Making the Case for Effective Assistants

From Calendar Keepers to Extended Brains

Jul 1, 2022

The Brief Case 📚→ 💼 → 📊 →📈

In The Organized Mind, Daniel J. Levitin recalls meeting with Jimmy Carter when Carter was campaigning for the United States Presidency: “[Carter] spoke as though we had all the time in the world. At one point, an aide came to take him off to the next person he needed to meet. Free from having to decide when the meeting would end, or any other mundane care, really, President Carter could let go of those inner nagging voices and be there.”

We are channeling Levitin (channeling Carter) in part to underline a simple, three-part reminder for leaders at or near the top of an organization: (1) They should be doing more of what they are uniquely good at; (2) they should be doing less of what distracts from what they are uniquely good at; and (3) what they are uniquely good at should be aligned with the organization’s goals and needs.

Ongoing alignment of this kind requires effective approaches and systems. For that reason, we are going to offer a vision for modern executive assistants. When effective, an assistant’s relationship with a school executive (i.e., leader) should generate approaches and systems that multiply the skills and talents of that executive, on behalf of the school. It is possible — and profitable — for these often backstage players to not only schedule the calendars of school leaders, but also to extend their capacities.

📚 The Learning Case for Effective Assistants

In the last nine months alone, many of the Heads of School that we know have had to get “up to speed” in ways both predictable (ongoing learning about their school’s financial picture, ongoing learning about diversity and inclusivity, etc.) and unpredictable (COVID surges, town ordinances with which they suddenly had to grapple, etc.). During such moments, if they cannot learn — well and quickly — then they cannot lead.

The learning case for effective executive assistants is, therefore, quite literal. The top leaders at a school need to be the lead learners of the school; they need to learn efficiently, at times deeply, and often in a manner that drives urgent decisions; therefore, assistants that make room for or facilitate such learning are worth their weight in gold. These colleagues are essential to the leaders they support, and assuming that those leaders’ talents are aligned to their schools’ needs and aspirations, essential to schools.

So what might such work look like? How might an effective assistant support and extend the learning capacity of a Head of School, Board Chair, Division Head, or area Director?

Here is an extended example:

Most school leaders spend much of their time in meetings — meetings that they either call in order to drive progress, or meetings that they attend in order to provide input or blessings. Given our school context, it helps to think of meetings as the “classes” of a school’s leaders. At times, they need to teach those classes so that others can leave with the right mindset, skillset, knowledge, or context. At other times, they need to attend those classes, and likewise, emerge with the right mindset, skillset, knowledge, or context. In this sense, school leaders’ calendars are filled with teaching and learning, learning and teaching, all day long, via a series of meetings that then feed decisions and actions.

With that frame set, or rather re-set, an effective executive assistant might facilitate a leader’s learning by building a clearcut discipline around that school leader’s meetings as follows:

⓵ Before the meeting

Work with their supported leader to prepare meeting agendas that relate to what has been learned or uncovered in prior, related meetings or to the big goals of any particular quarter or year.

Ensure that their supported leader has both the time and the prompting to “do the reading” before each meeting. This suggestion is not meant to imply that school leaders are children who need to be told to do their homework; likely, though, their calendars are often so packed that they cannot adequately prepare for meetings. By continually setting aside time in advance of meetings and working to keep this “meeting prep” sacred in a school leaders’ calendars, executive assistants can help school leaders to be prepared to make the most out of every meeting.

⓶ During the meeting

Take task-oriented notes. We believe that leaders should take their own notes as well, because that’s a good way for them to synthesize information and therefore learn. Executive assistants, however, should take a very specific kind of notes during meetings, extracting to-do items or follow-up items as they occur.
Serve as the time-keepers and agenda-watchers. When leaders are the ones to stop a conversation, or move an item to another day’s meeting, they risk sending an inadvertent, possibly untrue signal about their priorities. If, instead, assistants are given the responsibility to advance an agenda (and this is treated as a norm for the groups) then they can adjust, and even interrupt — politely of course — without introducing the power dynamics that can exist when supervisors are the ones making such calls.

⓷ After the meeting

Convert task-oriented notes into concrete tasks in leaders’ calendars. These could be anything from, “X decision was made, so it will need to be communicated in a letter to the community” [calendar event = Draft letter re. Executive Committee Decision] or “Y looked unhappy during the discussion, sighing audibly at one point” [calendar event = 1:1 with Tom]. Again, we’re not suggesting that school leaders won’t leave meetings with their own impressions and their own sense of next steps, but having an extra set of eyes in the room, one that works deliberately to extract meaning and value from meetings, allows the school leaders to concentrate on being fully present in the meetings, just like Jimmy Carter in our opening reference.
Send timely follow-ups with notes, action items, and information about the next meeting (if applicable) to all participants in a way that is routine, consistent, and clear.

In short, when supported by effective executive assistants, school leaders will be prepped on the way into meetings, present when in those meetings, and pushed forward by those meetings. By extension, meeting attendees will also be well served.

We picked meetings as our use case because they show up in every school leader’s life, likely every day. More importantly, they demonstrate the ways an effective assistant can move from logistics (just calling meetings) to being an essential part of an executive’s ongoing learning process and even taking on what might be called leadership activities. There is a necessary step away from the institutional default that would have executive assistants thinking of themselves in limited roles and executives thinking of their assistants in limited roles.

💼The Business Case for Effective Assistants

About ten years ago, ex-Google CEO Eric Schmidt encouraged busy executives to respond quickly to all emails and to think of themselves as routers, moving information where it most needed to go. The underlying implication? Leaders can get in the way. Sitting on emails can stall progress or halt momentum. A too strict hierarchy can leave a lot of value “at the top,” like a traffic jam waiting to resolve.

