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šŸ’» All Tech Tips — Year 1 (Part 2 of 2): Feb – Aug 2025

Second half of Year 1's Tech Tips

This post is a running compilation of the Thursday Things Tech Tips from February 13th, 2025 through August 7th, 2025 (the second half of Year 1), sorted by reverse chronological order.

This way you don’t have to dig through your old emails just to search for a specific tech tip you wanted a refresher on. šŸ‘

Why EAs need tools built specifically for their workflows (8/7/2025)

If you’ve ever wrestled with a tool that wasn’t designed for how you work (e.g. Google Calendar or Outlook), this might resonate.

Imagine you want to colorize a black and white photo.

You could ask a general tool like ChatGPT to do it.

It’ll kiiinda work, but it’s clunky, slow, and honestly not good enough.

Or… you could just use a specialized tool that was actually built to do that one specific thing.

That’s the difference between general AI tools and specialized software, and in this 18-minute presentation I gave at The EA Campus’s Innovate Virtual Summit, I break down exactly what that looks like in action. šŸ‘‡

If you’ve ever felt like your scheduling tools are fighting you, you’ll want to watch this.

Planning an offsite? 2 tools worth checking out (7/31/2025)

Offsites are fun after they happen. But planning them? It’s a lot…

Here are two tools I know about that can make organizing your next one easier, whether you're doing it solo or want someone to take it off your plate:

Offsite

Fun fact: Offsite is also based in NYC so we’re going to be hosting a fun event for EAs together soon, look out for that!

Think: ā€œAirbnb for team retreatsā€ but with two options: you can go the self-serve route and browse venues yourself or let their team plan the whole thing for you.

They offer:

  • Search over 1,000 vetted global venues and compare availability, amenities, and pricing in one place

  • Access curated local vendors from team-building activities to event production and transportation

  • Option to upgrade to full-service planning, including customized agendas, vendor booking, travel logistics, and on-site coordination all for a flat per-person fee

šŸŽ Offsite set up a discounted link for CCing my EA readers, which includes 10% off your first retreat when you use their full-service option.

Nowadays

I heard about Nowadays from a trusted Vimcal EA user who was raving about how actually helpful the AI features were, so I had to check them out.

Built from the ground up around AI and automation, it’s perfect if you want speed, reach, and a shared planning dashboard.

You get:

  • Access to 400,000+ venues/vendors, all searchable and instantly comparable

  • Automated outreach in the venue’s native language and real time negotiation

  • Help with flights, visas, city research, and attendee registration

  • One dashboard for quotes, maps, comments, and approvals

šŸŽ Nowadays set up a discounted link for CCing my EA readers that gives you 30% off their corporate planning fee (normally 10%, now 7%). If you have any questions, you can also reach out to them with ā€œCCing my EAā€ in the subject line.

ChatGPT prompting cheat sheet (7/24/2025)

I saw this ChatGPT cheatsheet on Reddit and thought it could be super helpful as a printout for you to have by your desk.

With that said, if you ever feel like using ChatGPT ā€œcorrectlyā€ is too complicated or technically complex, you might find some of the top comments on the Reddit post reassuring:

I'm gonna say this blunty and it's gonna sound rude - but using ChatGPT or any LLM AI model comes down to literally just talking. That's it. You are overthinking on how to use it. You simply just need to talk to it - and be good at talking helps better outputs.

All this ā€œpromptā€ stuff is bollocks for almost everyone. Just talk to it like you would a colleague that you trust but know you’ll need to double check the work of. Easy. Don’t overthink it

It doesn't require any specialized knowledge. It just requires a willingness to engage in conversation and exercise intellectual curiosity.

Clay for CRM (7/17/2025)

Note: if you're already using a different CRM tool, Clay will migrate you for free and send you a special gift! Just email them to get started.

If your exec knows hundreds of people but remembers zero birthdays, job changes, or who they had lunch with last quarter… Clay might be worth a look.

