Ask the CFO: The Human Side of Finance: Lessons from Family-Owned Businesses

Reflections from the October Ask the CFO Session

In our October Ask the CFO session, I decided to take a break from the usual financial headlines — tariffs, cost-cutting, and global uncertainty — and focus on something closer to home: the human side of being a CFO in a family-owned or privately held business.

After all, numbers are the easy part. It’s people, relationships, and trust that make the work meaningful — and often, challenging.

The Six Cornerstones of a Great CFO (Fractional or Full-Time)

Over the years, I’ve found that strong CFOs — especially in smaller or family-led organizations — serve as both financial stewards and trusted advisors. In our conversation, I shared the six areas that I believe define great financial leadership:

1. Trust and Credibility

Everything starts here. In any business — but especially family-run ones — your reputation is your currency. Acting with integrity, being transparent, and following through on commitments builds the foundation for every financial and strategic decision that follows.

2. Navigating Family Dynamics

Every family business has its stories, passions, and conflicts. The CFO often sits in the middle, balancing differing perspectives while keeping the company’s long-term health in view.
It’s part finance, part psychology — and it requires empathy, patience, and emotional intelligence (even if, as I joked, my three daughters tell me I have none).

3. Balancing Tradition with Change

There’s pride in “the way we’ve always done things,” but growth requires evolution. The healthiest businesses find ways to honor their history while embracing technology and process improvements. In other words, no more “SALLY” — same as last year.

4. Mentoring Future Leaders

A good CFO doesn’t just manage numbers — they grow people. Mentorship is about developing the next generation of leaders, even if that means they’ll eventually move on. When a former team member succeeds elsewhere, that’s a win for the business ecosystem as a whole.

5. Aligning Personal and Business Goals

In family businesses, personal goals and business objectives often blur. Some owners want to stay at their desks forever; others are ready to step back. Part of our job is to help clarify these motivations and ensure they align with what’s best for the company’s value and continuity.

6. Confidentiality and Discretion

Finally — and perhaps most importantly — we must protect the trust people place in us. Whether it’s a private conversation with a family member or a sensitive financial decision, discretion isn’t optional. It’s part of the job.

When Family Business Feels Like Family Life

One of our guests, Leah Richter, shared a memorable story about working with a family business that had seven relatives at the table — all with completely different visions for their company website. As she put it, “The people who need cohesion the most often have it the least.”

Her story got everyone laughing — and nodding in agreement. Whether it’s designing a website or planning next year’s budget, everyone pulling in different directions leads to chaos.

The lesson? Success in family-owned companies depends on clarity of vision, alignment of goals, and the humility to listen.

Employment vs. Ownership: Two Different Roles

Another theme that resonated was the distinction between being an employee and being an owner.
Just because someone has equity doesn’t mean they automatically have a job — and vice versa. Keeping those boundaries clear prevents resentment and protects the long-term health of the business.

This also came up in a discussion with John, one of our newest participants, who’s thinking about employee ownership as a potential growth strategy. It’s a powerful option, but as I reminded him, ownership comes with both opportunity and responsibility — and not everyone wants both.

What’s Next: AI, Technology, and the Future of Finance

As we wrapped up, Doug (who, I might add, agreed with me on everything this time — a rare event!) brought up the growing role of AI in business operations. We’ll be diving deeper into that topic in an upcoming session, exploring how automation and intelligent systems are reshaping finance for small and mid-sized companies.

Because while AI might dominate the headlines, many businesses are still catching up with basic automation tools that could save them time and money right now.

A Final Thought

This month’s conversation reminded me that finance isn’t just about spreadsheets — it’s about people. Every balance sheet tells a story of relationships, trust, and growth.

So, whether you lead a business, advise one, or simply want to understand the financial side of decision-making, remember this: business health is built on both numbers and humanity.

Join Us for the Next Ask the CFO Session
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