It’s 9:00am, Monday morning.
You’ve just finished your second cup of coffee for the day as you open your inbox. One email immediately stands out: It’s from Gina Hargreeves, a former-colleague-turned-founder you used to be close with.
It’s been six months since you last talked, and she wants to catch up. Excited about reconnecting, you write back that you’d be happy to catch up and CC your EA to lock in a time.
And with that, you don’t give it any further thought. They’ve got it under control, right?
Two weeks pass. It’s Monday morning again and, seemingly out of the blue, you remember that email from Gina. You check your calendar but don’t see anything locked in.
“That’s odd,” you think, “I wonder what’s taking so long.”
You reach out to your EA for an update, only to receive a profuse apology. “It must’ve slipped through the cracks,” they say. You’re frustrated, but understand mistakes happen. You ask them to get on it, and they promise they will. The call gets locked in for a week later.
You walk into the meeting, excited to catch up. The conversation goes well and, when she asks what’s new in your world, you share your struggles to find a VP of Engineering. Gina’s face blanches.
“You’re kidding, right?” she asks, “I really wish we’d talked sooner! A friend of mine just accepted a Director of Engineering role a few days ago—man, they’d have been perfect for you! I can still intro you, if you’d like?”
You accept, but know this ship has likely sailed—which is a huge bummer, because a referral from Gina would be worth its weight in gold. You try not to get frustrated but can’t help thinking there’s got to be a better way. After all, this isn’t the first opportunity you’ve missed because something as simple as scheduling isn’t running as smoothly as you know it should.
There’s got to be a better way, right?
There is a better way.
Scheduling mistakes aren’t an inevitable part of an EA/exec partnership. They’re typically the result of an ineffective system, rather than a careless assistant or demanding executive.
In fact, I want to pause and make one thing clear: Any EA who manages a calendar deserves a shout-out. Most people don’t appreciate the challenges that come with scheduling. It’s one of those things that looks easy on the surface, but has layers-on-layers of complexity. It’s hard work. So know this article isn’t meant to shame EAs who’ve made scheduling mistakes; it’s meant to empower them to reach their fullest potential.
So, to repeat: Scheduling mistakes are rarely the fault of a careless assistant. They’re the result of a broken system. But what is that system, and what are the problems?
Although it might look a little different from person-to-person, the basic approach to scheduling is mental juggling: Your EA is trying to manage dozens—if not hundreds—of responsibilities in their head.
Our brains simply aren’t built for that, and it can cause massive stress. When you try and track everything in your head, things will fall through the cracks. It’s just a matter of time. These stresses and oversights only heighten as more items are added to your plate. Which leads to the first problem: Structure, or a lack thereof. Most EAs don’t have a clear structure or workflow to track scheduling items.
The second problem is a lack of transparency. As an exec, you typically have very little transparency into how your calendar is being managed so you’re left wondering things like:
- Has the meeting with John been locked in?
- Have we followed up with Jamie?
- Where did my sync-up with Jin go?
These unknowns often add a subtle unconscious stress that eats away at you and sabotages your trust in your assistant. And these two problems—a lack of structure and transparency—ultimately create a recipe for disaster.
So what do we do about it?
Simple: We use a system with built-in structure and transparency. And if the success stories of my clients are any indication, you can kiss scheduling mishaps goodbye.
Here’s how it works.
Flipping the Script: Effortless Scheduling in Asana
Let’s work with the same situation as before. Don’t worry if the specifics don’t make sense yet—I’ll explain it all shortly.
It’s 9:00am, Monday morning.
You’ve just finished your second cup of coffee for the day as you open your inbox. One email immediately stands out: It’s from Gina Hargreeves, a former-colleague-turned-founder you used to be close with. It’s been six months since you last talked, and she wants to catch up. Excited to reconnect, you write back and CC your EA to lock in a time before moving on with your day.
The moment your EA sees the email come in he opens Asana and creates a new task to lock in your meeting with Gina. Once he’s reached out to Gina with a few available times, he moves the scheduling task to “First Contact Made.” He sets the due date for three days out and moves on to his other responsibilities. The whole process takes about 5 minutes.
Thursday morning rolls around, and Asana alerts your EA that Gina’s scheduling task needs an update. They realize Gina hasn’t responded to their initial outreach. After drafting a quick follow-up email, your EA moves the scheduling task from “First Contact Made” to “EM Follow-Up #1,” sets the due day for another three days out, and moves on with their day.