It’s a relationship management tool that actually works for EAs and is built to help you stay on top of your exec’s network across both personal and professional relationships. With shared access, smart integrations, and a clean interface, Clay helps you manage your exec’s relationships behind the scenes.

Here’s how you’ll want to start:

  1. Connect everything: Email, calendar, LinkedIn, iMessage, WhatsApp. Clay pulls in contacts, meetings, and interactions automatically.

  2. Clean up contacts: Use Clay’s duplicate detection to merge, edit, or enrich with job titles, notes, or personal context.

  3. Set reminders + notes: Schedule regular check-ins for important relationships, and take rich, searchable notes tied to each contact.

  4. Use the Home feed: It’s like a relationship briefing: job changes, social updates, birthdays, and who your exec hasn’t talked to in a while.

My personal favorite feature is the Map view though. It gives a quick, visual reminder of who’s physically nearby, which is especially helpful while traveling.

More than once, I’ve visited a city and completely forgotten someone I should’ve reached out to. Clay solves that in one glance!

To try out Clay, use this link to get an extended trial (normally 14 days, now 2 months) specifically for CCing my EA readers: clay.earth/partners/vimcal šŸŽ

Paste this into ChatGPT. It’ll change how you prompt. (7/10/2025)

Ever spent 10+ prompts trying to get ChatGPT to ā€œjust write the thingā€? Same.

A Reddit user had that exact meltdown and ended up creating Lyra, a prompt that flips the script. Instead of you guessing what ChatGPT needs, Lyra interviews you first.

In his words, it’s like upgrading ChatGPT into a ā€œ$500/hr consultantā€.

Here’s what to do:

  1. Copy the full Lyra block below

  2. Paste it into a new ChatGPT thread

  3. Give it your vaguest, messiest request

  4. Watch it ask smart clarifying questions and return a way better result

šŸ‘‡ Copy/paste this into ChatGPT:

You are Lyra, a master-level AI prompt optimization specialist. Your mission: transform any user input into precision-crafted prompts that unlock AI's full potential across all platforms.

## THE 4-D METHODOLOGY

### 1. DECONSTRUCT
- Extract core intent, key entities, and context
- Identify output requirements and constraints
- Map what's provided vs. what's missing

### 2. DIAGNOSE
- Audit for clarity gaps and ambiguity
- Check specificity and completeness
- Assess structure and complexity needs

### 3. DEVELOP
- Select optimal techniques based on request type:
  - **Creative** → Multi-perspective + tone emphasis
  - **Technical** → Constraint-based + precision focus
  - **Educational** → Few-shot examples + clear structure
  - **Complex** → Chain-of-thought + systematic frameworks
- Assign appropriate AI role/expertise
- Enhance context and implement logical structure

### 4. DELIVER
- Construct optimized prompt
- Format based on complexity
- Provide implementation guidance

## OPTIMIZATION TECHNIQUES

**Foundation:** Role assignment, context layering, output specs, task decomposition

**Advanced:** Chain-of-thought, few-shot learning, multi-perspective analysis, constraint optimization

**Platform Notes:**
- **ChatGPT/GPT-4:** Structured sections, conversation starters
- **Claude:** Longer context, reasoning frameworks
- **Gemini:** Creative tasks, comparative analysis
- **Others:** Apply universal best practices

## OPERATING MODES

**DETAIL MODE:** 
- Gather context with smart defaults
- Ask 2-3 targeted clarifying questions
- Provide comprehensive optimization

**BASIC MODE:**
- Quick fix primary issues
- Apply core techniques only
- Deliver ready-to-use prompt

## RESPONSE FORMATS

**Simple Requests:**
```
**Your Optimized Prompt:**
[Improved prompt]

**What Changed:** [Key improvements]
```

**Complex Requests:**
```
**Your Optimized Prompt:**
[Improved prompt]

**Key Improvements:**
• [Primary changes and benefits]

**Techniques Applied:** [Brief mention]

**Pro Tip:** [Usage guidance]
```

## WELCOME MESSAGE (REQUIRED)

When activated, display EXACTLY:

"Hello! I'm Lyra, your AI prompt optimizer. I transform vague requests into precise, effective prompts that deliver better results.

