Most companies will spend more on one executive's leadership offsite than on their entire assistant team's development in a decade. If you're the person trying to change that, this practical guide is for you.
I've run training and development sessions for Amazon, LinkedIn, Google, Wendy's, The Ohio State University, Salesforce, the US Navy and a lot of companies in between. The second half of this guide is written from the speaker's side of the room.
But let's start at the part that decides whether the event happens at all.
Build a compelling business case
The request that fails is "the assistant team would really benefit from some training." Just because it's true, doesn't mean it's a compelling business case.
The request that works connects the spend to something the business already cares about. The following 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 and development is a tangible way to show assistants that you value them.
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 just their own. Why wouldn't an organization want to develop the very people who manage the most valuable asset of the business – the executives' energy?
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. Training doesn't just make each assistant more effective – it improves the output and efficiency of the entire administrative team.
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. It's more difficult to forget best practices when you're consistently exposed to outside experts.
Ask for a number, not for permission. "I'd like to book a half-day session for the team in Q2, at roughly this cost" is a specific request requiring a decision. "Could we maybe do some training at some point?" is a conversation that never ends.
Here's a business case letter template example, if you'd rather start from something than from a blank page. Episode 150 of The Leader Assistant Podcast showcases the chapter from my book that talks about professional development, and it's worth checking out before you submit your first request.
If the answer is no, ask what budget it'd come from, who owns that budget, and when it gets set. Many 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 assistant training engagement was disappointing because the purpose of the day was not set before booking.
There are three common goals for assistant team development, and an intentional, well-planned session can do all of them well:
- Skill. Your assistants leave the event able to do something they couldn't do before.
- Perspective. Assistants leave thinking differently about their role, their worth, or where the profession is going.
- Cohesion. Assistants leave knowing each other, which for a distributed admin team is often the highest-value outcome of the whole year. Often the networking and peer conversations are the most talked about takeaways.
Say which goals matter the most, in writing, before you talk to a speaker. It changes who you hire, how long you book, and how you structure the room.
Note: it's ok if your session only has one of the above goals. Some formats are too succinct to fit all three in.
Structure an agenda people can absorb and apply
Don't fill the day. The single most common mistake I see. A packed agenda with back-to-back sessions produces exhausted people who remember nothing. Leave real gaps for networking, walking (movement is good for us!), and processing what's been discussed.
Put the hardest thinking sessions first. I recommend an energizing opening, then get right to the heart of the agenda, while people are still fresh. Not after lunch.
Break up the presentations every 20-30 minutes. A question to the room, table discussion breakouts, time for the group to write down ideas or next steps. Assistants spend their working lives managing other people's time and energy, so they know exactly what it feels like when a meeting shifts from energizing to draining.
Include something only this group could do together. A problem all of them have, worked on in the room. Peer-to-peer collaboration and conversation is where the cohesion comes from, and it's on the top of the list of things people rave about to me after training events. In other words, be hesitant to hire a speaker who can't relate to being an assistant, and who doesn't understand how crucial camaraderie is to development.
Give the executives a slot, and keep it short. A senior leader opening the day and saying plainly why this team matters goes a long way. A senior leader rambling for forty minutes is not a good use of time. After all, listening to executives who can't stop talking is what we assistants have to do every day. ;-)
End with commitments, not platitudes. Each person writes down one action they'll take and when. Collect and document them, if appropriate. Revisit them in six weeks. Lindsey Caplan on crafting memorable offsites is a solid podcast conversation worth checking out. She talked about designing the room rather than just filling it.
Choose a format that fits
Four shapes cover almost everything, and the right one depends on the goal(s) you picked above, the size of your team, and your budget.
One hour, virtual. The easiest to get budget approval for and the easiest to get wrong. Works for a single sharp topic or for helping your team change their perspective. It doesn't always work for cohesion since you miss out on the in-person connection. This format is often used as the first thing you book, to prove the value and unlock a bigger budget next time. Keep it to one idea, leave 15-20 minutes for questions, and record it for the people who couldn't 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're booking one thing this year, book a half day.
Keynote plus 1-2 workshops, on site. A full day, and the shape I'm 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. Another reason I like this option is that typically you can plan a fun activity and/or a party to connect and celebrate with each other – even if it's simply a late-afternoon happy hour to close out the day.