Not an hour later, Gina responds with a profuse apology for missing the email. She’s eager to meet, but the times your EA offered don’t work. Your EA offers a few new time slots, then moves the task from “EM Follow-Up 1” to “In Scheduling (Direct).”
One email later and the meeting’s locked onto your calendar for tomorrow at 11:00am. Your EA moves the scheduling task from “In Scheduling (Direct)” to “On Calendar.” He sets the due date for tomorrow (the day of the meeting), and lets you know everything’s good to go.
You walk into the meeting the next day and, when Gina asks what’s new, you share your frustrations around finding a VP of Engineering. Instead of blanching, Gina’s face now lights up.
“Really?” She exclaims, “What a coincidence!” She tells you about Georgia, an “insanely talented” friend of hers she thinks would be perfect for the role. And apparently the timing couldn’t be better: She’s looking for a new job and, although he’s in talks with another company, he’s not particularly excited about them. She asks if you’d be interested in an introduction, and you excitedly accept.
Shortly after the meeting, as your EA closes off Gina’s scheduling task, he sees he’s been CC’d on a new email—this time to lock in a meeting with Georgia. He opens Asana, creates a new scheduling task, and begins the cycle anew.
Same Situations, Very Difficult Outcomes
In the second story, your EA didn’t need to track everything in their head. Instead, they used a step-by-step workflow designed to guide scheduling tasks from initial outreach all the way through locking in the date.
But it’s not just about mistakes avoided—it’s about the massive reduction in mental load for you and your EA. Inefficient scheduling is stressful; most people don’t realize just how stressful it is until that weight is suddenly lifted.
And keep in mind: The story above only highlighted a single scheduling event. Most EAs are tracking dozens of scheduling items at any given time, and that’s where this system really shines. Once it’s up and running, here’s an example of how this approach might look:
Imagine your EA—or anyone, for that matter—trying to track all of that in their head (in addition to the dozens of other responsibilities on their plate). It’s impossible.
And yet that’s how most EAs try to manage a calendar. Is it any wonder things fall through the cracks? Now they don’t have to.
If you want to learn how to set up this system for you and your EA, read on.
Enter Asana: Your EA’s Secret Weapon
The backbone for this entire system is a Asana: A flexible and collaborative project management tool. We use it to run every aspect of our organization here at Mindmaven, and we’ve trained countless clients and their EAs on how to use to manage their priorities and ensure the things that matter most don’t fall through the cracks.
For the scope of this article, I’m focusing exclusively on how to set up Asana as a scheduling tool, but that’s just scratching the surface of what it can do. If you’d like to learn more about getting started with Asana, check out their Quick Start Guide here.
Note: These aren’t necessarily the best practices we teach our clients, but they’ll be enough to get you started.
You might be wondering why we recommend Asana for scheduling.
The reason is simple: Standard calendaring tools—like Google Calendar, Apple Calendar, or Outlook Calendar—aren’t built to run complex workflows; they’re built to display information.
But scheduling is a multi-step process. This leads many EAs to create their own hacked solutions, often culminating in their inbox being their task management tool. The problem? The inbox isn’t meant for complex workflows either. And so it’s inevitable things fall through the cracks.
Asana, combined with the right workflows, eliminates these issues once and for all.
Can you use other task management tools, such as Trello or Monday? Sure, but Asana’s the best we’ve found: It’s simple, collaborative, and straightforward—it’s the tool we train all our clients on, and the tool we recommend for you.
Note: For the sake of length, this article will only walk you through how to set up a scheduling workflow in Asana. For a step-by-step guide on how to use this system, download our free book:
Setting Up Asana for Scheduling
Configuring Asana for optimal scheduling is a simple three-step process, and shouldn’t take more than 7 minutes.
Step One: Create and Link Asana Accounts for You and Your EA
If you don’t already have one, you and your EA should sign up for a free Asana account. I recommend using your company email addresses, as it makes the process of linking your accounts automatic.
Having trouble? You can learn more about account creation and linking here.
Step Two: Create an EA Support Team
A Team in Asana is simply a collection of related Projects. In this case, we want to create a Team to house everything related to your exec/EA partnership.
Here’s how to create a team:
- Click the orange “+” button in the upper right-hand corner of the Asana window.
- Click “Team.”
- Under “Team Name,” write “NAME’s EA Support.” For example: Amanda’s EA Support.
- Under “Members,” add the email address your EA used to sign up for Asana.