Too often, this happens because the busiest people in an organization are often the same people who need to give final approval to, or budgetary support for, an idea. Or, they don’t believe that they have the time to explain to someone else how a project should be done. To coin a kind of reverse power law, there’s probably a lot of untapped value in most schools simply because the person in charge doesn’t have fifteen minutes (right now) to activate that value, see it through, and as a result, save fifteen hours (over the next six months).

Enter the most aspirational description of effective executive assistants: to become extended brains (and therefore extended doers, speakers, and listeners) for the leaders they support. When this happens, if this happens, executive assistants quite simply make their businesses (i.e., schools) better.

As extended brains, they might:

anticipate things the same way leaders might and bring them to attention;
execute tasks in a manner reflective of how leaders would (e.g., the way in which they reply to emails or perform tasks is a direct representation of the leaders with whom they work); and,
offer leaders multiple perspectives (think role play or devil’s advocate) around issues because of their proximity to the contexts (people and situations) that often are being discussed.

Best of all is when effective executive assistants complete delegated tasks or projects in better, clearer, or more delightful ways than the leaders themselves might.

A simple example: Reshan recently needed to pull together some articles and planning tools for a team to use during a day-long seminar that he was running. His version of “complete” for this task would have been to grab any folders he could find and to stuff the printed readings into them. This utilitarian approach would be sufficient (to him), and he asked his assistant to handle the task so that he could design the activities and think about the needs and learning styles of each of the participants. Case closed.

Except… his assistant produced school-branded folders, printed personalized labels, and organized school swag (a branded pen and a branded folio notebook) to add to the participants’ experience. She did not await direction or approval. She understood Reshan’s intent and thought of things she knew he would approve but also might not think of himself given his schedule that week. That’s the ideal state — for Reshan, whose end product was enhanced, and for the assistant, who added value to the seminar, and by extension, to the school.

We have seen assistants build websites in two weeks with information that had been sitting on a leader’s hard drive for two years. We have seen assistants take responsibility for a certain category of phone calls that used to go straight to a Division Head. And we have seen them build systems around everything from school outreach opportunities to student discipline matters. All because their capabilities rose in equal measure with the trust a leader was willing to place in them.

📈 Measuring the ROI of Effective Assistants

Ideally, leaders are hired, and then positioned, to make essential, unique contributions to their schools. For example, they may have years of deep expertise that can drive professional learning in a community, or they may have relationships that can help a school to navigate crises or fundraising challenges. These are the unique attributes for which leaders are compensated.

On the contrary, leaders are not necessarily valued by their ability to complete common tasks — tasks like scheduling, meeting notes, meeting follow-up, meeting reminders, proof reading, and so on. We’re not suggesting that common tasks are “beneath” the leader, and in fact, they should address them when needed. But, these tasks should lead to the same outcome every time, be consistently near-perfect, and be part of the predictable fabric of daily school life. As such, and by definition, they cannot be improved by adding a leader’s unique skillset or approach. They should be, therefore, the province of the leader’s assistant.

With that in mind, you can look at a school leader’s salary and time and an assistant’s salary and time in order to observe the return on investment for an effective executive assistant — one who can (1) handle common tasks with little to no input from leaders, (2) continually support leaders in doing more of what they are uniquely good at / paid to do, and (3) take on some leadership work on their own.

The basic ROI thesis is simple: if a school doesn’t pair its leaders with effective executive assistants, a leader’s time spent on common tasks is actually a net loss for the school in terms of its investment in that leader. When a school leader is spending time on something that someone else, with the right skillset and training, can be doing, that return on investment is negative when you measure that time at the cost of that other person (say, an assistant).

For example, let’s say that a school leader’s hourly rate works out to something like $67.50 an hour, and their assistant’s rate is something like $20.00 an hour. Any hour that the leader spends doing something that the right assistant could be doing is immediately a loss (-$47.50 in this case). Compound that over a week or a year, and the loss is significant.

An investment in effective assistants unlocks more from the leaders hired into the higher valued roles at a school. When the leader is spending more time on unique tasks and the assistant is able to take on some of those as well, not only does a school offset the loss, but also it gains value on the investment.

📊 Measuring the ROL of Effective Assistants

Most assistants help to schedule leaders into meetings. And most are good about gatekeeping, helping the leaders to see the people they need to see. They are usually good at handling the detailed setup of events, at serving as a front line for complaints, at adding grace notes from the school in the form of flowers, messages, etc. Many are good at proofreading.

If we take all of that as a given (the return of which is that all of these events and communications happen), then the return we want to be able to measure next is learning: the learning of executives and how it benefits their direct reports and teams.

Do they have the time and space to learn or are they always just barely fitting it in? Do they make prepared and precise use of their direct reports’ time? Do their schedules allow them to explore and understand the work of their direct reports and understand how they might offer support? Are their actions aligned with the mission of the school and inspiring to those choosing to spend their careers serving such a mission themselves?

To measure return on learning, a leader should use a monthly, anonymous survey with a 5-point scale that lets teams assess the leader’s capacity across three areas:

The leader’s respect of team members’ time and talents
The leader’s developing understanding of purpose within the team
The leader’s earned, growing confidence from the team

Each area should include a comment box to allow participants to explain their answers. A leader should be looking for growth across all three elements over time. In the absence of such growth, that leader should pay close attention to the comments and acknowledge them explicitly with the team. Likely, better utilization of an assistant will help to mitigate the articulated challenges (or ensure that they don’t arise in the first place).

School leaders who have access to a full-time administrative assistant and are still feeling overwhelmed/frantic are either not making good use of their assistant or have not hired or developed an assistant who possesses the modern skillset needed to assist effectively today.

Such overwhelm, too, is not simply a personal problem for the individual; it is also a problem for the school that the individual is charged to lead.

Making the Case