Recurring Tasks for a Virtual Assistant (or Executive Assistant)

Consistent tasks to outsource that provide compounding benefit.

Photo by Tom Wilson on Unsplash

Professionals encounter hundreds of minor inconveniences that reduce productivity and create tension. In many cases, we have grown accustomed to them. We troubleshoot these issues over and over again without realizing it.

It’s rarely 1–2 big things that zap our productivity. Instead, it’s death by a thousand cuts and victory by a thousand wins.

Assistants are a cost-effective way to remove these problems. Yes, it’s great to have some help with one-off tasks, but benefits compound the most from systems and processes happening in the background without you needing to be involved. Powerful use of an assistant comes with the delegation of routines and recurring tasks.

The following information lists my top categories of recurring tasks, specific tasks I’ve found helpful, why I do each, and simple examples. I even included copy/paste-able language to get your assistant started.

This post is long, so here is a summary of the tasks with links to jump down to whatever seems interesting:

• Every Morning, Resolve Schedule Conflicts.
• Every Morning, Review Inbox.
• Every End-of-Day, Confirm Reminders for Tomorrow’s Outliers.
• Every Thursday, Solidify my Schedule for Next Week.
• Every Thursday, Send Schedule Overview to Family.
• Every Friday, Send a Rollup of Meeting Followups.
• Every Friday, Send a Weekly Work Summary.
• Every Month, Submit Company Reimbursement Requests.
• Every Month, Review Meeting Priority List.
• Every Credit Card Purchase, Record Transaction.
• Every Trip, Build Itinerary with Trip Details.
• Every Reschedule, Prevent Double-Rescheduling.

Daily Tasks

Every Morning, Resolve Schedule Conflicts

Being double-booked seems to be unavoidable. The most common occurrence within my schedule is a personal appointment competing with a previously scheduled meeting. So, for example, a child’s medical appointment with a specialist conflicts with our weekly team call.

Unfortunately, because of the last-minute nature of these changes, I would rarely catch them in time. I’d either miss the child’s appointment or cancel on a team member last minute. Both outcomes erode trust and credibility over time.

Each day, my assistant should be keeping an eye out for double-booked meetings and subtle overlaps in timing. While better calendar options exist, I prefer Apple Calendar because it allows you to look at many unrelated calendars side-by-side. For example, I see a rollup of my personal, work, and side-project calendar in one place. Conflicts are obvious.

Wanna try? Here is a template to ask your assistant to start daily conflict resolution:
“I’d like to start double-checking my schedule for conflicts to avoid canceling on people last minute. Please set a time daily either the previous day or first thing in the morning, to ensure all conflicts are resolved. If the overlap is 10–15 minutes, see if you can shift slightly or reduce meeting time. If the overlap is more than 30 minutes, reschedule on another day.”

Every Morning, Review Inbox

I place a high value on being responsive, but the email inbox can become a productivity graveyard. Most of my email accounts are 8–15 years old, which means they’re a crazy cocktail of newsletters, spam, random messages, and urgent needs.

Making matters worse, the garbage is mixed among the gold. I regularly improve spam filters, go on unsubscribe rampages, and use all kinds of tools. But, regardless of what I’ve tried, a person is still needed to make sure important information does not get missed, but that person doesn’t need to be me.

Each day, I postpone my entry into the inbox to give a chance for my assistant to have the first look. Newsletters get sorted out, unsubscribe violates get escalated, important items get flagged as such, and more.

Wanna try? Here is a template to ask your assistant to start daily conflict resolution:
“I need help reducing the time I spend in my inbox. Please review the items in my inbox before 9:30am. Flag any urgent/important requests or stuff that’s been sitting in there for more than 48 hours. Sort newsletters into the “newsletters” folder. Archive anything that looks like blatant spam but keep stuff that looks like it was sent by a human.”

