What Leadership Searches Ask of People

Reflections on Candidates, Boards, and the Quiet Power of Getting the Process Right

Leadership searches are often described in procedural terms. Timelines. Shortlists. Interviews. Decisions. What is spoken about far less is the human experience that sits beneath all of this.  

For candidates, leadership searches demand extraordinary commitment. They prepare carefully. They reflect deeply. They open themselves up to scrutiny. They consider what it would mean to uproot their lives, move families, change communities and step into highly visible roles. The emotional and cognitive load is significant.  

And then there is the waiting.  

Waiting between interviews. Waiting while boards meet. Waiting to know whether a future is unfolding or quietly closing.  

This intensity is rarely visible, yet it shapes the entire experience. Leadership searches are not abstract exercises. They affect real people, real families and real lives. How these processes are held matters.  

Boards carry a different but equally real weight. They know this is the most important decision they will make, often with implications that extend well beyond their own tenure. Having served on boards myself, I recognize how heavy that responsibility can feel. The seriousness, the care and the pressure to get it right are very real, especially when decisions must be made collectively and under scrutiny.  

Many trustees are not educators. They bring deep professional expertise, strong judgment and governance experience, but they are often assessing a form of leadership they have not been trained to evaluate. They rely on frameworks they know, comparisons that feel safe and signals that offer reassurance.  

There is also pride. Pride in the school they serve. Pride in its culture, its reputation and its achievements. That pride is deserved. A strong reputation often reflects quality, stability and ambition. It becomes a natural reference point when evaluating candidates. The challenge arises when reputation becomes a stand in for understanding leadership impact, rather than a starting point for deeper exploration.  

Within this landscape, candidates can also be unintentionally compared with one another rather than anchored to the vacancy itself. Strengths become relative. Differences can appear as gaps. The core question can quietly shift from what the school needs next to who feels strongest in the room. This is human. It reflects responsibility, not a lack of care.  

Over many years of being deeply involved in leadership searches, I have learned how powerful these moments are. Not just in shaping outcomes, but in revealing patterns. I have seen how assumptions influence judgment, how reputation can overshadow impact and how pressure can pull attention away from purpose. I have also seen how clarity, alignment and curiosity consistently strengthen decisions.  

Leadership transitions act as mirrors. They reflect a school’s clarity, its alignment, its assumptions and its readiness for change. They show how decisions are made when pressure is present and how values surface in practice. When approached thoughtfully, they offer schools a chance not only to appoint a leader, but to understand themselves more deeply.  

At their best, leadership searches are not exercises in judgment alone. They are acts of exploration. Exploration of what leadership looks like now. Of what a school truly needs next. Of how values translate into practice. And of how a community wants to grow. When boards, candidates and advisers approach the process with curiosity rather than certainty, the experience becomes richer for everyone involved.  

As I have reflected, a few questions continue to surface. Not as critiques, but as invitations.  

• Are we assessing candidates by impact rather than reputation?  

• Are we anchored in the needs of the role rather than in comparisons?  

• Are we aware of the intensity candidates are carrying?  

• Are we clear on what our school truly needs next?  

• Are we allowing space for thoughtful decision making rather than urgency?  

This is not a call for perfection, but for presence and care in moments that carry real consequence.  

Leadership searches are not only about selecting someone. They are moments that ask a great deal of people on all sides. When these processes are approached with clarity, empathy and intention, they do more than lead to strong appointments. They shape the tone of leadership long after the search has ended.  

Leadership matters. And how we arrive there matters just as much.  

Connect with Pauline O’Brien on LinkedIn. Learn more about ISS Leadership Search services at ISS.edu