Leading a Montessori School in 2026-27: The Leadership Playbook for Families and Teachers

Leading a Montessori school today means navigating shrinking enrollment, teacher shortages, rising parent expectations and a growing load of administration. In this session, Tim Seldin, President of the Montessori Foundation, and Sandi Zorinich, Head of School at Rockridge Montessori School in Oakland, California, joined Anna Leichter of illumine to talk about how school leaders can attract and keep the right families and teachers, support a stretched team and protect their own time. Anna also showed how illumine simplifies observations and parent communication. This is the written recap. The full recording is at the top of this page.

Key takeaways

The reality Montessori leaders face

Tim said many Montessori schools are reporting that they are not full and that budgets are more stretched than ever. They face competition from free public programs, and from private schools that used to start at kindergarten and now take three- and four-year-olds as well as full-day five-year-olds. Recruiting great Montessori teachers is getting harder, and every departure hurts.

Sandi described how different two campuses can be. Rockridge's two sites are about ten minutes apart. The original site is full of applicants and attracts teachers easily. The second site, open for seven years, has seen enrollment fall since transitional kindergarten (TK) expanded over the last two years, and it is currently about half full. Finding qualified Montessori teachers for it has also been hard, so every resignation raises the question of who can replace them.

A poll asked what takes up most of leaders' weeks. Staffing and hiring came first, with families and enrollment, parent communication, and paperwork and compliance close behind.

For Sandi, enrollment is always top of mind. Because TK makes her January re-enrollment pool hard to predict, she is already forecasting for 2027-28: how many openings she will have, how to market, when to run tours and what her messaging should be now, around 11 months ahead. She is also hosting events to build community before families even enter the enrollment cycle.

Finding families who stay

We've been dating all the wrong people.

Tim said Montessori leaders tend to act like missionaries, wanting every family to become a Montessori family. Leaders reply that they have bills to pay, and he agreed. The answer is both: fill every place, and fill it with the right families. If a family leaves, he said, they take two more with them.

Constant refilling hurts more than the budget. Montessori is built on the years a child stays: the family's buy-in, the relationships between families and children, and the feeling that "this is our school". For three- to six-year-olds, the third year, the kindergarten year, is when everything comes together. Older children become the magnet younger ones want to follow, and they shape the whole class. When families keep leaving, teachers feel they must be doing something wrong, classes are harder to normalize and everything becomes a problem. Parents are under more stress since the pandemic, and so are children, so schools need the most stable, close-knit communities they can build.

The family's journey, not just the child's

Sandi said many parents are raising a child for the first time, with information coming at them from every direction, including social media. That puts schools in a strong position to lead. She sees her role as supporting the development of the child, the parents and the whole family: meeting them where they are, giving them tools to parent with less stress and helping them understand Montessori, so school and home work as partners.

When families do not see the value

Tim said parents often do not know whether Montessori is a franchise or a religion, and assume every Montessori school is the same. Most do not want to be educated, but schools need them to understand. The same handful of parents attend parent education nights. Families who are not bought in eventually leave, usually saying nice things on the way out, and a class erodes like a sandcastle in the tide.

Sandi shared what her school is changing. Parents see photos of their children with the materials but ask why it matters whether a child is using the red rods or the number rods. Her teachers now add a quick anecdotal note that explains the purpose of the activity, so a photo of blocks becomes a story about what the child is learning. Parents want to know the benefits, she said, and why they are paying for a Montessori education. If they do not understand it, they are harder to keep.

Anna added that linking each update back to the curriculum and lesson helps parents see the classroom through their child's eyes, rather than receiving a sheet of paper at the end of the day. Tim pointed to the Montessori Foundation's Montessori Family Alliance, which offers a weekly e-newsletter for parents, Tomorrow's Child magazine and resources that answer the questions parents feel too embarrassed to ask a teacher.

The real cost of the wrong teacher

One attendee shared that owners in their area are considering stepping away from the Montessori model because staffing is so hard. Tim's view was that Montessori has grown on its popularity, and there are now more Montessori classrooms than there are teachers to fill them. But a school that steps away becomes a generic preschool and loses its unique selling proposition. It then has to compete on art, STEM or other add-ons to keep enrollment up.

Money follows excellence.

Bringing in the wrong people as teachers, and not investing in them, is a serious mistake, Tim said. Getting the right people to run your classrooms is what sustains the school.

What burns teachers out

Sandi joked that parents might be the answer, then gave three real ones:

Tim said he first saw illumine when it exhibited in the US for the first time, at the Montessori Foundation's convention in Atlanta. It was the first software he had seen that might actually make a teacher's life easier. It does not solve every problem, he said, but once teachers learn it, it helps them work faster with less stress.

