Transcription
12 Strategies to work better with your assistant to buy back your time. If you're not doing these things, you're spending time on things that are sucking your energy and that don't make you any money.
See, I've been teaching people how to hire executive assistants and train them to get more leverage so that they don't build the business that they grow to hate, which unfortunately is how most entrepreneurs do it. That's why I teach the buyback principle: we don't hire people to grow our business; we hire people to buy back our time. Because if we do the second, we get the first. An executive assistant is one of the highest forms of leverage in your first hire.
Now, most people don't know how to do it right. That was my journey. I had to learn through trial and error, having somebody make huge mistakes, and trying to figure out the communication rhythm. How do I get them integrated into my inbox? How do I get my calendar to work? How do I make the whole system work so that I actually feel relieved, not stressed out that somebody is just one email away from making a huge mistake?
That's what I want to share with you. There are four key areas that we're going to unpack, with three strategies per area. Let's get into it.
The first pillar that I want to unpack is the inbox. A long time ago, my brother called me up and said, "Hey man, I think it's time that I hire an assistant. I see what you're doing. I see what you've done with clients. How do I do this?" So I sent him everything: the processes, the test project, the profiling assessment, the whole thing. He actually went on and hired somebody.
I remember a month later, I'm at his house, and I'm like, "Yo man, how's the new assistant? I'm excited to hear how they're buying back your time." He replies with a bit of a sigh, "I don't really see what the big idea is." When he did that, I knew exactly where he missed his opportunity. I asked him one question: "Is your assistant managing 100% of your emails that come into your life, or are you just CCing that person on tasks they need to do?"
He's like, "Oh, why is there a difference?" Yes, there's a difference. Essentially, your inbox is a public to-do list for strangers off the Internet on your time. Think about that. Your email is a sophisticated distraction machine from people that you may or may not know, who are just asking you for time or your attention or messing with your feelings. So having somebody take that over is key.
But most people don't know how to get that done right. There are three key strategies to really unlock an executive assistant when it comes to the inbox. The first one is your folder structure. You need to create a place where all the emails come into one spot so that they can triage it.
The key folder, out of the finance one and the respond folder and all of these others that I break down in my book, is the review folder. This is the folder where they will put all the things that they don't know how to handle. As long as you have a schedule to meet with your assistant to review that review folder, nothing will stay there for too long. That's your opportunity to train them, to coach them, to teach them how to think about your life and have them process things for you.
Now, the second thing is the daily meeting. It's the rhythm, it's the sync. What do you review when it comes to your email with your assistant? For me, it's always that review folder. It's always doing a quick scan of things in the to respond folder, which means these are her task list, things that they need to move forward.
It's also the things that are in the responded folder, so I know how they've been communicating to the people in my life. This helps me get comfortable with them understanding more context and doing things on my behalf.
Now, the third thing is the inbox SOP, the standard operating procedure. Here's how it works: as your assistant is processing your emails and talking to people and scheduling things and taking a lot of stuff off your plate, you want them to document what they're doing.
Let's say you get an email from somebody asking you to be involved in their charity. Create a response: one where it's, "Yes, I want to do this," and one where it's not. Have them add that as a template into your email system, but more importantly, into the inbox procedure. The more they add to it, the more they create, the more they respond to people on your behalf. You'll be able to add all these different nuances and scenarios into your inbox procedure so that they and future people can come into your life, support you in your inbox.
So you have the folder structure, the daily meeting for review, and the procedure to make that awesome.
The second pillar is the calendar. My rule is: nothing goes in or out of my calendar without my assistant being aware. Why? Because they own my time. When you can delegate your schedule to somebody else, then you can be free of knowing that you're doing the most important thing right now and not be distracted.
Not wondering if something is going to get missed or if something needs to be scheduled. You can just give that to somebody else, and they own it. Now, some of you are going to be freaking out. I know that when I was building my company Flowtown, my co-founder Ethan and I had a hard time scheduling things because I was the bottleneck.
I was the one that, when he'd send me an email saying we need to schedule this meeting, I would be like, "I don't want to get back to him right away," or "I don't know if I want to do that." I was trying to keep my Fridays open so maybe I could go skiing or whatever it was. Eventually, I brought in my executive assistant, and I realized that when it comes to the calendar, these are the three key areas you have to get right.
The first one is a perfect week. If you’re going to have somebody else manage your calendar, then you need to give them the blocks of time where you want to do certain things: where you want to do sales calls, where you want to have team meetings, where you want to go to the gym, where you have family time, where you have relationship time with your partner, and where you decide that you want to connect with your friends.
