Should I hire an Executive Assistant or a Chief of Staff?

Quite a few of my clients have recently asked: What’s the difference between an Executive Assistant (EA) and a Chief of Staff (CoS)? 

I’ve found that most early stage technical startups end up having a role like an EA or a CoS as one of their first non-technical hires. For technically trained leaders, hiring for a role like this is often much harder than hiring scientific or engineering talent. 

The truth is: Executive Assistant (EA), Chief of Staff (CoS), and even Chief Operating Officer (COO) are very similar flavors of roles. They are all roles that support the organization with systems, making sure that everything is moving in the right direction. The roles themselves are relatively amorphous; there isn't a standard job description for any of them. An Executive Assistant in one organization can often have responsibilities that edge right up against what a Chief of Staff may do in another organization. A Chief of Staff may crossover into Chief Operating Officer duties in another organization as well. 

Roughly speaking, here’s a way to think about the different between these roles: 

Executive Assistant

Executive Assistants usually work closely with the CEO; sometimes, EAs are shared across other C-Suite roles as well. Their role is to help keep the CEO organized with their schedule, supporting them with administrative tasks like collecting invoices and managing their schedule. An effective EA will ensure that the details have follow-up when the leadership team is focused on the bigger picture. Executive Assistants need to be extremely organized, detail oriented, proactive, and are effective communicators. 

Pro tip on hiring Executive Assistants: don’t hire some young whipper-snapper who sees this job as a foot-in-the-door at a cool startup. Although that kind of profile is extremely appealing (they’re young and eager and so smart!), you want to hire someone who actually likes doing EA work and has done it before. You don’t want someone on your team who is willing to do this work in order to get to the next job. You really do want someone who takes pride in doing great work in this space - and who can help train YOU on how to use an EA effectively since it’s likely you’ve never worked with one before. 

Ask around your network if anyone knows someone great that may be available. You can post on LinkedIn as well, but that’s usually a flood of resumes with a wide range on quality. EA’s don’t need to be in person necessarily so broaden your view. The best way to get the right person is to be extremely clear about what you’re looking for - and what you need as a teammate. I strongly recommend asking potential hires to do a brief assignment for you so you can evaluate their work realtime before you make an offer. 

One more thought: you can often hire EAs fractionally. I have an incredible teammate who supports me about 5 hours a week from California. She handles all of my contracts and coordinates with my accountant - she keeps my client records straight. She take a huge weight off my shoulders (thanks, Emily!).

Chief of Staff

I’ve been a Chief of Staff so I have a pretty good understanding of this role. This role is often someone who could be a CEO but is happy to be behind the scenes, supporting the work. A CoS is usually a little less in the details than an EA and a little more strategic. This is someone who can sniper in and kick-off a new initiative until that initiative has an organizational home. This is someone who can put together a board deck for you or who can lead your strategic planning process. Again, a very experienced EA could do some of this work, too, so you need to be really clear about what skills and competencies you’re looking for now - and in the near future. 

Getting a great CoS is a little like finding a unicorn. You are looking for a highly strategic operator who also is comfortable rarely getting public recognition for their work. In many ways, this role is like an invisible superhero. Someone who anticipates problems and solves them before most people are even aware of them. A CoS is the glue that keeps the organization aligned and moving forward. Maybe this role designs systems that help people communicate more effectively across teams. Maybe this role helps align the organization and stay on task with achieving their OKRs or KPIs. Sometimes a CoS is capable of being in a meeting instead of the CEO because they deeply understand how the CEO would think and make decisions, so they can act on their behalf.  

Sometimes CoS roles can be in charge of the CEO’s schedule as well, and sometimes they simply have visibility and access to the CEO’s calendar and someone else is managing the day-to-day. As you can see, a CoS can crossover into the EA space but I advise you to be careful not to combine too many detail-oriented tasks if you scope this out to be a high-level strategist; those two skill sets are rarely present in the same person.

If you can find a CoS through your network, that’s the best way to have someone who has been vetted by your trusted community. Even so, the match has to be so high here that I’d strongly encourage you to do a trial project together or time-bound some work together to make sure it’s a great fit before you make someone a formal offer. You really want to experience what it’s going to be like to work together in advance if you’re able to. 

Chief Operating Officer

In an early stage technical startup, the Chief Operating Officer (COO) may be someone who also manages your building and facilities. They may even have a technical background so they can help your science/engineering team with your lab and equipment. It’s not necessary - but it is possible. Eventually your COO will likely oversee your finance person and your HR representative - though some teams have a CFO play this role instead. 

An effective COO is someone who is truly keeping everyone moving forward by designing systems and processes for the organization. What’s different about the COO and the CoS is that this role typically grows into a manager who oversees big areas of the organization. A COO is part of the C-Suite; a CoS may not be on the C-Suite but is definitely supporting the C-Suite. Again there are no rules here so it may look a little different across organizations.

The big take-home message

As you can see, an EA, a CoS and COO are all similar roles - but they’re definitely not the same. The key is really clearly mapping out what you want this new role to do and what capabilities this hire needs to have - and the worry about which title is appropriate next.

Before you pick the title for your new role, start with a bottom-up approach: what will this role be doing on a daily, weekly, or quarterly basis. Make a list of the tasks and responsibilities and then figure out what skills and competencies you need.

You may even want to have two parallel job descriptions if you’re not 100% sure. You can have both roles open at the same time to see which one feels like the right match as a way of trying it on for size with actual candidates. If you’ve never worked with any of these roles, it may take you a little while to figure out exactly what you need and are looking for.

Regardless of whatever path you pursue, having a very clear job description and a highly structured onboarding process with rapid feedback will help you get this new person integrated onto your team as quickly as possible and get them operating as a key accelerant on your team.