Managing Email with an Assistant

Let me be honest. I am actually better at writing about delegation than actually doing it. This is especially true when it comes to email. I have always prided myself in being super-responsive. As a result, I like to process my email myself. However, that has become increasingly difficult.

Emal Hitting a Computer Screen - Photo courtesy of ©iStockphoto.com/mipan, Image #665423

Photo courtesy of ©iStockphoto.com/mipan

For starters, I now have more than one inbox. (Please don’t tell David Allen.) In addition to my physical inbox and my email inbox, I now have a Twitter inbox and a Facebook inbox. My volume of incoming messages has risen dramatically, primarily as a result of my blog.

A few weeks ago, I attended the Catalyst One Day Conference in Chicago. I was particularly challenged by Craig Groeschel’s talk on “Creating Personal Spiritual Momentum.” (My friend, Ron Edmondson, provides a great recap here.) I realized that my current workload was not sustainable. I could no longer process more than 300 email messages a day in addition to my other responsibilities. Something had to change.

I decided that I was going to delegate more of my email processing to my assistant, Vicki. She is more than capable, and I was simply under-utilizing her by insisting on processing all of my email messages myself. However, in searching the Internet, I could not seem to find any good resources for managing email with an assistant. So, I decided to experiment.

The first thing Vicki and I tried was creating a secret email address for me. I know several leaders that use this method, because I have their secret address! The idea is that Vicki would process my email inbox and forward the messages that required my personal attention to my secret address. I would also give this address to my direct reports. I would then delete my main inbox account from my email program.

This approach lasted about half a day. I soon realized that eventually:

  1. Too many people would have this address, rendering it ineffective; and
  2. I couldn’t easily reply from this address without blowing my cover.

Next, we tried creating a special inbox folder called “Mike to Handle” under my main inbox. The idea here was that Vicki would go through my inbox and drag the messages I needed to handle to my special folder.

The problem with this was that I couldn’t seem to refrain from viewing the messages in my main inbox. It was just too tempting to “sneak a peek.” This method lasted about two hours!

Finally, we reversed the process. We settled on creating a separate subfolder for Vicki called “Vicki to Handle.” I then set up several email rules that would automatically process the email that hit my inbox, so I would only see the message I needed to see.

Here are the email rules I created:

  1. In reply to me. This ensures that anyone who replies to a message I have initiated comes directly to me. In Apple Mail, the rule looks like this. (You could use the same logic in Outlook or almost any other modern email program.)

    Email Rules: Reply to Me

  2. Direct reports. This ensures that my direct reports get directly to me. The rule looks like this:

    Email Rules: Direct Reports

  3. Important contacts. I’m sure this will grow over time. Right now, it operates like a kind of “white list.” I have to specifically add people to the rule for them to get through Vicki. The rule looks like this:

    Email Rule: Important Contacts

  4. Move remaining messages. This rule moves every other message to Vicki to process. If she thinks I need to respond personally, she drags it back to my main inbox.

    Email Rule: Move Remaining Messages

This has worked remarkably well. It has dramatically reduced the volume of email messages I am handling on a daily basis. In addition, Vicki has taken my standard email templates and modified them, so that they are coming from her. This ensures a consistent response to the usual requests I get.

In addition, I can move email messages from one of my other accounts (my public BACN account or my personal accounts) to Vicki to process. I can do this with a single keystroke using Mail Act-On. The email rule looks like this:

I automatically “flag” the message, so that Vicki knows I have reviewed the message and want her to handle it.

I realize that not everyone has an assistant. If you are in this situation, you might want to read my post, “How Do You Delegate If You Don’t Have a Staff.” Nevertheless, hopefully, this will give you a place to start. If you have a way to improve on this system, I would love to hear it.

Question: If you have an assistant, how do you work with him or her to manage your email?
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  • http://intensedebate.com/profiles/gunfighter3w Geoff Webb

    Once again, thanks for sharing your experiments!

    What I like about your system:
    1. Transparency: By modifying your templates and avoiding secret addresses, people know whether they're corresponding with you or Vicki.

    2. Temptation Mitigation: It prevents you from casually "sneaking a peek" at mail you don't need to see.

    3. Trust: Vicki now knows – really knows – how much you truly trust her and believe in her. That's cool.

    Meanwhile, I've got to get back to processing my inbox… :)

    My recent post Why Empathy Isn’t Enough

  • Colleen Coble

    I've been toying with the idea of letting my assistant (hubby Dave) answer my reader mail. Most of the emails are similar so I could create a template for him from me that he could paste into the email. But then, I'm not sure I could follow through and NOT sneak peeks to read them. So it's a dilemma. I love interacting with my readers so I'm not sure I can actually do it. LOL Your solution sounds workable for you!

