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Our Top Executive Assistants Challenged ChatGPT To 5 Tests. Here’s What Happened.

There’s a lot to be excited about in tech today. Innovation seems the weekly norm. But no tool seems to get quite as much press as OpenAI’s ChatGPT.

  • It can write like Shakespeare…
  • It can analyze complex data sets in a flash…
  • It can write code…
  • It can do math homework…
  • It can translate language…

Heck, by Christmas it’ll probably be able to wrap our presents!

Of course, the AI tool has some notable drawbacks, like bias, plagiarism, and just plain making up nonsense. However, it’s still helpful for certain use cases.

We’ve covered how the tool can ramp up an already-rockstar executive assistant’s productivity. But, because our team is training extensively on this and other AI tools, we wanted to push its limits.

So, five top-caliber EAs from our team tested ChatGPT’s abilities with tasks they perform every day in these areas:

      1. Interpreting real-time data
      2. Human empathy
      3. Attention to detail
      4. Nuance and intent
      5. Following specific instructions

Here’s how our battle of the humans vs. the AI unfolded, along with a “✅Pass or ❌Fail” verdict for each use case.

Test #1: Can ChatGPT Interpret Real-time Data To Make Informed Decisions?

Our first test was using real-time data to make informed decisions.

Our EA reported: “In planning an itinerary, ChatGPT hit all the tourist spots. But what it doesn’t note is critical: [X location] is closed for renovations and you can’t actually tour it other than the outside!”

Oy! This blunder reveals a critical flaw: while the AI is great at generating lists with whip-crack speed, it struggles to integrate real-time, context-specific information.

This oversight might seem small, but imagine taking an Uber to a fun location after a demanding day, only to find a construction fence! That’s a lot of wasted time, disappointment, and frustration.

This is not the experience a great EA delivers. Ever.

It failed because of its inability to handle real-time data and its nuanced interpretation. ChatGPT, as efficient as it is with handling massive data, often stumbles when it comes to contextual understanding.

While generative AI is making impressive strides, it still has some distance to go in taking real-time, highly-relevant data into account when making decisions.

✅Pass or ❌Fail?


Test #2: Can ChatGPT Mimic Human Empathy?

Our second test was testing its ability to have empathy for, and be considerate of, everyone involved in a cross-timezone meeting.

Here’s what our EA found:

“I asked ChatGPT to find a good meeting time for a few clients; it suggested 10AM EST. But that works out to 4AM HST… I don’t think the Hawaii participants would appreciate having to get up that early for a meeting!”

This is a big one for us—as care and kindness are bedrocks of our culture!

While it accurately suggested a meeting time, it failed to consider how the time zone differences would affect actual humans. Sorry, Hawaii-based folks.

In a business context, an executive would either face disgruntled clients, no shows, or even missed opportunities. As advanced as AI might be, it’s still no match for human empathy and consideration. Failure to understand and adapt to the human element has real consequences.

This sets off a chain of future problems, too. What about other interpersonal dynamics beyond respecting personal time and preferences? This is something even the best prompt can’t reproduce to the standard premium EAs hold themselves to.

✅Pass or ❌Fail?


Test #3: Can ChatGPT Work With High Attention To Detail?

Our third test seemed pretty simple. Can ChatGPT handle the nitty-gritty details? It can handle thousands of cells of data in seconds—surely it could handle a few requirements, right?

Here’s what our EA reported:

“ChatGPT came up with 3 of the meeting spaces I had already looked into but some of the facts were not correct. For instance, it said one of the locations only could hold up to 14 people but the room actually holds 22 people!”

ChatGPT offered up locations already on our EA’s radar—a fair move. But, it stumbled on a critical detail: misjudging the capacity of a meeting room.

An oversight like this is more than a minor hiccup in the business realm. It’s not a huge issue for 14 participants to meet in a room that can hold 22. But what about 20 people arriving at a venue that only fits 14—with plenty having flown in for the occasion?

