What if we all had an Executive Assistant?

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If you, like me, grew up with the stereotype of the successful person always helped by a beautiful (or handsome) Executive Assistant (EA) able to proactively predict his or her needs, then, please, keep reading, I might be able to give you a hope!

It was 2005 and I was a Master student in search of adventures. I managed to visit the San Francisco Bay Area for the summer, hosted by Peter, a distant relative of mine. He was the CEO of a successful startup and, a few times, I visited his office to get an idea of what work was like in the world’s innovation heart.

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In that office, for the first time, I could see with my own eyes the value of an EA. His assistant, let’s call her Gina (fictitious name), was an absolute superstar. She knew Peter like her pockets, had a great relationship with his wife (key to success!), and was always able to anticipate his needs. She was fast in accomplishing tasks, organizing logistics at the office, and filtering/prioritizing calls and meetings. She blew my mind with her resourcefulness.

The questions I immediately asked myself were:

Are all Executive Assistants like Gina?

How long does it take to reach that level of productivity between EA and Executive?

Fundamental role despite its limits

At a high level, the role of the EA is to take care of mundane tasks delegated by the Executive, thus allowing the latter to focus on more fulfilling value-generating activities, and consequently accelerate the business.

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Over time, I had the chance to talk to several Executives who have an EA, and I came to the conclusion that the key functions Executive Assistants carry out are: managing calendar, being a firewall and handling logistics. There are additional minor functions that contribute to the overall value, however, the ones I mentioned appear to be the most compelling in terms of Executive’s time savings.

Managing calendar

Intuitively, this activity entails scheduling and rescheduling events in the busy calendar of the Executive. The EA collects needs and requests from all the stakeholders trying to get a hold of the boss. She/he also collects priorities and needs directly from the Executive, and uses them to rank and prioritize events based on her/his best judgement. Then, the EA spends time figuring out each stakeholder’s availability through a ton of emails, instant messages and calls back and forth. Finally the EA can schedule or reschedule events.

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Being a firewall

Throughout the day, many people try to get in contact with the Executive via phone calls, messages, emails, in person visits and other means. The EA filters the noise and lets through only what truly matters in light of the current goals.

Handling Logistics

The Executive is busy and often traveling. Every trip comes with a considerable amount of effort to book flights, hotels, cars and create the infamous expense reports that require a constant fight with constraints dictated by corporate policies. Often, an important meeting is happening at the office and the EA prepares the meeting room, buys food for everyone and facilitates the meeting start.

No EA, no business

Without a doubt, if the Executive were to manage her own calendar autonomously, she would be able to accomplish a tiny fraction of her normal output, due to an insurmountable amount of mundane tasks: all distractions that do not allow the Executive to focus on creating value and growing the business.

But there’s still coordination cost

Let’s get back to Gina. Despite being at Peter’s office for just a few random days as a visitor, I could witness a few occasions when Gina and Peter closed themselves in a meeting room for long sessions to discuss priorities and sync on calendar events. A couple of times, frictions arose between Peter and Gina due to misunderstandings, and Gina had to promptly course correct.

By observing these dynamics, I figured that, no matter what, Gina would have never been able to optimize Peter’s day with accuracy. Simply, she was not equipped with enough current knowledge of the facts and business wisdom to avoid frequent syncs, plus mind reading isn’t really a thing yet.

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How long does it take to get on the same frequency with your experienced EA?

Every person is different, and chemistry definitely plays a role. Probably, it would take a couple of months of working together before starting to see a visible impact. Instead, it will take years to reach Gina’s level of productivity.

Is it worth having an Executive Assistant?

Hell yeah! Without a doubt. You are paying a salary to an individual, pleasant to be with, who is making your life so much easier, while enabling you to focus on your strengths and what you like to do, therefore generating a great positive impact on your business, several orders of magnitude more valuable than the price you pay for the EA.

How long before Artificial Intelligence (AI) replaces your Executive Assistant?

Not long, bear with me…

We have seen that the main EA functions are managing the calendar, being a firewall and handling logistics.

