As a CEO, the demands on my time are relentless. 

From high-stakes meetings to strategic planning, my schedule often feels like a chaotic puzzle, with little room to breathe. 

Every executive knows this struggle (I hear it too often in our Lead with AI community)—too many decisions, too many emails, and not enough hours in the day. 

That’s why I turned to AI assistants. 

By building a tailored team of AI tools, I’ve managed to reclaim my precious time, boost productivity, and sharpen my focus on the high-impact work that truly matters.

And I won’t gatekeep this information – because I believe everyone deserves their team of relentless AI workers. 

So, let’s dive into the AI assistants you shouldn’t live without:

The Core Gen AI Platforms: The Brains Behind My AI Team

At the heart of my AI assistant team are the core generative AI platforms—ChatGPT, Microsoft Copilot, Claude, and Google Gemini. 

These powerful AI platforms are the foundation for personalized assistance across various tasks. 

• ChatGPT: This is my first choice and go-to, especially for brainstorming, drafting content, and conducting research. It's my go-to for tackling complex questions and generating content quickly. Especially with the new voice features and the ChatGPT o1 (chain of thought) model, it’s clear why the #1 AI tool in our AI Top 100 is unbeatable. 
• Claude: Developed by Anthropic, Claude is designed with safety and context understanding in mind, but what I appreciate the most is its creative writing capabilities and the Artifact feature. 

• Copilot: While my team is on Google Workspace, I know many of our Lead with AI community are on Microsoft 365, so I’ve been familiarizing myself more with Copilot. I love how it automates routine tasks within familiar apps like Word, Excel, PowerPoint, and Teams, helping me save time on document creation, data analysis, and meeting management. 
• Gemini: Google’s Gemini offers seamless integration with Google Workspace, providing intelligent assistance in everything from drafting emails to managing calendar conflicts. I’ve just gotten access, and believe it’ll deliver similar value as Microsoft Copilot, although it doesn’t have their impressive ‘assistant home.’ Gemini also stands out as the LLM with the largest context window.

But while these platforms provide the cognitive power behind my AI team, I wouldn’t quite call them assistants. That’s where GPTs, Projects, and Copilot Agents come in:

Personalized Assistants: Tailoring AI to My Specific Needs

One of the biggest game-changers for me has been the use of personalized AI assistants. These customized versions of the core platforms help me tackle specific, high-value tasks.

• ChatGPT GPTs: Custom GPTs allow me to set up personalized AI agents that know my preferences, streamline tasks, and provide targeted insights. For example, I have GPTs dedicated to writing podcast questions, editing newsletters, and helping me close deals. (If you want to know more, I have a free workshop to create your first GPT.)

• Claude Projects: Similar to GPTs, Claude Projects are tailored AI setups that handle specialized tasks, like managing research initiatives or coordinating complex project plans. I used them similar to GPTs, but specifically for writing assignments, like crafting a newsletter. 
• Copilot Agents: These personalized copilots within Microsoft 365 apps are configured to my workflow, providing intelligent suggestions and automating repetitive tasks based on my unique needs. They are part of the recently introduced “Copilot Wave 2,” and I will discover them in more detail soon.

As I shared in my free workshop, the key to making these AI ‘employees’ work for you is to get as specific as possible. Create a GPT, Project, or Agent (Google has ‘Gems,’ but I haven’t tried those) for each repetitive workflow – don’t try to create one big ‘digital clone’ that can do everything (they can’t!) 

Calendar Management and Task Prioritization

Time is the most valuable asset for any executive, and managing it effectively is crucial. It’s also where AI truly shines. 

To keep my calendar and tasks under control, I use a tool called Reclaim. Reclaim combines calendar management with task prioritization, automatically adjusting my schedule based on my deadlines and workload. 

It’s like having a personal time management coach and personal assistant in one. It also integrates Calendly-like meeting scheduling links, which are trained on your priorities.

Other platforms in this category include:

• Motion: Motion automatically organizes meetings, tasks, and deadlines, reshuffling priorities as your day evolves. It’s similar to Reclaim but a bit more advanced (and expensive.)
• Clockwise: Similar to Motion and Reclaim, Clockwise optimizes your calendar to create blocks of focus time, a powerful tool to protect your time for deep work.
• Clara: Clara handles scheduling via email and coordinates meeting times with contacts seamlessly. It’s the closest thing to having a real-life assistant copied on your emails to handle your calendar.
• Calendly: An essential tool for managing external meetings, Calendly streamlines appointment booking, integrates with any calendar, and minimizes the back-and-forth of scheduling. (Although, the priority-based scheduling links in Reclaim and Motion are a lot more powerful!)
• Trevor AI: Trevor AI integrates directly with your calendar, and focuses on ensuring your tasks are prioritized and scheduled in the best possible way. I found (after testing) that it’s easier to use one of the abovementioned platforms that has these features integrated, but you may want to give Trevor a try.