Every End-of-Day, Confirm Reminders for Tomorrow’s Outliers

I have a healthy, long-standing morning routine. From wake-up until arriving at the office, I’m largely on autopilot. An important part of my schedule is delaying when I check my email and my calendar.

From time to time, however, there are meetings or events that occur outside of normal business hours. When I am in a sales-heavy role/season, it’s the norm. These outliers present a problem. Deviations from my usual schedule are easily overlooked.

If I don’t check my calendar until 9am, I could easily forget a random 8am coffee appointment. In the past, hours have passed without me recognizing the oversight.

When my assistant sets an appointment outside my typical work window, they schedule a text reminder as well. Then each day, they review to make sure the meeting or event is still on and that my special reminder is set to go out. In some cases, they might even include a special message the day before.

Disclaimer: The effectiveness of the text reminder is in part due to how I communicate with my assistant. Slack and email are our default communication channels. Texts are only used in emergency situations, so I’m trained to treat them with more importance.

Wanna try? Here is a template to ask your assistant to start checking for outliers:
“Please start reviewing my schedule for meetings or events outside my typical work hours/days. Set a text reminder for first-thing in the morning on the day of these pre/post-work events so I don’t miss them.”

Weekly Tasks

Every Thursday, Solidify my Schedule for Next Week.

I like to plan the upcoming week each Friday afternoon. It helps to have details and dates solidified the day before. It’s never perfect, but the more confirmations I can secure before my weekly planning, the stronger the odds my week plays out as I expect.

Scheduling for most people is a “squeaky-wheel situation.” If the squeaking wheel gets the oil, I want to make sure my meetings don’t fall through the cracks. If the meeting isn’t important, I should cancel. Otherwise, I want to lock in the timeslot before something else on their calendar gets priority.

Wanna try? Here is a template to ask your assistant to start checking for outliers:
“Each Thursday morning, follow up with any unresponded meeting invites for the following week. Prompt people (politely) to confirm or reschedule. If I haven’t replied to an invite, remind me too.”

Every Thursday, Send Schedule Overview to Family

Implementing this one task singlehandedly removed the largest stressor from my marriage. No one likes surprises. Surprises are particularly challenging when two areas of life collide. For example, I was consistently encountering frustrations at home when a work event would overlap with personal time. I made matter worse by under-communicating the overlap until the last minute.

My wife would regularly learn about an important work dinner the night beforehand. In plenty of cases, I would inform her only hours before I was scheduled to arrive.

In my defense, appointments regularly appear and disappear off my calendar. Our team might put two events on the calendar, only expecting to use one. Travel plans could make something highly tentative. Approval or rejection from a single attendee could invalidate the need for a meeting altogether. The list goes on.

Either way, it was shitty for my wife. She had every reason to be frustrated.

Despite what you might be thinking, this is not a promotion for better “work-life balance” (though you can read my thoughts on that topic here). In some ways, it’s allowing personal life and work-life to play nicer together.

Every Thursday, my assistant sends a summary email to my wife and me. It outlines the next two weeks of events that fall outside my normal work hours and days off. By getting two weeks’ worth of appointments sent weekly, it leaves plenty of time to make changes or discuss why it’s worth me borrowing from our family time. It also gives my wife plenty of time to arrange a babysitter if the event calls for it.

Wanna try? Here is a template to ask your assistant to start a weekly schedule summary for the family:
“Each Thursday evening, please email a summary of every meeting for the next two weeks that is outside my normal work hours. Group them by ‘before work’, ‘after work’, ‘weekend’, and ‘travel’. Include my wife in the email and send even if no events exist.”

Every Friday, Send a Rollup of Meeting Followups

I am bullshit on following up after meetings. It’s one of the easiest ways to stand out as a professional. My rule: “Follow up, every time, and with everyone.”

While I place a high value on following up, I’m not immune to forgetting or yielding to distractions. Getting a rollup of my meeting follow-up ensures nothing falls through the cracks.

