Skip to content

Looking to hire
ridiculously
talented staff?

Get Started

Ready for the dream
job you never
thought existed?

Meet Boldly

Beyond ChatGPT: How To Learn AI Tools As An Executive Assistant

Written by: Katie Hill
Executive assistant sitting at her home office, talking on phone while looking at her computer.
Executive assistants can learn AI through a mix of EA-specific training, professional communities, and hands-on practice with the tools they’ll use in their daily workflows. A good starting point is with a general assistant like ChatGPT or Claude for everyday productivity, then layer in targeted skills through courses built for administrative professionals and organizations where EAs learn alongside peers. Three use cases deliver results soonest: AI-assisted inbox triage, automated meeting prep, and calendar protection. AI literacy is now a core part of the executive assistant skillset rather than an optional extra.

 

Executive assistants are entering a new era where being tech-savvy is no longer a preference. It’s a must.

According to the 2025 Workplace Learning report by LinkedIn, 4 out of 5 people say they want to learn more about how to use AI in their work — but only 26% of organizations say they’re actively teaching their employees to use AI tools.

Even Forbes is talking about how AI implementation fundamentally alters workflows, job roles, and business models. From improving email and calendar management to creating content ideas for blogs and social media, nearly every industry is utilizing AI as a tool to increase productivity and efficiency.

With all of the information available for using AI, how are executive assistants wanting to upskill supposed to find great training in AI? Thankfully, we’ve answered this question so you don’t have to spend your time sorting through endless Google results.

Boldly branded promotional image asking, 'Looking to build your AI skills as an administrative professional?' encouraging viewers to download a free guide titled 'Getting Started with AI.' The guide aims to help executive assistants and administrative professionals enhance their AI proficiency."

How To Upskill In AI As An Executive Assistant

Executive assistants’ skills have moved firmly into the digital age and AI is the newest piece of that digital skillset. Here’s how to stay ahead of the crowd.

AI Training For Executive Assistants

There are already an overwhelming number of search results for “AI courses for executive assistants” and “AI executive assistant.”

But many of them are generic AI courses not meant specifically for executive assistants. The rest are AI tools for productivity. So here are two resources specifically teaching EAs how to use AI:

  • The Leader Assistant hosted by Jeremy Burrows, offers trainings, webinars, and live events for growth-minded executive assistants, including a growing library of AI-specific resources.

Professional Organizations For Executive Assistants

Numerous industries use professional organizations, and administration is no different. Connecting with other executive assistants gives you the opportunity to learn and develop skills alongside others with similar responsibilities as you.

  • Executive Assistants Organization is a professional organization that was founded by a C-suite executive assistant with the goal of building a community. They offer community forums, webinars, and mentorships as part of their membership.
  • The American Society of Administrative Professionals is the largest international association for executive assistants and administrative professionals. Their free membership has resources and partner discounts. The paid membership allows for access to their webinar library.

Sites such as LinkedIn or Meetup can help you find local organizations.

Practically Using AI As An EA: Three Places To Start

But three use cases show up consistently across EA communities right now:

  1. Inbox triage. AI can read through an executive’s inbox, flag what’s urgent, and draft first-pass replies for you to approve before anything is sent. For anyone managing a shared inbox or running point on a high-volume exec mailbox, this is where time savings show up fastest. Separate the “respond now” messages from the “later” pile, draft the reply, get the approval instead of starting from scratch on every email.
  2. Meeting prep. Before any important call, Claude can pull together attendee context, recent correspondence, open action items, and a few sharp questions to ask packaged into a briefing in under three minutes. Most useful for board meetings, investor calls, and recurring internal meetings where context shifts week to week.
  3. Calendar protection. Tools like Motion and Reclaim.ai automatically place tasks into open slots, preserve focus blocks, and reschedule lower-priority work when the calendar shifts. If your executive runs on Outlook, Motion tends to be the better fit. Google Calendar users will find Reclaim.ai easier to integrate, and it’s cheaper.

It is a best practice to explore the tools and get to know their features before shifting over to using them. This is one area where practice makes perfect.

ChatGPT & Claude For Executive Assistants

If you are looking for a place to start with AI, ChatGPT or Claude are great options. There are numerous ways to incorporate AI tools into your day-to-day, but the most common use is to boost productivity. The downfall is that your AI-generated results are only as good as the information you enter to start. If you want to improve these results, try using prompts.

The bottom line is that using AI is now an intrinsic part of the executive assistant skillset. The question is, how are you going to keep up?

FAQs

How can executive assistants learn to use AI?
Executive assistants can learn to use AI through a combination of three approaches: take training built specifically for administrative professionals, join professional organizations where you learn alongside other EAs, and practice directly with the tools. Starting with ChatGPT or Claude for everyday tasks is the simplest on-ramp before moving to more targeted skills.
What are the best AI tools for executive assistants?
ChatGPT and Claude are strong starting points for general productivity. For calendar management, Motion works well for executives on Outlook, while Reclaim.ai integrates more easily with Google Calendar and costs less. The right mix depends on the systems your executive already uses.
How can executive assistants use AI day-to-day?
There are three use cases that deliver results fastest for executive assistants who want to use AI on a daily bases. AI can triage an inbox by flagging urgent messages and drafting first-pass replies for approval, pull together meeting briefings with attendee context and action items in minutes, and protect the calendar by slotting tasks into open time and rescheduling lower-priority work automatically.
Do executive assistants need to know how to use AI?
AI literacy is increasingly becoming a core executive assistant skill—not an optional extra. Four out of five workers say they want to learn more about using AI on the job, yet only about a quarter of organizations are actively teaching it, which leaves room to stand out.
Are there AI courses made specifically for executive assistants?
Yes. Most search results return generic AI courses, but a few are built for EAs. The American Society of Administrative Professionals offers a ChatGPT prompting course framed around real EA tasks, and The Leader Assistant provides trainings, webinars, and a growing library of AI-specific resources. You can also look for AI training courses as they are becoming more prevalent and available with both paid and free options.
What’s the difference between ChatGPT and Claude for executive assistants?
Both are strong general-purpose AI assistants useful for boosting day-to-day productivity. Results from either depend heavily on the quality of the information and prompts you provide, so learning to write clear prompts matters more than the choice between them.
Should an executive assistant use Motion or Reclaim.ai?
It depends on the calendar your executive uses. Motion tends to be the better fit for Outlook users, while Reclaim.ai is easier to integrate with Google Calendar and is the cheaper option. Both automatically place tasks into open slots and reschedule lower-priority work as the calendar shifts.
About the author Katie Hill is a Content Writer at Boldly, which offers Premium Subscription Staffing for demanding executives and founders. When she isn't writing about remote work or productivity, she can be found adventuring in Colorado's backcountry.

You might also like

Smiling executive assistant working remotely from a bright home office, seated at a desk with a laptop, coffee, and workspace essentials. The image accompanies guidance on how to find a qualified executive assistant replacement during a leave of absence or role transition.

How To Find Your Replacement As An Executive Assistant

Remote Know-How
Woman with glasses on phone, looking at computer screen.

Chief Of Staff vs. Executive Assistant: Who’s Your Next Hire?

Move Your Business Forward
An executive assistant works thoughtfully from a home office, reviewing documents beside a laptop and coffee cup. The calm, organized workspace reflects the professionalism, dedication, and appreciation high-level executive assistants bring to the people and businesses they support.

The Best Ways To Say “Thank You” To Your Executive Assistant

Growth Tips