Slow Down and Listen: Lessons from the Start of a Fractional CFO Engagement

by John Illges

I recently became a father, and one of the most rewarding aspects of my new role is watching my little daughter encounter new things for the first time. She lives in a world of many firsts: first swing, first prune, first ball pit, first time hearing Fleetwood Mac. I am privileged to witness the magic of her encountering “new” with caution and curiosity. Eventually, the new wears off and caution turns into confidence, curiosity into familiarity. The little ball she held in her right hand became more than an object to scrape her teeth on and then throw. Upon encountering it again and again, she knows exactly where it goes and deftly drops it right into the hole in the box. The prune puree is devoured without a second thought, and she smiles and bounces with glee whenever she hears the first notes of “Silver Springs.”

When I first started as a fractional CFO, my new client engagements worked much the same way. The first few weeks were full of caution and curiosity. After a few years of new client engagements, you get familiar with the process and can begin to template your approach: we go from addressing immediate known issues in the books to developing a financial package, to holding monthly financial meetings, and then customizing KPIs and dashboards to the client’s specific business. That approach typically works; after practicing a hook shot many times over, it becomes muscle memory. However, not all clients are the same. I was reminded of that last year when we were approached by a new client, O’Leary Asphalt.

O’Leary was started decades ago by two brothers. They grew the business into a vital and respected component of the DC metro and wanted to begin handing it off to their sons. As they began the transition, they wanted a strategic partner in the room, so they approached us for CFO guidance. Similar to previous new client engagements, they knew what they needed. With equal confidence, I thought I knew what they needed. Every new engagement starts with alignment, and it soon became clear that the O’Leary team had a clear view of what they needed, and it was different from the familiar playbook I had become accustomed to running.

The next few weeks became an alignment process: how do we stitch together the client’s priorities with what I see needs to be done? We spent many hours on calls working to surface the issues at hand. Once we had a grasp of those, we could begin to negotiate priorities and layer theirs on top of my own. My automatic starting point is the balance sheet; it’s usually where the problems lie, and my push to address the few things I found there was met with a very studied and deliberate approach by the O’Leary team. After addressing balance sheet issues, I strongly push for financial review meetings, even though we know the numbers won’t be clean yet. The goal is rhythm: a set meeting where errors get caught and corrected. Instead of the whole engagement becoming error-hunting, we silo that into part of our monthly cadence.

We ran that playbook, and it worked for what it was. We fixed what we could, but the client kept steering me back to the P&L. They were smart and deliberate in their questions: Is the chart of accounts set up so we can really determine what is going on? Usually, the P&L is second or third on my list of priorities, but the client’s questions kept pulling the conversation toward the P&L, and we were rewarded for it. There wasn’t any tension or resistance, just intentionality. And it forced me to adapt.

The client’s questions kept pulling the conversation toward the P&L, and we were rewarded for it.

I still made sure to get some quick wins on the books. The important issues I found were addressed; we made substantive changes to the customer deposit process, though we agreed to leave other areas in place for now, because the risk of changing the records and the processes behind them outweighed the benefits. The slower, more deliberate pace ended up improving the work rather than hindering it. The consistent scrutiny of the P&L and the organization behind it led us to create a deep backlog of specific, important procedural and material changes we wanted to address throughout the organization. These early meetings gave us a clear agenda for 2026: job costing, budgeting, reporting metrics, and technology.

I became familiar with new client engagements and thought I had the approach nailed down.

Like my daughter familiarizing herself with the taste of a prune, I became familiar with new client engagements and thought I had the approach nailed down: balance sheet review, to fixes, to financial review meetings, to continued tweaks and improvements in the accounting function, to core financial strategy development and monitoring. Familiarity can also be a little blinding. The O’Leary team served as a helpful reminder that each client deserves a fully tailored approach, and requires me to listen more than drive. The rich backlog we built together, the kind I now try to build with every client, came directly from their careful attention to what the business actually needed. Their clarity about what they needed let them get more out of my expertise than a standard engagement usually allows.

So, the lesson for me was this: slow down, listen more, and hone my approach. The lesson for those considering hiring a fractional CFO is this: come to each meeting with an agenda and speak your mind. These two approaches, combined, will yield fruitful results.