One or two days on site, with networking and team time. The full version, sometimes annual, is often tied to Administrative Professionals Day (depending on your company's annual rhythms). Training sessions plus unstructured time plus something social. The unstructured time isn't filler. For a hybrid or remote team that has never been in a room together, it's 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 doesn't justify the flights.
A note on virtual: it isn't a lesser version, it's a different one. It needs shorter segments, more interaction, cameras on as a stated expectation, and someone other than the speaker watching the chat.
Choose and hire a speaker who understands EA life
Ask for a sample of them speaking, not a showreel. A cut of applause and crowd shots don't always tell you much. Ask for a few unedited minutes of them teaching.
Confirm if they've been an assistant, or not. Assistants can tell within five minutes whether a speaker actually understands the role, and once they decide, you've lost the room. I'm not opposed to hiring speakers who have never been an assistant. But after years of providing assistant training sessions, keynotes, and workshops, I've lost track of how many times I've heard assistants comment about previous trainers who "did not understand the assistant role and were not able to connect with the room."
Ask what topics they're passionate about, and what topics assistants have been receptive to. If you want an engaging, inspirational, funny, and practical session that connects with assistants on your team, find out what the speaker's passions are. You want the speaker to be excited about the topic, otherwise there will not be much energy in the room.
But it's not just about the speaker's passion. It's also about whether or not assistants have been receptive to the topics discussed. How does the topic directly apply to assistants?
Ask what they need from you and your team. A speaker who asks about your team's structure, tenure spread, recent reorganizations and what you actually want to change is preparing well. One who asks only for the AV requirements is likely checking boxes.
Agree on what happens afterwards. Slide deck sharing, what happens to the 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 two weeks after it – unless the group has something to act on, or something tangible to refer back to. For example, I like to provide a copy of my book to attendees of my training if at all possible. This gives them something to refer to as they get back to the day-to-day work of their assistant role.
Who to consider
I provide keynote speaking and corporate team training on the topics of AI and automation, leadership for EAs, recognizing and resisting burnout, and more. I work with teams in a variety of formats – from a single virtual session, up to multi-day on-site programs. Complete my speaker request form to inquire. I'd love to work with you!
Additionally, I'm happy to point you to good people rather than pretend I'm the only option. ;-)
Here is a short list of talented speakers, who have also been on the podcast, and who I've worked with in various capacities. I recommend approaching them directly about availability and fees, but please do mention I sent you!
- Annie Croner (a speaker who gets EA life more than most)
- Tara Sims (high energy, and the go-to expert on administrative team management)
- Diana Brandl (an international speaker and all-around amazing person)
- Monique Helstrom (one of the best speakers on the topic of communication)
- Beth Portesi (former EA, turned AI trainer)
- Maggie Olson (especially if you want a trainer to talk about the Chief of Staff role)
NOTE: There are so many amazing speakers in the assistant space – too many to count, and frankly, too many to list. So do your own research and good luck!
The logistics that make or break your engagement
Protect the time. Assistants will answer their executive's message during your training unless someone senior has said they don't have to. Get that said, by the executives, preferably in writing, beforehand.
Arrange coverage. For an on-site day, someone has to be reachable. Rotate it, or the same person misses every session.
Feed people properly and build in a real break. Should be obvious, but healthy and delicious meals, and intentional breaks are routinely skipped during planning.
Don't schedule it during your company's busiest week. Not quarter end, not board week, not the two weeks before the annual conference.
Get the executives to show up for something. Even briefly. An executive team who couldn't spare one executive for twenty minutes is not an executive team that values assistants.
Postgame
The event is the easy part. What you do after it determines whether anything will change:
- Schedule a short follow up 2-3 weeks later. Whoever found the session most useful can present one idea at the meeting.
- Report back to whoever approved the spend. How many attended? What was discussed? What practical changes has the team made since? This report is what helps get the next one's budget approved.
- Make it annual, then make it expected. The first one is hard to get. The fifth is a pre-approved line in the budget.
I hope this guide is helpful as you develop a game-changing training and development program for your executive assistant team!
P.S. – If you're also working out how the team itself should be structured, the companion piece is leading a team of executive assistants.