I think we’ve got this scheduling process sorted out, and I really really like it. It turns out that I didn’t have to fuss about with lots of templates or worry so much about exceptions.

When I’m reaching out by e-mail, all I have to do is cc: my assistant and add a short paragraph with details. She knows how to handle things. She knows my preferences for in-person and online meetings. She can follow up and make things happen.

So far, amazing. Things appear on my calendar! I can send Criselda a long e-mail with the AngelHack schedule for the weekend, ask her to pull out just the 2:15pm demo and block off 1h before / 2h after for travel, and it appears on my calendar with the venue information and other things I need to know. I feel comfortable asking her to coordinate with multiple people. This is good.

Here are a few things we’ve done to make it nice and smooth:

• I used Google Calendar to share my calendar with her so that she has full edit access to it without being able to access the rest of my e-mail. Stephan Spencer has his assistants process his e-mail for him – I’ll get to that level of trust someday!
• I set up an account for her on Google Apps. Because she uses a @sachachua.com address, I feel like I need to explain less about who she is, and I worry less about offboarding.
• I add the person’s name to the subject line: That way, when she’s reviewing her inbox, she can easily distinguish the different conversations.
• We use Trello to keep track of task status: I want to be able to see whom we’re waiting for a response from and the status of other tasks I’ve assigned her, and Trello makes it easy to do that. I do most of the Trello task updates, but I hope we’ll get the hang of updating the boards together.

Who’s interested in talking about delegation and scheduling? We can look into scheduling a Google Hangout!