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      I'm not sure my solution would work for anyone except me. And even then, I might change it next week. I thought I'd share it as a “work in process.” For right now, it is working great! Thanks.

    • http://www.facebook.com/TimothyFish Timothy Fish

      I'm sure you get a lot more reader mail than I do, but I think I would quit writing before I quit responding to reader mail.
      My recent post Thoughts on Christian Fantasy

      • http://intensedebate.com/people/michaelhyatt Michael Hyatt

        I definitely won’t stop responding to reader mail. That's precisely why I am employing a system like this. However, many of the messages—probably more than 50%—are questions that my assistant can readily answer. I would rather ensure that they get their question answered by someone than stack up in my inbox unanswered.

  • http://www.4u2live.com Peter Eleazar

    Michael, I have always admired responsiveness and I hold it as a value. I once reported to a CEO with 30,000 employees, who still managed to personally respond to his employees, albeit briefly and delayed. He uses a team to filter his mails, because there is a lot of noise in it all. Some mails just need info, some need to be redirected, some even need a simple delete. But I encourage you to hold on to one of the things that I think may have defined you – never forget that it is people who got you there and keep you there, so honor your constituencies. A skilled PR assistant could effectively ghost you and convey your heartbeat, without displacing you.

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      That’s a good word. Thanks.

  • http://www.4u2live.com Peter Eleazar

    I have been on the receiving end of a secret mail list exclusion – it is cold, heartless and I don’t think it does you justice. The business world has become so impersonal, with computer generated voices or mails. Never let go of the human touch as it offers sustainable competitive advantage for your personal brand and for TNP – but do manage it. Yes delegate, but one thing I learnt about marketing is that what matters is perceived value – you don’t have to do it all to still maintain positive perceptions.

    That said, you would be wise to manage expectations so that people don’t abuse your mailbox. That too can be managed sensitively e.g. a gentle redirection or an email rule with a graded initial response, etc.

  • http://www.4u2live.net Peter Eleazar

    I must add this: don't be a slave to the technology, make it work for you. Know who you are – accessible, responsive, human, interesting etc., and use technology to sustain or harness all that whilst also enhancing your effectiveness.

    One practical option would be to use your email only for your in-list. Then direct all other new mails to you (using an email rule) to a "non-public" (CEO's) internet template. There you can force all kinds of rules relating to text length, subject filters, redirects, automated responses, attachments and filters.

    My recent post Ignorance is a real cause for real crisis

  • http://intensedebate.com/people/johnmrowley johnmrowley

    This is really good Michael. I am getting close but not there yet but I am using your other email rules with outstanding success.

    Question. I am a mac and iphone guy. I was using google apps for email and calendar but I like the mac applications better (mail, address book, calendar) do you use the mail, address book and calendar on the mac? Do you use mobile me? Do you use Plaxo as well? Too many things I I really respect your opinion.

    Thanks and God bless!

    John
    My recent post The Importance of Monday-Seize Monday!

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      I use Apple Mail on my MacBook Pro, iPad, and iPhone. I use Google Calendar across all three as well. I have it set up to work with iPad and iPhone, but it requires a pretty convoluted set-up to make all five calendars appear there—but it works! I don't use Mobile Me for anything other than an online photo gallery. Flickr is a lot cheaper. I don't use Plaxo. Thanks.

      • http://intensedebate.com/people/johnmrowley johnmrowley

        thank you Michael!

      • Chris Fowler

        Michael – Do you still use a BCC type system for tracking delegated items? If so, I’d appreciate understanding how you were able to set that up in a rule for Apple Mail. Thanks! – Chris

        • http://www.michaelhyatt.com Michael Hyatt

          Actually, I am not using that presently. I have switched my task management from Things to Nozbe. I am waiting on an AppleScript from Nozbe before I can implement it.

  • Jenni Baier

    You deserve a lot of credit & kudos for tackling this level of delegation with material that can sometimes be quite sensitive.

    However, your first mail rule has a fatal flaw. You've just told the entire internet how to format their email to get your attention :) Anyone can put "Re:" in the subject line. In fact, a lot of spam is formatted this way in an attempt to trick you into opening them.

    I agree that the "secret box" method is also flawed, but it is possible to set it up in such a way that the "secret" address is not exposed when replying to a message. But another effective strategy is just the opposite: have a "junk" address — a lower-priority email account that you use for things that you won't need to handle personally, and for those occasions where you are required to give an email address and you'd really rather not!

