Pairing with an assistant to slay the email beast

By | July 8, 2014

Keeping up with the 150 or so emails I get every day is a challenge, one that I fail at quite regularly. Happily, I’ve recently had a breakthrough on this thorny problem. Pairing with Jamie Lystra, our incredibly able assistant, has tamed the email beast. I’ve improved my responsiveness, reduced my mail-induced anxiety, and found an implementation that balances the conflicting forces of leverage, confidentiality, and privacy.

My first experiment with getting email help from an assistant didn’t go very well. I didn’t get the leverage I’d hoped for, and having full access to my email account proved to be a problem in the end. I wish Alexandra Samuel’s HBR article on delegating email to an assistant had been written a year ago. She has some great ideas and advice, and it could have helped me avoid some pain.

While the first experiment failed, the need for help didn’t diminish. A new approach was called for. My colleague Shawn Crowley suggested that rather than share full access, I think about a filtering and forwarding approach.

Baseline requirement: a great assistant

I believe the primary factor for success in getting help from an assistant, whether in email or any other area, is the person him or herself. Jamie is justifiably proud of the important work she does. She’s gratified by helping me, Mike and Shawn. She seeks out new ways she can help us. She’s thoughtful, reflective, and pro-active. She’s loyal, steady, discreet, and optimistic, and exercises good judgment. With an assistant like this, any strategy for getting help with email would probably work.

Filtering, forwarding, and digesting

While our company email is hosted by Google, I continue to use a desktop mail client with IMAP. I like having all my email in my laptop, and being able to read and respond to mail without a network connection. My mail client of choice is OS X’s Mail.app. Mail has a feature similar to forwarding known as “redirect”. The difference between forwarding and redirecting is that redirect preserves the original sender in the From: header. When I redirect a message to Jamie, she sees the message as if it came from the original sender, not me. This helps her process my mail, and makes it easier to respond if appropriate.

Here’s how we’ve worked out an effective way to pair on my email. Throughout the day, Mail.app automatically:

  1. pulls all mail with IMAP
  2. leaves mail from anyone in my company in my Inbox
  3. leaves selective mail from outside the company in my Inbox
  4. archives and redirects everything else to Jamie

During the day, Jamie processes the mail that is redirected from my laptop. At the end of the day, she produces a daily digest of my emails in three categories:

  1. Important, response required
  2. Read, no response required
  3. Not sure what this is

I use the daily digest to read mails that matter from my All Mail folder. The third category provides a natural feedback loop to help Jamie learn what matters and improve her handling and efficiency. Since Jamie’s monitoring mail throughout the day, she will occasionally text or call me with something that’s urgent.

Results

The overall results after just two weeks have been very good. I’ve been able to stay caught up on email. My responsiveness has improved. My anxiety level has decreased. Jamie is learning quickly what matters and what doesn’t. She can respond on my behalf on some mails. She’s more aware of what’s happening in my life, which has opened up new ways she can assist.

Our approach has reduced the total time I spend on email. That means there are things I’m missing, and serendipities lost. For example, I don’t see as many Basecamp messages on projects I’m close in. Interesting tidbits from newsletters, LinkedIn, and yes, even FaceBoook, can no longer catch my eye. Since she can’t possibly know when to add this stuff to the digest, Jamie has unsubscribed me from a bunch of lists.

The only downside to how we’ve implemented our strategy is that my laptop needs to be up and running in order to receive and redirect messages.

The level of loyalty, discretion, and diligence that Jamie brings to her job are critical to success since they build my trust. Keeping internal emails out of the redirect stream is a reasonable compromise between confidentiality for other employees and efficiency.

Inbox 0 is now a very attainable goal on a daily basis.
 

Carl Erickson (70 Posts)

Carl is the president and cofounder of Atomic Object, a software product development company with offices in Grand Rapids, Detroit, and Ann Arbor. Learn more about Carl.


 


4 Comments

Gordon Whitehead on July 8, 2014 at 3:21 pm.

Great post Carl. As I’ve grown accustomed to seeing, AO innovates on more than just technology. Thanks for sharing – I’m going to use this.
gw

Reply

Carl Erickson on July 8, 2014 at 4:17 pm.

Thanks, Gordon. I’d enjoy hearing how your experiment goes.

Reply

Julie Shears on July 10, 2014 at 7:24 am.

What a great process to tame the email beast. I don’t have an amazing assistant to help but I do try to limit the time my time on email during a day. I have tried to clearly set the standard I am not going to respond immediately to requests that are not urgent. It seems we have become very dependent on expecting a response immediately. This has allowed me to help shift that dial on that expectation every so slightly.

Reply

Carl Erickson on July 10, 2014 at 8:16 am.

It’s a wonderful thing to have Jamie’s help. But if I had to live without it I’d go to a scheme where what I had previously forwarded to Jamie got automatically moved to a triage mailbox. Then I’d process that mailbox daily to pull the important stuff back into the Inbox.

And I couldn’t agree more about the expectation. Responding by the next day is an improvement for me, but probably still longer than some people expect.

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