TheGmailGenius

Paint us a snapshot of what your inbox looks like right now.

On the one hand, I keep my inbox pretty tidy. I really stay on top of unreads so usually I won’t have more than 10 or so (obviously this is higher in the morning, etc). On the other hand, I know my inbox would STRESS certain people out because I keep almost everything. I delete things like newsletters, but any form of conversation or active communication gets kept basically forever.

For me, the main benefit of using Gmail is the ability to search and access just about anything that’s ever come my way. I don’t have to remember as much because I know it’s somewhere in my inbox and I can usually search and find it very quickly. So deleting and pursuing Inbox Zero is not only unnecessary but actually wasteful because then you lose one of the key benefits of Gmail – a built-in archive of all past communications.

What’s your email strategy? Please break it down for us. (This is a good place to discuss how you think about the role of email in your life, daily routine with it, any rules you subscribe to…)

The inbox is one of my to-do lists (other lives on a Moleskine Smart Writing Set, which automatically digitizes my handwritten notes and syncs with Evernote.) Anything marked unread is a to-do list item, and when it’s done, it gets marked as read and automatically pushed to the second half of the page.

I don’t use any labels, and I don’t organize my inbox beyond marking things as “Read” or “Unread.” I know there are ton of organizational tricks and options, but I like to keep it really simple and just lean heavily on the search and storage benefits.

You’re an ultramarathoner and recently completed a 100-mile race (holy cow!). I’m guessing all that running provides a good break from email…

Haha – yeah, running definitely gives me time away from email. And I’ve found that, especially when I’m really working hard to get a deal finalized or I’m waiting on something from a client, just stepping away seems to make things happen. Not sure on causation or how factual that claim is, but probably something about less is more 😉

Are there any specific Gmail tools you can’t live without?

I’m a big Boomerang user, and I lean on it in a few key ways. Like I said, my unreads are my to-dos, so I want to get those cleared out ASAP. But I also don’t want to look like a psycho who responds within 1 minute, so I’ll often schedule something to go out in an hour. That way I can get that task off my plate but not look like I’m awkwardly eager in replying. Kind of petty, I know, but ¯\_(ツ)_/¯.

I also use Boomerang when reaching out to potential clients. A lot of times these are cold-emails, so follow up is key if I don’t get a reply after the first note. So I will send an initial email, then open the sent message, hit reply all, bcc another tool I use called FollowUpThen to set a reminder in 1 week, add a canned follow up message, and schedule that 2nd email to go out in one week if nobody replies. That way I will have my first email sent, my second follow up email scheduled to go out in 1 week if no one replies, and a reminder to send a 3rd and final follow up email set for 2 weeks after the initial email has gone out. Sounds complicated but it’s second nature now and has been huge in keeping follow up from slipping.

Is there anything about email that really drives you nuts?

One issue that vexed me for too long was all the back and forth that usually goes into setting up a call or meeting. Five emails to find a time that works for us both to talk? I just can’t. So I’ve started using a tool called ScheduleOnce to just put my availability out there and have the other person grab a time that works best for them. So much more efficient, but you REALLY have to have your calendar buttoned up otherwise people can book times when you aren’t available.

I know these schedulers are nothing new, and I always felt like people who used them came off as a bit self-important, but the efficiency was too much for me to resist. Highly recommend.