    Good luck taming your inbox!

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      Great catch!

      I got an email from someone else mentioning the same thing. However, I think I have fixed it. I have added another condition to that rule: “Sender is in my address book.”

      Thanks for bringing this to my attention.

    • http://intensedebate.com/profiles/gunfighter3w Geoff Webb

      Thanks Jenni – hadn't heard or thought about the "Re:" issue – this helps us all!

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      I just changed the screen capture graphic on this, Jenni, just in case someone didn’t read down this far in the comments to see the fix. Thanks again.

  • http://www.fredmckinnon.com Fred McKinnon

    Michael,
    I just love it that you share how you struggle to peak .. .that’s hilarious. I’m the same way. I delegate more and more, yet constantly peek in and try to take over. Best thing for my staff would be for me to disappear without internet for a while.

  • http://www.lynnrush.com Lynn Rush

    Great post. I always wondered how you handle all the emails you must get. I get around 100-150 a day and have several rules set up in iMail already. . . but 300+? Jeepers. :-)

    Anyway, thanks for sharing. Have a great day.

  • http://intensedebate.com/people/success2you John Richardson

    Great insights, Michael. I get hundreds of e-mails from school districts in California each week pertaining to a new state mandated student data system (CALPADS). Since there are over 4000 districts in the state, the e-mails come from a variety of people and require me to fix a particular student record, or Anomaly as they call it, when a student enter/exit date differs from my records to theirs. It's crazy that the state decided to use e-mail to process these records which really is a huge database flaw in their program.
    I have recently had some help processing these records, but it has been a challenge delegating and then having them round-trip back to my inbox when my co-worker sends them back to me and off to the other district. I actually get double the e-mail this way.
    I'm looking for solutions in Outlook to better filter incoming mail that doesn't have a consistent subject line and can come from hundreds of different people and also better round-trip solutions to have a digest e-mail instead of separate e-mails for every record from my co-workers.
    I'll have to try some of your ideas above.
    My recent post Meet Me in Chicago

  • http://Www.ignitiongarage.com Brett Eddy

    How apropos Michael- I am reading your blog while in the airport thinking about the To-Dos for today and tomorrow, processing which gaps in my schedule between meetings I will begin to knock off the prioritized tasks. Was then thinking “boy I miss my old Exec Admin”, she was worth her weight in gold to pre-think my needs for the day. I think I will forward this article to her for when we bring her on board, it’s a great post. Much appreciated. Blessings.

  • http://thatguykc.wordpress.com K.C.

    As an assistant this is great material to help me "manage up" to my executives and to my own assistant in the future.
    Thanks, Michael!
    My recent post A Man’s Guide to Birthday Success

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      I'd love to interview a dozen top executive assistants to see how they do it. It might be interesting.

  • Greg Williamson

    I claimed e-mail bankruptcy on Feb. 13/09. I have although noticed I am sneaking back a bit. At the time I had maybe 100+ messages a day. From then to know I went to about less then 10 per day. I have noticed that I have gone up to closer to 20 now and am concerned.

    I noticed that if I put it out there to friends and close colleagues that I do not use e-mail and would prefer a text, twitter DM or facebook message, or best of all a good old fashioned phone call then people did not e-mail me. I also noticed that how I treated others in e-mail would be how they treat me! No jokes, stupid reply alls, and other useless information would never come from me again. If I want you to see something I would tell you through Facebook or twitter, NOT e-mail. For direct reports I use Yammer, Michael you may like this. It is basically identical to twitter, but is closed to only people with the same e-mail extension.

    Here are my random thoughts on my journey this past year. I absolutely LOVE having virtually no e-mail habit, but I NEED more publicity because as you correctly pointed out I have not figured out yet how to make my e-mail address private or show my public e-mail when sending from my private e-mail?

    Next, by forcing people to text, yammer, tweet, or Facebook then the message I get is always short and to the point.

    Thanks for your post, there isn't many of us out there who are doing anything about their e-mail addiction

    Greg

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      This maybe just where our styles are different, but I like the email trail. I certainly use Twitter DM a lot, but not much related to business. I really need to keep the history.

  • http://www.tikesbestfriend.wordpress.com Tim Dahl

    I've become very appreciative of your transparency. I've never really expected to have actual contact with you. As the CEO of Thomas Nelson, I expect to work through your assistant. Yet, after a personal email and a twitter response, I became very appreciative of your personal touch. Knowing that the amount of contacts you have to deal with, not only will I expect to go through your assistant (if I've ever a felt need to contact you); but on the off chance there is a personal contact from you I'll feel all the more blessed. Also knowing the huge amount of interaction that people desire of you, I won't attempt needless contact. I wouldn't desire to be a part of your problem.

