
Apply HN: AskWhen – An Executive Assistant for Everyone - raymondyu8
We’re building a calendaring system that treats people&#x27;s schedules as a constraint satisfaction problem.  Most calendaring software (gCal, Outlook, etc.) does an excellent job of ensuring people know when &amp; where they are supposed to meet and aren&#x27;t double booked.  However, they do a poor job of ensuring that people are able to make the best use of their time.  Indeed, one of the main tasks of executive assistants is to play &quot;Calendar Tetris&quot;, actively managing the schedules of busy executives in response to new meeting requests and an exec&#x27;s high level directive as to how they want their days to be structured.<p>In contrast, with our system, a user specifies with whom they want to meet and a time frame in which a meeting needs to happen.  Our software will then automatically find an opening, adjusting participants&#x27; schedules as needed to make space for the meeting.  More generally, our software takes the place of a calendaring assistant: users paint a broad picture of how they want their days, weeks, and months to look (ex. what gets priority, when meetings need to happen, who needs to be invited, where meetings should be held, etc) and we work out a specific schedule that best fits those needs.<p>By understanding the “who, what, when, where, and why” behind each calendar event, we’ll make sure people spend less time coordinating, and more time doing.
======
buss
Something like this is sorely needed.

Do all participants need to be using your software for anyone to benefit, or
will I see the value by running it myself even if my coworkers aren't?

How will you prevent meetings from bouncing around my schedule multiple times
a day? eg I thought I was meeting with Bob at 9am today, but as I'm driving to
work your software rearranges my schedule to meet Bob at 4pm because he just
got a slightly more optimal pairing with someone else at 9:15. So I arrive at
work ready for a meeting and get annoyed that I didn't even need to be there
yet, I could have made that stop at Starbucks after all. Too many days of this
and people will stop using it.

How will you make money?

(aside: this business looks a lot like an interview question I got asked at
Google!)

~~~
raymondyu8
> Something like this is sorely needed.

Thanks for the vote of confidence!

> Do all participants need to be using your software for anyone to benefit, or
> will I see the value by running it myself even if my coworkers aren't?

Individuals could also benefit from this. For example, most corporate jobs
have work to be done outside of meetings, and time blocking is very effective
at reducing the overhead caused by context switching. Outside of work, we can
promote work-life balance by helping you find time for family, friends,
exercise, etc.

> How will you prevent meetings from bouncing around my schedule multiple
> times a day? eg I thought I was meeting with Bob at 9am today, but as I'm
> driving to work your software rearranges my schedule to meet Bob at 4pm
> because he just got a slightly more optimal pairing with someone else at
> 9:15. So I arrive at work ready for a meeting and get annoyed that I didn't
> even need to be there yet, I could have made that stop at Starbucks after
> all. Too many days of this and people will stop using it.

The last-minute reschedule is sure to result in a poor user experience, and
it’s an area where user feedback would be hugely beneficial. Here’s a couple
of our ideas:

\- Users can fix certain meetings; ie. once booked, they won’t be subject to
rescheduling.

\- Constraints based on time: ex. no rescheduling of same-day or next-day
meetings, or meetings where, if rescheduled, take place too far in the future.

\- Constraints based on participants: is anyone not using the calendaring
system? Would it affect external customers? How hard was it to get the meeting
in the first place? Is the meeting with your boss? Etc.

> How will you make money?

We would look to charge a recurring subscription fee for this, primarily as it
is more transparent and least prone to perceived conflicts of interest. Every
moment of a worker’s time has some associated cost, and if we can reduce the
time wasted on scheduling ping-pong, and improve the use of available time, we
believe we can quantify a value add.

Happy to hear your thoughts!