Grow your own teachers

Responding to an attendee whose school had started its own training program, Tim described founding the Institute for Advanced Montessori Studies at the Barrie School in 1982. Running a teacher education program builds a professional learning community, attracts people who want to become teacher trainers and gives you first pick of the people who want to become Montessori teachers. Good pay and good hours matter too. Schools need the resources to do the job right.

Tools that help, and tools that do not

Asked how much time illumine saves, Sandi estimated an hour or two a day. It has helped most with teachers who speak English as a second language and find written reports hard: observations are quicker, translation is built in and those teachers are more confident. The teaching team also works more collaboratively.

Tim added that parents often do not read email, and when schools use several communication tools, parents do not know where to look. Apps that do not notify parents of new messages often go unseen. He also noted that the average teacher is not a great writer. He has been advocating a return to long narrative report cards, which means a lot of writing. AI trained for early childhood education lets a teacher speak into a phone or tablet and get a clear, coherent report quickly.

See it in action

Anna walked through two areas of illumine:

As a head of school, Sandi said she uses the timeline to see everything teachers have posted and group messaging to see how parents and teachers are communicating. Her school created a parent group inside the system, so families can talk to one another, which supports community building and replaced a separate group email tool. She can filter incidents, see late arrivals and review check-in and check-out. Her bookkeeper particularly likes the billing reports. For a deliberately lean leadership team, she said, it streamlines a lot. Learn more about illumine's Montessori software, including parent communication and record keeping.

What only the head of school should carry

Tim said your staff do not need to know how worried you are about payroll or enrollment. Every leader needs someone outside the staff to turn to, whether that is a board, the Montessori Foundation, the American Montessori Society (AMS) or the Association Montessori Internationale (AMI). Sandi agreed that it is lonely at the top, and said leaders should find confidants in the industry who hold similar roles.

Hard conversations are the work

Tim said parents want far more information than schools usually provide. They will not read your emails, but they are "like baby birds hungry for positive information about their child", while teachers already feel they are on a hamster wheel. Some conversations are hard for many reasons.

Sandi said documentation is what makes those conversations possible. For a child who is having a difficult time, her staff record staff-only observations in one place on the child's profile, rather than sending them to parents. Everyone can see what each teacher has tried, the team stays on the same page and they have clear documentation to share when it is time to talk with the family. Read more in our recap of The October Danger Zone.

If you could hand off one thing tomorrow

A final poll asked what leaders would hand off first: parent emails and calls, staff schedules and coverage, licensing and compliance paperwork, or billing and tuition follow-ups. Sandi guessed staff schedules and coverage, which she called "a Tetris game", and she was right: 13 of 20 respondents chose it. Tim said licensing and compliance reports were the most aggravating part of his own time as a head. He also noted that illumine tracks attendance, including geofencing, so schools know who is on campus and who picked each child up. For help with schedules, see how to master staff scheduling with AI.

The three great jobs of a head of school

Montessori leadership isn't about eliminating anxiety, your own or others'. It's about becoming a steady presence within it.

Heads of school juggle fundraising, volunteers, admissions, parent concerns, documentation, incident reports and legal issues. But Tim, who has been sharing this framework for 20 years, said there are three main jobs:

Everything else, such as bookkeeping, can be hired.

Questions from the session

How do we support burned-out teachers in the toddler room?

Tim joked that you could change the diapers for them, then said the real answer starts with hiring people who have a strong nurturing instinct and love being with infants and toddlers. You cannot make someone love the work, but you can tell them, "I see you," and help them see why it matters so much. Toddler rooms are physically exhausting. Sandi said open communication between co-leads and co-teachers helps, so everyone follows the same policies and is kind, firm and consistent with the children. Toddler-specific Montessori professional development has also helped her teachers find new activities and keep their spark.

Do you have strong onboarding procedures that help new teachers connect and stay?

Tim said the Montessori Foundation has whole programs on onboarding staff and parents, covered in its twice-weekly webinars, articles and YouTube playlists, and offers a free consultation. For more ideas, see our guide to effective staff induction and staff retention strategies for childcare centers.

Should we step away from Montessori if we cannot find Montessori teachers?

Schools are entitled to, Tim said, but they pay a price: they lose what makes them distinct. His advice is to invest in finding and developing the right people, including by running your own teacher training.

Does illumine include a Montessori curriculum?

Yes. Tim said schools can load any curriculum they want, and curriculum from the Montessori Foundation has been loaded into illumine.

Resources mentioned

• A professional development certificate, the recording and information on Tim's latest book, emailed to attendees.
• The Montessori Foundation's Montessori Family Alliance, with parent resources, a weekly e-newsletter and Tomorrow's Child magazine.
• Earlier sessions with Tim Seldin, recapped in The Montessori Leadership Playbook for 2026 and AI and the Future of Montessori Leadership.

What to do next

For more on Montessori leadership, read Tim's strategies to hire and retain preschool teachers, his take on the childcare staffing crisis or our guide to preventing teacher burnout. To see how illumine supports Montessori schools, book a live demo.