How does AI perform today with regard to these three activities?

Managing calendar

Unfortunately, we are still far from replacing Gina. We start to see some smarter calendar automation, however, we are still far from being able to ask a Virtual Assistant to execute tasks like:

“Organize a meeting with Frank, Margaret and Josh from ACME Corp., at our earliest convenience”

There are still many limitations that prevent the fulfilment of this request; above all, the security reasons whereby your assistant can’t access Josh’s calendar, since it’s outside the domain of your organization.

Being a firewall

Also in this case, Gina can relax; just think about all the spam calls you receive. When you see a number you don’t know that leaves a 5 sec message in your voicemail you already know it’s a bot that made that call, and you put that phone number in the black list.

The blacklist approach is binary, either black or white; once a number is in the list, you don’t get a second chance to answer that call. Gina, instead, answers for you, listens, judges and prioritizes the interactions based on your goals.

Mainstream AI solutions aren’t smart enough to recognize spam calls, let alone prioritize interactions for you.

Handling logistics

There are a few Virtual Assistant companies in the world that made use cases like booking a flight a reality, although, they still perform just a little better than a prototype and do not account for the myriad of variables and trade-offs that play a role in choosing a certain itinerary versus another.

“Should I fly through Atlanta and risk waiting there for hours due to the usual delay caused by bad weather, or have a longer overnight layover at grandma’s house in Chicago?”

Again, Gina’s job is not at risk anytime soon.

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Gina’s threats come from breakthrough innovations and paradigm shifts

When we consider incremental innovation on top of existing technologies, interaction style and rules of engagement, then Gina is safe.

However, what if a breakthrough innovation happens, the rules of engagement change and suddenly the AI is able to deliver more value than Gina in some specific fields?

Still, the new paradigm would not be able to fully replace a human, however, imagine the monetary benefit of the new AI paradigm plus the money saved by firing Gina were higher than Gina’s overall value minus her salary and minus the value of the time required to coordinate with her.

The future is in the works

Let’s focus only on two EA functions only: managing the calendar and being a firewall.

Visualize a future where calendars become obsolete, people focus on what they love doing, while the AI orchestrates the interactions among them, according to a grand scheme that maximizes the overall organizational outcome.

You give orders to your Virtual Assistant (VA):

“I need to talk to Frank before the end of the week”

“I need 5 min of Shelley’s time on Friday to show her the latest floor plan”

“Put me in contact with Ashley at ACME Corp asap”

After a request to the VA, you forget about it because you know that it is going to happen. So, you get back to what you like and fulfills you. Then, magically at the right time, you get connected with the right people through the channel that best suits your intent (e.g., you need a communication app capable of screen sharing to show Shelley the floor plan on Friday), and you have your live collaboration session without constraints like scheduled boundaries.

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This new approach changes the rules of the game and solves the hard problems of the managing calendar function, by simply making calendar management not needed. As you might remember from my previous articles, calendars limit your productivity by dividing your day in coarse 30-min chunks. You only have a limited number of those chunks, usually 16; the more you use your calendar, the more you are limiting what you can achieve in a given day.

Now, imagine someone you rarely interact with wants to talk to you and makes a wish to the Virtual Assistant. The VA notifies you of his/her intention to talk and allows you to accept or reject; now, your reaction is a significant data point that, along with other conditions, allows the AI to learn your preference, your habits, the way you prioritize, resulting in the VA ability to act as a firewall and let the important interactions pass through automatically, while stopping the ones that are inappropriate for a certain moment.

The firewall function gets automatically fulfilled by the VA, and the accuracy increases over time based on your interactions with the VA itself.

All of the above value gets delivered to you without the periodic alignment sessions and misunderstandings Peter used to have with Gina, at a price which is between free and a negligible fraction of her salary.

Get ready to experience a new kind of Executive Assistant for everyone, have less scheduled meetings, focus on what matters and achieve a better work-life harmony.




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Dario De Santis

Dario De Santis

Long-termist visionary technology Entrepreneur and Product Leader, with a strong passion for improving people's productivity through innovative solutions.