Tweaking my scheduling process for delegation

Scheduling stresses me out. I’ve had several calendar hiccups before: wrong dates, ambiguous locations, no contact information (or incorrect ones!), and so on. I want to fix that so that I can get better at meeting people and following up.

What would success look like? I think it would be awesome to get to the point where I can easily set lunches, coffees, and calls with people. This is how that process might look like:

  1. I bump into people in person or get an email from them. If I meet them in person, I scan in or take a picture of their business card and add it to my file.
  2. I introduce my assistant through e-mail and ask him/her to schedule lunch/coffee/a call. I use an e-mail template on my computer or a snippet on my phone to make sure that I include all the information necessary. My assistant also refers to a note with my preferences and processes.
  3. My assistant contacts the person and negotiates schedule / location using or manual scheduling through e-mail, following up in case people don’t respond. If possible, we’ll suggest a venue with good WiFi near the person’s office or location. He or she would create a calendar entry for the meeting as well as travel/preparation time around it.
  4. We have a task board where I could see where people are in the process, so I can be sure that nothing slips through the cracks. My assistant updates it, and we review it periodically.

It’s important to me that the process doesn’t make people feel like I’m standoffish or self-important. I also want to make sure that we don’t drop the ball even if I change assistants or take tasks back, so I want to use something like Trello to track scheduling status.

Here are some templates that I’m thinking of using:

Sample e-mail introducing the assistant and asking her to set things up

Hello, John!

I’d love to meet with you for lunch to discuss sketchnoting – my treat. Criselda (cc’d here) will be helping us set up something that works with your schedule. Criselda: Could you please organize lunch for maybe the second week of December? Thank you!

Sacha Chua

Sample e-mail from assistant

Hello, John!

I’m Criselda, and I’m looking forward to helping you and Sacha get together for a great conversation about sketchnotes. For lunch, would either Dec 10 (Mon), Dec 11 (Tue), or Dec 13 (Thu) work for you? 12pm usually works, but she’s happy to meet earlier or later if needed. Alternatively, if none of those dates work for you, you can check her availability at or send me a few dates and times that fit your schedule.

Also, where will you be at that time? If you’ll be near your office at 123 Anywhere Street, I can find a restaurant nearby. If you’ll be elsewhere, tell me and I’ll look for somewhere close – anywhere near the subway line would be fantastic. Got a favourite? We’d love to find out about it!

What phone number would be the best to reach you at in case something comes up?

Best regards,
Criselda Hernandez

Sample calendar entry

Subject: Lunch: John / Sacha – sketchnotes
Attendees: [email protected]
Location: Restaurant Name (123 Restaurant Address St., Toronto)
Sacha’s phone: 416-823-2669
Your phone: 123-456-7890
Restaurant website:
On Yelp:
To reschedule, please contact Criselda at ______ . Need to reschedule on the day of the event? Please call Sacha.

<agenda / notes from e-mail>

Sample confirmation

Hello, John!

This is Criselda again. I’ve set up the calendar invitation for your meeting with Sacha for 12pm on Dec 13 at Restaurant Name. Please tell me if you’re having problems adding it to your calendar. If you need to reschedule, please feel free to get in touch with me. You can check for Sacha’s updated availability. If you’re rescheduling on the same day, please call Sacha at 416-823-2669. Thank you, and I hope you have a great conversation!

Criselda Hernandez

What do you think? If I used a process like this to schedule something with you, would you feel weird about it? What would make it better? Have you delegated or are you in the process of figuring out how to delegate! I’d love to talk to you!

  • James

    Weirdness kind of depends on the person… I think anybody who’s familiar with you and your leanings would “get” this. To me, it feels more tech/productivity geeky than self-important or bureaucratic, so I’d be fine with it; just my view, though.

    Since you seen open to random thoughts, I guess my question would be re: the fuss-to-benefit ratio. Presumably to some degree you’ve still got to interface w/the calendar and your assistant (plus, the meeting attendee), so you likely know best here. VAs tend to provide max utility in high-throughput-type things in my experience.

    Probably worth a try if stuff is falling through the cracks now. I use a super-crude GTD-type system myself, even manually inputting stuff into both a Google calendar (so family can see) and an Outlook calendar (for work), and it doesn’t take long.

    But if you’re doing this a lot and the people require a lot of back-and-forth, maybe the VA will be a help? Good luck and keep us posted! ;-)

  • James: Thank you for the encouragement and validation! =)

    There’s more fuss than benefit at this point, but I need to get through that part in order to get to the point of being able to reduce my stress and benefit from people helping me. =) So I still think that’s worth it, and it’s probably good for me to increase my throughput in terms of talking to people anyway.

    Things don’t fall through the cracks that often. I just happen to be good at keeping track of the times they do, because I end up doing post-mortems on my blog. There’s a lot of back-and-forth and looking-up that’s hard for me to do on my smartphone, though, and I’d love the peace of mind that might come from having someone doublecheck. =) Looking forward to sharing the experiment! Canonical process document is now over at Scheduling.

  • Josh Tolle

    I would not be bothered at all by that series of emails.

    However, coming from Corporate America, it wouldn’t strike me as remotely strange to only interact with your assistant. I know a number of people who have transitioned into senior management and C-level roles over the years, and one of the most difficult and beneficial transitions they have had to make is reliance on assistants, which means completely turning over management of their calendars to their assistants.

    If it were me, I would probably set up a centralized calendar that you and your assistant both have access to, keep where I’m at in that calendar, and then just fire notes to my assistant to schedule lunches/coffees with people. The notes would include a little background on where and when I met the person and what kinds of things I think we’ll be chatting about, the dates I’m available to that person, the acceptable proximity in which I’m willing to meet (I’m not spending half a day on buses to get to a lunch…in most cases), and the appropriate “please” and “thank you.” The note might look something like this:

    “I would like to have coffee in the afternoon with Sacha Chua (see contact information below) during the week of January 7. Sacha and I met at the Sketchnoting 2012 in Boston in November, and I would like to discuss some ideas on sketchnoting more in-depth with her. Since I will be in Toronto that week at a conference, but I don’t have anything concrete planned in the afternoons. Please see if she is free to meet. Thank you!”

    The email to the person with whom I would like to meet might look something like this:

    “Hello Sacha,

    I am emailing on behalf of Josh Tolle who you met at Sketchnoting 2012 in Boston last November. While he is attending a conference in Toronto, Josh is interested in meeting for coffee to discuss more about sketchnoting. I am scheduling this for Tuesday, January 8th, but Josh is free during the afternoons the week of January 7, so if another day that week works better for you, please let me know. Thank you!

    Best regards,
    Criselda Hernandez
    Assistant to Josh Tolle

    Keep in mind that I’m coming from Corporate America where life is a little less personal on a regular basis. And I come from the Five Sentences Email ( school of thought, and that bleeds into the number of emails I send/receive, too: less is more. That’s my unsolicited $0.02.

  • Whew! I’m relieved to hear that it’s not weird. I definitely don’t want to be cut out of the loop – I like having those e-mail conversations as well. =) I find that cc:ing is a great way to set up the context and help people remember who I am, so that’s what I’ve been doing. Thank you so much for taking the time to share your ideas on templates!