That’s the issue! Inattention to detail creates delays, wastes valuable time, and is a poor look on the company hosting the meeting.

✅Pass or ❌Fail?


Test #4: Can ChatGPT Understand Subtleties, Nuance, And Intent?

Test four dug into the AI’s ability to grasp a human’s intent behind the prompt.

Here’s what our EA shared:

“I asked for free things to do around a nearby city. Even though I tried wording it differently several times, it kept showing me the same attractions that have an entrance fee.”

What happened here? The assistant was on the lookout for budget-friendly recreational options, yet ChatGPT persistently offered paid attractions. Clearly, this misses the mark.

This scenario sheds light on a particular struggle faced by AI. It often stumbles over the crucial nuances that play a significant role in real-world contexts. Whether it’s accommodating a client’s preferences or planning a team activity within a limited budget, EAs need to nail the minutiae.

Even the most sophisticated AI can struggle to comprehend subtle differences in language or intent. In this case, ChatGPT efficiently provided a list of attractions, but overlooked the “free” part of “fun.”

This showcases where the human touch is indispensable, bringing nuance and understanding, grasping subtlety and intent, and having a deeper understanding of who the client is as a person.

✅Pass or ❌Fail?


Test #5: Can ChatGPT Follow Specific Instructions?

Our fifth and final test deals with the complexities of travel, itineraries, and following instructions.

Here was our EA’s summary:

“I asked ChatGPT to modify its trip suggestions by removing all museums. The revised itinerary had at least one museum on it!”

Our assistant had a straightforward request: a travel itinerary excluding museums. However, ChatGPT’s updated itinerary disregarded this specification, resulting in a museum still being part of the plan. Every time.

This highlights a significant hurdle AI might face: comprehending and acting upon specific instructions. Again, deleting a museum visit from an itinerary doesn’t seem like the end of the world. However, our tests were designed to pinpoint failures so we could extrapolate to more serious consequences.

Scale inability to follow specific instructions to operations, planning, or any other key business output, and you have much higher consequences from a seemingly innocuous error. An error, by the way, that might be difficult to track down and correct.

✅Pass or ❌Fail?


AI + Humans = Winning

And there we have it. A glimpse into the world where AI and human minds collide rather than collaborate. These tests from the trenches of executive assistance show us that while AI tools, like our friend ChatGPT, are genuinely impressive, they aren’t ready to fly solo just yet.

Our AI assistant can handle a heap of tasks, churning out itineraries and suggestions at lightning speed. But, it can sometimes get things wrong that have real consequences. Some are small, but others are severe.

Powerful tools like ChatGPT can boost human productivity. But, it takes a highly-trained executive assistant to get the right output and scan for inevitable errors.

Whether it’s planning a meeting that doesn’t have your Hawaii clients waking up at 4AM, or tailoring an itinerary that ditches museums, getting these details right isn’t optional. It’s required. Because it’s what we do. And that’s why we need the human touch.

So, where does that leave us? We think in a pretty exciting place.

AI and humans, working together, can achieve amazing things. AI takes the grunt work, freeing up humans to do what they do best: think, create, empathize, and grasp the nuances that make us human.

In a nutshell, AI is a powerful tool, but it’s not the be-all and end-all. The magic really happens when AI and humans work together. That’s when we’re on track to see some real game-changing stuff in the business world.

In the end, it’s not about AI vs Humans. It’s about AI + Humans. That’s the future we’re looking forward to.


In the kaleidoscope of innovation that defines our age, AI tools like OpenAI’s ChatGPT have stolen the limelight, dazzling us with their ability to weave text as a human would. They promise us streamlined tasks, more efficient operations, and yes, even the prospect of replacing certain roles. Yet, when the rubber meets the road, they’re not quite hitting the mark.

Consider the stories of five executive assistants who decided to put ChatGPT through its paces, delegating tasks they routinely handle in their day-to-day. The results? Less than stellar.

