How to partner with an executive assistant.

January 28, 2020. Filed under management 102

One of the magic moments you’ll experience as a senior leader is the first time you get support from an executive assistant. Starting at that moment you’ll slowly uncover more and more possibilities that you had – in order to preserve your sanity – intentionally blinded yourself to. It is, you’ll gradually relearn, actually possible to reschedule large meetings, get all those one-off meeting requests scheduled in a timely fashion, and to plan good offsites that bring the team together.

Busy leaders so often drop these sorts of seemingly low leverage tasks, that their organizations are hamstrung not by an insufficiently extraordinary vision but rather by an absence of the fundamentals. Bringing a strong executive assistant onto the team is the most effective way I’ve found to reverse that trend.

That said, it can be unclear when you ought to start hiring executive assistants, there’s a real learning curve to partnering with them well, and it’s common for the executive assistant career path to be ambiguous or absent. Let’s talk through all of these.


This topic is inspired by David Loftesness who brought it up during a recent dinner, where I also learned a bunch from Kimber Lockhart’s experiences. Thanks also to Steffi Hoydich and Jennifer Shorr for reading and suggesting a number of important improvements.

Assistants, administrators and so on

The role of executive assistant goes by a number of different names, and I’ll stick to executive assistant, abbreviated to EA, throughout this piece. I’ve not found any name-of-role distinctions to be particularly consistent across companies except, so I won’t attempt to identify a taxonomy. Similarly, I’ll refer to the folks that are supported by an executive assistant as “leaders.” This is for clarity only, and an entrant into the endless redefining of management and leadership.

When to hire?

The general hiring pattern I’ve seen is that CEOs hire an executive assistant early on, likely before the company reaches thirty folks, but that there is little additional EA hiring until the company gets much larger. Once sub-organizations, e.g. product, engineering or operations, cross one hundred folks, it’s common for companies to add the next layer of EAs. Generally by the time a company crosses 1,000 folks there are five to ten EAs supporting the leadership team.

Most companies never hire the third layer of support even as they grow larger, to the chagrin of folks who are leading teams of hundred-plus nestled within organizations of thousands. Rationales for not hiring vary, most frequently concerns around cost or that hiring additional EAs will create a cycle that requires hiring more EAs. I’ve found that folks leading large organizations without EA support tend to roll their eyes at folks with EAs voting to curtail additional hiring.

The rules of thumb I’d offer up are

  1. Anyone leading an organization with more than fifty people should get part-time EA support for offsites and scheduling large meetings.
  2. Folks leading more than a hundred should get full-time support, starting with calendaring and extending to a deep partnership.

This is a larger investment than most companies I’m familiar with have made, although Facebook seems to have successfully done something along these lines, but I think it’s a worthwhile investment.

Leveraging support

When you first start working with an executive assistant, it can be hard to figure out what to offload to them. It can also feel weird, since these are often tasks you’ve personally deprioritized – probably because you’ve felt they’re less important than the work you’re doing – and now you’re asking someone to do them for you.

Your homework before you start partnering is to talk to as many executive assistants within the company or at peer companies as you can, try to talk to three or four, and ask them what’s worked for them. Also dig into which kinds of tasks have been most and least effective to delegate. Then do the same thing with three or four folks who’ve been supported by an executive assistant.

Once you start partnering with an executive assistant, your first step is to establish a rapid feedback loop between the two of you. For your first few weeks, you should maintain a daily fifteen-minute meeting at the beginning of the day to tweak coordination based on the day before, align on priorities for the day, and moderate workload. Too much? What can be more efficient or take back for now. Too little? Identify next tasks to transition.

After two weeks, take an hour together to review how the work is going and whether you should reset approach or if you’re heading in the right direction.

