Why Scheduling Is Still Broken.

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I want to make a quick comment about a problem which has been hounding me for the last two or three years, reaching a breaking point this year. This problem is that of scheduling. We all have to do it, we all hate it, and we’re all patiently waiting for someone to fix it. For those of us who cannot afford for someone to do it for us, scheduling tends to go something like this:
Me: Let’s get together.
Her: Totally. How about Thursday?
Me: Can’t do Thursday. Monday morning?
Her: How about Monday afternoon?
And so on. It’s painful. I’ve estimated that I spend almost 5 hours a week emailing people just about whens and wheres. That is half a work day. I’ve tried the tools out there: doodle, tungle.me (RIP), Baydin Calendar. I even sometimes try my friend Sahil’s method of only taking meetings within 3 blocks of where I live and work, or another friend’s method of devoting a half (or even full) day to open office hours, where I’m “on call” for meetings at the same time every week. I have close friends who have worked at big companies where they used Microsoft Exchange internally, and I’ve worked at smaller companies where we all used Google Calendar. None of these strategies work. The personal hacks and tools mentioned above all fail as solutions for a couple reasons:

– While I am thorough about my calendar, including both work and social events, and scheduling blocks of “me time” to write, read, or think, I am unpredictable about my time. (And I bet most people are, if they can help it.) Sometimes I wake up sick, or frustrated, or get into a great groove with one thing or another. Sometimes a meeting runs long, and sometimes I’m just feeling more protective of my time than normal. Rescheduling is just as painful (and often more so) than scheduling in the first place.

– Different people warrant different meetings. While I might take a half-hour lunch with an office mate who I see every day, I might want a full-hour for a meeting with a client, or a potential outside partner. While I might put one meeting at the very top of my priority list, another might be very low priority. And finally, critically, the felt power between two participants of a meeting is rarely equal. One person usually asked for the meeting. And tools that automate the scheduling process lose that nuance in a way that breaks the experience.

My calendar and my communication interface are separate. Deciding to have a meeting, and even deciding on the location, happens in one interface. Marking that meeting in a database happens in another. It’s a process that doesn’t work at all over mobile devices, and is still inelegant on the web.

I want a product where I can express intent to someone else, or receive a request from someone else, and appropriately bucket that person according to the nature of the request, and my relationship with the person. A database as simple as a calendar should surely allow such functionality, right? I want a product where I can decide to take only half my meetings, or none of my morning meetings, or to free up everything non-urgent in my afternoon. Yes, the topic of felt power is one we avoid in polite conversation, and nobody talks about it, but it matters.

Felt power is nowhere more, err, felt, than with executive assistants. Every successful woman and man in business either has one, or has considered hiring one. They are the silent gatekeepers, managing the felt power of relationships, deciding which deals get done when, and who meets with their boss, and for what amount of time. They soften the blow of a declined meeting. They add powerful subtlety in the form of “So-and-so is booked all month” or “so-and-so only has 15 minutes to chat on the phone.” As the networking word to the wise goes, “you want to get on a [important person’s] calendar: be nice to the EA.”

Software has obviated many aspects of the secretary’s former function — from the word processor to email, from the spreadsheet to wireless internet and smart phones. A modern-day executive assistant and a mid-20th century secretary look very different in almost every way except one: scheduling. There must be wisdom to that. As a wise friend of mine once suggested, perhaps making that felt power too obvious will make a product like this necessarily fail. Maybe our collective avoidance of the subject is what keeps the wheels turning. I wonder. And for my sanity, I hope I’m proven wrong. Soon.

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