Nobody Handed Me Strategic Work: I Built It With AI

Courtney Johnson shares her story of using AI to become a strategic partner – without permission, without a coding background, and without waiting

“You’re now ready to be a strategic partner” – said no one ever.

“Strategic partner” has become the buzz phrase of the last few years in the world of executive support. Most Assistants I know don’t want to stay buried in clerical work. We’re ready to step up, to influence outcomes, to be seen as key contributors to the success of our leaders.

But here’s the truth no one tells you: strategic work is rarely assigned to us. No executive is going to suddenly walk into your office, drop a confidential initiative on your desk, and say, “You’ve proven yourself worthy. Here’s your first strategic project.”

I know because I used to wait for that moment. But it never came. Instead, I had to create the opportunity. And the first step came in the form of a single, powerful question: How can I give my executive more of his most valuable asset: his time?

That question led me down a path of innovation, frustration, persistence, and ultimately, transformation. Not just for my executive, but for me, my peers, and the broader admin community I’m so fortunate to be part of.

This is the story of how I used AI to become a strategic partner – without permission, without a coding background, and without waiting.

The Pain Point Was Obvious

I was supporting the Global Chief Information Security Officer (CISO) at the largest alternative asset firm in the world, an incredible executive with a packed schedule. From the moment he walked in until the minute he left, his calendar was solid wall-to-wall meetings. Sometimes double- or even triple-booked. There were no focus blocks. No space for high-level thinking.

If you support a senior executive, you’ve likely seen this too. They’re running from one Zoom link to another, grabbing lunch in five minutes, with little to no time to breathe.

That wasn’t good for him, and it wasn’t good for the firm. I saw an opportunity to make a meaningful contribution. Not by organizing a birthday cake or taking minutes, but by helping him get his time back.

So I said to him, “I want to do a recurring meeting audit. Let’s see what we can clean up on your calendar.”

He was intrigued. So was I.

The Problem? I Had No Tool… And No Clue

In the interview for that role, I had promised to provide calendar audits. At the time, I assumed there would be a plug-and-play solution. Surely, I thought, there was a calendar analytics tool out there that could do this automatically – Vimcal, Cabinet, Reclaim, Zapier… the usual suspects.

But I quickly hit a wall: SEC compliance. I worked at a firm with $1T in assets under management; we couldn’t integrate with any third-party apps or plugins that touched calendar data. Security was sacred.

So now I had a problem: I had promised something that I couldn’t deliver. And the alternative – doing a full calendar audit manually, line by line – wasn’t going to happen. My goal was to save time, not just for him, but for dozens of other leaders across the firm that I hoped to help later. I had no time to take on a manual calendar audit.

Most people would’ve dropped the idea at this point. But I couldn’t let it go.

The Turning Point: I Asked AI for Help

I had been hearing about ChatGPT and other large language models, and something clicked in my head. Maybe, just maybe, AI could help me find a workaround.

I opened a new chat and typed: “I need to extract a list of all recurring meetings from an Outlook calendar into Excel. Can you help?”

It responded with code. Now, let me be clear: I am not a programmer. I had paid developers before to build tools at past jobs, but I never thought I could write or run code. VBA (Visual Basic for Applications) was a total mystery.

But I copied the code anyway, asked for step-by-step instructions, pasted it into Excel… and nothing worked. So I did the next best thing: I copied the error message and pasted that into ChatGPT and asked, “What now?”

And so began a months-long journey of trial and error, late nights, and small wins. I’d get an error, copy it into ChatGPT, read its explanation, test a fix, and break something else. I didn’t know what half the messages meant, but I kept going. Each tweak got me a little closer.

At some point, I stopped feeling like I was failing and started feeling like I was building.

The Tool That Changed Everything

Eventually, it worked.

I had a working Excel-based script that connected to Outlook and extracted every recurring meeting from my executive’s calendar. It gave me:

• Meeting title
• Day of the week
• Meeting length
• Frequency
• Owner
• Location
• Date of next occurrence

I took the data and sorted it. Patterns emerged – meetings that had lived on the calendar for months, long after their purpose had passed. Weekly syncs that could be monthly. Hour-long sessions that could be 30 minutes if we tried.

I asked my executive for 30 minutes. We sat together and went through the list line by line. For each, we asked:

• Can this be shorter?
• Can it happen less often?
• Do you even need to be there?

We made changes. And when I added it up, I had saved him 389 hours per year.

389 hours. Let that sink in. That’s nearly 10 full work weeks. Imagine what a CISO can do with that kind of time back – mentoring, vision work, deep strategy, or maybe just not being on calls while eating lunch in a stairwell.

The Strategic ROI

This wasn’t just a time-saving win. It was a business case.

Although we didn’t quantify the dollar value of those 389 hours, we didn’t need to. Everyone understood what it meant to get that kind of executive time back. It meant leadership had more time to lead. And that’s priceless.

What started as a clever side project turned into something far bigger: a scalable, repeatable tool that could be used across the firm. So I started sharing it.