Getting a bit more concrete, some sorts of tasks that typically delegate well are:

  • Time management - this is both managing your calendar, reviewing time allocation and suggesting improvements (maybe that weekly meeting really isn’t that useful anymore), and also routing requests to maximize focus and minimize interrupts
  • Drafting communications - coordinating clean communication, especially for sensitive organizational changes, requires great attention to detail and also ensuring you loop in the right folks
  • Recurring meetings - at some point most companies end up with recurring operational meetings, and executive assistants can coordinate the agenda, presenters, timing and action items
  • Planning offsites - a great team offsite will gel a team and provide focus in your execution, and an executive assistant can do a great job of alchemizing a general theme into an agenda, a rented room and a date
  • All hands meetings - most organizations bring the company together to talk about their work, progress and priorities, and an executive assistant can coordinate the presenters, give feedback on the presentations, run practice sessions, and coordinate execution of the meeting itself

That said, the partnership between a leader and an executive assistant is more custom-fitted than most, and you ultimately you should find the intersection between what the leader needs, what works for both of you, and the executive assistant’s career development.

Being supportive

Executive assistants do a tremendous amount to make their leaders successful, but the social contract goes both ways. Folks whose executive assistants are tremendously impactful approach their relationship as a partnership built on trust and communication. Folks who don’t support their EAs at best get a pair of hands instead of both head and hands, and at worst find themselves rebuilding their partnership with a new EA every couple quarters. While the EA role is to support you, they can’t do that unless you support them as well.

A surprising number of folks get this wrong, so I’ll share the core secret to supporting your executive assistant effectively: support them as you would any other member of your team. Have one-on-ones with them that are about them, not just your schedule. Work with them on their career development. Identify stretch assignments. Give them feedback that helps them grow in addition to feedback that helps the two of you partner effectively.

Leader-aligned or centralized

One of the tricky decisions in designing the role of executive assistants in your company is whether they report to the leaders they support or whether they report into a centralized manager. As is often the case for specialized roles, these different approaches represent a tradeoff between alignment on one hand and career development on the other.

Switching between models is surprisingly disruptive because in the former your first team is the team your leader supports, and in the later your first team is the other executive assistants. Many organizations flip-flop between approaches, which is often a primary source of frustration. Both models can work with proper investment.

In the leader-aligned model – where EAs report directly to their leader – then the biggest challenge tends to be a lack of professional and career development. In the centralized model the biggest challenge is a lack of alignment between leaders and the central organization’s management.

Another wrinkle is whether the EAs support a single leader or multiple leaders. Sometimes you’ll see EAs supporting multiple leaders with very different responsibilities and who have distinct – potentially inconsistent – views on what the role of an EA ought to be. This is a source of considerable stress for folks in such arrangements. One way to reduce that stress is asking your executive assistant to share with you what they’re doing to support any other leaders they are supporting. This has two benefits: first is understanding their workload, and second is that it ends up being an amazing way to learn from peer leaders about practices you might want to adopt!

The model that I’ve found most successful is having the executive assistant dedicated to supporting a single leader who is their direct manager. The EA provides full support to that leader, and limited support to the organization that leader supports. This approach maximizes continuity, creates a clear community and team for the EA to be part of, and also provides support for folks within the organization who often would end up unsupported.

Career development

The most obvious downside of the leader-aligned model is a lack of career path. How do you develop your career in the context of supporting a single leader? I’ve seen a couple different approaches work here, but either way start with the fundamentals: ensure you’re having monthly career discussion in addition to 1:1s that focus on execution.

The first is by working with your manager to develop a career narrative. Identify skills you want to develop, and work together to find projects that develop those skills. Watch the leader you support, understand where they’re spending time, and find the intersection of taking work off their plate and the skills you want to develop. This approach can culminate into a Chief of Staff style role as the organization grows.

Another approach is treating the executive assistant role as a stepping stone role, building expertise and relationships within the company, and after a year or two transitioning into a different role. I’ve seen folks move into business operations roles, program management roles, customer experience roles, and a handful of others. Depending on your personal goals, it can be an effective way to slingshot into a successful role with your internal network and existing business context flattening the new role’s learning curve.

Exceed the precedents

I’d offer two major points to take away. First, most organizations underinvest into making their executive assistants successful, which unsurprisingly makes them less successful. Second, most organizations underinvest in hiring executive assistants, which limits the leverage their existing leaders can bring to the company. Don’t be afraid to buck both trends.