Partnering with an Executive Assistant (EA)

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I was lucky enough to have an Executive Assistant (EA) for a few years and this gave me an opportunity to think more deeply about time management  (Thanks, Bel and Annette!). I’ve invested ~20+ years thinking about personal productivity (YouTube, Presentation), and what follows are my best practices on how I maximize focus and impact by partnering with an EA. 

EAs transform a professional’s productivity and effectiveness. EAs adapt your calendar to match your energy levels, support your projects, improve team culture, and identify root causes of inefficiencies to improve your operation. 

Also, as AI permeates knowledge work, professionals must effectively partner with EAs to deliver maximum impact in their professional lives.

What follows are my best practices of partnering with EAs and time management. 

• Who needs an EA?
• What’s the Role of an EA? 
• Production Planning Tool: Calendar
• Meeting Timing, Coding, and Facilitation
• Preparation Blocks
• EA Guidance
• Operational Excellence: Variances and 5 Whys
• Project Management and Communications
• Team and Talent
• EAs in the Age of AI 

Who needs an EA?

“Everyone with more than one or two meetings a week should use a service or assistant,” per Cal Newport in his excellent book, World Without Email (book notes). Jonathan Swanson in his incredible X thread writes: “Matt Mochary has been CEO coach to Naval, founders of OpenAI, Notion, Coinbase, Reddit. His first requirement: Hire an EA.” Swanson’s post also shares an overview of various high performers’ use of EAs:

Knowledge work depends on specialization. Therefore, the fewer responsibilities that a knowledge worker has, the more opportunity there is for the knowledge worker to focus on an opportunity and deliver a breakthrough impact. Per Newport, knowledge workers should be “aggressive about identifying work that can be delegated.” By “hiring more support staff…Knowledge work can become massively more productive and sustainable.”

Imagine four busy knowledge workers across multiple time zones needing to meet within the next week. Each of their calendars are packed with meetings with some meetings being more or less important than others. Ultimately, it requires human judgment to review each person’s calendar, identify lower-priority meetings, weigh tradeoffs, and present the most viable options to the knowledge worker.

Unfortunately, business leaders have mistakenly believed that automation has eliminated the need for EAs. Some believe that online calendaring, calendly, and automated room scheduling software eliminates the need for EAs. I disagree. While technology makes the EA role more efficient, there is still a need for EAs at all levels of the professional hierarchy. 

As Newport describes it, “firms have leveraged technology to decrease intellectual specialization.” The knowledge workers are investing time in calendaring, tracking, organizing, event planning, project planning, and more. These are all tasks that can be more efficiently taken up by an EA, rather than the knowledge worker. 

What’s the Role of EAs? 

The role of an EA is to help business partners manage their time and attention in order to maximize their impact. Michael Hyatt, in his book, World Class Assistant (book notes), writes, “the power of an EA is adding margin to your life…Margin is like a savings account full of creativity, energy, well-being, and perspective…”

Each time a knowledge worker does work that could be handled by an EA, this is a double loss for the organization. 1) A potential EA is losing an opportunity to do work aligned with their skills and interests that adds value to the organization. 2) A knowledge worker is losing the opportunity cost, time, and broken attention that could be invested in more impactful work. 

I think of EA work as falling into 4 buckets: Operations, Project Management, Calendar Management, and Team Building. I will go more into depth on these topics below.

Production Planning Tool: Calendar

Andy Grove, in High Output Management (notes) writes, “Your calendar can be a valuable production-planning tool.” My calendar is my most important production planning tool for my most valuable resource - my time. How much effort do I forecast a piece of work will take? I put it in the calendar. What types of tasks will flow most efficiently through the system, dependent on my energy and creativity levels? I tend to focus better on deep work in the mornings so I keep my mornings open. I tend to be more creative and social in the afternoons so I do more 1:1s and brainstorming in the afternoon. Following the concepts in Kanban: Evolutionary Change in Technology (book notes), I limit my work-in-progress (WIP) commitments to ensure my production does not run over capacity. I also rate limit the number of speculative meetings and schedule those for late Friday afternoons so that I can focus on my most high impact work during the middle of the work week. Finally, I keep a buffer in the operation, so that my system can handle unplanned tasks or variable demand on my time. 

