Executive Summary
The fastest path to a Group CFO seat is rarely a straight line up one discipline. The professionals who get there earliest are the ones who built the broadest perspective the soonest.
This article draws on a conversation with Dave DeFreitas, who held 18 roles across 32 years at Caterpillar before retiring as Group CFO, to explore what early career design actually looks like in practice.
You will learn why lateral moves compound into leadership judgment, what the mindset shift from accountant to operator really demands, and how to lead people who know more than you do.
You will leave with a clear picture of what it actually takes to build toward a Group CFO role, and the specific moves, mindsets, and leadership frameworks that make the difference.
The Real Career Path Behind A Group CFO Title
Most finance professionals assume the fastest path to CFO is a straight climb up one discipline. Stay in FP&A, get better at it, get promoted, repeat. The problem with that logic is it produces technical experts, not business leaders. The Group CFO seat at a large company is not a technical expert role.
What actually gets finance professionals to the top is breadth. Enough experience across functions and business contexts to understand:
How a company creates value
Where the real risks live
How to lead people who are smarter than you in their own area
That breadth has to be designed. And the time to design it is in the first five to ten years, not the last five.
I explored this in depth on the podcast with Dave DeFreitas, who retired as Group CFO of Caterpillar after 32 years and 18 different roles. His path is one of the clearest examples of what intentional early career design looks like. You can listen to the full conversation here
🎧 Also worth listening to: Jack McCullough on Secrets of Rockstar CFOs: Jack McCullough on Developing the Next Generation of CFOs explores what senior finance leaders look for when they decide who to bring along and what separates the professionals who get to the top from the ones who plateau.
The Lateral and Stretch Roles That Build CFO-Level Judgment
The single most underrated career move in finance is the lateral. Not a promotion. Not a step up. A move sideways into something unfamiliar, where you build credibility from scratch and learn how a different part of the business works.
Most finance professionals avoid laterals because they feel like a delay. They are not. They are an investment. But only if you make them early enough and consistently enough for the perspective to accumulate.
Here is what that looks like in practice:
Seven different roles in six years: internal audit, legal entity accounting, P&L coordination, budgeting, and cost accounting
Zero promotions during that stretch
Ten levels of promotion in the six years that followed
The mechanism is not mysterious. Each role adds a new vantage point on how the company creates value. The professional who has run a P&L for a $2 billion entity, coordinated a budget across an entire business unit, and done cost accounting inside a manufacturing facility asks different questions than the one who has spent six years in the same FP&A process. They think differently under pressure. They see around corners that specialists cannot.
The stretch move that proves this most vividly takes a finance professional entirely out of finance. Leading a full product line across engineering, manufacturing, marketing, and 650 people, with no prior experience in any of it. The instinct is to say no. The right move is to say yes and figure out the gaps as you go.
“You don’t have to be an expert in engineering. You have an engineering manager that knows that stuff. What you have is the ability to step back and say: what does done look like? If we all have the same picture of done, we can plot the route together.” — Dave DeFreitas
That ability to establish a shared destination before anyone starts mapping the route is not a finance skill. It is a leadership skill. And it only develops through roles where technical expertise is not enough.
The other shift that comes from stepping outside finance is moving from minimizing cost to optimizing outcomes. An accountant’s instinct is to cut. But sitting across from a customer who tells you their harvest failed because your product broke down in the field changes the calculation entirely. The question is no longer how to reduce the warranty expense. It is what it takes to delight that customer enough that they come back.
This shift from reporting steward to business partner is what I explored in Supporting a Strategic CFO: Why CFO Direct Reports Matter More Than Ever. The CFO who has lived on the operational side of a business brings that perspective into every finance conversation they have for the rest of their career.
🎧 Also worth listening to: The Art of Becoming a Strategic CFO with Dr. Tamer Alsayed goes deeper on what the shift from technical expert to strategic leader actually requires and how to bridge vision and execution without losing credibility.