**What I need to know:**
- **Target AI:** ChatGPT, Claude, Gemini, or Other
- **Prompt Style:** DETAIL (I'll ask clarifying questions first) or BASIC (quick optimization)

**Examples:**
- "DETAIL using ChatGPT — Write me a marketing email"
- "BASIC using Claude — Help with my resume"

Just share your rough prompt and I'll handle the optimization!"

## PROCESSING FLOW

1. Auto-detect complexity:
   - Simple tasks → BASIC mode
   - Complex/professional → DETAIL mode
2. Inform user with override option
3. Execute chosen mode protocol
4. Deliver optimized prompt

**Memory Note:** Do not save any information from optimization sessions to memory.

Give it a try and let me know how it goes!

Emojis for saved Google Maps lists (7/3/2025)

Back when I was backpacking China and SE Asia from 2018-2019, I desperately wanted a way to visually separate saved food spots from museums and scenic viewpoints. Instead, I was stuck with Google Maps’s 5 generic default icons. šŸ˜’

Turns out, Google quietly fixed this in September 2023!

Now, when you create or edit a saved list in Google Maps (on iOS or Android), you can assign it an emoji icon: like šŸ” for restaurants, šŸ–¼ļø for museums, šŸŒ„ for viewpoints, etc.

The emojis will show up on your map, making it way easier to scan at a glance.

Wish 2018 me had this but better late than never!

Search browser tabs shortcut (⌘ + Shift + A) (6/26/2025)

Right now, I have 61 Chrome tabs open. And yes, I actually counted. 😱

If that sounds like you, here’s a much needed shortcut I just discovered that I’m kinda obsessed with:

  • ⌘ + Shift + A on Mac

  • Ctrl + Shift + A on Windows

This opens a little search bar where you can type anything (e.g. ā€œLinkedInā€, ā€œGoogle Docsā€, ā€œcalendarā€) and instantly jump to the relevant tab.

Bonus: You can close tabs right from the same search box (perfect for removing duplicate tabs).

Extra bonus: The tabs are sorted by last opened them, so it’s easy to spot mummies. I found 13 tabs I haven’t touched in 64 days… 😭

Copy-paste text without messing up your formatting (6/19/2025)

Ever copy-paste something into an email or doc, only to spend the next minute fixing the weird font sizes, colors, and spacing?

Here’s a shortcut I use constantly to get around that:

  • Shift + ⌘ + V on Mac

  • Control + Shift + V on Windows

This pastes just the plain text, so it’ll automatically match the formatting of whatever you’re pasting into.

No more unintentionally copy pasting Comic Sans font!

Note: If you’re on Mac, this is literally the same effect as right clicking and then selecting ā€œPaste and Match Styleā€.

Stop manually scanning emails for scheduling and just let AI do it (6/12/2025)

You get an email:

ā€œCan you do Tuesday 2-5pm, Wednesday 11am-1pm, or Thursday 3pm-6pm?ā€

And suddenly you're stuck flipping back and forth between your email and calendar trying to see what works.

If this sounds familiar, take 10 seconds to watch this šŸ‘‡

With Vimcal EA’s AI Free Time Finder, you can:

  1. Screenshot the message

  2. Drag the screenshot into your calendar

  3. Instantly see which times actually fit for you

Calendly links work too: just copy-paste the link and Vimcal EA will show you the overlapping availabilities directly inside your calendar.

Little things like this save way more time (and brainpower) than you’d expect.

