How Executive Assistants & Chiefs of Staff Can Effectively Work Together to Lead Up

A common question I get is, “What is the difference between an Executive Assistant and Chief of Staff?Over the course of my thirteen years in the professional workforce, I’ve spent about five of those years as an Executive Assistant and about six years as Chief of Staff. I’ve seen the commonalities and overlap in these roles and I’ve also seen where they diverge and become two distinct and important positions in an organization.

Yes, there is often overlap between the two roles. Yes, a top EA may work on special projects in a strategic capacity as one CEO’s Chief of Staff, while another EA may be more administrative and tactical. Yes, in some cases, the titles are interchangeable. However, when both an EA and COS exist in an organization, the roles are quite unique, yet interdependent.

I think the biggest differentiation between the two roles lies in both the time and overall responsibilities. How EAs and Chiefs go about getting the job done involves both strategy and tactics; they are simply working on different parts of one big, important, high-impact job. Both positions thrive in a supportive leadership role and both are Force Multipliers. Read this post for more information about the differences between an Executive Assistant and a Chief of Staff.

Now, that we’ve got the differences and distinctions between the roles out of the way, let’s dive into how Executive Assistants and Chiefs of Staff can effectively work together to lead up and support their Principals and the organization.

Establish clear job descriptions

Because of the overlap in the roles, it can be challenging to navigate who does what. The most basic, and perhaps the most helpful, thing to do is write out clear job descriptions. Go beyond the usual responsibilities and get granular. Determine the responsibilities for the respective roles on a daily, weekly, monthly, quarterly, and annual basis.

Sometimes the challenges in working together don’t come from each other, but rather from the leaders in the company. Once the job descriptions are established, share them with each other, with your Principal, and with the leadership team. It is your responsibility (EA and COS) to clearly communicate to the organization who does what and how you can each help support and provide value to the various parties.

Stay in your lane

Once the roles have been clearly defined, it’s important to stay in your lane (I’m probably talking to myself here more than you!). This can be especially difficult when a former Executive Assistant grows into a Chief of Staff position (and certainly when it’s in the same company). I know this from personal experience! There is a lot of ownership and ego tied up in our work and it can be hard to let go. But let go, we must!

As Chief of Staff, if you are constantly jumping into the work of the Executive Assistant then I guarantee you are not focused on your most important activities to move the company forward. And Executive Assistants, if you are always bumping up against the Chief of Staff, what might you be missing? If you both don’t stay in your lane and respect each other’s roles, there may be redundancies and inefficiencies, which can ultimately lead to one or both of you dropping the ball on your primary responsibilities.

Hold regular meetings and briefings

Equally important to establishing boundaries between the two roles is constant communication and collaboration. Just like Force Multipliers need their leader to thrive, so too, do Executive Assistants and Chiefs of Staffs need each other. This is where very clear and intentional communication will come into play. You will both likely be talking to the same people, getting internal and external requests that cross the lanes of your job descriptions, get questions and projects from your Principal or leadership team that require both of your time and attention, and more. Remember, you are both working on the same core mission – to ensure your Principal’s vision/agenda is clarified, communicated, and executed throughout the organization. You are each just accomplishing this mission by using your unique skills and strengths.

Depending on the communication channels between the COS, EA, and the Principal, the Principal may be going to either the EA or COS more regularly for their various needs. That’s fine. That just means that it’s even more important to keep open lines of communication between EA and COS so items don’t get missed. For example, in our company, largely based on the long-standing relationship between myself and Adam, my Principal, a lot of new initiatives, scheduling changes, new projects, etc. are communicated to me first. I, in turn, must make it a priority to loop in our Executive Assistant and any other parties to get the work done.

If you haven’t already, make sure you have set up several touch-points throughout the week to stay in sync with your counterpart. I’m a fan of the Monday meeting where the Chief of Staff and Executive Assistant go over priorities and projects for the week. During this time, we also review the company calendar, as well as the Principal’s calendar to ensure everything is covered, prepped, shifted, rescheduled, added, etc. as needed.

Throughout the week, I also recommend regular check-ins to download information and brief each other on any pressing issues that could affect the other person’s work. This could be a morning check-in, a mid-day coffee and catch-up, or a call during the evening commute. The key here is to establish regular touch-points so you both have the information you need and are sharing relevant information consistently. This can significantly cut down on the EA and COS stepping on each other’s toes or assuming that one person or the other is handling a particular task.

Depending on the reporting structure of your company, you could also implement the 5 Daily Accountability Questions. For example, if the Executive Assistant reports to the Chief of Staff, at the end of every day, the EA would send their 5 Daily Accountability Questions to the COS. This is a great opportunity for the Chief of Staff to see where the EA had successes for the day, where the struggles were, how he/she overcame them, and where their mindset is for the day. It also provides the opportunity for the COS to answer questions, coach the EA, and in general get on the same page in terms of projects and any personal issues that could be affecting their staff member. In turn, the EA could use this tool with any of her/his direct reports.

Regardless of how you choose to set up your daily and weekly briefings, get them scheduled and on the calendar. A structured time for communicating and exchanging important information will keep you both on the same page, running fast, and getting results.

Meet regularly with your Principal

As I mentioned above, your Principal may tend to lean more on their Chief of Staff or Executive Assistant. That’s fine as long as the COS and EA are communicating regularly and working together. In addition, it is important for all three of you to meet together. We like to do a monthly touch-base where we look at the calendar for the month ahead, go over any personal obligations in the months to come, and decide on any changes or additions to major projects and initiatives. Once again, this keeps everyone on the same page for the most critical items. It also helps the EA and Chief of Staff hear the same vision and important items at the same time from the Principal to ensure a cohesive execution.

It’s also just a great way to keep the strategic partnership strong! We’re all busy and running hard to hit our various goals. Yes, we all touch base regularly, but having a monthly extended meeting as a team, helps us strengthen the relationship between us all and keep us rowing in the same direction.

Invest time into the partnership

And finally, the best way for a Chief of Staff and Executive Assistant to effectively work together to lead up is by investing time into their partnership. You are probably spending a lot of time together. You rely on each other to get work done and achieve results for the organization. You lean on each other in difficult times and when you need to vent or just to think through a challenge. Like all important relationships, the only way to create a deeper, more meaningful, and ultimately more effective relationship is by investing time into the other person.

Whether you do weekly check-ins or monthly coffee (or cocktails!) or vacation together with your families, more than anything, it is making sure you have each other’s back. Know each other’s professional and personal goals and support each other in making those happen.

At the end of the day, the most effective Executive Assistants and Chief of Staff partnerships are the ones who are committed to developing their partnership, helping each other succeed, and who communicate, communicate, communicate!

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