AI for Executive Assistants: What Works and What Doesn’t

AI has become the new buzzword, with industry leaders praising its efficiency and task automation capabilities. In fact, the dominant narrative has been that AI will replace executive assistants by taking up roles such as scheduling and email management.

However, executives who have tried to switch to AI systems have quickly realized that the best way to maximize their performance is by onboarding a great EA and then pairing them with the right AI tools.

This empowers your EA to create systems and workflows that turn random requests into predictable tasks, reducing disruptions to your schedule.

This article covers everything to know about AI for executive assistants, including the best AI tools and common mistakes to avoid when incorporating AI into your workflows.

Why AI Does Not Replace Executive Assistants

AI offers invaluable benefits, including workflow automation and significant time savings, but executives still need human-led EA support if they are to truly reclaim their time and maximize their performance.

Even the best AI tools need executive assistant input for the following reasons: 

• AI Can’t Replicate Human Judgment: AI tools can schedule meetings based on incoming requests and even identify conflicts, but may struggle to prioritize which meeting is the most important based on changing context. In contrast, your EA leverages their deep understanding of your business and priority scoring system to identify the meeting that has the most strategic importance.
• AI Lacks Human Credibility: Stakeholders, such as board members and clients, will likely respond differently when they receive a meeting decline from your EA vs. an automated response by an AI. In the case of AI, they might wonder whether you even saw their request at all, which could sour stakeholder relationships.
• AI Only Adds an Acceleration Layer: Elite EAs provide high-quality support even without using any tools. As such, AI only simplifies the tasks, allowing your EA to complete them faster and with higher accuracy. An example would be your EA using AI to summarize a 100-page report in seconds, which would otherwise take them at least an hour to skim through.
• AI Lacks Most Executive Superpowers: Experienced executive assistants leverage their superpowers, such as ESP and synchronization, to tailor schedules to their principals’ rhythms and productivity cycles. This means your EA may cancel or reschedule a meeting just because they realize you are not in the right headspace at the moment or they may time-block your schedule to give you time to rest and refocus.

Where AI Improves Executive Assistant Workflows

AI tools shouldn’t replace executive assistants; rather, they should streamline workflows. Instead of your EA spending hours building templates, they can leverage these tools to work faster, stay organized, and support you better. 

Here is a table comparing tasks an EA does manually vs. with AI assistance:

Other ways AI will impact your EA’s performance include:

Speed and Drafting Leverage 

EAs can use tools like ChatGPT to generate first drafts for routine communication, including emails, status reports, and meeting agendas, in minutes.

This means your EA will only need to refine the message to match the target recipient rather than create it from scratch. 

Better Meeting Prep and Recaps 

Your EA can use AI-powered meeting assistants to transcribe and organize agenda items, and then use the output to prepare summarized reports that you can quickly scan through before meetings.

This ensures your EA doesn’t miss important agenda items, such as due to fatigue after long working hours, and helps them stay organized when sharing reports with you or other team members. 

Smarter Inbox and Calendar Triage 

Your EA can use AI to organize messages based on themes or stakeholders.

This saves time when managing large email volumes and reduces the chances of missed messages, which could otherwise jeopardize stakeholder relationships or cost you business.

Executives can get the best out of AI by partnering with an elite EA who can develop a deep understanding of their business and build workflows that turn tasks into predictable cycles.

At ProAssisting, we partner executives with EAs who have experience leveraging tools and software to streamline workflows. Additionally, we offer customizable support models to help executives with a full-time EA transition to a fractional executive assistant after automating most administrative tasks. This way, you can utilize ⅓, ½, or ⅔ of a ProAssistant’s capacity depending on fluctuating support needs.

Schedule a call to explore how to leverage AI for executive assistants to streamline your workflows.

Best AI Tools for Executive Assistants 

Your EA should use AI as part of their executive assistant tools for operational support and to automate repetitive tasks, allowing them to focus on strategic support. 