    Thanks for all that you do!

    Tim
    My recent post Violence Against Women, by David Lowrie

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      You are welcome, Tim. Thanks for your kind words.

    • http://www.4u2live.com Peter Eleazar

      I echo your views Tim – Michael may never get to know us, but he is allowing us to know him a bit and I hope we honor that trust. Its not just his vunerability and transparency that resonates for me – its his values. Michael, if you are looking for spiritual momentum, you may be overlooking what you have already started – for the real power of the kingdom vests in relationship.

      By the way, Tim, your personal photo may need a bit of updating, otherwise you are a really young writer??

  • http://intensedebate.com/people/patriciazell patriciazell

    I am not deluged with e-mails like you are–50 to 75 a day via 3 accounts–but, if I ever do, I will listen to you. I know your post on dealing with each e-mail just once really has helped me with my 2 personal accounts, and I now have a file system that works. This summer I'm going to set up a file system for my school e-mail account. I'm also glad you know the value of "tweaking" when something just doesn't fit right–making changes can save us from frustration.

  • http://deliverbliss.com Tim Sanchez

    Hi Michael,

    You mentioned you couldn't find anything on the internet about managing your email with an assistant.

    If you haven't been there before, please allow me to introduce you to Manager-Tools.com (Mark Horstman and Mike Auzenne). They are the absolute best resource on management I've found online (and maybe anywhere).

    Check out this podcast for some great info on how to utilize your admin for email:http://manager-tools.com/2006/11/your-admin-and-y

    Hope you find it useful.
    My recent post Embrace Selflessness to Deliver a Blissful Experience

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      Thanks so much for this resource. I will check it out!

  • http://blog.cyberquill.com Peter G.

    When you open a post with “Let me be honest,” does that mean honest as opposed to usually?

  • http://www.facebook.com/chriszaugg Chris Zaugg

    I love this, Michael! Thanks for the post and the screen captures. I have been fighting the battle of email bombardment and "personal touch" for quite some time, and this just may be the ticket to some modicum of technological freedom.

    By the way….can you add me to your address book? LOL! =)
    My recent post Mickelson, Woods and “Blink”

  • D Rob

    Regarding your reason #2 for scrapping the first private e-mail idea, I don't know if you have heard of Fastmail, but it does offer the easy ability to send from the Fastmail e-mail system as another e-mail account.

    You can even make up e-mail addresses from their list of domains and send or receive e-mail through the fake (alias) e-mail addresses.
    http://www.fastmail.fm

    Thanks for the blog and sharing your life.

  • http://twitter.com/abbylive @abbylive

    I get people who are trying to sell me something use the "RE:" trick. They email me something with "RE:" in the subject line when I never wrote them in the first place. It gets my attention, but only makes me mad when I read the email. :)

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      That's why I added that the sender must be in my address book.

      • http://twitter.com/abbylive @abbylive

        Good idea!
        My recent post what i'm reading

  • http://www.facebook.com/likesalt Richard Morton

    Good article. Here is a post on reducing your inbox. Frictionless Work: How to Clear Your Life of Non-Essential Tasks http://zenhabits.net/2010/04/minimalist-work/ I liked several of his ideas. Thought you might as well.

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      That is a very challenging article, especially the part about eliminating comments. Wow.

  • michael

    I'm confused about #3. You move your "important contacts" to the "!vicki to handle" folder? I thought you wanted to see those yourself?

    • http://intensedebate.com/people/michaelhyatt Michael Hyatt

      Good catch. I actually used the wrong screen shot. It should stop processing and leave the message in my main inbox. I have corrected in the post above. (You may have to clear your local browser cache to see it.) Thanks!

  • http://intensedebate.com/profiles/reflectionsbypj reflectionsbypj

    I giggled when I saw the title of this blog come through in my email, primarily because I just received an email from you (of which I was very surprised to receive, I was expecting marketing to respond). I also giggled due to the fact that I have so many inboxes (linkedin, twitter, facebook, myspace, blog, college, personal) and would love an assistant. Granted, I have no where near the volume you do but when my own mother says "you never responded to the email I sent you", it leaves me longing for an assistant, a clone, calgon, or an easy button – anything other than time management skills. (wink)

  • http://dmbaldwin.wordpress.com Dave Baldwin

    Thank you Michael for this great post. It reminds me of a three part podcast that Manager-Tools.Com does on how to work with your administrative assistant. Mark & Mike talk about this area of working with your admin as well as a myriad of other aspects of our work. It's worth the listen.
    Manager-Tools.Com is just a plain good old podcast if you want to be a better manager and leader. I stumbled across them when I read a book on Transformational Leadership and the authors wrote that if one is to be a great transformational leader they must have some level of management acumen. I started looking for some management resources on the web and ran across Manager-Tools.com. Anyone who wants to lead better should subscribe to this excellent resource.
    Blessings,
    Dave
    My recent post What Difference Does Your Small Group Make?