How to Think About Risk, Timing, and Saying Yes (or No)
The question most finance professionals get wrong about lateral moves is the timing question. They ask: is now the right time? The more useful question is: have I finished learning what this role has to teach me?
The right amount of time in any role is:
Long enough to contribute meaningfully and absorb what the position has to offer
Not so long that the role becomes a comfort zone
A good mentor moves people every six months to two years. Not on a fixed schedule, but based on whether the learning curve has run its course.
When a stretch opportunity appears, especially one that feels too big, the bias should be toward yes. The roles that feel largest in the moment tend to look smallest in the rearview mirror.
The harder version of this challenge is leading a team where your direct reports are older, more experienced, and not shy about either fact. Becoming a divisional CFO at 35 with six direct reports, four of whom are 60 or older, is a leadership test no training program simulates. The instinct is to assert authority or over-manage to prove you belong. Neither works.
What works is matching your approach to where each person actually is. For the experienced expert who has been doing the job for 15 years:
Agree on the goals clearly
Get out of their way completely
Show up without fail when they need you in their corner
Consistent presence at the moments that count is what earns trust across a team with wide experience gaps.
“Don’t judge others by the years and yardstick of your own experience. Understand where they are in their journey. That’s what situational leadership is.” — Dave DeFreitas
Signs You’re Actually on a CFO Track (Even If Your Title Isn’t There Yet)
Title is a lagging indicator. The things that actually predict whether a finance professional will reach the Group CFO seat show up years before the promotion.
You explain why, not just what. The professional who can tell you not only that revenue missed by 6 percent but why and what it means for the decisions ahead is developing the instinct the CFO role requires. The one who stops at the number is still thinking like a staff accountant, regardless of their current title.
You take the uncomfortable option seriously. Every stretch opportunity that feels too big is a test of whether you are building a career or managing one. The professionals who reach the top at large companies almost always said yes to the role they were not fully ready for, then figured out the rest.
You lead the team you could have, not just the one you have. The best finance leaders do not coach to current capability. They assess potential and push toward it. That means giving people room to form their own plans, make their own mistakes, and build the confidence that comes from doing, not just being told.
You are building a personal board of directors. Finance professionals on a genuine CFO track are not waiting for mentors to find them. They are actively building relationships with people who push them into uncomfortable roles, tell them the truth, and open doors in rooms they are not in yet.
Not sure where your gaps are? The free CFO Readiness Assessment at diaryofacfo.com gives you a personalized view of which skills to prioritize next.
FAQ
How early should a finance professional start thinking about lateral moves?
As early as possible. The return on breadth is highest in the first five to ten years. Seven roles in six years builds a picture of how a business works that most straight-line climbers take decades to develop, if they ever do.
What is the most important mindset shift for a future CFO?
The move from minimizing cost to optimizing outcomes. The accountant asks how to cut the expense. The CFO asks what it takes to deliver the result the business needs and what it is worth to get there. That shift only happens when you get close enough to operations and customers to see what the numbers actually represent.
How do you lead people who are more experienced than you?
Agree clearly on what done looks like, then get out of their way. Be present without fail on the rare occasions when they need you. Over-managing an expert is as damaging as ignoring a new hire. The skill is reading where each person is and calibrating accordingly.
Is a role outside finance worth taking on the path to CFO?
Almost always yes. The credibility that comes from leading a real operating role, P&L ownership, customers, engineering, manufacturing, is something no amount of finance experience replicates. The CFOs described as unique by their senior leadership are almost always the ones who have lived on the other side of the numbers.
To learn more about what business judgment looks like in practice across different finance functions, listen to Beyond the Numbers: Leadership Lessons from Three-Time Nonprofit CFO, Teri Kozub and Learning and Leading as a Modern CFO with Basem Waheed on The Diary of a CFO podcast.
About The Author:
Wassia Kamon is a CFO and the host of The Diary of a CFO, where she interviews finance and business leaders on strategy, risk, and leadership. She writes about finance leadership and governance in small and mid-sized organizations, including what works, what breaks, and how leaders manage growth and complexity without burning out.