Questions Answered

It's a five-week training program for executive assistants and office managers. Each week covers one operational area: calendar management, travel booking, meeting prep, inbox triage, and building institutional knowledge. Sessions are in person in Chicago. You leave each session with a working tool or template, not just notes.

No. The program does not lead to a credential or certification. It's a practical skills training program. Participants receive a completion document, but the emphasis is on the tools and systems you build during the program, not on a credential at the end.

The program has been running in its current form since 2022. The curriculum has been revised based on what participants found most and least useful in earlier iterations.

Yes. The program is designed for people who are already working in administrative or office management roles. It assumes familiarity with standard office tools and focuses on building more sophisticated systems on top of that foundation. Participants typically have at least two years of relevant experience.

Yes. The curriculum applies to both roles. Office managers who handle executive support as part of a broader role find the calendar, inbox, and knowledge modules particularly relevant. Executive assistants tend to engage more deeply with the travel and meeting prep modules, but all five modules are relevant to both roles.

Yes. Supporting multiple executives adds complexity rather than changing the fundamentals. The templates and frameworks in the program are designed to be adapted, and the working sessions give you time to think through your specific situation. If you support multiple executives, that context is worth mentioning when you reach out.

Sessions are in person in Chicago at 2501 Des Plaines Ave. The in-person format is intentional — the working sessions require focused time away from the usual work environment, and the small group discussion is more productive in person. There is no online version of the program at this time.

Each session is a half day, typically from 9am to 1pm, with a short break. The schedule is designed to fit within a workday without requiring a full day out of the office.

Cohorts are kept small — typically six to ten participants. This is deliberate. The working sessions are more useful when the facilitator can engage with each participant's specific situation rather than running a large group through generic exercises.

A laptop and access to the tools you use in your current role (calendar system, email, whatever you use for documents). The working sessions involve building tools within the systems you actually use, so having access to those is important. Printed materials are provided at each session.

Each participant receives the full template library for all five modules, printed reference materials for each session, and digital copies of everything. The templates are designed to be adapted for your specific organization and role, not used as-is.

Yes. A structured check-in session is included three weeks after the final module. This is a group session where participants can raise questions about implementation, share what's working and what isn't, and get input on specific situations they've encountered since the program ended.

Yes. Organizations sometimes send two or three people from the same team, which can be useful for building shared systems and language. Contact us to discuss whether this makes sense for your situation and whether there are any scheduling considerations.

Contact us through the contact form or by phone. We'll discuss whether the program fits your current situation and schedule, and confirm availability in the upcoming cohort. There's no online enrollment form — we prefer to have a brief conversation first.

The next cohort starts September 8, 2026. Contact us to confirm availability and discuss scheduling. Cohorts run multiple times per year, so if the September cohort doesn't work, we can discuss future dates.

Many participants have their employers cover the cost as professional development. We can provide an invoice in whatever format your organization requires. Contact us to discuss the specifics.