I have been fired more than once for having too much of a filter problem. I am from New Jersey, I have opinions, and earlier in my career I did not always understand that being right and being effective are two different things.
But getting fired, challenging bad leadership, uncovering financial misconduct, and eventually becoming a CEO taught me something important: integrity, financial clarity, and hard work matter. You just have to learn how to deliver the truth in a way people can hear.
Key Takeaways
- Strong CFOs translate financial data into the story leaders need to make better decisions.
- Documented processes create accountability and allow businesses to close their books faster.
- Integrity can carry short-term consequences, but dishonesty creates far greater long-term risks.
- Effective leaders keep their conviction while learning to communicate disagreement with respect.
Table of Contents
- From Aspiring Actor to Financial Detective
- The Four Areas I Assess as a Fractional CFO
- Financial Intelligence Means Telling the Story Behind the Numbers
- Why CFOs Can Become Strong CEOs
- Early Lessons About Ego, Greed, and Respect
- When Integrity Costs You a Job
- Learning That How You Say It Matters
- Financial Detective Work: Finding Fraud in the Details
- Navigating the Boardroom and Becoming CEO
- Getting Off the Hamster Wheel and Becoming a Fractional CFO
- The $400,000 Website Problem
- A Fractional CFO Is Not There to Pay Every Bill
- Every Person Is a Client
- Keep the Work Ethic, Tame the Filter Earlier
From Aspiring Actor to Financial Detective
When I was younger, I wanted to be an actor. I have always felt that I had a decent balance between the creative side of my brain and the analytical side. Numbers came naturally to me, though, and I grew up poor. Acting felt like a path where I might spend years struggling, waiting tables, and hoping for a break that never came.
Finance looked like a path toward stability. It was a way to build a better life.
College also gave me something I badly needed at that point in my life: a place to live, a purpose, and a direction. Rutgers had recently introduced a finance major through its business school, and it fit my strengths. I decided to lean into what I was good at, even if it was not the original dream.
I started down the accounting path at first, but repetitive accounting work was not for me. I respect accountants, but I was drawn much more to financial analysis. I liked digging into numbers, finding what was wrong, and spotting opportunities other people had missed.
That is why I think of finance as detective work. Good financial work is not merely calculating numbers. It is figuring out what the numbers are trying to tell you.
The Four Areas I Assess as a Fractional CFO
When I enter a company as a fractional CFO, I begin with an assessment across four core areas:
- Profit: Are the financials accurate, timely, useful, and understandable?
- People: Do the right people hold the right jobs, with the skills and support to do them well?
- Process: Are essential workflows documented, consistent, and accountable?
- Systems: Does the company have systems that fit its current size, needs, and reporting requirements?
These four areas are connected. Poor systems create weak reports. Weak reports make it difficult for people to make good decisions. Missing processes make accountability nearly impossible. And all of that eventually shows up in profitability.
The Biggest Blind Spot Is Usually Process
In small businesses and startups, the biggest gap is often process. Many companies are running on habit, memory, and whatever somebody was taught by the last person in the role.
A monthly close is a perfect example. Some companies take 20 or 25 days to close their books. That means leadership may be deep into October before it can see August results. By then, the information is stale.
Without a documented close process, nobody knows what should happen on day one, day two, day three, and so on. When the books are late, the manager gets explanations but has no real way to determine whether those explanations are legitimate.
In most of the companies where I worked, we had a five day close because people knew exactly what had to be completed and when. A documented process creates clarity. It also creates accountability.
Systems Are Not Just Software
Many companies begin with QuickBooks, which can be perfectly appropriate. The question is whether the company has outgrown it, whether it is configured correctly, and whether the team knows how to use the reporting available inside it.
Having a system is not enough. Leaders need reports that help them run the business.
That means defining meaningful key performance indicators, or KPIs. The CEO should know what to look at daily or weekly to understand business performance, employee performance, cash needs, sales activity, and operational issues before they become expensive problems.
Financial Intelligence Means Telling the Story Behind the Numbers
A CFO has to evaluate people, not just spreadsheets. When I meet a finance team, I speak with each person about their background, responsibilities, frustrations, and understanding of the business.
Then I discuss the numbers with them.
If an expense spikes in September, I want to know why. If the answer is always, “I do not know, ask the CEO,” that tells me something. It does not automatically mean the employee should be fired. They may be overwhelmed, unsupported, poorly trained, or excluded from important business decisions.
You need to look at the entire context:
- How much support does this person have?
- Who works beneath them?
- How long have they been with the business?
- Do they understand the financial statements?
- Are they equipped to make strategic decisions?
- Were they promoted beyond the level of their current skills?
A strong controller is not automatically a CFO. A CFO needs strategic judgment, financial analytics, communication skills, and the ability to explain what leadership should do next.
I have worked with data analysts who could slice and dice numbers in every possible way. But slicing and dicing is not the full job. The numbers have to tell a story.
If a CEO does not come from a finance background, they need someone who can explain what the data means, what is changing, where the risk sits, and where the opportunity is. A report without interpretation is not leadership.