Here are the best AI tools for executive assistants:

1. Generalist AI Models 

These are multi-purpose tools that your EA can use to automate administrative tasks, such as drafting emails or summarizing documents.

Some AI tools to consider include:

• ChatGPT: EAs can utilize this AI tool to draft emails or for general research when writing reports. 
• Claude: Helps EAs summarize large volumes of documents, prepare briefs, and organize complex reports into scannable summaries and briefing notes for the executive.

2. Inbox and Email Assistant

Your EA can leverage the following AI tools to get your email inbox under control once and for all:

• Superhuman AI: Processes emails and provides prompt response suggestions, giving the EA communication control when managing large inbox volumes. 
• Fyxer: Organizes emails and filters out spam, eliminating low-priority “noise” that EAs encounter when sorting emails manually. 

3. Scheduling and Calendar Agents 

These are tools your AI can use to optimize your itinerary and identify and resolve scheduling bottlenecks. Notable tools include:

• Cover Reclaim: Minimizes the manual coordination EAs face when balancing meetings and productivity time by suggesting possible schedule changes to optimize executive performance. 
• Lindy: Automates repetitive workflows, such as reminders, follow-ups, and scheduling, allowing EAs to focus on other tasks without worrying about urgent matters. 

4. AI Notetakers and Meeting Tools 

Your EA can use the following AI tools to record meeting minutes and prepare reports:

• Cover Granola: Creates structured summaries with little to no human input, allowing EAs to manage simultaneous executive meetings effectively.
• Otter: Integrates with Zoom and Google Meet to transcribe and take notes, which the EA can use to pull information about the meeting without reading the transcriptions. 

5. Knowledge and Workspace AI

Your EA can leverage the following AI tools to automate workflows:

• Cover Notion AI: Streamlines workflow by creating a centralized workspace for EAs to pull important executive documents from integrated platforms, such as Google Drive and Slack. 
• Glean: Saves EAs time by providing a unified enterprise search for finding meeting notes, historical documents, executive briefings, and past correspondence. 

Where AI for Executive Assistants Falls Short

AI tools majorly excel in tasks that require pattern matching or mass output generation, like customizing emails to 1,000+ clients at a time.

However, they may be unreliable in handling tasks that lack clearly stated instructions or those that require interpersonal nuance, as outlined below:

AI Fails in Tasks With Gray Areas

Executive requests often fall in gray areas where the instructions are incomplete or priorities are clashing. As such, the right answer depends on contextual factors like team morale or stakeholder mood, which AI can’t read.

For example, your EA may remember that the last call they had with a client was tense because their order had not yet been processed. Consequently, your EA may escalate this issue to you and prioritize it over a board meeting if it risks costing the business its biggest client.

AI Lacks Trust-Building Capacity

A huge part of integrating and onboarding an executive assistant into your world is assigning them tasks to gauge their capabilities, after which you can increase their workload based on their performance. 

Over time, you learn to trust your EA even with tasks that have a strategic impact on your business because they have shown that they are dependable.

This remains a major concern with AI because its dependability and output can change due to external factors like version updates, altering how the software processes and executes tasks.

AI Cannot Function Independently During Crisis Management

Unforeseen circumstances, such as delayed or flight cancellations, require quick judgment and intervention, as they can disrupt your entire itinerary.

AI may fail in such instances that require improvisation and human reassurance to keep you at ease. However, your EA may leverage AI to quickly find backup solutions, such as available flights, and then choose the option that disrupts your schedule the least.

AI Cannot Represent You in Meetings

AI falls short when you need someone to represent you in meetings or philanthropic events because of your hectic schedule. You can use the software in online meetings to take notes in your absence and summarize them into brief notes. However, you may not be willing to have the AI commit to future meetings on your behalf. On the other hand, your EA can function as your extension and represent you in meetings, ensuring your presence is felt.