These tools collectively give me more control over my schedule, helping me find hidden pockets of time and reduce the stress of constant rescheduling.

Meeting and Transcription Assistants: Turning Meetings into Actionable Insights

Meetings are a necessary part of any executive’s role, but managing them effectively can be a challenge. 

As a first principle, the best way to solve meeting challenges is to organize and attend fewer meetings. (This is one of the principles of AI Time Management, and discussed in my course.)

Beyond that, these AI assistants help create more effective team meetings and save a ton of time:

• Otter.ai: One of the most popular AI productivity tools, Otter records and transcribes meetings, providing accurate notes and summaries that you can refer to at any time. It ensures that no critical detail is ever lost, and takes screenshots of slides for full context. A bot lets you ask questions about any meeting. (You can also try Notta, Tactiq, or Read AI.)  

• Zoom AI Companion: Integrated directly into Zoom, this AI assistant summarizes meetings, generates agendas, and organizes follow-ups, making virtual meetings far more productive. One of my favorite features is that you can ask questions as the meeting is going on.
• Copilot for Teams: This is another tool that lets you ask questions as the meeting is ongoing. It also offers real-time meeting insights, automates action item tracking, and streamlines post-meeting workflows. You can ask Copilot if you’ve been mentioned in meetings you didn’t attend and generally any questions about them. To use Copilot in Teams you need Microsoft 365 Advanced Plus Copilot (around $45/user/month.)

• Granola: A newer kid on the block, Granola is a privacy-focused meeting assistant that works locally on your device. This means you don’t see it as a participant in a meeting, like Otter, Read or Fireflies.

With these tools, meetings go from time drains to opportunities to generate clear, actionable outcomes. HOWEVER: please be mindful of the amount of sensitive data these tools capture. Ensure you trust the tool you choose. Also understand that they may record more than you bargained for – see this recent piece in the Washington Post for some scenarios you surely would want to avoid.

Pro Tip: Check your existing meeting platform for AI assistants. Don’t pay for an additional AI meeting notetaker if you already pay for Copilot, Zoom, or Gemini for Google Meet.

Writing and Content Creation Assistants: Boosting Communication Efficiency

Clear communication is crucial in my role, but drafting content can be time-consuming. These AI assistants speed up the writing process while maintaining quality:

• Grammarly: Beyond just checking grammar, Grammarly enhances the tone and clarity of my writing, ensuring every email or document is polished and professional. Additionally, it can create entire documents and emails, shortcutting regular drafting time. Because Grammarly works on nearly every platform, it’s easy to see why it once again made the Top 100 AI for Work Tools in September 2024.

• Copilot for Word and Gemini for Docs: These AI assistants make document creation in Word or Docs effortless, providing real-time suggestions and formatting tips to enhance productivity. Having them embedded in your word processor means enjoying two key benefits. One, you don’t have to toggle between ChatGPT and your writing application. And two, it can base new documents on ones you’ve created before.
• WriteSonic: An all-in-one tool for generating marketing copy, blog content, and even visuals. It’s my go-to for creating high-quality, SEO-optimized content. 

Some other popular AI writing assistants include:

• Jasper: Jasper drafts blog posts, marketing materials, or any content that needs a creative touch.
• Rytr: Rytr provides quick content generation with customizable tones, perfect for drafting social media posts or internal communications.
• Copy.ai: Focused on marketing, Copy.ai helps generate engaging copy across multiple platforms, saving teams significant time on content creation.
• Lex: Lex is a writing tool our team loves, highly tailored to where professional writers need help the most.
• Writer.com: An enterprise copy platform, helpful for large teams who need to write consistently from an existing knowledge database.   

These tools ensure that I can maintain a high standard of communication without spending hours at the keyboard. 

Whether these tools will survive is a question, though, as Copilot for Word (and Gemini for Docs) provides you with writing help right where you need it, and ChatGPT launched ChatGPT Canvas to help with the rest. 

In your quest to find the right set of AI tools, weigh which platform you are gifting your training data – the lifeblood of AI’s effectivity. 