The Ripple Effect

I was invited to present the tool to all the administrative professionals in my firm’s Technology and Innovation division. I walked them through how to use it. Some were intimidated at first. Code? Macros? Scripts? It was a lot.

But it was so simple to run. The entire admin team of my division now had the ability to run recurring meeting audits for all senior leadership.

Time is the most finite resource a leader has. And we were giving it back to them, hours at a time. We weren’t just managing calendars anymore. We were shaping them.

Could I Make a Google Version?

Eventually, as word got out in my various EA networks, I was being asked to present this magic script. But they all wanted a Google version.

This time, my process was much quicker. I knew how to master the art of prompting by this time. What took me months to do initially now took one day.

I built a second version of the tool for Google Calendar using Google Apps Script. I wanted to support my peers outside of Microsoft environments and prove that these skills were transferable. ChatGPT helped me every step of the way, just like it had with the first version. This time I pulled five times more data than I had with the first version, such as:

• Dates the series started and ended
• Attendee participation percentages
• Date an occurrence was last edited
• Did the meeting end early?

Now, whether your team uses Outlook or Google, this recurring meeting audit can be run, reviewed, and revised to maximize your executive’s time. There’s no limit to how far this can go. We’re now exploring automatic dashboards, AI-powered suggestions to shorten meetings based on participation percentages, and visualizations that help EAs spot time drains instantly.

As I continued to share the recurring meeting audit in different circles, something unexpected happened. I was contacted by the team at Vimcal – one of the most talked-about calendar platforms for executives. They had heard about my work through EAmafia, an elite community of top-tier Executive Assistants. After a brief call, they asked me to demonstrate the tool I had built.

I walked them through my process and explained how I had used AI to solve for SEC compliance barriers and build something fully internal, functional, and scalable. They were blown away. Johnny Wu from Vimcal said, “Courtney’s solution was so simple, so effective, and so aligned with what EAs actually need that we ended up spending the next month incorporating her solution into our product. It became our biggest feature launch of the year.”

Watching a Silicon Valley calendar startup implement my idea into their roadmap? That was surreal. It proved that Assistants don’t just consume tools; we create them.

Lessons for Assistants Ready to be Strategic

Here’s what I learned, and what I hope you take from this:

1. Don’t wait for permission

Strategic work rarely comes wrapped in a bow. See something broken? Try to fix it. Don’t get discouraged if you don’t have the support of your peers. I was told that this type of work was not part of my job and that I needed to remove it from my annual goals. In the beginning, my own administrative manager, a lifelong EA, told me this was not in my job description and that I needed to stop. I was dumbfounded. But I wasn’t going to let someone’s inability to see the big picture derail me. So I worked every night of the week for months and kept it to myself until it was finished. I didn’t need her encouragement or validation.

2. Start with a pain point

Look for inefficiencies, bottlenecks, or complaints. That’s your starting line.

3. Ask AI for help

You don’t need to know the solution. Just describe the problem in detail and let the AI walk you through it.

4. Expect failure – and keep going

My script didn’t work the first, second, or fiftieth time. But every error taught me something.

5. Track impact

“389 hours saved” is a headline. Find your version of that number. Data speaks louder than effort.

6. Share what you build

Don’t gatekeep. I can’t stress this enough. The more you empower your peers, the more strategic visibility you earn. Sadly, not everyone will cheer you on. Never be that manager that stifles innovation. Be the one who sees the bigger picture. Be curious. Be hopeful. Champion others. Encourage growth. Innovation doesn’t always come with permission.

What Happened Next

This experience reshaped how I approach everything.

I don’t just wait for tasks. I listen for pain points. And I think, how can I solve this?

I’ve built automations to streamline household operations and tools to track multiple entities, and even started sharing my story publicly. And then I created this:

AI for Admins

After seeing how powerful AI could be in my work, I started a free weekly Zoom group called AI for Admins. It started with a handful of Assistants from World50 and has grown into a global community made up of more than 400 tech-hungry Executive Assistants who support key decision-makers at some of the largest companies in the world.

We demo tools, share prompts, support each other through projects, and cheer on each other’s wins. There’s no gatekeeping – just growth.

Everyone is welcome, whether you’re brand new to AI or building scripts already. If you’d like to join, connect with me on LinkedIn and I’ll send you the invite. We’re all in this together.

The Final Word: Start Building

If you’ve made it this far, thank you. You’re probably someone who wants more strategic work but maybe hasn’t found the doorway in. Let me be the one to say: don’t wait. Don’t wait for an invitation or a new job title or a “strategic” label.

Go build your own door.

I’m so glad I chose not to listen to that person at my last firm and stop working on this because it “wasn’t something I was hired to do.” I believed I was making something that could make an impact. And that’s exactly what I did.

Use AI. Use your voice. Use your unique perspective as an Assistant who sees everything and spots what could be better.

Nobody handed me strategic work.

I built it with AI.

And so can you.