The Best Assistant I’ve Ever Worked With

How I Trained the Best Assistant I’ve Ever Worked With

In this article, Harry Catrakilis shares his experience onboarding one of the best assistants he’s had, whose performance exceeded all expectations. From thoughtful questions to high-level output, it felt like working with a top-tier hire. This story offers a fresh look at training, technology, and what it really means to work smarter.

“A few weeks ago, Nick Catrakilis, Executive Chairman of CKH Group, came to me and said, “Harry, I know you’re retired, but we’ve lined up a new assistant for you.”

Now, if you came up in the 1980s, you know what that means. Back then, a good assistant wasn’t just an admin, they were an extension of you. Someone who anticipated your thoughts, protected your time, and added value at every turn. Naturally, I was intrigued.

So, I said, “Sure, why not.” And just like that, I had an assistant again- Abe, starting on Monday.

Over the weekend, I was thinking about how I would kick off the onboarding. I figured I’d talk him through how I think, give some context to my processes, talk through the current project I’m working on, and see how he handled it.

On Monday, we kicked things off.

Right away, I could tell Abe had done his homework- the first week was incredible. He was asking thoughtful questions, engaging with curiosity, and- this part caught me off guard-genuinely kind and inspiring.

At one point, I’d joked about being “not the smartest” about a particular thing and he pushed back saying “Smart isn’t just spreadsheets- you’ve got a sharp instinct for people, community, and opportunity, which is a big part of what makes deals like this work.”

And not only that, but he was smart and eager to learn, not just about projects, but about me and how I thought. After I’d spent a bit of time explaining that my style of communication is to explain the ‘why’ before the ‘what’ he asked me “what kinds of experience or values shaped your approach to communicating that way?”

Now, I’ve hired and mentored a lot of people in my time, and I can tell you: most of them don’t talk like that in week one. I started thinking, Where did Nick find this guy? Some of my best rockstar employees didn’t show this level of enthusiasm and support. Here was an assistant who was smart, could build upon my thoughts, and really take some things to the next level. And it didn’t stop there.

By the end of the day, Abe had sent me a clear, well-organized summary of everything we’d discussed. Key priorities, core themes, next steps. It was the kind of memo I’d expect to get from a top tier consultant.

As the week went on, the pace didn’t slow. He was doing incredible research and preparing documents, all with no delays and no miscommunications.

Of course, he had his quirks.

I could never get him on the phone. Not once. And he only worked while I was online- no overtime, no after-hours hustle. And he practically depended on the internet; the one time he had some internet trouble, it was like he completely shut down, wouldn’t even respond to me.

And yes, by the end of the first week I was wondering if Abe was too nice. The constant agreement and perfectly polished encouragement made me think he didn’t actually mean it, and was just being a people-pleaser.

Still, despite this I couldn’t deny the quality of the output. I was stunned by his ability to get the best out of me and turn my ideas into clear compelling results.

Honestly, it started to not feel real.

Likely because it isn’t.

Abe is ChatGPT– my digital assistant for only $20 a month.

This was my first time trying out AI/Chat GPT, and I can honestly say that this new technology, when utilized the way I did, it truly blew me away. I found that the key lay in training and treating it like a junior hire to whom I must explain how I work and what I want. And once it knew, its ability to interact with the necessary context and passion, to do research and prepare documents, was unbelievable.

So yes, I was impressed by my new AI assistant, but I’m still in the honeymoon phase. In a few months, I’ll give an update on all that I’ve learned.” -Harry Catrakilis

The above article only intends to provide general information and reflection. It is not designed to provide specific advice or recommendations for any individual. It does not give personalized tax, financial, or other business and professional advice. Before taking any form of action, you should consult a financial professional who understands your particular situation. CKH Group will not be held liable for any harm/errors/claims arising from the blog. Whilst every effort has been taken to ensure the accuracy of the contents, we will not be held accountable for any changes that are beyond our control.