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  • http://www.letsgo.com/profile/mabeljohnsonn how much should i weigh

    lmao cool info man.

  • Vincenzo Vecchio

    Maybe I'm still not ready to "giving" control of my email to someone else…

    One tool I must admit I found very useful and that has really changed the way I handle email is GTDInbox (http://www.gtdgmail.com/). A plug-in for Firefox and Chrome.
    It is one sure way you will never miss an email (either inbound or outbound).

    The only problem is always time… even if emails are now very well formatted tasks, there is always a need for a lot of time to take care of them :)

  • http://intensedebate.com/people/todshuttleworth todshuttleworth

    Great idea. I have to find a better email solution. Janet and I will investigate. Thanks!!

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  • Joe

    Just curious, was this the system that you settled on with your assistant? Or, were there some additional tweaks over time?

    • http://michaelhyatt.com Michael Hyatt

      Yes, it was.

  • Steve

    Hi Michael, thanks for this post. I’d be interested to know how your assistant manages your calendar too.

  • Jon_neal23

    Hey Michael!

    Really appreciate your words here.  Currently trying to figure this out as I am an assistant much like Vicki.  Do you have any more information as to how to set this up?  For example, was it POP or IMAP?  I guess I’m just confused how you both got the system to work when you use separate computer programs.  Maybe it’s just an issue I’m facing as my boss uses Outlook, which doesn’t seem to give an easy way to do this.

  • Eugene Sim

    I’m trying to use your mail rules for my apple mail but it doesn’t give me the “every message” option.  Was that an applescript? (i’m running mountain lion)

    • Eugene Sim

      sorry found it. haha.

  • Navneet

    Thank you Michael for this great post. http://www.javamazon.com

  • Rich

    Michael, do you use IMAP for sync your email to Mac Mail? It was clear from this article. Thanks!

    • Rich

      Sorry, I meant to say “it wasn’t clear…”

    • http://michaelhyatt.com/ Michael Hyatt

      Yes, I do. Thanks.

  • http://www.cloudstaff.com/downloads/assistants Armie Cabrera

    This is a very helpful article on managing emails with the help of an assistant. The insights that you have shared are indeed very informative. Thanks for sharing.

  • Matthew Ware

    Michael, thank you for this post. I recognize it is several years old, but still seems to be one of the best resources available for dealing with this topic. I’m just beginning to tackle this exact issue with my assistant, and had a few questions.

    1. Where does the “Vicki To Handle” folder live? I use the same platform and tools you do (OSX), but I’m unclear on where this folder exists.

    2. Does this method require your assistant to have your login credentials, or is it some sort of public folder she can access?

    3. Do you still utilize this same basic approach, or have you changed/updated your method?

    Again, thanks for writing about this. I’m looking forward to experimenting and spending my time on the right things!

    • http://michaelhyatt.com/ Michael Hyatt

      I probably need to updates this post. I have a radically different procedure today. I use Rhino Support, which is a help desk system. All my public email goes there. My entire team has access to this, so messages can be reviewed, discussed, and assigned as necessary.

  • http://www.scottrossonline.com/ Scott Ross

    Michael,

    This post is more than 4 years old but I am just now hiring an assistant and searched your site for archives that might be helpful. This is hugely helpful, but I am curious about 2 things. 1: How do you set up the permission in Mac Mail for Vicki to see the “Vicki to Handle” folder? 2: Have you discovered any tweaks since writing this you think I should know.

    Thanks for the mountains of value you provide to all of us!

  • Kassy

    Hi Michael!

    Thank you for writing this – super helpful! However it has been a while since this article was written, so I wanted to write and see what your process looks like currently.

    I recently became an Executive Assistant for the very busy owner/founder of a rapidly growing startup in San Francisco. Before this job, I have never been an EA, and my boss has also never had an EA. We were trying to come up with ways for me to help manage his email load, and this seems like a great option that I am going to recommend to him.

    I’d like to know how this system has evolved over the years? Has this method, or a version of it, continued to work for you?

    Thanks so much!
    Kassy