Bonus Tech Tip: 2 recent AI updates useful for EAs

Wanted to throw in an extra tech tip this week that isn’t about Vimcal EA and is 100% worth knowing about:

The ā€œ3-word ruleā€ to make ChatGPT give expert responses (6/5/2025)

A few months ago, our CTO shared his four-part prompt formula to help you get quality responses from your AI tools.

Today’s tech tip essentially boils that four-part prompt formula down to a 3-word phrase you can add to your AI prompts to get quality answers. All credit for this tech tip goes to Amanda Caswell via Tom’s Guide.

Before we get started, as per Amanda’s post, ā€œNo, the three little words are not ā€˜I love youā€™ā€. šŸ˜‚

ā€œThe concept is simple: Add a short, three-word directive to your prompt that tells ChatGPT how to respond. These three words can instantly shape the tone, voice and depth of the output. You’re not rewriting your whole question. You’re just giving the AI a lens through which to answer.

Here are a few examples that work surprisingly well:

  • ā€˜Like a lawyer’ — for structured, detailed and logical responses

  • ā€˜Be a teacher’ — for simplified, clear and educational explanations

  • ā€˜Act like Hemingway’ — for punchy, minimalist writing with impact

It’s kind of like casting the AI in a role, and then you're directing the performance with the specifics in your prompts.ā€

ā€œNeed a few starter ideas? These formats work across writing, research, translation and even creative tasks:

  • ā€˜Summarize this article like a journalist’

  • ā€˜Explain dark matter like a professor’

  • ā€˜Give feedback like a mentor’

  • ā€˜Write a poem like a songwriter’

  • ā€˜Translate this message like a diplomat’

You can swap in almost any role or voice that fits your needs: CEO, therapist, designer, coach, teenager or just about anyone else. The more specific, the better.

Each tweak helps ChatGPT interpret your request through a more useful lens, and the difference in quality is often immediate.ā€ - Amanda Caswell

2 Shortcuts: ⌘ + ↓ (bottom of page) and fn + ↓ (next page (5/29/2025)

Ever found yourself mindlessly scrolling down a 40-paragraph blog post or dragging your mouse to hit a tiny scroll bar just to reach the footer of a website?

Here’s a faster way:

On Mac

  • ⌘ + ↓ instantly jumps to the bottom of a document or webpage

  • fn + ↓ moves you down one full page at a time

On Windows

  • Ctrl + End instantly jumps to the bottom of a document or webpage

  • Page Down moves you down one full page at a time

Why you shouldn’t sleep on niche AI tools (5/22/2025)

My parents recently sent me some old black-and-white photos of themselves from 40+ years ago that they were reminiscing over.

Papa and Mama Wu 🄰

I thought it’d be fun to surprise them by colorizing the photos with AI, so I first tried my go-to AI tool, ChatGPT.

Despite explicitly prompting ChatGPT to ā€œcolor the photo in realistically while keeping all of the original details intact and without taking creative libertiesā€, the result still looked cartoonish.

(ChatGPT) Who’s that?? 🤨

Then I tried Gemini with the same prompt. While it did a better job of maintaining some of the realism, it melted their faces and turned their clothing into plastic.

(Gemini) At least the rocks look pretty good… 😐

But then I found a niche AI tool on MyHeritage that was specifically dedicated to restoring old family photos and the difference was night and day: the colors were true to life while every wrinkle, shadow, and smile remained intact. Best of all, I didn’t need to do a thing beyond uploading the original image — not a single prompt needed!

The result speaks for itself.

(MyHeritage) Whoaaa that’s literally them!!! 🤯

The main point I’m trying to make here is that while general-purpose AI tools like ChatGPT and Gemini are super convenient and great for getting simple work done, they’re going to fall short when compared to single-purpose tools for more complex tasks.

If you’re trying to get the best result, whether it’s restoring a decades-old photo, transcribing a meeting, or calendaring meetings for your exec (Vimcal EA anyone? šŸ˜‰), niche tools built for one job are going to outperform general-purpose AI tools every time.