Why CFOs Can Become Strong CEOs
Traditionally, plenty of CEOs came from sales or marketing. That makes sense because sales drives revenue. But a CEO focused only on top-line revenue can miss the rest of the picture: people, process, profit, and systems.
A sales-led CEO may be excellent at generating business but still need a strong CFO to ensure that revenue actually turns into profit and cash.
Over time, I saw more CFOs becoming CEOs because they understood profitability. They saw how operational decisions affected margins, cash flow, staffing, investment, and long-term value.
When I became a CEO, I did not replace myself as CFO because I already knew the financial side of the business. My job was to build strong support around my weaker areas, especially sales, marketing, and HR.
That is a lesson for any executive: know your strengths, know your blind spots, and hire people who are better than you in the areas where you are weak.
Early Lessons About Ego, Greed, and Respect
My first firing was not from a CFO job. It was Burger King. I had been there for two weeks, wanted to leave for summer vacation, and decided I was going anyway. That did not work out particularly well for my career in fries.
My time on Wall Street came next. I worked in a back-office analyst role and was quickly made supervisor of a department. I was making $17,000 a year, and when bonuses came around, mine was $1,000. I had a very New Jersey response to the director who handed it to me.
I was not fired, but I became disgruntled and chose to go back to graduate school. The experience taught me that people remember whether their work is valued.
Wall Street was also exactly what many people imagine it to be, especially in the 1980s. There was money, excess, ego, drugs, alcohol, and a culture where people could get pulled into a lifestyle quickly. That environment did not fit me. I did not want a career where I was simply told what to trade and paid well enough not to ask questions.
I wanted to use my brain. I wanted to investigate, analyze, and build something.
When Integrity Costs You a Job
One of my early CFO roles was with a distribution company that had been acquired by private equity. A new CEO came in, and I had trouble respecting him because of his decisions and behavior in the office.
Then came the real issue.
It was shortly after September 11, and the head of the private equity firm asked me to tell vendors that late payments were related to 9/11. That was not true. He wanted me to use a national tragedy as an excuse for why the company was not paying its bills.
I had lost people in 9/11. I could not do it.
When I was let go, I was told I was not a team player. My response was simple: if that was what being on the team required, I was fine leaving.
Integrity can be expensive in the short term. It can cost you an opportunity, a title, or a paycheck. But there are lines that should not be crossed, especially when people are being asked to lie to vendors, employees, investors, or customers.
Learning That How You Say It Matters
Early in my career, I had an incident at a company dinner where a salesman was making a married colleague uncomfortable. I told him directly that he was making her uncomfortable. That was all I said.
The next day, I was instructed to apologize to him because I had made him uncomfortable. I was young, did not understand the corporate pecking order, and was told I could lose my job if I refused.
So I gave the kind of apology people recognize immediately: I apologized if he felt bad about what I said, not for what I actually did.
I hated doing it. It felt like I had acted against my character. But it taught me a hard lesson about working inside organizations: sometimes you need to save face, pick your battles, and understand the power structure around you.
That does not mean abandoning your values. It means learning how to be strategic about when, where, and how you speak.
Financial Detective Work: Finding Fraud in the Details
In another CFO role, reviewing the CEO’s travel and entertainment reports was part of my responsibility. I began noticing odd items: duplicate flights, paintings, jewelry, and personal expenses that did not appear to have been properly identified.
At first, I asked innocent questions. Was this duplicate flight a mistake? Where was this painting being used in the business? Was this item personal?
The explanations did not add up.
I looked deeper and found that one duplicate flight was actually two seats next to one another, one for the CEO and one for his girlfriend. I found jewelry classified as gifts for an all-male sales team. I found $300,000 that had been taken from the company.
I reported the findings to the parent company’s CFO. They asked me to investigate further. The next day, police arrived and the CEO was arrested.
Then, about a month later, I was fired without cause.
That can happen. You can do the right thing, find the issue, protect the company, and still become inconvenient. It is one reason finance leaders need to document their work, escalate concerns through appropriate channels, and understand that uncovering misconduct can create political consequences.
Navigating the Boardroom and Becoming CEO
After that experience, I joined another company where I would spend 20 years. Within six months, I discovered the CEO was hiding losses.
He was not taking money for himself. Instead, he was using cash from new deals to make older losing deals look as if they had broken even. He never wanted to admit that the company had lost money. But the business was losing roughly $1 million to $1.1 million that the board did not know about.
Because of what I had just been through, I was careful. I did not immediately confront everyone. When board members noticed my facial expressions during meetings and asked me what was wrong, I told them I could not simply go around my CEO. I suggested they ask specific questions in the board meeting and require me to show the numbers.
That is what happened.
The CEO and board president attempted to blame me, even though I had only been there six months. I knew they were going to do it, so I came prepared. I had the facts, the numbers, and the evidence to respond directly.
The CEO was fired on the spot.
Then the board asked me to become temporary CEO. I said no. I would become permanent CEO, but I would not be temporary CEO.
It was a gutsy move, especially after being fired before. But it worked. They trusted me, gave me the opportunity, and I led the company for two decades.
