CFOs face compounding pressure from every direction. They’re expected to lead distributed teams, navigate economic uncertainty, deal with tighter margins, provide strategic insight, improve financial visibility and integrate AI into the finance function.
From the outside, the role looks like the natural next step for experienced finance professionals. On the inside, it’s a constant balancing act between competing priorities, imperfect information and difficult conversations. Yet the gap between expectation and reality rarely gets talked about.
At Pleo, we’ve built relationships with many mid-market CFOs. While every finance leader’s journey is different, some experiences seem universal.
So we asked CFOs to share the realities of modern finance leadership, plus the lessons they’ve learned along the way. This is the first in that series, featuring Lisa Press, Fractional and Interim CFO, and founder of Lisa Press Consulting.
One of the biggest misconceptions about the CFO role is that it’s all about high-level strategy. The reality is that many days are spent juggling priorities and balancing competing demands.
Lisa noted that the worst weeks typically stack up the same three things: “Fundraising pressure, systems that aren't automated enough yet to keep up and a dozen stakeholders each convinced their request is the most urgent.” She added that you can’t do all of it well at once. “The job in that moment isn't getting everything done; it's figuring out fast what actually needs your attention first and letting the rest wait.”
The most effective CFOs are constantly prioritising what matters most, making trade-offs and accepting that some tasks simply have to wait until tomorrow.
Senior leaders are often associated with confidence and certainty. But many CFOs still experience imposter syndrome. For Lisa, this hit hardest when stepping into a new industry, while taking responsibility for a large team.
Her approach didn’t involve faking her way through it, but rather working hard to close the gap.
“I built knowledge deliberately, outside work hours, until I could genuinely hold my own in the room. Confidence followed competence, not the other way around.”
It’s an experience many new CFOs can relate to. Promotions don’t eliminate uncertainty, and sometimes they introduce even more of it. The key is learning to make decisions to the best of your current ability, while continuing to build your expertise.
Finance teams have more tools than ever. Automation has cut down on manual data entry, dashboards update in real time, and agentic AI can now handle routine tasks like sorting expenses or flagging anomalies.
Despite these advances, CFOs are still dealing with incomplete data. “Even now, revenue data is rarely as granular as I'd like,” said Lisa. She added that this visibility gap means CFOs are often making seven-figure calls without the full financial picture.
That uncertainty doesn’t stop the decision-making process. “It just means you’re deciding with a level of humility most people outside finance never see,” added Lisa.
Of course, the CFO role isn't just about financial data. Building and maintaining relationships with other leaders and departments is just as critical a part of the job. Whether challenging assumptions, balancing priorities or managing expectations, finance leaders have to navigate their fair share of difficult conversations.
Lisa recalls one conversation with a CEO whose revenue targets didn’t match up with reality. “He was attached to the number, not the maths. What moved the conversation was sharper data, not opinion. That's the only currency that works in that room.”
Lisa also noted that building cross-functional relationships with other departments has shifted from seeing finance as a gatekeeper to seeing finance as a partner.
“The turning point was automation. Once we could get other teams their numbers faster, we stopped being the department that slows things down and became the one that speeds decisions up.”
One of the biggest traps for new CFOs is thinking they should know the answer to every question. Lisa admits acknowledging this was one of the biggest lessons of her own career.
“I assumed I could personally master every specialised corner of finance, M&A, tax, treasury, all of it. I couldn't, and trying to was a mistake.” She added that maturity in the CFO role isn’t about knowing everything, but it’s knowing exactly which specialist to bring into the room and when.
The hardest parts of being a CFO aren’t listed on the job description. While the expectation is that you’ll be managing budgets and forecasts, the reality is a bit messier. In truth, the role also includes becoming comfortable with uncertainty, building relationships and getting to grips with new technology.
That’s why conversations like this matter. Being a CFO might feel isolating at times, but Lisa’s reflections are a reminder that many finance leaders are dealing with the same challenges. The truth is that behind every dashboard and decision sits someone making high-stakes decisions with imperfect information.
Looking for more insights from finance leaders? Visit the Pleo blog, and keep an eye out for the next article in this series.