Future of Work
How to get the most from an AI executive assistant

How to get the most from an AI executive assistant

Judy Tsuei
November 20, 2023

How to get the most from an AI executive assistant
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No matter your title — individual contributor, manager, freelancer — chances are you’ve got a lot on your plate. And an even more painful truth: most of it is likely busywork. In the 2023 Anatomy of Work Global Index, Asana reported that knowledge workers spend 58% of their workday on “work about work” — that is, duplicated work, unnecessary meetings, and switching between apps.

An AI executive assistant can help you manage your day-to-day, especially when it comes to busywork. That means more time (and mental bandwidth) for you to focus on high-level tasks like decision-making, creative thinking, and strategy.

In short, advancements in AI technology can help you find more freedom in your workday — without having to hire a personal assistant.

How does AI work?

Artificial intelligence is designed to mimic human thinking and problem-solving by learning from data (a technique called machine learning). 

Keep in mind that automation and artificial intelligence are not one and the same. Automation describes rule-based tasks (if this, then that) and doesn’t necessarily require intelligence. On the other hand, AI is all about mimicking human intelligence in machines, in order to perform tasks like: understanding natural language, recognizing patterns, and making decisions.

Pro tip: For a major boost in productivity, use both automation and artificial intelligence in your workflow. 

What can an AI assistant do?

There’s no replacement for the personal connection that only human assistants can bring. But the reality is that not everyone has the resources to hire an administrative professional. That’s where an AI assistant comes in.

We’re all familiar with tools such as Alexa, Siri, and those customer service chatbots you usually see at the bottom of a webpage. However, that’s only a slice of what AI can bring to the table. AI can assist in areas such as:

  • Project management
  • Calendar management
  • Administrative tasks
  • Content creation

Below are our favorite AI assistants for you to get started.

3 AI tools to try today

ChatGPT: Best for versatility

ChatGPT is an advanced language model created by OpenAI, an artificial intelligence research company. As a language model, ChatGPT is designed to understand the patterns between words, phrases, and sentences (a.k.a. language). It can then respond, in a natural-sounding way, within the context of the conversation.

Along with being a language model, ChatGPT is also a chatbot, which means you interact with it through a messaging interface. Simply open the chat, enter a prompt, and get an instant response. You can use ChatGPT for a wide variety of use cases including: explaining complex concepts, brainstorming new ideas, and even writing code snippets.

As of September 2023, OpenAI is also rolling out a new functionality that lets you carry voice conversations with your ChatGPT assistant. The new rollout uses Whisper, OpenAI’s speech recognition system, to identify and transcribe your spoken words. It then responds to you, in voice, using a text-to-speech model.

Key features:

  • Supports Zapier and Slack plugins, which enable language models to perform actions for you
  • Allows you to tailor ChatGPT’s responses to your unique needs via custom instructions
  • Saves and labels conversations, so you can continue or reference them later
  • Currently rolling out new voice and image features (as of September 2023)

Pricing: ChatGPT is free with access to GPT-3.5 model, standard response speed, and regular model updates. ChatGPT Plus costs $20 per month and includes GPT-4, faster response speed, and early access to new features like plugins.

Clockwise: Best for scheduling and time management

One of the top reasons for hiring virtual assistants? For scheduling meetings, of course! If you feel like you spend way too much time managing your calendar, let us introduce you to Clockwise.

Clockwise is a time orchestration platform that puts your schedule on autopilot. Start by telling it your unique scheduling preferences (e.g. how much Focus Time you want, when you prefer to have meetings) — then Clockwise will work to design your ideal day, every day. Clockwise resolves meeting conflicts automatically, optimizes your schedule for greater productivity, and coordinates time for your entire team or company.

Even better, Clockwise is gearing up to release Clockwise AI, a first-of-its-kind calendar experience powered by GPT. Clockwise AI makes scheduling as easy as having a conversation. Just type a request like “I need to meet Sasha today after lunch” via chat, then Clockwise AI will coordinate for you. Click here for first access. 

Key features:

  • Creates more Focus Time in your schedule by rearranging your existing meetings
  • Suggests best meeting times for you and your colleagues, taking into account over ten different factors (e.g. time zone, preferred meeting hours, Focus Time)
  • Connects Google Calendar to your Slack status through the Slack app
  • Makes it easier to schedule external meetings with scheduling links
  • Lets you schedule and manage your calendar via chat (Clockwise AI coming soon)

Pricing: Join Clockwise for free and get started with your smart calendar assistant. The free version automatically finds the best time for your tasks and routines; protects your personal time for meals, travel, and appointments; and integrates your calendar with your favorite productivity tools.

Upgrade to advanced features like Focus Time and Clockwise Links starting at $6.75 per user per month. Best for automatic transcription and meeting notes

This next tool is a must-have if you’re looking to get the most of your meetings. Otter records and transcribes meetings in real-time and even generates summaries — so you can focus on the conversation, instead of your meeting notes.

Otter is also a great assistant because it can attend up to three meetings at the same time, a huge advantage for busy people.

Key features:

  • Uses speech recognition to automatically record and transcribe your meetings
  • Lets you import audio and video files for transcription
  • Supports English (U.S. and U.K.) and can handle a variety of accents
  • Provides playback speed options
  • Allows you to share and collaborate on notes
  • Connects to your calendars and automatically attends meetings for you (Microsoft Calendar, Google Calendar, Dropbox, Zoom, iOS Calendar)
  • New AI live feature called Otter AI Chat, helps teams get answers to meeting questions instantly
  • Available on mobile or desktop, including iOS, Android, and web 
Pricing: Otter is free for up to 300 monthly transcription minutes and includes core features. For more minutes and advanced features, upgrade to Pro for $10 (per user per month) or Business for $20 (per user per month).

Going forward

The thing about to-do lists: not every item is the best use of your time and energy, but it’s still got to be done. For shallow work like scheduling meetings, try adding an AI executive assistant to your workflow. Try Clockwise for free today.

About the author

Judy Tsuei

Judy Tsuei is a Simon & Schuster author, speaker, and podcast host. She’s been featured in MindBodyGreen, BBC Travel, Fast Company, Hello Giggles, and more. As the founder of Wild Hearted Words, a creative marketing agency for global brands, Judy is also a mentor with the Founder Institute, the world's largest pre-seed accelerator. Judy advocates for mental and emotional health on her popular podcast, F*ck Saving Face. Follow along her journey at

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