Case in point: “In the planning itinerary ChatGPT hit all the tourist spots. But what it doesn’t note is critical: [X location] is closed for renovations and you can’t actually tour it other than the outside!”

ChatGPT, in its bid to craft the perfect itinerary, ticks all the tourist boxes. But, it trips over an important hurdle – real-world, real-time context. It doesn’t catch that [X location], a must-see spot, is currently out of bounds, under renovation. Sure, the AI can whip up a laundry list of attractions in a flash, but it misses the beat on the here-and-now status of these sites.

This slip may seem small, but to an executive on a tight leash of time, it can spell chaos. Picture the scenario: an executive, arriving at a remote location, only to find it off-limits. The wasted time, the derailed schedule – it underscores the importance of the human element in these roles.

The crux of the matter? Real-time data and its nuanced interpretation. AI, as embodied by ChatGPT, might be a powerhouse of data processing, but it often falters when it comes to deciphering context. This leads us to an important revelation: AI has made leaps and bounds in shaping the business landscape, but it’s still got some ground to cover before it can truly mirror the subtlety and discernment of human judgment.


Our narrative unfolds with another executive assistant navigating a unique conundrum. Their story goes, “I asked ChatGPT to find a good meeting time for a few clients; it suggested 10AM EST. But that works out to 4AM HST… I don’t think the Hawaii participants would appreciate having to get up that early for a meeting!”

This tale offers us a stark illustration of the indispensable role of human insight and situational awareness in the world of business – an area where AI still seems to be finding its footing. Here we see ChatGPT ticking the ‘meeting time’ box but tripping over the hurdle of time zones, failing to consider the convenience of participants spread across different locations.

For a business executive, this stumble could mean navigating choppy waters of client dissatisfaction or, in the worst case, opportunities slipping through their fingers. This real-life instance drives home a critical truth: AI, despite its dizzying advances, has yet to match up to human empathy and consideration. It underscores the pressing need to comprehend and incorporate the human factor in a business environment.

AI, with all its prowess in crunching numbers, may still stumble when it comes to the delicate nuances of human interaction – the respect for personal time, preferences, and convenience. ChatGPT, in this case, missed the human-centric angle of the task, a miss that could impact relationships and potential business prospects.

To wrap it up, while AI tools like ChatGPT excel in processing a vast volume of data and tasks, they still need a human at the helm to steer their outputs towards accuracy and appropriateness. This reaffirms the need for a harmonious blend of AI and human judgment, an alliance that continues to be integral in shaping the modern business landscape.


On we march with our narrative, landing on the experience of another executive assistant. They shared: “ChatGPT came up with 3 of the meeting spaces I had already looked into but some of the facts were not correct. For instance, it said one of the locations only could hold up to 14 people but the room actually holds 22 people!”

So, what unfolds here? ChatGPT replicates a list of venues already on the assistant’s radar – not a miss, per se. But the real snag comes with the misstep on key facts, like understating the capacity of a meeting room. It’s akin to a pianist hitting the wrong note at a key crescendo.

In the orchestra of the business realm, these seemingly small errors can transform the symphony into a cacophony. Picture a meeting planned for 20 attendees, but the room falls short, accommodating only 14. It’s a mismatch that could lead to discomfort, especially when you have top-tier executives jetting in for the event.

This episode provides us with an invaluable lesson: even the most sophisticated AI can slip up on the details. And it’s not just the minor trivia, but the meaty, make-or-break facts. It underscores the importance of the human element in the chain – the fact-checker, the meticulous one ensuring all the i’s are dotted and t’s crossed.

In a nutshell, while AI boasts a remarkable prowess and potential, it hasn’t quite earned its wings to fly solo. We still need that human touch, that sense of fine-tuning to ensure seamless execution. It’s this symbiosis of AI and human talent that’s poised to transform businesses into well-oiled, high-performance engines.


Our journey brings us to the next chapter, a story by another executive assistant: “I asked for free things to do around a nearby city. Even though I tried wording it differently several times, it kept showing me the same attractions that have an entrance fee.”

