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 they were asked to manage the administrative team.
It's a genuinely different job, and the skills that got you where you are as an executive assistant are only about half of what's needed. This guide is a sampling of what I've learned from interviewing assistant team leads, and my own experience managing assistants.
First, decide which structure you're actually running
There are two common models, and much of the confusion in admin teams comes from nobody saying out loud which one is in force.
The dotted line
Assistants report to the executive(s) they support. Performance reviews, pay and priorities belong to those executives. You lead the group: development, community, standards, hiring input, vacation coverage, and so on. You've got influence, but no formal authority.
The solid line
The assistants on your team report directly 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 I recommend listening to our conversation for insight.
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 supervisors who disagree, and a team lead accountable for a standard they can't enforce.
Some assistants want to report to another assistant, and some want their executive and nothing else. Not only do you need to decide which structure your team will adhere to, you need to make it clear to those you're considering adding to the team.
What changes the day you take the team
You stop being measured by 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 not as easy to quantify, 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 so helpful: your job as team lead is to coach, mentor and grow your assistants. How they support their executive is theirs. You don't need to tell a capable assistant how to manage a calendar.
Cara Silverman spent part of her career leading 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 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 on the output – how a briefing doc looks, what a handover contains, response times. Don't micromanage the process for getting there; that belongs to each strategic 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, or to highlight a problem someone is stuck on.
Goals that are the team's, not the executives'. Jillian Hufnagel on OKRs for an assistant team is one of the earliest conversations I had about goal setting, OKRs, and KPIs for assistants – and it's still the most practical.
Hiring and assigning
Assign for fit, not availability. The EA <-> executive 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. Can they identify problems worth solving?
Say what the structure is, out loud, in the interview. Make sure the job description clarifies it in writing as well. 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. Add those conversations to your "up next" playlist to dig deeper.
Where admin teams go wrong
The lead is still doing the work. Usually because it's easier to do something than it is to teach someone else to do it. Don't fall for this trap. Delegate and develop your 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 aren't a leader. If your company won't cover the whole team's attendance, send a delegate to attend and report back.
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 met – and exceeded – their goals. This is more important than a clean inbox.
Going deeper
The following three sessions in the Premium Membership library go further on the mechanics, and are worth subscribing for:
- 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
Learn about administrative management from an expert
Almost nobody gets trained for this job, which is the problem the Administrative Management Accelerator exists to solve. It's Tara Sims' course, built from her real world experience including pitching, designing, and leading an administrative function that did not previously exist inside a large organization.
If you're stepping into leading a team, or have been doing it by instinct for a while and want a structure underneath, enroll in Tara's course -> Administrative Management Accelerator. Additionally, her podcast episode is a good sample of how she thinks about leading an admin team.
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 formats.