Use ChatGPT to prepare for tough conversations (5/15/2025)

This tech tip is a simple and self-explanatory, but also powerful use case of ChatGPT.

Here’s the template from above that you can copy and paste into ChatGPT:

I need to [bad thing]. Help me think through:

- Two different ways to approach this conversation

- Emotional reactions they might have

- Common objections they might raise

- Phrases I should avoid using

- How to close with clear next steps

- How this might affect their relationships with other team members

QR Code Not Scanning? Try This (5/8/2025)

This tip is so simple, I almost didn’t share it. But it saved the day so many times at the EA Ignite conference, I figured it’s worth passing along.

If your camera won’t scan a QR code, don’t close the app. Just switch to ā€œVideoā€ mode, then back to ā€œPhoto.ā€ That quick toggle refreshes the camera, and more often than not, the QR code will scan right away.

Switch to ā€œVIDEOā€ and then back to ā€œPHOTOā€

Try it now using the same QR code we displayed at EA Ignite. Who knows which David you’ll get? šŸ‘€

Roll the camera-dice. Will it be David Ryan or David Nguyen? šŸŽ²

Calendar views and Find shortcuts (5/1/2025)

Our recent tech tips have been rather AI-heavy, so this week we’re taking a break from that to highlight a couple simple but seriously underrated keyboard shortcuts.

The first group of shortcuts comes from Shelley Trask at Udemy and it works in both Google Calendar and Vimcal EA!

Did you know that you can just press ā€œDā€ in your calendar to switch it to day view? Pressing ā€œWā€ switches to week view, and ā€œMā€ brings up month view. These quick toggles make jumping between views super easy when you’re scanning availability or juggling meetings.

While these work great in both Google Calendar and Vimcal EA, Outlook makes things a bit more… involved. šŸ˜• 

To switch views in Outlook, you’ll need to use:

  • Shift + Alt + 1 for day view

  • Shift + Alt + 2 for work week view

  • Shift + Alt + 3 for full week view

  • Shift + Alt + 4 for month view

On another note, are you using ⌘ + F (on Mac) or Ctrl + F (on Windows)? If not, you really HAVE to start using this ā€œFindā€ shortcut immediately. It lets you instantly search for specific words or phrases within any document or webpage.

For example, if I wanted to search for every mention of ā€œChatGPTā€ in our 2025 State of AI in the Executive Assistant Industry report, I’d simply press ⌘ + F, type ā€œChatGPTā€ into the search box, and it’ll highlight every instance of ā€œChatGPTā€ as well as count how many times it was mentioned.

These shortcuts might seem small, but using them regularly can save you serious time and mental energy. Give them a try this week and let me know if there are other time-savers you swear by, I’d love to share them in an upcoming tip!

Create office tunes from zero to song in minutes (4/24/2025)

Thank you to Molly Medvecky for this fun tech tip!

Want to make a song from scratch in minutes? Just type a simple prompt into SUNO and boom — you’ve got a track. Seriously, it’s that simple. šŸŽ¶

Extra tip: When creating your song, make sure to select the ā€œCustomā€ option so you can take advantage of their AI lyric generating feature.

200+ AI-Powered side-hustle ideas (4/17/2025)

This tech tip was surfaced by Jenelle D. Allen-Daniels, an ambassador of EAs to the Rescue! ā›‘ļø

Hubspot just dropped a pretty interesting resource: 200+ Ways to Make Money with AI.

After entering your email, you’ll get access to their spreadsheet that contains 205 ideas for AI-powered side projects.

Now I’m not saying you need a side hustle… but if you’re curious about building something of your own, picking up new skills, or even earning a little extra, this is a fun place to start.

At the very least, it’ll be an idea-generating read!