Another habit I’ve developed is the concept of MITs or Most Important Tasks borrowed from Leo Babauta. The idea is that I will set one goal per day, per week, or even for the entire year. This helps bring clarity to my goals. As a side hack, I try to complete this MIT before anyone wakes up in the morning so that I can feel less mental overhead during the day. This requires careful and thoughtful MIT selection. 

I am a firm believer that work will take 140% of the capacity that you allocate to it. There is always more work to do. That is why I am such a fan of Cal Newport’s fixed schedule productivity.

“The system works as follows:

1. Choose a schedule of work hours that you think provides the ideal balance of effort and relaxation.
2. Do whatever it takes to avoid violating this schedule.”

Calendaring is one of the most essential roles of an EA. This could be scheduling meetings, 1:1s, skip levels, internal meetings, customer meetings, and more. 

EAs should constantly groom their business partners’ calendars to ensure tasks line up with the energy level, priorities, and judgment of the business partner. 

Here is an example of what my calendar might look like that lines up my tasks with my energy flows and ensures I do not violate my fixed schedule:

My EA managing my calendar creates positive impact and margin for me, my wellbeing, and productivity. While it is possible to manage my calendar and meetings myself, it’s much better for the organization to provide EA assistance. Going back to Swanson’s X thread, “…Mochary believes in what he calls ‘cognitive offloading’ - your EA becomes your second brain. They manage all the details and follow-ups so your mind stays clear for the hard problems only you are uniquely positioned to solve.”

Meeting Timing, Coding, and Facilitation

EAs enforce standards around calendar invites. For example, whether I’m working at home or in an office, I am often in back-to-back meetings. Therefore, I need buffer to account for times walking to elevators or commute time between meetings. For a “30 minute” block, I like to call a 20 minute meeting that starts at either :05 or :35 and ends at :25 or :55. This allows for some buffer in between meetings to use the restroom or walk around. 

I also expect calendar invites to have a clear agenda, ‘This meeting will be successful if,’ facilitator, links to supporting documents, and pre-reads specified. EAs ensure that calendar invites have the required information before asking the business partner to invest time. 

My EA understands that we need to collect this information in advance of any meeting and include it in the calendar invite. This rigor saves the business partner time and confusion, and also helps every person with whom the business partner is interacting. 

I also categorize my 4 meeting types represented as different colors on my calendar:

• Meetings with Other People (Blue)
• Professional Tasks for Myself (Purple)
• Personal Meetings (Orange)
• Personal Tasks (Yellow)

This helps me keep a visual cue of the types of tasks upcoming in a day.

I take this all a step further. I set alarms for each transition on my phone each morning. This serves as an added layer of guidance and nudging to ensure I am on time for each of my meetings and commitments. 

Preparation Blocks

I’m not a fan of ‘tasks lists’. I like project plans that list out each work item that needs to get done, start time, end time, and status. But I do not like endless personal tasks lists that seem to add more and more items faster than I am able to complete them. As an alternative, I prefer to schedule time or tasks or commitments directly in the calendar. 

Cal Newport in his post, Beyond To-Do Lists, does a great job of summarizing my process. 

I was talking recently with a friend who is a [product manager] at a tech company who happens to also be particularly interested in productivity strategies. He told me about a fascinating habit he’s been deploying with great success in his own work life. Instead of maintaining endless to-do lists, when he takes on a new obligation, he puts it on his calendar: scheduling a specific date and time when he will tackle it. As he clarified, this approach applies even if the obligation is just to “think some about this topic.”

This might sound extreme, but it shouldn’t. What my friend is really doing is acknowledging that he has a limited amount of total time to spend on tasks. By scheduling each obligation, he’s confronting the reality of how much time each item will actually take, and identifying where these mental cycles will come from.

