substantial experience, and strong references. One shares the superintendent's philosophy, communicates in a familiar style, and offers reassuring answers about continuing the district's work. The other has a different background, questions some longstanding practices, and offers credible evidence of having led successful change elsewhere.

Who gets the job?

Too often, I suspect, the candidate who makes everyone feel more comfortable.

But the question shouldn't be which candidate feels most familiar. It should be which candidate brings the knowledge, judgment, perspective, and demonstrated capacity the organization needs to become better. That doesn't mean disregarding organizational values. An applicant unwilling to embrace the fundamental commitments of public education, professional integrity, and student success isn't a good match, regardless of how impressive the résumé may be. But shared values are not the same as shared opinions. And cultural alignment should never become an excuse for intellectual conformity. School boards and hiring committees can make this distinction more explicit. Instead of asking whether candidates will fit into the existing culture, ask them to describe a time they challenged a widely accepted practice.

What evidence informed their position? How did they engage people who disagreed? What happened? And perhaps most revealing, what did they learn that changed their own thinking?

Then evaluate the answers against clearly defined criteria rather than relying on how comfortable everyone felt during the interview. After all, selecting an educational leader shouldn't resemble choosing someone you'd enjoy having dinner with. Although, admittedly, that would make for a more interesting interview process.

Standing Out Rather Than Fitting In

Jim Collins, author of Good to Great, popularized the importance of getting the right people on the bus. But the right people aren't necessarily those who resemble the passengers already aboard. They're the people capable of helping the organization reach a destination it hasn't yet reached.

Wayne Gretzky, another pretty successful fellow, famously emphasized skating to where the puck is going rather than where it's been. The organizational equivalent seems obvious. Why hire exclusively for the culture you already have when the purpose of leadership is to help create the culture you need?

This requires a certain amount of courage, particularly from superintendents and school boards. Hiring someone who will challenge your thinking means occasionally being uncomfortable. It means accepting that the best idea in the room may not be yours. And it means understanding that loyalty to an organization's mission sometimes requires disagreement with its leaders.

Wooden understood that distinction. He didn't advise surrounding yourself with people who would agree with you. He advised finding smart people willing to argue with you.

Of course, the challenge isn't merely finding those people. It's creating an organization where they can thrive.

What's the moral of this story?

Stop looking for people who fit the organization you already have. Find people who can help you build the organization you want.

And if you're the one looking for your next leadership opportunity, here's my advice:

Go somewhere you can stand out, not just fit in.

Just make sure they're willing to listen.