To ensure every meeting gets a follow-up, my assistant creates a ‘send follow-up emails’ task on my to-do list (I prefer Asana). Within the task is a list of each meeting from that week and whether I’ve sent the follow-up yet.

While I regularly send 50% of my follow-ups before I see the task, it’s a useful reminder while closing out my week.

[INCLUDE SCREENSHOT]

Wanna try? Here is a template to ask your assistant to send a rollup of meeting follow-ups:
“Each Friday, create a task for me to ‘send follow-up emails’ and include a list of everyone I met with from the week. One task with a bulleted list in the description. Review my inbox to confirm whether or not I’ve sent a follow-up yet and specify the status beside their name.”

Every Friday, Send Weekly Work Summary

I’m not a fan of micromanaging an assistant. I do, however, like to get a baseline understanding of what’s being worked on and how long a given task takes. I’m constantly looking for ways to operationalize my requests for my assistant and I’d hope the same tasks get faster over time.

A weekly summary helps accomplish that.

While I hope they’re assembling this along the way, every Friday my assistant sends a summary of what they’ve been working on and how much time they spent.

WARNING: If you overanalyze this summary or question things too often, you risk creating an adversarial relationship with your assistant. Think of it as a tool to improve your processes, not nickel and dime their efforts.

Wanna try? Here is a template to ask your assistant to start sending a weekly summary:
“Each Friday, please send a spreadsheet of tasks you worked on this week. Add a column with an estimate of how long it look. Feel free to round to the nearest 5 minutes. Please send the report weekly, but I strongly suggest you log things throughout the week as you do them.”

Monthly Tasks

Every Month, Submit a Company Reimbursement Request.

While our company has individual cards for employee expenses, there are some edge cases where company charges end up on personal accounts.

For example, I lost my wallet. My personal card was the first replacement card I received but I needed to buy something for work. Also, I travel to Mexico for work. There are plenty of examples when the work card declines a transaction (likely assuming fraud).

Instead of delaying my assistant, they have permission to switch cards to complete a purchase or task. It’s not a major problem, but I need to be reimbursed eventually.

Each month, my assistant makes sure any company reimbursement gets submitted directly through our company reimbursement system. Since they do it on my behalf, I love seeing the confirmation email come through.

Wanna try? Here is a template to ask your assistant to start submitting company reimbursement requests:
“Each month, please submit any reimbursements you have on your list. Before you send, please check in with me to make sure there isn’t something on my list as well.”

Every Month, Review Meeting Priority List

A few years ago, I mapped out every type of meeting I’ve encountered. From ‘weekly internal, all-hands meeting’ to ‘external sales meeting. The different variations number between 30–40 different types of meetings.

Much like email, however, not all meeting types are created equal. To provide clarity for my assistant, I have adopted a similar framework our executive team uses to align company priorities.

The framework is “Even, Over Statements.”

The idea is simple: highlight the key tensions within a system and, using a series of statements, establish a baseline for how to reconcile the items against each other. Even, Over Statements do not imply that one item isn’t important nor that both can’t coexist. Instead, it guides decision-making in the event a tradeoff needs to be made. Once created, we then work to place them in a hierarchy, with the most important items first.

For example, here are some “even, overs” I’m workshopping for my assistant:

• Family Emergencies, even over everything.
• Executive Responsibilities, even over Meetings.
• Internal Team Members, even over External Partners.
• My department goals, even over other tasks.
• Focus time, even over last-minute changes.

Wanna try? Sorry, no template here. Step 1 is figuring out how you prioritize tensions within your work-life. Any easy place to start is within areas where your team or assistant look to you to choose between multiple options.

Event-Based Tasks

Every Credit Card Purchase, Record Transaction.

Some people are nervous about giving their assistants access to purchasing power. It’s reasonable. Assistants tend to have access to a lot of personal information. Carelessly combining that with access to finances could be a recipe for disaster.