40+ Guided workflows with EAwiz’s ChatGPT bot (4/10/2025)

This tech tip comes from Courtney Johnson, creator of EAwiz! šŸŽ‰

She’s built a free custom ChatGPT bot that’s specifically tailored for the needs of Executive Assistants.

EAwiz offers guided, step-by-step help for 40+ high-impact workflows using simple hashtag commands (like #calendar, #budget, #branding, etc.). Here's how:

  1. One Question at a Time: Like a productivity coach, EAwiz asks one clear question at each step so you're never overwhelmed.

  2. Customized Output: You get three tailored versions of every result:

    • Concise āœ…

    • Detailed šŸ“‹

    • Creative šŸ’”

  3. Smart File Integration: Upload documents, and EAwiz can extract or optimize info from them on the spot (e.g., resumes, reports, calendars).

  4. Tool Suggestions: EAwiz will recommend free tools first, and only premium ones when necessary.

Hope you find this helpful with your day-to-day EA needs!

Creating an agent through Copilot (4/3/2025)

This tech tip comes from CCing my EA reader Kayla Southards at RRM Design Group!

ā€œI have a tech tip that is pretty neat! Our architectural design firm is in the process of implementing a new ERP system. I created a bot (agent) through Copilot studio. Basically, you feed it knowledge, such as documents, and create prompts with answers. I built it to answer questions for our employees, such as how to create a new timesheet or enter a new expense report.

ā€œI just had a meeting with our COO and ERP implementation team, and we decided that post-implementation, we are going to turn this agent into a general use bot for the company to answer all things RRM.ā€

Amazingly, Kayla has put together a step-by-step PDF on how to set up a Copilot agent. She’s included her email address on the first page in case you want to reach out to her with more questions. šŸ‘

Using ChatGPT for image generation (3/27/2025)

Earlier this week, Open AI released their update for ChatGPT’s image generation feature.

By far the most prevalent use so far has been transforming pictures into Studio Ghibli’s art style like I did with my cat, Apex. 😼

However, there are WAY more practical uses for this update because:

  • Text rendering is now reliable

    • This opens the door for creating mockups and posters that you can actually use

  • Fine control over details

    • You can iterate and refine on images instead of rewriting the entire prompt

This means you can actually create assets like illustrated metaphors for slide decks, graphs and charts for data visualization, or even posters and thumbnails for social media, without weird sloppy-looking text.

For example, here’s an image I generated to help illustrate the exact points I made right above.

If you want to try out ChatGPT’s image generation feature for yourself, just hit the ā€œā€¦ā€ and select ā€œCreate imageā€ before you submit your next prompt.

Doubling down on the Four-Part Prompt formula (3/20/2025)

This past Tuesday, 127 EAs joined us for an AI Prompting webinar!

Now, I know I shared a Four-Part Prompt Formula tech tip a few weeks back, but I think it’s an important enough tech tip to highlight this deeper dive.

I want to stress that the Four-Part Prompt Formula is especially useful because it’s an enduring technique that will remain applicable across any chat-based AI tool, and most AI tools are conversational chat-based tools.

In the webinar, our CTO, Mike, broke down the Four-Part Prompt Formula and then put it into action with live, hands-on practice.

You can watch the 26 min recording on YouTube (5 min were for Q&A), and I’ll also link to the accompanying slides as well.

Just one tip though: I think the real value of the webinar was in actually practicing the prompts, so if you’re watching the replay, make sure to try writing a few yourself! šŸ‹ļøā€ā™‚ļø

Don’t just take my word for it, here’s Mary literally putting what she learned into practice!

"Send Later" for Texts on iOS 18 šŸ“± (3/13/2025)

This tech tip comes from CCing my EA reader Renee Viens at Alkami :)

Apple’s iOS 18 finally lets you schedule text messages! This is a game-changer for anyone (but especially EAs) juggling reminders, nudges, and updates for their execs.

To schedule a message, you just need to be in an iMessage conversation, tap the ā€œ+ā€ icon, and then tap ā€œSend Laterā€.

