How to: Onboard your AI assistant

Do you remember your first day at work at your very first job? Awkward? Nerve-wracking? Possibly a bit overwhelming as you contemplate how much you need to learn to contribute meaningfully?
No new hire magically knows what to do or how to do it. They need to learn everything from the most basic aspects of work—where to sit, where to get coffee, where the bathrooms are—to the elements that are specific to their role—how your company has configured Google Analytics, which email service provider you use for marketing campaigns and on and on.
As a manager, it’s your job to show them the ropes during their first days. You introduce them to the team, set up their email and Slack accounts, and point out where to get coffee (and beer on tap ;-). These first steps are essential before any new employee can dive into real work. Do them well, and you’ll have a relaxed and effective employee; do them poorly or not at all, and they’ll take up even more of your time asking basic questions.
We like to think of hiring Amy and Andrew to schedule your meetings in a similar way. The hitch is that this may be the first time you’ve ever hired an assistant, let alone an AI assistant.
Not to worry. Getting Amy and Andrew up to speed isn’t hard; it just requires a bit of focus. First you need to do basic setup. On, you need to connect your calendar(s), let them know your phone number and addresses and set your preferred meeting hours (no meetings after 4PM on Fridays? No problem, just make sure Amy knows).
Now that you’ve taught Amy and Andrew the basics, you can turn to more advanced preferences, such as who your VIPs are (boss, co-founders, mom?) and how you’d like your AI assistant to sign their emails (“Andrew Ingram | AI Commander of Raquel’s calendar”).
With initial setup of a new hire out of the way, you typically start them on smaller tasks. You want to be sure they understand what you need before you throw them complex jobs or sticky problems to solve. With Amy and Andrew, you might feel the same way. So you schedule a meeting with a friend or your mom, to test the waters.
Trust, however, might not come instantly. And that’s no surprise. In the real world, it takes any new employee about 10 weeks to become fully productive in their role. And that on-ramp isn’t always smooth. Good managers will give direct feedback to new employees to keep them on track.
Amy and Andrew aren’t that different. Our data shows that it takes about 13 meetings before you really find a groove with your AI scheduling assistant. Along the way, you may need to fine tune your settings. You may realize that 9:00AM may be a slightly more realistic scheduling start time than 8:00AM or that you’re sick of your go-to lunch location and want to change it to the new spot that opened around the corner.
Once you hit that 13 meetings mark, the real magic happens. At this point, you’re probably ready to give Amy and Andrew the toughest scheduling challenges in your inbox. And mostly they rock them.
But back to our human example: just as a new employee might miss a deadline or forget to update a campaign budget, Andrew and Amy might occasionally flub. No good manager expects any hire, even their top performers, to make zero mistakes. They do expect their employees not to repeat the same mistakes over and over. Same goes with Amy and Andrew (machines aren’t infallible, after all). If they mess up, you can let them know. Better yet, take a quick peek at to see what actually happened. You may find out Amy and Andrew have been doing their job just fine, and it’s the humans who have erred.
Onboarding any new hire takes some real effort and time. Invest some time in setting up and getting to know Amy and Andrew and then watch those extra hours pile up—the ones you used to spend playing that tedious and often fruitless game of email ping pong.
More tips from Amy & Andrew’s human help.
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