Financial accountability is why I prefer assistants who live within the United States. Our legal system is clear on what constitutes theft, and tracking someone down is way easier. Of course, the financial cost is higher, but so is my peace of mind.

It’s unlikely I’ll convince anyone one way or another. My personal preference: There is more to gain by trusting others than there is to be lost by hoarding control. Be generous with responsibility, then hold them accountable.

At the risk of over-indexing on a moot point, here are five precautions I take to safeguard against payment issues. Heads up, the first 4 are good ideas, whether or not you plan on giving your assistant access to your spending:

1. Share credit card details (via password manager) but not bank account information.
2. Freeze your credit with each of the four major credit bureaus.
3. Communicate spending limits.
4. Set up alerts to notify you when one of your cards is used or a financial account is accessed.
5. Ask them to record transactions they initiate (with receipt and proof of my approval)

Wanna try? Here is a template to ask your assistant to start recording transactions:
“Every time you use one of my cards, log it within the “Assistant Transaction Spreadsheet.” Please include the date, a description, the cost, a screenshot where I consented, and any account information that’s associated (such as Amazon Prime, etc.). If you have to set up an account to make the purchase, please make sure the account details are added to the ‘Assistant Vault’ in 1password.”

If Travel, Build Itinerary with Trip Details.

Travel can produce a flood of details. Most details are relevant, but some are disproportionately valuable.

For flights, expected traffic to the airport, departure times, in-flight accommodations, and delays can change quickly.

For ground transport, ridesharing and car rentals are not always equally accessible. In plenty of cases, they should be scheduled in advance to ensure availability.

For hotels or Airbnbs, there always seems to be a door code, hidden entrance, or secret handshake that’s needed to gain entry.

When travel is booked, an assistant should begin building an itinerary for the trip. The goal is not to dump every detail. Instead, the focus should be on primary pieces of context or information needed to maneuver from A to B.

Wanna try? Here is a template to ask your assistant to start building an itinerary with trip details for travel:
“Every time I travel, I’d like a simple itinerary with essential information. Ideally, it’s a 1-pager with highlights (key times, access codes, addresses). Add full details after the 1-page overview in some sort of labeled appendix. Bonus points for including 4–5 star coffee and food options near the destination. Send me the URL once you create it AND the day before departure.”

Every Reschedule, Prevent Double-Rescheduling.

I have a higher threshold for people needing to reschedule on me than I have for myself rescheduling on them. I’ll let someone reschedule on me 3–4 times before pushing them on whether or not the meeting is important to them.

I avoid rescheduling back-to-back at all costs. My assistant knows this.

Every time I need to reschedule, my assistant first confirms I haven’t already rescheduled on that person. If it looks like I’m at risk of rescheduling twice, they’re instructed to follow up with me to confirm. If I’m going to reschedule on someone back to back, I at least owe them a further explanation. I often opt for handling this personally and with a phone call.

Wanna try? Here is a template to ask your assistant to prevent double-rescheduling on an appointment:
“Before you initiate the rescheduling of an appointment, please confirm the meeting hasn’t already been rescheduled. One reschedule is normal. Two, especially back to back, is flakey.”

Conclusion

One of my favorite parts about recurring tasks like those mentioned above: Certain tasks set up a chain reaction that snowball into serious advantages. Take travel, for instance. Travel makes an appearance across the following recurring tasks. Each task compounds to save time, increase peace of mind, reduce stress, and improve my overall output:

• Resolve Schedule Conflicts.
• Confirm Reminders for Tomorrow’s Outliers
• Solidify my Schedule.
• Send Schedule Overview to Family.
• Send a Rollup of Meeting Followups.
• Send Weekly Work Summary.
• Submit Company Reimbursement Request.
• Record Transactions.
• Build Itinerary with Trip Details.
• Prevent Double-Rescheduling.

I look forward to hearing what you think. Please pass them along if you have recurring tasks your assistant provides.