What to do when you’re falling behind
How I use a virtual assistant to keep up when I can’t do it all
If you scheduled a meeting with me, there was probably a 1 in 3 chance it would actually happen. During this period of time, I didn’t remember your birthday, I didn’t know what our last 1x1 meeting was about, I got a haircut only after half of the people I met on a given day demanded it, and I drilled into a candidate for an hour about the nuances of performance marketing…when he was really interviewing for a product role.
Ouch. But guess what: it was pulling teeth for me to even remember these times. Beginning in a few sentences this story is going to turn into a best practices article about staying meticulously organized when your workload expands. How can I write both? I’ll start by quickly telling you how to become a professional disaster and show you how I escaped.
The first ingredient to becoming very, very disorganized and losing all control of your day starts with growth. When the functions you manage, the scope of what you do, and the number of direct reports you work with expands, make sure you don’t change a thing about how you manage your time — that’s the best way I’ve found to sink. The next most important step is to be very embarrassed about asking for help. In fact, don’t even admit you have a problem. After all, it’s a sign of weakness. Further justify this with the financial cost to the company, and the cultural precedent it would set if you needed to hire someone to help you. And that just about sums up how I got into the mess we saw in the first paragraph.
In the end, I got an executive coach who told me I should try a virtual assistant (VA). Talk about delegation! But it changed everything. And good thing: at the time I was organizationally topped out the company needed so much more from me. With a little help I was able to get ahead of our startup.
Over the years I have now worked with several virtual assistants, and thought it would be valuable to share some of the practices and routines we’ve developed together. If I refer to my virtual assistant as ‘my secret weapon’ at work, these daily projects are the tools that weaponized her.
My favorite virtual assistant power moves
Inbox: Waking up to an inbox with 6 new e-mails instead of 60 is an incredible treat. Using gmail delegation and a prioritization system, each morning my VA will go into my inbox and clear out not just junk mail but anything that doesn’t truly require my attention. I know you wrote back to say “thanks” after our last exchange — but I never actually see that e-mail. Everything that remains gets properly classified so I know what needs to get done first. And all of this happens before I wake up because I always hire VAs at least one time zone ahead of me. Since my VA also has the context of what was important from yesterday, she can take stock of important things that are still pending — and have probably increased in priority.
Calendar Review: While my VA manages all of my calendaring and scheduling, it’s important to also have a sanity check once a day. In the morning review my VA makes sure there are no conflicts, she’ll e-mail to re-confirm all external meetings I have offsite, ensure that there is sufficient travel time built in between appointments, see if the rooms are still available, etc.
Daily Digest: Once these steps are done, she’ll send a short e-mail with what’s most important for me to work on today. Since she has skimmed my incoming e-mails she’ll also flag anything particularly urgent. There will be a few reminders, and probably several questions for me. Each day this is the very first e-mail that I read no matter what because my VA is my secret weapon and a huge source of leverage for me. Thus, if she is missing context or has a question outstanding for me I want to make sure I can clear it up as quickly as possible so she can keep working.
Code words: Of course no partnership would be complete without a secret language. My favorite part about having a VA is setting up a meeting with a quick e-mail cc reply saying “Great, adding Tracy to help” — and forgetting about it until one day when the meeting is magically the next appointment on my calendar. I used to lose so many in scheduling: I’d respond with times, somebody wouldn’t follow up and it would get lost forever. Today I’m operating on a new level, and I even set up code works with my VA to signal how long I want the meeting to be, the format (coffee, drinks, dinner, do we need a room reserved) whether I am willing to travel to their office, and whether the meeting is “clear out my schedule urgent” or “Let’s find time to meet in the next few months.” I won’t share my particular vernacular but it’s a good tip to create your own.
Priority Keeper: in the past I never succeeded at blocking out time to get certain tasks done — especially if didn’t have a looming deadline. I would either schedule over it, or someone else would. Having a VA accountable to actively guard that time makes a night and day difference. The biggest payoff I can remember was last summer when I got invited to speak at Dreamforce. I didn’t think it would be much work to be on a panel, so I agreed. A few weeks before the event I learned they wanted me to be on stage alone speaking for an hour. My VA immediately cleared and protected time every single day for me to get ready. I know what would have happened if I were left to my own devices to prepare, and I assure you I wouldn’t be writing a story about it. Today almost every minute of my day is actively blocked off for something, and it’s not fluff. Instead I get to be highly organized about when I get things done. Wanna see me? I have a time for that. Want me to review your board slides? I have a time for that, too.
Birthdays and work anniversaries: I have never had a VA send an e-mail on my behalf (and Gmail’s delegation system makes it obvious if you do), but I do love to have drafts created for me to fill in and send. In my morning digest e-mail, my VA Kara might flag “There are 3 birthday drafts in your inbox” already addressed to the right person on the right date, I just need to fill out a personal message and click send. This helps me enormously without being disingenuous.
Plus: always look for new projects: I always find the best projects for my VA by starting with “Wouldn’t my life be incredible if….” One of my favorite projects was having my VA pull together a list of everyone I met for coffee, dinner or drinks in the past two years. I then spent a few minutes going through the list and coming up with the people who I really wanted to stay in touch with but struggled for whatever reason. I set a goal of how many times a year I’d like to connect with each person. This way whenever I had a gap in my schedule my VA could go to my list and see if I could use the time to stay in touch with an old friend or colleague.
How does it work? The Details.
My VA gets all of this done for me in 10 hours a week. I pay $35 an hour, or about $1600 a month. It’s hard to quantify the benefit HoneyBook receives in exchange, but if you re-read the first paragraph of my story I think it’s fair to conclude that I’m at least twice as good when supported by a VA, maybe substantially more. All of these things, above, help me to be a better manager, a better peer, and even a better friend.
If you’re interested in exploring more, there are many places to look and I can’t offer any advice beyond: just give it a shot! Wait wait — that’s not true: I did write an article with tips to onboarding and working with a VA. But actually finding the perfect match takes some luck and the willingness to iterate if the partnership isn't’ perfect, so it’s better to just get started.
If you like the above list of things I’ve developed with my virtual assistant send me a note because sometimes my own VA is looking for more hours. And do share your own secret weapons, I’d love to hear from you.