I can’t count how many times I had to pause my work just to manually remind my exec before a meeting. Now with ā€œSend Laterā€ I can pre-schedule reminder texts instead of interrupting my workflow to send them.

Plus, each text is easily modifiable and can be deleted if no longer needed!

For iMessage Mac users, you’ll be relieved to here that ā€œSend Laterā€ is also available on Sequoia. 🄳

Just in case, here’s a link to the full guide on how to use this feature.

Color Code your Google Drive Folders šŸ“ (3/6/2025)

This is a quick tech tip from fellow CCing my EA reader, Jenelle!

Color coding Google Folders is a simple but effective way to organize your drive.

Creating this quick "at a glance" color system can help to focus your eyes, alleviating the information overload of searching for docs.

Manage multiple executives and calendars? Consider matching the Google Folder color to correspond with the calendar color assigned to each executive. 

Maybe an oldy but still a goldie tip!

The Four-Part AI Prompt Formula šŸ“‹ (2/27/2025)

This four-part prompt formula has recently been making its way around the Internet because it helps you get precise and high-quality responses from AI on the first try.

You should think of AI as a genius 8-year-old — it will do a great job of following your instructions, but only if your instructions are sufficiently clear. And that’s exactly where this four-part prompt comes in :)

Let’s break it down:

1. The Goal: Set Clear Expectations

This is where you tell the AI exactly what you need and who you want it to be. It's like briefing a new team member on a task!

Instead of: "Find me a hotel in Chicago."

Try: "I'm an EA booking a crucial business trip for my executive. You're a seasoned corporate travel expert who understands what business travelers truly need — reliable Wi-Fi, convenient meeting spaces, and easy airport access."

This immediately focuses the AI on your specific needs rather than generic travel advice.

2. Return Format: How You Want Your Answer

This tells the AI exactly how to package its response for you. Remember, AI will follow your formatting instructions precisely!

If you're:

  • Building a spreadsheet → Ask for CSV format

  • Creating a presentation → Request bullet points with clear headers

  • Sharing with your IT department → Specify JSON format

This small step saves enormous time by eliminating reformatting work later.

3. Warnings: Help the AI Avoid Common Pitfalls

Just like you might caution a colleague about potential issues, this section prevents frustrating mistakes before they happen.

For a travel booking prompt, add something like: "Double-check that recommended hotels are actually open during our travel dates, have consistently positive business traveler reviews for Wi-Fi reliability, and aren't currently undergoing renovations."

This anticipates problems and saves you from that dreaded back-and-forth.

4. Context Dump: Share Your Insider Knowledge

This is your secret weapon! The context section allows you to share all that valuable background information that makes you so effective in your role.

Consider including:

  • Your executive's preferences ("My executive prefers quiet rooms away from elevators")

  • Past successes and failures ("The Langham worked perfectly last quarter because...")

  • Special requirements ("Always needs early check-in due to flight schedules")

  • Timing constraints ("Meetings begin at 8am, so proximity to the conference center is essential")

The more relevant context you provide, the more the AI response will feel like it came from someone who truly knows your executive.

Just to make it more clear, here’s an example of how you might prompt something like ChatGPT to help prepare a Meeting Brief:

  • Goal: I'm an executive assistant preparing a brief for my executive before an important meeting. You're an expert briefing specialist who can organize complex information into concise, actionable summaries. Create a comprehensive yet scannable meeting brief that highlights essential information.

  • Return Format: Structure the brief with these sections: Meeting Objective, Attendees (with relevant background/history with our company), Key Discussion Points, Recommended Talking Points for my executive, Potential Challenges, and Next Steps.

  • Warnings: Ensure the brief remains under two pages when printed. Avoid including speculative information. Highlight any conflicting interests among attendees. Make sure each talking point aligns with our company's established position on the topic.

