Most companies will spend more on one executive's leadership offsite than on their entire assistant team's development in a decade. If you are the person trying to change that, this is the guide I wish I could hand you.
I have run these sessions for Amazon, LinkedIn, Google, Salesforce, the US Navy and a lot of companies in between, so the second half of this is written from the speaker's side of the room. The first half is the part that decides whether the event happens at all.
Build the business case in the language your company uses
The request that fails is "the assistants would really benefit from some training." It is true, and it is not an argument anyone can approve.
The request that works connects the spend to something the business already cares about. Four arguments land most often:
Retention. Replacing an experienced executive assistant is expensive in ways finance understands – recruiter fees, months of reduced executive output, institutional knowledge that walks out. A day of training is a rounding error next to one resignation.
Executive capacity. Your assistants are the leverage on the most expensive salaries in the building. Anything that makes them better multiplies against those salaries, not their own.
Consistency. If eight assistants each invented their own way of running a briefing doc, an onboarding or a board pack, shared training is how that becomes one standard – which is a quality argument, not a nice-to-have.
Risk. Assistants handle confidential material, travel, expenses and access. Untrained is the expensive option and a single incident makes that argument better than any slide you could write.
Ask for a number, not for permission. "I would like to book a half-day session for the team in Q2, at roughly this cost" is a decision. "Could we maybe do some training at some point?" is a conversation that never ends.
The Premium Membership includes a business case letter template for exactly this, if you would rather start from something than from a blank page. Episode 150 is the chapter on professional development, and it is worth reading before you write the request, because the first question in it is what you actually want to change.
If the answer is no, ask what budget it would come from, who owns that budget, and when it gets set. Most training requests fail on timing rather than merit – the money was allocated in October and you asked in March.
Decide what the day is actually for
Almost every disappointing session I have seen was disappointing because nobody answered this before booking.
There are three honest goals, and a session can do two of them well:
- Skill. They leave able to do something they could not do on Monday.
- Perspective. They leave thinking differently about their role, their worth, or where the profession is going.
- Cohesion. They leave knowing each other, which for a distributed admin team is often the highest-value outcome of the whole year.
Say which one matters most, in writing, before you talk to a speaker. It changes who you hire, how long you book, and how you structure the room.
Structuring a session people remember
Do not fill the day. The single most common mistake. A packed agenda with back-to-back sessions produces exhausted people who remember nothing. Leave real gaps.
Put the hardest thinking early. First session after the opening, when people are fresh. Not after lunch.
Break up the talking every twenty minutes. A question to the room, a pair discussion, something written down. Assistants spend their working lives managing other people's meetings and know exactly what a badly run one feels like.
Include something only this group could do together. A problem all of them have, worked on in the room. This is where the cohesion comes from, and it is almost always the thing people mention afterwards.
Give the executives a slot, and keep it short. A senior leader opening the day and saying plainly why this team matters is worth a great deal. A senior leader talking for forty minutes is worth less than nothing.
End with commitments, not applause. Each person writes down one thing they will do differently and when. Collect them. Revisit them in six weeks. Lindsey Caplan on crafting memorable offsites is the best conversation I have had about designing the room rather than just filling it.
Choosing a format
Four shapes cover almost everything, and the right one depends on the goal you picked above.
One hour, virtual. The easiest to approve and the easiest to get wrong. Works for a single sharp topic and for perspective; does not work for skills or cohesion. Best used as the first thing you book, to prove the value and unlock a bigger budget next time. Keep it to one idea, leave fifteen minutes for questions, and record it for the people who could not make it.
Half day, virtual or on site. The best value in the set. Room for one keynote and one working session, so you can pair perspective with skill, and short enough that nobody has to clear a whole day. If you are booking one thing this year, book this.
Keynote plus two workshops, on site. A full day, and the shape I am asked for most often. The keynote sets up the thinking, the workshops turn it into practice, and the day has enough space that people actually talk to each other between sessions. This is where an admin team stops being a list of names on an org chart.
One or two days on site, with networking and team time. The full version, usually annual, often tied to Administrative Professionals Day. Training sessions plus unstructured time plus something social. The unstructured time is not filler – for a team that has never been in a room together, it is frequently the part with the highest return. Two days needs a genuine reason: either the team is large enough that small-group work needs the space, or people are traveling in and one day does not justify the flights.
A note on virtual: it is not a lesser version, it is a different one. It needs shorter segments, more interaction, cameras on as a stated expectation, and someone other than the speaker watching the chat.
Choosing and hiring a speaker
Ask for a sample of them speaking, not a showreel. A cut of applause and crowd shots tells you nothing. Ask for twenty unedited minutes of them teaching.
Check they have done the job, or have spent years around people who do. Assistants can tell within five minutes whether a speaker actually understands the role, and once they decide you have lost the room.
Ask what they will change about it for your team. Anyone who will deliver the same talk to a four-person team at a nonprofit and a two-hundred-person admin org at a bank is selling you a recording.
Ask what they need from you. A speaker who asks about your team's structure, tenure spread, recent reorganizations and what you actually want to change is preparing. One who asks only for the AV requirements is not.
Agree what happens afterwards. Slides, recording, a follow-up session, something the team can use in six weeks. Most of the value of a training day leaks away in the fortnight after it.
Who to consider
I speak and train on this, so treat the first line as an interested party: my own speaking and training covers AI and automation for assistants, what holds assistants back from leading, and recognizing and resisting burnout, and I work with teams from a single virtual hour up to multi-day on-site programs.
I would rather point you at good people than pretend I am the only option. Everyone below has been on the podcast, which is the extent of what I can vouch for – approach them directly about availability and what they cover:
- Annie Croner of Whole Assistant, on burnout, confidence and mindset. She has been on the show more than a dozen times and is the person I recommend most often alongside myself.
- Diana Brandl, an international speaker and host of Executive Office Insights, for European and globally distributed teams.
- Monique Helstrom, on communication, interviewing and how assistants present themselves.
- Beth Portesi, for AI enablement specifically, from twelve years as an EA. She and I ran a workshop for assistants together if you want to hear how she teaches.
- Maggie Olson of Nova, if the team's question is about chief of staff and career paths.
The logistics that quietly decide it
Protect the time. Assistants will answer their executive's message during your training unless someone senior has said they do not have to. Get that said, by the executives, in writing, beforehand.
Arrange cover. For an on-site day, someone has to be reachable. Rotate it, or the same conscientious person misses every session.
Feed people properly and build in a real break. Obvious, routinely skipped.
Do not schedule it in your busiest week. Not quarter end, not board week, not the fortnight before the annual conference.
Get the executives to show up for something. Even briefly. A team whose leaders could not spare twenty minutes has learned something, and it is not what you wanted to teach.
Afterwards
The event is the easy part. What determines whether anything changed:
- Ask for the commitments in writing, and diary a check-in at six weeks.
- Run one thing in-house afterwards. Whoever found the session most useful presents one idea at the next team meeting.
- Report back to whoever approved the spend, with what changed rather than how much everyone enjoyed it. That report is what gets the next one approved.
- Make it annual, then make it expected. The first is hard to get. The fifth is a line in the budget.
If you are also working out how the team itself should be structured, the companion piece is leading a team of executive assistants.