Common Mistakes Leaders Make with AI Assistants 

While it’s undeniable that AI assistants have streamlined workflows, one common mistake leaders make is to try to replace executive assistants with these tools. Other pitfalls include: 

1. AI As a Replacement for the EA 

Eliminating EAs to save costs backfires because these tools often miss interpersonal nuances. For example, Superhuman AI will promptly respond to client emails, but without human oversight, it won’t provide an emotional tone that’s important when cultivating a good relationship with your clients. 

Additionally, AI recommendations don’t include executive preferences, which your EA would know because of your existing relationship, which compounds their knowledge of your business.

2. Tools Stacks Without a Workflow 

Installing many AI tools without a clear direction leads to tools that offer similar services, resulting in unnecessary AI subscription expenses. 

Instead, you should partner with your EA to create systems and workflows, and then determine which touchpoints would benefit from AI assistants to boost efficiency and performance.

3. No Human Review on AI Output 

Even AI-generated schedules can sometimes provide fake meeting dates or invite the wrong people to board meetings if left unsupervised. 

As such, an executive assistant plays an important role in reviewing AI-generated outputs to ensure accuracy and to add the human element needed to foster a strong organizational culture. 

4. Thin EA Training on AI

Failing to train your executive assistant on how to use AI tools results in poor workflows and underutilized software.

Your EA will need time to learn how to write effective prompts, which tasks to automate, and how to customize outputs using AI to meet your executive expectations. 

The Future of AI for Executive Assistants

As with most technologies, AI for executive assistants will continue improving, requiring less and less human input. However, this does not mean that at some point it will replace human-led EA support. Instead, it will become more embedded into workflows, improving EA efficiency and performance.

Here’s how we predict AI will impact the quality of EA support you receive in the next 5 years to a decade:

• EA Will Take Up More Strategic Roles: AI adoption will automate labor-intensive tasks like data entry, giving your EA more time to learn about your business. Consequently, your EA may take up more strategic roles, such as executive decision support and stakeholder management, further multiplying your performance.
• AI Proficiency Will Become a Core EA Skill: Among the top questions to ask when hiring an executive assistant will be their knowledge of AI, with proven experience being an added advantage.
• Human Support Will Remain Irreplaceable: Even with advanced AI tools, you will likely want human oversight for tasks involving confidential information, conflict resolution, and leadership support. For example, while your EA may use AI to create and send client agreements, you may want them to attend the onboarding sessions.

Frequently Asked Questions (FAQs)

Below are answers to common questions executives ask about AI for EAs. 

Will AI Replace Executive Assistants? 

No. AI will not replace executive assistants even as the technology evolves and becomes more advanced. AI will help in routine tasks, such as scheduling, drafting quick emails, creating templates, and idea generation, leaving the human element to EAs. 

How Can an Executive Assistant Use AI Without Slowing Down? 

An executive assistant can use AI without slowing down by using the tools to automate repetitive tasks, such as drafting emails, transcribing meeting minutes, and generating summaries in a few minutes. 

This will allow an EA to focus on tasks that have a strategic impact on the executive’s performance.

How Should Executive Assistants Evaluate AI Tools? 

EAs should evaluate AI tools based on how much time they save, how well they integrate into their current workflows, and whether they simplify their job. 

The best AI tools for executive assistants solve a specific work problem instead of automating random tasks.

How Do You Train an Executive Assistant on AI? 

An effective way to train your EA on AI is to use a practical approach. For example, starting with simple tasks, such as drafting emails or using AI to summarize meeting notes. 

Additionally, you can create internal prompt libraries that your EA can use before they master how to generate AI prompts.

Conclusion

AI provides leverage for executive-assistant partnerships looking to streamline their workflows. This explains why the gap between an average and elite EA widens with the introduction of AI instead of bridging it.

As such, executives should prioritize finding the right EA first before exploring the available AI tools.

At ProAssisting, we provide seasoned executive assistants with experience creating workflows and supporting C-suites in global brands like the WNBA, Comcast, and Oracle. Additionally, we have a rigorous vetting process that results in less than 5% of applicants qualifying for the ProAssistant role.

Book a call with Ethan Bull, our co-founder, to discuss how you can partner with an EA to integrate AI into your workflows.