  • Context Dump: The meeting is with a potential strategic partner in the healthcare technology sector. My executive has met with their CEO twice before but not with their full leadership team. Our company is exploring potential integration of their patient management system with our healthcare analytics platform. Previous discussions revealed concerns about data security protocols. My executive tends to focus on long-term strategic benefits but may need prompting to address specific technical compatibility questions that will likely arise.

I know this seems like a lot of extra work and we’d all prefer to take shortcuts, so I’ll clarify that the decreasing order of importance for these 4-prompts is as follows: 1. Goal, 2. Context, 3. Return Format, 4. Warning.

Hope this helps you get more out of your AI chatbots!

Use Perplexity for web searches and answering questions šŸ”Ž (2/20/2025)

Last week, I shared a tech tip on how you can use ChatGPT with your writing, which is kind of its bread and butter.

However, ChatGPT is not necessarily great for web research or answering questions because it’s trained on past data and you’ll often receive outdated (or simply wrong) answers.

That’s where Perplexity.ai comes in!

Perplexity delivers:

  • Up-to-date information. Perplexity provides current information including even for live events

  • Easily digestible information. Perplexity consolidates information from multiple sources and presents it in an easy-to-read format

  • Direct answers with citations. Perplexity responds directly to your search queries (as opposed to giving you a bunch of websites to sort through), complete with source citations for sanity checks

I feel like Perplexity is what search engines were supposed to be, but it’s hard to really convey its benefits without seeing it in action. So, here’s a query I made on both ChatGPT and Perplexity (beginning with ChatGPT) about the recent passage of the Global Executive Assistant Mobility Act of 2024 and its effect on the international career opportunities for EAs.

Pretty good! But here was the same question asked with Perplexity.

Yup, I made that piece of legislation up. There’s no such thing as a ā€œGlobal EA Mobility Act of 2024ā€. šŸ˜›

While ChatGPT hallucinated an answer that sounded legit, Perplexity correctly identified the legislation as totally fabricated!

I highly recommend trying Perplexity as your go-to search engine for a day to see whether you like it. There’s no need to create an account to use it a few times either.

Please lemme know how you end up liking it!

Training ChatGPT to edit your writing āœļø (2/13/2025)

In response to our 2025 State of AI in the Executive Assistant Industry report, many EAs emailed me asking for practical AI use case examples.

So, I’ll show you how I regularly use AI to help me edit my writing! It’s a two-part process: you first train the AI to learn what you’d like for it to do, and then you actually apply it.

For example, let’s say I’d like to use ChatGPT (the most popular AI tool EAs use) to help me edit an email I’m sending out to organize a company offsite.

Here’s exactly how I’d do that:

  1. Tell ChatGPT to learn what it can from a webpage teaching email tips

  2. Have ChatGPT to remember what it learned

    • This way you can reuse this particular bot for any future emails you want it to edit. You’ll know you did this right when it says ā€œMemory updatedā€.

  3. Ask ChatGPT to apply what it learned to your email draft

    • You can quickly write the main points you’d like to get across in your email without worrying about proofreading or perfect grammar. That’s kinda the point of having an AI editor. šŸ˜‰

  4. That’s it! ChatGPT will spit back an edited version of your email draft

    • I highly discourage using exactly what ChatGPT spits out. You wouldn’t accept every single edit a human editor suggests, so don’t do that with AI either. That said, it’s a pretty great editor, right? :)

Extra tip: You can train your ChatGPT bot to learn from more than one resource as well! If you found, say, 5 resources you thought all had golden writing lessons you’d like to use in your writing, you can have your AI learn and then apply all of those in one go!

I hope this helps you speed up your future writing efforts. As mentioned in our 2025 State of AI in the Executive Assistant Industry report, of the EAs who are currently using AI tools, 86% are already using ChatGPT. If you haven’t started playing with it yet, today is a great time to give it a try! šŸ’Ŗ

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