Once you give them that scaffolding, they can easily review the demands on your time, things that you've asked them to add, or emails that come to you to get scheduled. They can put it in the right place and the right frequency so you don't feel overwhelmed. You don't feel like somebody is just taking stuff and you've always got to be the filter.
So that's the first step. The second thing is you need to make sure that you review the calendar with them, and I call it calendar complete. When I look at my calendar on Sunday night, I expect my calendar to be complete from the previous Friday.
What that means is that everything I need, every meeting that was scheduled, all the details, the calendar is complete. Now I can review all the projects and the goals that I've set for my own life and add any open spots, the projects or the creative activities that are going to help move those forward. They could be phone calls, right? But the calendar has to be complete for the following week so that you can add your things and make sure that the activities to achieve your goals are in there.
The last thing is using your notes for context. In every calendar invite, there's a description section, the notes section. I essentially ask my assistant that whatever I need for that meeting—if it's a link to a project file, if it's a resource file, if it's a booking confirmation, if it's literally everything, the context—if it's a podcast interview, I want to know who I'm speaking with and what questions they've sent ahead of time for me to prep on.
That way, I know that the calendar's got the context for me to move forward so I can go from meeting to meeting to meeting and quickly ramp up before I have those conversations. It saves me a lot of time.
Now, I'm going to give you a tip. If sometimes other people schedule with you, where your assistant might book a Calendly link in their calendar because you've requested the meeting, then you can add a second meeting called notes. In the description of that, which coincides with the original booking, you can add all the information for the context of that meeting.
Oftentimes, I'll ask somebody for a meeting, but by the time I have that conversation, which could be two or three weeks later, I'll forget what it was about. My assistant will put notes in there and tell me. They'll literally copy and paste the original email in there so I can see that and go, "Oh, there's notes for this conversation." I'll read the email, get the context, and be able to show up with perfect information so I can really deliver for that person.
Number three is travel. When it comes to understanding where I am, what I'm doing, and who I'm talking with, there is a special person in my life that needs to know what's going on to synchronize, and that is my wife.
Now, she doesn't care who I meet with. She doesn't want to be the last person to know that I'm meeting with her sister to help her with her business or her best friend to help her business or another friend to work on a charity thing. She just wants to be informed.
Oftentimes, because my life is pretty chaotic, I've got a lot of different business interests, and I'm always moving forward really fast, I don't always know, and I don't manage my own calendar. So as it pertains to travel, booking flights, seating arrangements, all that stuff, we delegate that to other people.
But I had to create tools to allow me to make sure that everything was in sync. I want to share those with you because if you're struggling right now with having somebody else book your travel and schedule your hotels and trying to get different people synchronized, you're going to want to implement these three.
The first one is the preloaded year, and it's a template. You can click the link below to download my whole workbook for Buy Back Your Time, and it's included. Essentially, it's a one-page document where I can look at my whole year at a glance.
Every day is a little dot on this month, and there are 12 months on this page. At a high level, I use my iPad and highlight things, circle them, and put in where I'm going to be, what I'm going to do, if my wife's doing stuff, if we’ve got our family vacations, if it's my events that I do, some key launches, or whatever it is. It's all the big stuff on her part, our family, integrated into one place.
Any time we're talking to somebody about going on a trip or speaking at an event, I always pull up this document so that I can see at a glance my whole year in one spot. It helps her as well because I have it synchronized on my phone. Very simple. She has a link to it. She can go, "Oh, Dan’s mountain biking this week. Okay, we're going to do it the following week," or "We'd love to go to this thing with a couple that we just met, but we can't do it because we're going to this other event."
So having a one-pager helps with everything. The second thing is what we call trip files. Trip files are essentially a Google Doc that's created any time we travel. What it has inside of it is the accommodation, the transportation, the information about where we're going, what we're doing while we're there, and some high-level agenda.
It's always linked up in all the calendar invites so that if my wife's like, "Who's picking us up at the airport?" I won't know that because my executive assistant managed it. But the information is always in the trip file. We have an ongoing Google Doc with all of our different trips and vacations, etc. We highlight the date and link it to the trip file so that we always know where to go find the one for our next trip.
It's added in all of the calendar entries, and it's just a template that my assistant copies and pastes, putting all the information that's in my inbox into this one document. My wife and I know where to go.
