Letter to a New Head of School: Anchoring Your First 90 Days

Hi,

Congratulations again on stepping into this role. The first 90 days as Head are a unique window—one where you're setting tone, building trust, and gathering insight. Here's how I suggest you think about this season:


Three Anchoring Principles

  1. Listen Broadly. Decide Deliberately. Act Intentionally.
    Resist the urge to jump into solutions. Instead, treat this period as a listening tour across the school's ecosystem—students, parents, faculty, board, and community partners. Every conversation is data. Patterns will emerge. Let those patterns—not personalities—inform your early moves.
  2. Earn Trust Before You Spend It.
    Trust is your currency. These early months are less about proving you're the smartest person in the room and more about showing you're the most present, curious, and committed one. Be visible. Be human. Follow up.
  3. Signal Stability Before Change.
    Even if the school needs a reboot, lead with care and clarity. People—especially in a school—want to know what’s staying the same before they can embrace what might change. Be clear about what’s enduring before previewing what may evolve.

Five Specific Priorities for Your First 90 Days

Priority

What to Do

Why It Matters

1. Conduct a Listening Tour

Meet with every team, group, and stakeholder—faculty, staff, board, student groups (if age-appropriate), alumni, parent reps. Use a few framing questions: “What’s working well?” “What concerns you?” “What should I never stop doing?”

Builds relational capital and surfaces root issues

2. Clarify the Narrative

Begin drafting a short “What I’m hearing” memo or presentation after 60 days. Share themes (not solutions) in community updates or board meetings.

Shows you’re paying attention and building shared understanding

3. Understand Your Team’s Strengths & Gaps

Observe your direct reports closely. Where are they thriving? Where are they surviving? Begin building an internal bench strength plan.

Leadership isn’t a solo act—you need the right people in the right roles

4. Align with Your Board Chair

Meet regularly, even informally. Clarify mutual expectations, communication norms, and how decisions will flow.

A strong Head–Chair partnership sets the tone for healthy governance

5. Be Present in Student & Parent Life

Attend drop-off, recess, events, and walk the halls. Send handwritten notes home. Make “visible leadership” real.

Builds warmth and approachability while showing what matters to you


A Few Watch-Outs

  • Don’t over-schedule yourself—create white space to reflect and regroup.
  • Don’t assume alignment across your leadership team. It’s likely that people are not yet rowing in the same direction.
  • Don’t promise change timelines until you understand the school’s cycles—culture, calendar, and capacity.

What You Can Say (Even When You’re Not Sure Yet)

  • “I’m still learning.”
  • “Thank you for trusting me with that.”
  • “Here’s what I’m hearing so far.”
  • “I don’t know yet—but I’ll follow up.”

These phrases buy time, show humility, and keep people close.


Closing Thought

You’re not just the new Head—you’re the steward of the school’s next chapter. Your presence, curiosity, and early instincts will shape what’s possible. You don’t have to do everything at once—but you do have to show up with consistency, care, and clarity.

You’ve got this. And I’m here anytime to think through strategy or gut-check what’s next.

Warmly,
Nishant