- Click “Create Team.”
Step Three: Create a Scheduling Project
Once you’ve created your Team, it’s time to create your scheduling project. A Project in Asana allows you to organize all the tasks related to a specific objective. In this case: Calendar Management.
Here’s how to create your scheduling project:
- Click the orange “+” button in the upper right-hand corner of the Asana window.
- Click “Project.”
- Select “Blank Project” for the list of options.
- Under “Project Name,” write “NAME’s Ongoing Scheduling.” For example: Amanda’s Ongoing Scheduling.
- Under “Team,” ensure the EM Support Team we setup in Step Two is selected.
- Set “Default View” to “List.”
- Set “Privacy” to “Public to NAME’s EA Support.” This ensures your EA will have access to the Project.
- Click “Create Project.”
We’ve now created the Project, but it’s just a blank slate that looks like this:
We’ll need to use Sections to turn this Project into a step-by-step scheduling workflow. Your EA will use these Sections to move scheduling events from beginning (initial outreach) to end (the meeting taking place).
Here’s what it’ll look like once we’re done:
I’ll walk you through how to create those in just a moment but, first, let me explain the purpose of each Section above. Note that you’re going to see two terms:
- EM: Engagement Manager. This refers to your assistant. An Engagement Manager is a powerful hybrid between a skilled EA and a chief of staff. You can learn more about turning your EA into an EM here.
- Exec: Executive. This refers to you, as the one who ultimately “owns” the relationships your EA is interacting with.
Okay, let’s talk about the Sections:
- First Contact Made – Indicates your EA has reached out to the other party to begin the scheduling process.
- EM Follow up 1 – Indicates your EA didn’t receive a reply to their initial outreach within three days, so they sent a follow-up email.
- EM Follow up 2 – Indicates your EA didn’t receive a reply to their first follow-up after three days, so they’ve sent a second follow-up email.
- EM Follow up 3 (Alternative Outreach) – Indicates your EA didn’t receive a reply to their second follow-up, so they’ve followed up for a third time. When possible, they’ll try a new medium (such as a phone call or text message).
- Exec Follow up 1 – Indicates your EA did not receive a reply to their third follow-up after three days. At this point, it’s time for a check-in email directly from you. If your EA has access to your inbox, they can draft the check-in email for you to send.
- Exec Follow up 2 – Indicates you didn’t receive a reply to your check-in after three days, so your EA drafted a second follow-up email on your behalf.
- Exec Call List – Indicates you didn’t receive a reply to your second check-in email after three days. At this point, you can either choose to try to call the other party, or decide to stop following up.
- In Scheduling (Direct) – Indicates your EA received a response directly from the other party and they’re in the process of locking in a time and date.
- In Scheduling (Via EM) – Indicates your EA received a response from the other party’s assistant, and they’re in the process of locking in a time and date.
- On Calendar – Indicates that the date and time for the meeting have been confirmed with the other party and the event is on your calendar.
- On Hold – Indicates that a scheduling item is on hold. A scheduling item might be On Hold after multiple follow-ups with no reply, or if the other party requests to push off finalizing anything for a couple months.
As you can see, that covers each step of a standard scheduling workflow. It’s worth noting, though, that you’re free to customize the process. Want more follow-ups? Fewer? Want to be involved sooner? Simply add, remove, or rearrange Sections.
Speaking of which, here’s how to create Sections in your scheduling Project:
- Navigate to your Ongoing Scheduling Project.
- Click the “+ Add Section” button at the bottom of the page.
- Insert the appropriate Section name.
- Repeat steps 2 and 3 for each of the 11 Sections.
Also ensure they’re in the appropriate order. If they’re not, simply hover over the out-of-order Section(s) until two rows for vertical dots appear on the left-hand side. Click and drag those dots to move the Section wherever you’d like.
Turn Your EA into a Rockstar
And that’s it: In three steps, you’ve created a powerful scheduling workflow. I hope this glimpse into how we manage scheduling in Asana has been as helpful for you as it has for many of our clients.
All that’s left now is populating the Ongoing Scheduling project with calendaring tasks and moving them through each of the sections as they progress. Note that each stage in the process has its nuances; if you’d like to learn more about how to use this workflow to it’s fullest potential, I recommend downloading our free book:
It’ll give you everything you need to ensure scheduling items never fall through the cracks again—all while reducing stress and giving you (and your EA) the mental whitespace to focus on the things that matter most. Download it here.