In knowledge work, we often ignore these realities. We pass around obligations like hot potatoes, via dashed-off emails and Slack eruptions, often pushing ourselves beyond what we can realistically accomplish, compensating by dropping things or completing them at a low quality level. This can’t possibly be the best way to organize cognitive work. And as my friend demonstrates, it’s not the only way.

I’ve been writing all week about how the disruptions in knowledge work we’re facing in the current moment might be an opportunity to spark radical new ideas about how this sector operates. This particular issue, confronting how we’re actually allocating our attention, is as good a place as any to start.

Each morning from ~5am to ~7AM, I like to schedule a ‘preparation block.’ This is a deep work block on a specific topic. In general I try to get my most important work done before my ‘normal’ work day starts. I will also try forecasting how many ‘preparation blocks’ I might need on a particular topic. For example, I might need 5 ‘preparation’ blocks in order to write a first draft of a strategy and incorporate comments. I also rate limit the number of ‘deep work’ blocks each day. My energy is highest in the morning, so I will often schedule my deepest work in the morning. In this case, my mornings may look something like this:

This combination of 1) rate limited ‘preparation blocks’ and 2) long uninterrupted chunks of ‘deep work’ combine to ensure I have clarity on my A+++ priorities and I’m investing my most important time in getting this work done. 

I often give guidance to my EA, such as, “I’d like 3 hours of prep blocks to review [XYZ] request that came in from the executive” or “2 hours of prep blocks to write that strategy” etc.  In general, I try over-estimating the amount of time that I need to complete a task. This serves three purposes:

1. I do not overload my schedule 
2. I ensure I’m crystal clear on my top priorities
3. This creates a buffer for myself - which can always be filled with email, catch up, and other work.

EA Guidance

One of the most critical artifacts that I leverage in partnership with my EA is our joint EA and Business Partner Guidance. This is a playbook or set of instructions that guides the way that my EA and I collaborate. I do not want to repeat guidance because that creates friction in our operations and collaboration. Therefore, I’d rather create a general  ‘rule’ or ‘guidance’ on how we are collaborating and store that in a shared document. This way, any time the EA wants to understand my approach to making a decision, he or she is able to look at our shared guidance together. 

Here is example guidance on how I like to operate:

• For any meetings with XYZ person, please ensure I have 2 prep blocks and 1 debrief block
• Please do not move the following meetings: XYZ
• When I make a request, please either A) complete the request within 48 hours or B) create a ‘project’ with that request, task list, expected ETA [including weekly updates on all open projects and statuses]
• When scheduling a ‘meet and greet,’ please ensure they are 45 minutes
• In advance of our 1:1, please plan to: groom at least 3-4 weeks of the calendar (ie. identify conflicts, prepare your questions for me, etc.), ensure questions/conflicts are documented, make sure project statuses are updated, and try synthesizing and documenting ‘principles’ from how we interacted into general guidance
• When someone asks for my time for a group meeting, can you please put in the invite clear
• Please prioritize exec meetings over other meetings. 
• Please keep meeting times consistent if we reschedule (ie. don't shorten 45 min meeting to 20 mins to make space)
• Please make sure meetings start at :05 or :35 and end with either :05 or :10 before the hour or half hour
• Please give weekly updates on open projects and how we're tracking against our ETA and status updates.
• Please give a heads up in advance if you're not able to respond to requests from stakeholders within ~1 business day
• If folks do not accept 1:1s the day before a meeting is scheduled, please cancel the calendar invites and remove them from the calendar
• Please confirm with me before scheduling on top of "buffer" slots.
• Please avoid recurring 1:1s before 9:30AM PST 
• Please update / groom our shared guidance in the spreadsheet ongoing as I adjust expectations
• Please email me your proposed changes to our joint guidance 
• For situations where you are not aware of the 'guidance' or I introduce something new, please proactively add it to our joint spreadsheet and confirm with me that you added it
• Please add the following earnings calls (ABC, 123) to the calendar as soon as you know the dates and 1 ‘prep block’ per earnings call to read each quarter

Operational Excellence: Variances and 5 Whys

EA is a highly operational role. EAs must hold a high bar in terms of reliability, consistency, and predictability. Operational work may include: business-partner specific workflows, distribution list management, travel briefs, travel planning, expense management, and more. For example, if the business partner hosts a monthly strategy meeting, then the EA can manage the spreadsheet of topics, manage the invites, ensure the pre-reads are completed and distributed in advance, confirm with the presenter, etc. 