Here’s the crux of the matter: the assistant was in the hunt for leisure activities that wouldn’t weigh down the purse, yet ChatGPT repeatedly pitched ideas that carried a price tag. Not quite hitting the target, is it?

This paints a vivid picture of an AI challenge. It often trips over the minutiae – those critical subtleties that bear significant weight in real-world situations. From catering to a client’s unique preferences to organizing a team event on a shoestring budget, picking up on these nuances is essential.

This tale accentuates a salient point: even a brainy AI can find itself in a fix when it comes to deciphering subtle variations in language or meaning. While ChatGPT was able to serve up a list of attractions, it missed the ‘free’ in the ‘fun’. This reminds us of the confines within which AI operates and underlines why the human role in the equation is irreplaceable.

In summing up, while AI impresses us with a plethora of abilities, it falls short when it comes to detecting the finer details. That’s where the human touch comes in, providing the nuance and understanding, particularly when things get intricate. The aim is to harness the power of AI, whilst capitalizing on human ability to navigate the subtleties.


Our narrative ventures forward to the next account from the front lines: “I asked ChatGPT to modify its trip suggestions by removing all museums. The revised itinerary had at least one museum on it!”

Here’s the inside story: The assistant had a particular ask – a travel plan devoid of museums. Sounds simple enough, right? But when ChatGPT delivered the updated plan, voila, there stood a museum, uninvited.

This brings to the fore a critical AI shortcoming: At times, it’s not quite on the money with particular requirements. You may believe you’ve spelled it out with absolute clarity, but AI could still end up veering off target. In the arena of business, missing specific markers can spell a breach of trust.

Visualize yourself servicing an elite client who has made their aversion to museums unequivocally clear. Then a museum appears on their tour plan. That’s a tough pill to swallow.

This account emphasizes a profound truth – AI, no matter how cutting-edge, can occasionally falter on exacting instructions. It may miss the essence of the request or falter on the delivery. That’s precisely why we still require the human factor to ensure impeccable execution.

In essence, while AI packs a punch with its capabilities, it’s not infallible. We still need the human touch to ensure every checkbox is ticked off accurately. When we manage to fine-tune the harmony between AI and human effort, we strike gold. That’s a future we can look forward to with optimism.


And there you have it, a riveting look into the frontier where silicon intelligence encounters the human mind. These stories, plucked from the battleground of executive assistance, illustrate that while artificial intelligence, personified by our associate ChatGPT, is quite a marvel, it isn’t quite prepared for a solo flight.

Our digital aide is adept at juggling myriad tasks, producing schedules, and offering suggestions at breakneck speed. But it can occasionally slip up, misunderstanding subtle cues or missing specific directives. This is precisely where we humans maintain our advantage.

In the high-stakes world of business, the minutiae – the nuances, the specifics – they carry weight. Whether it’s orchestrating a meeting that doesn’t rouse your Hawaiian clients at the crack of dawn, or fashioning an itinerary sans museums, acing these details can be the difference between a soaring success and a lost cause.

And this is why we need the human element. Because we humans excel at comprehending the small things, the bespoke requests, the unique needs. AI might be a dab hand at wrangling vast amounts of data and repetitive tasks, but when it comes to deciphering the more intricate, nuanced facets of our existence, nothing rivals the human intellect.

So, where does this leave us? We believe it’s a pretty exhilarating spot. AI and humans, in concert, can unlock incredible potential. AI tackles the heavy lifting, liberating humans to do what they excel at – thinking, creating, empathizing, and honing in on the subtle details.

In essence, AI is a potent ally, but it’s not the panacea. The true magic ignites when AI and humans collaborate. That’s when we’re poised to witness some truly transformative shifts in the business sphere.

In the grand scheme of things, it’s not about AI versus Humans. It’s about AI augmented by Humans. That’s the future we eagerly anticipate.

About the author Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.

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