in Early Stage Startups

Amy Etiquette

About six months ago, I got an email from a person named Pear about an “early christmas present”.  A friend who was affiliated with from the VC side had been kind enough to spend the keystrokes and relationship capital to enable me to be an early beta user of Amy.  Amy, or, which is the name of the company, is a gmail based personal assistant that magically schedules meetings with the power of artificial intelligence (and I assume a good bit of human “training” as well).

In my 15+ year professional life, I’ve never been in a situation where someone’s job was to be my personal assistant.  I can say unequivocally that Amy has made my life easier and I’d be pretty bummed out if she left me.  I’d like to share a few pointers that might be interesting for non-users, but perhaps more importantly, share some etiquette for users of Amy.

Don’t expect most people to get that Amy isn’t a singular human being, but, don’t sweat it when they assume that she actually is.

You might notice someone responding to the CC and being really polite to her – just go with it.  It’s going to take longer to explain Amy to your former wall street buddy what she is, than the time she will save you from all that looking at your google calendar and throwing around dates.

Later, when you chat, many intelligent people will have uncovered that Amy is part of some startup-thing and you guys can discuss her when you chat and have a chuckle.

“I totally thought she was a person!”  (Smiles.)

Don’t brag about having Amy in your emails or in your life.

“CC’ing my amazing artificial intelligence personal assistant Amy” Don’t be that guy or gal, it’s just bad form.  If being a part of a product beta is the most exciting thing you’ve got to say about yourself, well, then I guess go ahead and brag about it.  No one wants to hear about how hooked up you are..  Some people from the startup scene might actually be a bit envious of you and will ask you for the hook up because they read about Amy in tech crunch or something.  Be humble and appreciative that you’re able to participate in this.

You don’t have to send “Please” and “Thanks” to Amy*

*Except when she’s on a CC.  On a CC, you should always be polite with Amy because if you’re not you might seem disrespectful to people who don’t understand that she’s not really a singular person and you don’t want to look like a jerk.  Tangentially, if you have an actual personal assistant and you treat them without a that small amount of grace and appreciation in emails, then you’re kind of a jerk in my book.

Also- please don’t allow other people be nasty to Amy in emails, even if they know the story with her being a Mecha and all. The reasoning is there are probably still some real live human beings looking at these emails since is still an early stage startup. I’ve had people jokingly say “what’s wrong with you Amy are you an idiot?” and it pissed me off. Plus- why are you putting that crappy energy out there?

When it’s just me and Amy though- I’m beyond blunt, and typically don’t’ “please” nor “thank you”.

I also typically exclude punctuation.  She knows I’m a good person already. “No meetings 6-18” all subject line w/ no body — or a forwarded calendar invite with a “reschedule this” is a typical exchange from me to Amy.

When you’re scheduling a meeting with someone who is doing you the favor of connecting, don’t use Amy.  Schedule it old school by throwing out some dates, or use

They probably know someone at FirstMark, too, big-guy.  And if they’re not from the startup ecosystem/bubble/echochamber- how she communicates may confuse them.  Not to mention looks tacky that you can’t be bothered to schedule something personally with them, or you’re trying to be too cool for school with your assistant and all.

Your coworkers without Amy will come to hate Amy.

My team is not a fan of all the Amy emails.  They’re not jealous or anything.  If you have team members that participate in a majority of your calls/appointments, she can constitute a good portion of their inbox and it can be a bit noisy for them.  I don’t have a solution for this- but I’m also not dumping her either.

Expect half of the calendar invites she sends to be unanswered.

I think it’s a gmail tabs/spam/not compatible with some calendars thing.  What I do (when I am on my game) is confirm all my appointments, responded to or not responded to, the day before by forwarding the original invite with a quick note.  It’s probably a practice to do this even if you don’t use Amy actually.

Be pretty liberal with blocking out dates and times.

That Monday you get back from vacation, she will schedule that coffee meeting with your cousin’s friend who wants to break into startups first thing upon your return.  So don’t just block out the dates of your vacation/travel, but also the day you get back.

Always give yourself good buffers.  You can tell her “I need an hour between in-person meetings” and “I need 15 minutes between calls”, so you don’t have that dreaded back-to-back-to-back-to-back calls thing.  Also, she doesn’t care if you eat lunch, so if you’re using her for a road trip, you’d better tell her when you’re having lunch.

I have no idea how it works when both parties have Amy either.

My fiancee has Amy, too and we haven’t had any issues, nor have we experimented with an email like “Amys- schedule time for us next week to visit the wedding venue”, but maybe we should.  From their FAQ:

Q. What happens when I try to schedule a meeting with someone else that also uses Amy? Won’t she get confused?
A. Quite the opposite actually. Amy is usually blind to the availability of the guest, which is why she’ll engage in a dialogue on when and where, but if the guest is also a user of, Amy can skip the dialogue and schedule freely within the personal preferences of host and guest. It increases satisfaction and dramatically shortens the time to schedule. This is something we are very eager to see happen as often as possible. Scheduling nirvana! 🙂

But my final word is: should Amy (and her “twin brother” Andrew) become so big that this use case is not unusual, don’t send an email to anyone, under any circumstances, saying “Have your Amy talk to mine”.

Next steps- If someone feels like putting it together, I’d really love to see a subreddit or something with lots of tips and ideas for working with Amy.

There’s just not enough community out there yet- and I wonder why that is.