Robert Land Academy: The Retention Problem

Robert Land Academy:
The Retention Problem

Prepared for Michael Maislin · February 2026 · Confidential

37% retention — 2,171 alumni — 26 yearbooks

2,171 names tracked across 26 yearbooks, 1978–2011.

On average, roughly two out of every three students did not reappear in the following year’s roster.

Independent schools today ~90%

Robert Land Academy ~37%

Not a like-for-like benchmark — different eras, different measurement. The magnitude of the gap is the point.

For you

In your experience running businesses, is there a model where 63% annual turnover is normal — or does a number like this usually signal something about the product itself?

Did it ever change?

Each dot below is one year-to-year transition. The dashed line is the 30-year average. The grey bands are gaps in our yearbook collection.

Year-to-year departure rate — 21 consecutive yearbook pairs, 1981–2011

The rate doesn’t appear to respond to leadership changes, enrollment size, or decade. Our yearbooks cover several clear RLA staff transitions. We suspect this holds even after Scott Bowman’s departure. You may be able to confirm.

Four transitions. Four decades. Zooming in.

Entry Year Year 2 Retention

82–83

Your era

42%

92–93

A decade later

35%

04–05

Your board

32%

09–10

Last data

33%

Where did everyone go?

61%

39%

One-year — 1,320 Multi-year — 851

Here’s a working thesis:

Two-thirds of students leave after one year. They don’t form peer bonds that create a real alumni network. A kid who arrives in September and leaves by June has no reunion group. He is part of a group that left as soon as they could.

The churn rate we are seeing describes an enrollment pattern and indicates a customer retention problem. It may be the case that the Facebook groups, which act as ad hoc alumni hubs, reflect this, too.

For you

You stayed multiple years — you’re in the 39%. When you think about the guys who were there for a year and then disappeared, do you stay in touch with many of them?

Three things I need your help with

1The gaps. Our data has seven missing yearbook years. Your 1984–85 and 1985–86 yearbooks are two of them. If you can snap a few phone photos of the roster pages, I can fill in your cohort and send back the corrected numbers.
2After 2011. The yearbooks stop in 2011 but the school ran until 2024. You were on the board for most of that. Did the pattern hold? Did it change? Only you know.
3Your read. Does this match what you saw from the inside — or am I missing something about the model?