For email or Slack or Teams management, I am a fan of Inbox 0. 

For day to day work, there will always be slip ups. Meetings will be missed, the wrong folks might get invited to a meeting, emails might be missed, projects may not be completed within the expected ETA, and on and on. I think missing or ‘variances’ are a normal part of operational work. 

But I also think we should diagnose any misses to ensure that we reduce the likelihood of them reoccurring. One method I’ve encouraged EAs to use is ‘5 whys.’ The idea is that each time there is a miss, ask yourself ‘why’ 5 times to get to the root cause of the variance. 

We want to understand the learning from each variance. For example: was my guidance unclear? If we fell behind in calendaring during a planned vacation, do we have rigorous procedures  / coverage plans for what to do if someone is sick? 

All this can be improved by constantly asking ‘why’ and then trying to change our habits and guidance. 

I also encourage EAs to keep a list of ‘learnings’ from doing the ‘5 whys’ process to ensure we continuously improve our operational excellence. 

Project Management and Communications

Project Management is another area for EAs to scale their impact. At the lowest level, this might include tracking next steps, updating statuses, and proactively communicating with business partners about a project. But project management can scale in complexity to involve multiple stakeholders and larger, more complex projects. 

Another critical aspect of project management is scope management. An EA should be able to respond and give ETAs for requests, and proactively communicate if those ETAs will be missed. An EA should manage their own capacity and say ‘no’ to requests if they are beyond the capacity for the EA to do quality work on the task. 

EAs should be very clear on what is and is not within the scope of a certain engagement. For example, I had an EA who, given capacity, would help with: expenses, calendaring, booking travel, and managing distribution lists, but would not work on note taking or social media management. 

Team and talent

One of the biggest superpowers of EAs is helping curate the culture of the team. For example, EAs can be great partners in organizing events, helping with celebrations, giving gifts and appreciations, and informally checking in with teammates about their happiness and engagement. I’m a fan of employee voice surveys (see my post Dear New Group Product Manager), to understand the happiness and engagement of the team, and EAs can play a central role in ensuring the organization follows through on commitments from the employee voice surveys. 

I also believe EA talent should be developed and led like any other top talent in the company. This means having regular 1:1s with EAs, understanding their career goals, supporting them with understanding their strengths and potential growth opportunities, securing mentors for them, training them, and coaching them to achieve high performance. 

EAs in an Age of AI

I believe demand for EAs will only grow with the advent of AI. Time will remain our most precious resource, and people will continue to value thoughtful, caring, and insightful support to manage their time.

I don’t believe AI will replace entire job families. Rather, AI introduces automation to portions of tasks that are already part of a job, enabling the employee to handle more scope, complexity, and challenges. 

In the case of EAs, I believe the role will remain to help business partners create margin in their lives and manage their time more effectively. This requires human judgment to align with values, maintain operational excellence, build relationships, and use AI tools effectively.

One company thinking deeply about the future of EAs in an age of AI is Athena. They’re training EAs on the latest AI tools such as ChatGPT, Zapier, and FirefliesAI, while offering career paths to EAs in social media management, payroll, event planning, and more. They also create playbooks to streamline tasks, from grocery automation to accountability check-ins to vacation planning and more. (Side note - the Swanson X thread is the co-founder/CEO of Athena).

As AI improves, more professionals will have access to EA support, increasing demand for the profession. I imagine a future of AI-powered EAs leading teams of AI assistants, guiding their work, while helping their business partners achieve even greater focus and impact

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