During that time, I learned another major leadership lesson. In one argument, a board member reminded me that he owned the company and I reported to him. Human being to human being, I do not believe anyone is inherently above anyone else. But in an organization, reporting relationships are real.
I learned that disagreement has to be respectful. You can keep the fire. You can maintain the conviction. But you need to communicate in a way that respects the role, the audience, and the business relationship.
Getting Off the Hamster Wheel and Becoming a Fractional CFO
After selling the company, I worked for the acquirer and eventually left with a one-year non-compete that prevented me from working in healthcare. That was the first real chance I had to step off what I call the hamster wheel.
Most people get on that wheel after college and do not get off. There are jobs, mortgages, children, responsibilities, and financial pressure. You keep moving because you have to keep moving.
For the first time, I had the ability to stop for a year and breathe. I acted, wrote, explored business ideas, and did things I had wanted to do for a long time.
When the opportunity arose to become a fractional CFO, I was ready to return, but at a slower speed. I did not want to go back to a conventional nine-to-five office routine. COVID had also shown me how much better I worked without constant interruption.
Fractional CFO work allowed me to help multiple businesses, apply decades of experience, and get back to the financial detective work I enjoy.
I can help companies identify what is not working, improve their reporting, build their processes, and find the right people. After that, what they do with the advice is up to them.
The $400,000 Website Problem
One current example shows why financial visibility matters so much.
I worked with a retail business generating roughly $10 million to $20 million in revenue. The owner was personally handling accounts payable, HR, legal matters, IT implementation, and more. Bills arrived in his email, and he paid them one by one without a clear system showing what was due in 30, 60, or 90 days.
He had no real back-office support. His bookkeeper was expensive, and the financial information being produced was convoluted and unhelpful.
The books were a confusing mixture of accrual and cash accounting. To understand the financials, I had to drill down through the system, entry by entry, until I could see what was actually happening.
Then I found the website spending.
I asked the owner how much he thought had been spent building one website. He guessed around $100,000.
The real number was $400,000.
He was stunned, and understandably so. That is what a lack of financial transparency can do. When the data is unclear, leaders can spend massive amounts of money without realizing it.
The same issue often appears in marketing and sales:
- Companies have no budget.
- They do not know their return on marketing investment.
- They pay salaries and commissions without tracking sales by salesperson.
- They cannot identify whether someone is producing, underperforming, or simply living on a comfortable salary.
A business does not need to become obsessed with spreadsheets. It does need visibility. Leadership needs the data that drives the business and exposes what is hurting profitability.
A Fractional CFO Is Not There to Pay Every Bill
A fractional CFO should not become the company’s bookkeeper, accounts payable clerk, collections person, or reconciliations department. The role is to improve how those functions operate.
If the company needs a better bookkeeper, a finance manager, or a controller, the CFO can help define the role and find the right person. If the reporting is weak, the CFO can establish the processes, reports, and KPIs needed for better decisions.
The real value is not in doing every task. It is in helping the company create a financial function that can operate effectively after the CFO is gone for the day.
Every Person Is a Client
One of the most valuable lessons I learned over time is that everybody has different drivers.
In a large organization, people can become competitive, political, and untrusting. There may be one promotion available, and everyone may be fighting for it. But not everyone wants the same thing.
Some people want more money. Some want recognition. Some want balance. Some want status. Some want a promotion. Some simply want to do good work without carrying more responsibility.
As a fractional CFO, I think of my client as my boss. My role is not to tell a client what they want to hear. My role is to explain the truth in a way they can understand and use.
That same mindset applies to colleagues and peers. Treat people as clients. Learn what matters to them. Understand their drivers. Then communicate in a way that helps them get where they need to go while still protecting the business.
Keep the Work Ethic, Tame the Filter Earlier
Through all the career ups and downs, the thing that has carried me through is my work ethic. People may remember the humor, the directness, and the occasional fiery personality. But they also see that I work hard and that I can analyze a problem deeply.
That balance matters.
If I could offer one piece of advice to CFOs, CEOs, and anyone trying to lead through difficult situations, it would be this: stay true to your values, do the hard work, and learn how to communicate with respect.
Keep the humor. Keep the conviction. But tame the filter a little earlier than I did.
To connect professionally, find Tom Crooks on LinkedIn.
Frequently Asked Questions
What does a fractional CFO do?
A fractional CFO provides strategic financial leadership on a part-time basis. The role focuses on reporting, cash flow, profitability, KPIs, systems, finance team structure, and better decision-making rather than routine bookkeeping tasks.
What are the four areas a CFO should assess in a business?
A practical CFO assessment covers profit, people, process, and systems. Together, these areas reveal whether a business has accurate information, capable staff, accountable workflows, and suitable technology.
Why are KPIs important for CEOs?
KPIs give CEOs timely information about the activities that drive business performance. They can reveal sales productivity, spending patterns, cash needs, operational problems, and profitability issues before leadership is forced to react too late.
Should a fractional CFO also handle bookkeeping?
Usually, no. A fractional CFO can help improve bookkeeping processes and identify the right bookkeeper or finance hire, but the CFO’s primary role is to build financial clarity and guide strategic decisions.
