How to use an AI assistant for important meetings

Recently, an entrepreneur asked me whether I thought investors would be put off by an early-stage startup founder arranging meetings through an AI assistant like Amy or Andrew. He worried that some investors might be soured by having to reconcile the contradictory image of someone seeking money while simultaneously employing an executive assistant. That’s a worry I’ve heard before. Whether you’re a job seeker meeting a recruiter, an account manager calling a customer, or a novice getting coffee with an industry veteran, handing off communications to an assistant might give you pause. You might worry that you’ll blow the opportunity, come off impersonal or worse, arrogant.

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Cost-effective intelligent agents are taking over the functions of human assistants, and the perception of assistants is changing.

[/pullquote] But that’s a holdover from a time when human assistants were expensive luxuries, reserved for the C-suite at established companies. The social stigma of using an assistant is largely independent of whether the assistant is human or machine. As technology becomes more integrated, societal stigmas tend to disappear over time. It happened with talking on your mobile phone in public, for example, and it’s happening with AI assistants, too. Cost-effective intelligent agents are taking over the functions of human assistants, and the perception of assistants is changing. Worries like the one shared by that friendly entrepreneur soon won’t even be on the radar.

But there’s something else to consider here. Using an AI assistant shouldn’t change the nature of your human interactions. How you communicate with your AI and your human colleagues has more effect on your relationships than the fact that you use an intelligent agent.

You can dispel the preconceptions that linger from the time before AI democratized access to assistants by how you handle the handoff to your assistant. Take the following simple examples of the many ways an entrepreneur might set up that investor meeting through Amy:

Really bad:
“Amy can help you find some time on my calendar.”

“Amy, help Josh from Softbank find some time on my calendar.”

“Amy, please be so kind and help find some time for Josh and I next week.”

“Amy, please be so kind and help find some time for Josh and I next week. I am happy to go to his office.”

“Amy, please be so kind and help find some time next week that fits into Josh’s busy schedule. We can do between 8am and 7pm any day next week and I’ll, of course, go to his office.

Really looking forward to this Josh and appreciate you taking the time to listen to our vision.”

There’s a wide spectrum here in framing. The first (“Really bad”) example says, “I barely have time to care about this email, so I’m going to put the work of setting up this meeting I asked for back on you.” The last (“Great”) example says, “I really appreciate you taking time out of your schedule to meet with me, and I want to make this as easy as possible for you. Oh, and I’m also a pretty nice guy who treats his team well, even the non-human members.”

The words you use telegraph a lot about your personality. Good, honest people tend to stay good, honest, and kind, even when they use an AI assistant.

There’s also a more practical reason the last setup is so great. Each of these examples, in addition to getting progressively more genuine and kind, also progressively add detail and clarity.[pullquote align=”right” cite=”” link=”” color=”” class=”” size=””]Just like human assistants, AI assistants are not omniscient.[/pullquote] The “Great” example will make the process easier for everyone because it adds much needed context and specificity to the instruction to Amy. Just like human assistants, AI assistants are not omniscient. The more detail you can provide in your ask, the better your results on the other end.

AI assistants, like their human counterparts, struggle with commands that lack detail and context. Imagine an assistant designed to book travel. If you say, “Book me a flight to San Francisco,” without any other context, that assistant — AI or human — probably won’t get you the flight you want. What day are you going? By when do you need to arrive? If you instead add detail, context, and clarity, you’ll cut down on errors and get better results. “Please book a flight to San Francisco for Thursday. I need to arrive in time for a 6pm PT dinner in SOMA. Prioritize nonstop flights over my preference for JFK.”  

So should you use an intelligent agent while you court investors? I kindly asked for (and raised) $34M and did 200+investor meetings for using Amy, and it was never a problem (and I agree that raising capital for using Amy is unique, funny, and interesting all at the same time). However, I always make sure my messages clearly portray my genuine positive attitude and appreciation when someone is willing to spend time listening to our story at the same time give clear information to Amy, my AI assistant.


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