Presentation Assistants: Making Presentations Effortless

Presentations are a staple of any executive’s role, and these AI Presentation Generators help me craft compelling decks quickly:

• Copilot for PowerPoint: With smart design and content suggestions, Copilot for PowerPoint helps me create presentations. Microsoft's structured approach to AI in presentations takes you through important steps, like writing an outline to increase the final quality. Using your Microsoft Graph (personal data), you can even tap existing Documents or PDFs and turn them into a full-fledged PowerPoint. 

• Gamma AI: If you don’t have Copilot, I suggest Gamma AI, which I find the best tool outside of Copilot. It focuses on creating fully designed presentations from a simple prompt, and recently announced it’ll let you use your existing brand template. Other options include Beautiful AI, Canva AI Presentation Maker, Tome, and Visme, 

These assistants allow me to focus on the message rather than just formatting, ensuring presentations are always polished and persuasive.

Knowledge Management: Staying on Top of Information

In a fast-paced environment, keeping track of information is crucial. If you’re on Microsoft 365, then Copilot is your best bet, quickly turning Sharepoints into a full-fledged knowledge base.

Some other tools to discover here include: 

• Notion AI: Notion AI augments the popular Notion platform with AI-driven content creation and task management, making it indispensable to knowledge workflow for teams using this platform.
• Coda AI: Coda AI enhances document creation with automation and interactive data, helping you manage knowledge and collaborate more effectively.
• Slack AI: Integrated within Slack, AI helps you keep track of conversations, summarizes threads, and extracts key insights from discussions. 

• Dropbox Dash: A powerful organizational tool that helps you manage and find files quickly, ensuring that nothing gets lost in the clutter.
• Enterprise knowledge management tools like Glean, Moveworks, and Leena: These are massive platforms, pulling in data from all sources including Microsoft, Salesforce, and Workday. 

Whichever platform you end up using, these tools provide structure and clarity, helping you access the right information when I need it.

Sales, Customer Support, and Workflow Assistants: Enhancing Team Performance

If you’re in sales and customer service, these AI assistants streamline operations and provide valuable insights:

• Zendesk AI: Automates customer support workflows, providing instant answers and recommendations that help your team resolve issues faster. Hubspot recently launched a similar feature called Breez, which does the same.
• Gong: Analyzes sales calls to extract insights, helping your sales team refine their approach and close deals more effectively.
• AgentForce: Salesforce’s AI-driven sales agents engage leads and automate follow-ups, driving revenue growth with minimal human intervention.

Task Management and Project Management Assistants: Keeping Projects on Track

Managing tasks and projects is critical to staying organized and productive. Some options for AI-powered task trackers include:

• Todoist: Integrates AI suggestions to help create an action plan, prioritize tasks, and keep your to-do list manageable.
• Asana: Asana’s AI features automate action items delegation, track progress, and optimize workflows.
• Atlassian's Rovo AI: Enhances project management within Atlassian tools, offering predictive insights and automation.
• ClickUp AI: AI-driven task management and workflow optimization, streamlining your team’s operations.
• Monday.com AI: Provides suggestions and automations to keep

AI Assistants: The Bottom Line

With a growing array of AI assistants available, it’s easy to feel overwhelmed by the options. 

But the key isn’t to adopt every tool—it’s to strategically build a team of AI assistants tailored to your specific needs.

Start by identifying the areas of your day that consume the most time or cause friction while considering the work you like doing least. This is prime for an AI takeover. 

Whether it's managing your calendar, handling meetings, or drafting content, there's an AI tool designed to streamline these tasks. Begin with core platforms like ChatGPT, Copilot, or Claude, and expand into specialized tools that address your unique workflow challenges.

But don’t just look at the upside – consider the cost as well. Not just the monthly fee, but also:

• How long it will take to learn the tool. Especially in context of the possibility that one of your existing productivity tools will adopt this feature
• The potential future costs of this tool/company:some text
  • Having a data breach (data privacy and security)
  • Going out of business (vendor stability and reliability)
  • Not being able to grow with your demands (scalability and flexibility)
• The data you’re training this tool on for months or years versus training a platform more likely to stick with you long-term (since AI thrives on data.)

Pilot a few carefully selected assistants, measure the impact (for example, by tracking time through a time management tool like Activtrack or the abovementioned Reclaim) and refine your setup as you go. 

Remember, the goal isn’t just to automate tasks but to reclaim your time and focus on what truly drives value in your role. Start small, iterate, and build a personalized AI ecosystem that works for you. 

I often quote Seneca, who said that “your time is your most valuable asset” — so let AI help you protect it. Then, you can focus on what matters and be meaningfully productive.

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