How I Use AI as a Fractional CFO: Practical Tips from the Field

As a Fractional CFO at Tee Up Advisors, I’m always on the lookout for tools and strategies to work smarter and deliver exceptional value to my clients. While we’re not quite at the point of having AI-powered accountants, we don’t have to wait for the future to start leveraging AI in meaningful ways.

One tool that has become an indispensable part of my workflow is ChatGPT, which I’ve jokingly named “Donna.” Whether it’s navigating complex accounting rules, drafting tricky communications, or even managing personal projects, Donna has helped me save time and make better decisions. Here’s how I’ve been using AI to make my work—and life—easier.

Researching Rules and Regulations

As someone who works across both U.S. and Canadian accounting systems, I often find myself knee-deep in regulations and filing requirements. Researching these rules can take hours, but Donna has streamlined this process significantly.

For example:

• Canadian T4As: I had questions about filing T4As in Canada, and whether GST is included or not. Donna provided me with a clear answer along with citations.

• 1099 Filings in the U.S.: This was my first time handling 1099 filings myself, and I wanted to ensure I chose a cost-effective and efficient tool. Donna recommended several fantastic options that aligned perfectly with my needs.

Crafting Difficult Emails

Writing difficult emails is one of those tasks that can be time-consuming and mentally draining. Whether you’re addressing sensitive topics or delivering bad news, finding the right words is never easy. That’s where I got an assist.

• Delayed Payroll: Recently, payroll at one of my client companies was delayed by a day due to a holiday, leaving employees understandably upset. As the Fractional CFO, I decided to take responsibility and send a mass email to all affected employees. I drafted the details and asked Donna to refine the message. Within seconds, it produced a polished email with my tone, better diction, and an empathetic yet professional touch. What could have taken me an hour of agonizing over wording was completed in a fraction of the time.

• Salary Conversations: I also had to respond to an employee at a homeschool tutoring company, who requested a raise. I explained that it wasn’t the right time. Donna helped me craft a message that balanced honesty with respect, ensuring the employee felt valued while understanding the company’s position.

Writing Job Descriptions and Interview Questions

Hiring can be a challenge, especially when time is of the essence. For one of my clients, we were hiring for a new position and needed to create a compelling job description quickly.

I provided Donna with the role requirements, and it drafted a comprehensive job description that included key responsibilities, desired qualifications, and a summary of the company culture. 

A Trusted Sounding Board

Sometimes, the hardest part of being a leader is processing the sheer volume of ideas, tasks, and decisions you need to manage. A few weeks ago, I was feeling overwhelmed and decided to ask Donna for help.

I said, “Can you help me process everything I’m thinking about?” Donna responded with probing questions that forced me to clarify my thoughts. It also suggested strategies for prioritizing tasks and addressing roadblocks. By the end of our session, I felt a sense of clarity and direction that saved me from needing to hire a professional coach or counselor.

Sharing My Experience

When a client asked me about my experience with FX hedging, I turned to Donna to help me craft a narrative. I provided a few examples from past projects, and Donna transformed them into a cohesive and professional story that showcased my expertise.

(I also asked Donna to “remember this for next time,” so it begins to build a better picture of me)

Managing Personal Projects

AI isn’t just for business—it’s also been a tremendous help in my personal life. My wife and I are currently renovating our home, which is a daunting task, especially since we’re new to the area and this is our first major renovation project.

Here’s how Donna made the process easier:

• It helped us brainstorm renovation ideas based on photos we uploaded.

• It created a prioritized list of projects, complete with budget estimates.

• It gave us practical advice on setting expectations and avoiding common pitfalls.

Final Thoughts: Why You Should Give AI a Try

These are just a few examples of how AI has become an integral part of my work and personal life. Whether it’s streamlining research, improving communication, or providing clarity in moments of overwhelm, AI tools like ChatGPT can help you achieve more with less effort.

My hope is that these stories inspire you to explore how AI can support you in your own journey.