Help! Who Should I Interview? Screening School Leadership Candidates in the Age of AI

Last updated: October 2026 · By Davina Spillmann, Managing Director – Leadership Search, IndySchool Consultancy

When candidates can polish every résumé and cover letter with AI, schools need to screen for clues that AI cannot fake: specific, relevant accomplishments, a genuine voice, a clear understanding of this particular school, and a career path that makes sense. For candidates, the lesson is the reverse: use AI and keywords to get through applicant tracking systems, but make sure your own voice and specific experience come through.

I see LinkedIn comments every day about hiring for attitude and capacity for growth, and I agree. But I also hear from people who applied for roles they were perfect for, only to receive a canned rejection before the interview round. After years of interviewing candidates as a senior administrator, I felt confident reading between the lines of a résumé. With AI-polished applications and keyword-optimized materials, that has changed dramatically.

What should hiring committees look for in an application?

• An authentic voice. I still believe a cover letter is essential. Like a strong college essay, what matters most is an authentic voice, and this is where AI-written content still falls short. Generic polish is a signal, not a strength.

• A strong summary. It is often the first thing I read. A good one shows the candidate understands the role and the school, and communicates clearly and briefly.

• Specific, relevant skills. Budget forecasting, admissions experience, marketing expertise or specific tools, not a list of everything the candidate has ever done.

• Evidence they researched your school. Applications addressed to a person, or that reference the school directly, show real effort.

• A career path that makes sense. I look for clues like an archaeologist. Frequent moves? Ask why. Experience in other industries? That can mean valuable range, so ask how it applies now.

How can leadership candidates stand out?

1. Play the system strategically. Use the keywords in the job description so applicant tracking systems find you, and use AI for clarity if it helps, but make sure your voice comes through.

2. Use the summary and skills sections wisely. Show you understand the role and the school's culture, and highlight strengths beyond the basics.

3. Tailor every application. Many candidates share the same qualifications. Show why you are right for this school, this role and this culture.

4. Personalize your approach. Address your letter to the Head of School, the HR director or the relevant leader. Few things put me off more than "Dear Hiring Manager."

5. Write a thoughtful cover letter. Specific details stand out: a CFO candidate who is also a CPA and holds a real estate license, for example, may be exactly what a school planning to expand needs.

Frequently Asked Questions

Should schools still require cover letters for leadership roles?

Yes. A cover letter remains one of the best ways to hear a candidate's authentic voice and see whether they understand the school, especially when résumés are increasingly AI-polished.

Is it acceptable for candidates to use AI on their applications?

Using AI for clarity and keyword optimization is reasonable. The problem is generic, AI-written content that hides who the candidate really is.

How ISC Helps

This is not rocket science, but in a competitive market it takes time and judgment to find the candidate who will truly make a difference. IndySchool Consultancy's team reviews every candidate in depth, so schools see a prepared slate rather than a stack of polished applications. If you would like help with your next search, we are here for you. Candidates can also explore current opportunities.

Davina Spillmann is Managing Director – Leadership Search at IndySchool Consultancy and a former senior independent school administrator.