How Can a Chief of Staff Effectively Support Multiple Executives?

The chief of staff role can look different depending on the organization, the executive who is

being supported, and the culture of the workplace involved. Chiefs of staff can be deeply embedded within the organization, working as a right-hand to their executive, but they can also be fill-in support of administrative tasks that need to get done but can’t fall under the wheelhouse of important c-suite leaders. Because the chief of staff role can be so variable, it is possible for one chief of staff to support multiple executives, as long as they know just what they’re getting into and they prepare themselves ahead of time.


As an organization that supports multiple clients in all varying industries, we have certainly had chiefs supporting multiple clients at one time. We have a couple of trade secrets for how to make those partnerships work so that everyone benefits.


#1: Have Crystal Clear Expectations

This may seem obvious, but we can’t say it enough. There have to be very clear expectations in place from each client that the chief is supporting so that they can determine exactly how much bandwidth they’ll need to give to each client in order to determine how they’ll be spending their time and ensure they’re keeping up with their responsibilities.


Once you are clear on expectations, you can do a rough estimate of time percentages that you’ll need to dedicate to each client. Is one executive deeply involved in a bigger project with a looming deadline that they need your support on? Are you doing minimal busywork that can be completed at any time during the week (or weekend) for another client? Do you support an executive at an startup that is in the early stages and it’s all hands on deck?


Remember, too, that your situation will change from time to time, depending on what each client has going on. For different organizations, there will be peaks and valleys of workloads. Try to prepare for these periods as much as possible so that you can manage your own workloads between clients.


#2: Capitalize on Efficiencies

When a chief of staff is planning out how they will support multiple executives, it’s important to take a broad scope view of things. If you are supporting multiple executives at the same organization, how often do those executives’ work streams cross paths? And how can you use that to create a more efficient model of your time? For example, could you plan leadership team meetings that involve both the executives that you’re supporting? When leaders have work that is aligned, it is a natural fit for the shared chief of staff to support team activities that both of those leaders are involved with.


#3: Establishing Prioritization

When a chief of staff is supporting multiple executives at the same organization, there will most likely be times when competing priorities come into play. The value of communication and organization cannot be stressed enough here. Be proactive and hash out situations where there might need to be prioritization ahead of time, so that all parties are equally prepared. How will the chief of staff’s time be divided in these scenarios? Determining a process for those decisions before you actually have to make them is key. Have a plan in place with metrics for analyzing prioritization so that you can make an informed, level-headed decision when the time comes to split hairs and determine to which project or leader the chief is going to dedicate their precious time. And make sure it is a team effort--don’t put all of the expectation for the prioritization process on the chief of staff. The leaders should be involved as well. Of course, if a chief of staff is operating between multiple organizations, the onus will be on them to determine how to delegate their time, but they will have much more success in doing this if they keep the lines of communication open with all of the executives they are supporting.


#4: Feedback Matters

Another very important part of the planning process if there is a shared chief of staff within an organization is determining reporting structure:

  • Is the chief of staff actively reporting to multiple executives?

  • Is each executive giving that chief feedback on a regular basis?

  • Who is making decisions about advancement for the chief of staff, performance reviews, etc.?


#5: Supporting Multiple Executives at Multiple Organizations

You may be wondering if it’s possible for a chief of staff to support multiple executives at different organizations. We are very familiar with this concept as this is how many of our chiefs operate and our business model is set up to accommodate this very scenario, given the right mix of client and chief.


We spoke with one of our chiefs, Lindsay Hoag, who has supported three clients simultaneously from different industries: college, think tank, and ecommerce. Because the college client has set hours and her role requires collaboration with many people, including the executive leadership team, she spends the majority of her time with this client.


“It is a team environment and often work deliverables require frequent communication and total focus,” says Hoag.


For the remaining two clients, she only works a few hours per month supporting them and the work is “conducive to independent performance,” according to Hoag.


For example, the working group that she supports at the think tank only meets every 6-8 weeks, so she can predict that the week leading up to the meeting will be busy with coordinating the agenda, attendance, and speaker calls.


In addition, her work with the ecommerce client consists primarily of independent tasks like performing research or updating product cost, work which she can complete during irregular hours like evenings or weekends.


Hoag’s top tips for supporting multiple executives at one time:

  • Know your deadlines.

  • Communicate frequently with your clients.

  • Get organized: whether that’s with a white board, online or written calendar, to-do list, etc. Hoag likes to write out tasks and deadlines where she can see them.

  • If you manage three email accounts, one for each client, send the meeting invites to your personal email calendar so that you keep track of all the meetings

It is entirely possible for a chief of staff to support multiple executives at one time. But both parties will definitely want to consider how they want the chief-executive relationship to look, what the expectations will be for the chief’s duties, and how they can balance all the work to be done. Having realistic expectations for yourself as a chief is crucial before you commit to more than one executive.