The third thing I'm going to encourage you to add is a weekly sync with your executive assistant and your partner. I have to do this because, again, I'm not aware of everything that's going on in my life. Part of that weekly sync is really scanning forward: what are we doing the next two or three weeks? What's going on with childcare? How are you going to go to that event? I'm doing this event, and having two busy entrepreneurs in the same family requires this level of coordination and conversation.
When we didn't have this weekly sync meeting, we were always tripping over each other. We'd always have moments where one person was supposed to be driving a kid to some event, and the other person was like, "Well, I've got this talk I have to give," or "I'm going live," or "I'm shooting my podcast," or "I'm creating content for YouTube." Whatever was going on, it was always us stepping over each other.
We added this weekly sync, and it solved it all. A very structured agenda. We review the key items, our travel, our weekend schedule, and anything that we need. We can action it off, get it put in there, and it is ready to go.
The fourth core pillar is communication. If you've had an assistant in the past and they didn't work out, it's probably because you didn't set up a rhythm to communicate that allowed you to stay in sync for the person to understand your preferences or build context.
What I call a context map about your world to be able to respond and move things forward without your involvement. If you don't have these three things, this is probably what's holding you back. These are advanced strategies that I know, if you have an assistant today, will unlock a new level of communication to allow you to get more freedom and buy back that time.
Number one is you have to have a daily sync with your executive assistant to review what's going on in your life. You need to give them the context, the conversations. You have to explain to them what that email means. You have to explain what that person means to you. You have to tell them the story of how decisions were made.
Over time, they will understand how you make decisions, who is important to you, and how they get work done if they need to work with a legal team, a finance team, your travel agent, or whoever it is. Your assistant can help broker communication and move projects forward if you have a daily sync that unpacks the nuances for how you want them to interact with those people.
The second is what I call rerouting communication. Oftentimes, I've got hundreds of emails coming at me. I've got dozens of messages through social media platforms coming to me every day. What I've learned, and it’s one of my rules, is that you will teach people how to treat you.
If somebody messages you over SMS or WhatsApp or Facebook to coordinate something, and you're like, "Man, I really wish they would’ve emailed me so I could have this interaction in my inbox with my assistant," I'm not the person they should be asking directly because I don't know. But if you keep replying, you taught that person that that's how they should communicate with you.
What I do is reroute. When somebody messages me, like my buddy did today, and he's like, "Hey man, I want you to speak at our October event," I can screenshot that reply, loop in my assistant on text messages or Facebook or email, and just post that screenshot. Then I leave my context and move it to email with my assistant.
She now knows to understand what the request is, that it's something I want to do, and that subtly cues the person to know, "Oh yeah, Dan likes when I email him." You could politely remind them, "Hey, it's always better to email; that way it doesn't get stuck on me." That's the reroute process.
The third is closing the loop, and this is something you need to ask your assistant to do every day and check that it gets done. Most entrepreneurs have a hard time letting go because they're worried that something's going to get dropped.
What happens is at night, you're laying in bed, thinking about your day, and you're like, "Oh jeez, did they reply to that? I didn't see that email. Oh no. Did that get scheduled? Or, oh my gosh, I had that big opportunity. I wonder if anybody got back to them. Or, oh my gosh, I'm flying next week, and I don't think I booked whatever it is." Those are the open loops that will drive you crazy.
So what I ask my assistant to do is we have a private Slack channel just for us. She'll post closing the loop at the end of her day to write down all the things that she got done or moved forward. It's not a micromanagement thing; it's just a way for me to quickly scan and go, "Oh, cool, all these things are done. Good."
I only honestly check it when I have a question because I don't want to bug her. That way, she has almost like a personal accountability process to work through and get things done, leaving them there as kind of FYIs. I never have to wake up in the middle of the night and go, "Oh, did we ever book my mountain bike for that mountain bike trip?" and then go find out, "Oh, there it is. Okay, it got done last week. Perfect."
Closing the loop is a powerful strategy to free up your mind and trust your assistant to keep moving things forward.
Now, if you want to take things to another level, be sure to pick up a copy of my book, Buy Back Your Time. Get unstuck, reclaim your freedom, and build your empire. In my world, an empire is not this big, crazy, scary thing. It's literally a life of unlimited creation you never have to retire from.
That's what I want for you. So if you're sick of building the business that you grow to hate, be sure to get a copy of my book to unlock opportunities in so many ways, to show up as a leader, to really buy back your time, and build your empire.
As per usual, I want to challenge you to live a bigger life and a bigger business. I'll see you next Monday.