Leading a team of assistants is a job almost nobody is trained for. Most people arrive at it the same way: they were very good at supporting an executive, the company grew, and somebody had to look after the other assistants.
It's a genuinely different job, and the skills that got you here are only about half of what it needs. This guide is what I've taken from interviewing people doing it at Comcast, Duolingo, Cedar and a lot of companies you have not heard of, plus the assistants on the other side of those teams.
First, decide which structure you're actually running
There are two common models, and most of the confusion in admin teams comes from nobody saying out loud which one is in force.
The dotted line. Assistants report to the executives they support. Performance reviews, pay and priorities belong to those executives. You lead the group: development, community, standards, hiring input, cover when someone is out. You've influence and no formal authority.
The solid line. The assistants report to you. You run reviews, you decide who supports whom, you own the headcount, and the executives get an assistant rather than a direct report. Amy Tilley ran this version with nine or ten direct reports and is clear that it worked because the whole leadership team, from the CEO down, had agreed it was the structure.
Neither is better. What's fatal is having one on paper and the other in practice, which is where most admin-team pain comes from: an assistant with two bosses who disagree, and a team lead accountable for a standard they can't enforce.
Some assistants actively want to report into another assistant, and some want their executive and nothing else. Amy raised it in interviews for exactly that reason, and that's a habit worth stealing.
What changes the day you take the team
You stop being measured on your own output. This is the hard one. The work that used to make you feel effective by 10am now belongs to someone else, and your contribution is slower, less visible and harder to feel good about.
Your executive relationship changes. If you still support someone directly while leading the team, you now have two jobs and they'll compete. Decide in advance which one loses on a bad week, and tell both parties.
You inherit other people's relationships. Every assistant on your team has their own partnership with their own executive, built over years. Those aren't yours to manage, and the fastest way to lose a team is to start reaching into them.
Amy's rule on this is the best I've heard: your job is to coach, mentor and grow your assistants. How they support their executive is theirs. You don't tell someone how to run a calendar.
Cara Silverman leads executive support at Duolingo and Lexi Gunther has done both at once – team manager and EA – which is the shape more of these roles take than the job titles suggest.
Onboarding new executives is harder than onboarding new assistants
This surprises people, and it comes up again and again.
A new assistant joins and learns how the team works. A new senior executive joins from a company where they had one assistant, entirely theirs, doing things exactly their way – and now they're being told there's a team, a structure, policies, and someone else deciding who supports them.
Amy found this the single hardest part of the job. What eventually won people over wasn't the argument, it was the experience: once an executive realized they no longer had to deal with PTO coverage, performance reviews, or two assistants not getting along, they stopped minding.
So build the onboarding. A short document explaining how the team works, what the executive gets, and what they no longer have to handle. Have it ready before the next hire, not after the first argument.
The things a good admin team actually has
From the people running the strongest ones:
A clear leveling structure. What separates an assistant from a senior assistant from an executive business partner, in writing. Without it, promotion is a negotiation every time and pay drifts apart for no defensible reason.
Real backup. Who covers for whom, agreed in advance, practiced before it's needed. Elizaveta Usyaeva built a team from scratch and this is the kind of thing that separates a team from a group of people with similar jobs.
Shared standards, not shared methods. Agree the output – how a briefing doc looks, what a handover contains, response times. Don't agree the process for getting there; that belongs to each partnership.
A reason to meet that isn't status. A team meeting where everyone reports what they did is a waste of eight people's time. Use it for training, for a problem someone is stuck on, or for the thing nobody else in the company understands.
Goals that are the team's, not the executives'. Jillian Hufnagel on OKRs for an assistant team is the earliest conversation I had about this and still the most practical.
Hiring and assigning
Assign for fit, not availability. The pairing matters more than almost any other decision you make. A brilliant assistant matched to the wrong executive looks like a performance problem and isn't.
Involve the executive, but own the decision. They should meet candidates. They shouldn't run the process, or you've given the structure away on the first hire.
Interview for judgment. Task competence is easy to test and easy to teach. What you can't teach quickly is whether someone can tell what matters.
Say what the structure is, out loud, in the interview. Some strong candidates will opt out, and that's the process working.
In episode 114 of The Leader Assistant Podcast, I talked with Tara Sims, who previously led administrative services at Comcast, and in other episodes I spoke with Chandra Severin, Izzy Gousby and Nicki Cave – each walked through their experience managing an administrative team.
Where these teams go wrong
The lead is still doing the work. Usually because it's faster. It's faster once, and it costs you the team.
No air cover from the top. A team structure the CEO hasn't visibly backed will be ignored by the first senior person who wants their own arrangement.
Development that's only for the lead. If you go to the conference every year and your team never does, you have a retention problem you have not noticed yet.
Grief nobody names. Reorganizations, an executive leaving, a long-standing partnership ending – assistants absorb these hard, because the relationship was the job. Amy's episode is about this as much as it is about team management, and it's the part of the work least likely to be in anyone's handbook.
Measuring the wrong thing. Response time and inbox zero are easy to count and tell you almost nothing. What you want to know is whether each executive could do their job without their assistant, and the answer should be no.
Going deeper
Three sessions in the Premium Membership library go further on the mechanics, and they're members-only:
- Administrative Team Levels, Reporting Structure, and Support – the leveling question in detail
- Attributes of a High Performing EA Team
- The Pros and Cons of Managing EA Teams – including the honest case for not doing it
If you want to be taught this properly
Almost nobody gets trained for this job, which is the problem the Administrative Management Accelerator exists to solve. It's Tara Sims' course, and she runs administrative services at Comcast leading a team that supports a division office – so it's taught by someone doing the job at scale rather than someone who has read about it.
If you're stepping into leading a team, or have been doing it by instinct for a year and want a structure underneath, that's where I'd send you. Her episode is a fair sample of how she thinks about it.
If what you're working on is training the team rather than structuring it, the guide on running a training event for your assistants covers the business case and the formats.