The first 90 days: What a new CFO actually walks into

Most new CFOs arrive with a plan. Understand the cash position, meet the team, learn the systems, then start making things better. The plan makes sense in theory, but the first week rarely cooperates.

We spoke to four finance leaders who step into struggling finance functions for a living. Between them, they have decades of experience walking into businesses mid-flight and sorting out what they find. None of them described a tidy onboarding. They described the things the 30/60/90 plan tends to skip: numbers that look fine until you scratch the surface, spend no one can see, and the slow work of becoming a partner rather than a gatekeeper.

Their advice maps the (sometimes rocky) terrain below the 30-60-90 roadmap.

The basics are often broken 

Raymond Gong is a senior partner at Profitability Partners, a fractional CFO firm that takes over the finance seat for trade businesses. He's done the first 30 days more times than most CFOs will in a career, and his advice is blunt: before you touch strategy, check that the plumbing works.

"Make sure AR, AP and payroll work," he says. "You need to confirm that you can actually invoice and collect from customers, pay your vendors and pay your team on time." He says it’s not unusual to find books kept on a cash basis with a poor chart of accounts and no real metrics, which makes it almost impossible to understand what's happening.

Then there's the admin no one warns you about. "In a lot of businesses, the basics are missing in terms of administrative organisation," Raymond says. "Things like logins to vendor portals and software can be all over the place." Centralising those data sources is unglamorous work, and it's often where week one really goes.

His warning to incoming CFOs from private equity, banking or consulting backgrounds...don't put the cart before the horse: 

"They're strong at modelling, capital allocation and strategy. But for many businesses, you need to sort the steps that come before the high-level strategy first. Once the basics are right, you can shift focus to the higher-level work." Raymond Gong - Senior Partner, Profitability Partners 

The reports look fine, but there's a problem underneath 

Glen Morgan, CEO of itsettled and a working-capital specialist who has advised the UK government on late payments, has seen plenty of finance functions that read well on paper and creak underneath.

"Many finance challenges are actually operational challenges in disguise," he says. Delayed invoicing, unresolved customer queries, poor communication between departments, unclear ownership: all of it slows cash conversion, and none of it shows up cleanly in the monthly accounts. His advice for the first weeks is to look past the numbers and at the culture that produces them. "Are there formalised processes and procedures, and are these followed? Spend time understanding relationships, incentives and behaviours across the organisation."

Des Cooney, a financial consultant at Axis Financial Consultants, makes a similar point about what hides behind a clean-looking report. The reports may appear normal to outsiders, he says, while most of the real trouble comes from day-to-day friction inside teams: people who can't get timely spend information, budgets reviewed only once a quarter, two reports that give different numbers for the same metric. When that happens, he notes, "you have both a data issue and a reporting issue" to fix.

Spend visibility is usually worse than advertised 

Ian Wright, managing director of PayrollPrices.com, treats the first 90 days as a diagnostic sprint, and he looks for very practical red flags.

"If the team is spending too much time copying data from one spreadsheet to another, there’s already a significant amount of spreadsheet debt.  If no one can rapidly tell you how much was spent in a particular category during the previous month, there is limited spend visibility." Ian Wright - Managing Director, PayrollPrices.com

Glen sees the same pattern from the cash side: month-end reporting that leans on stacked spreadsheets and a couple of people who understand how it all fits together, plus poor visibility of discretionary spend. When processes depend on people rather than systems, the risk climbs.

This is the gap a tool like Pleo is built to close. Pleo is a spend management platform that gives finance teams a real-time view of company spending, rather than waiting for month-end reconciliation to reveal what happened. With that kind of view, you can see what's been spent, by whom, as it happens, and answer the "how much did we spend on that last month" question in seconds instead of days.

Your first job is trust, not "no" 

Every leader we spoke to landed on the same theme: credibility comes from being useful, not from guarding the budget.

Des is direct about the fastest way to fail. "The number one way to fail in the first 90 days is to act as though the role of finance is simply to limit spending," he says. Spending control matters, but if every meeting starts with a "no", you become the roadblock. Finance exists to help the business make better, faster decisions.

Ian's route to trust is to get out of the finance office and meet every department head. "When a CFO understands the pressure points their departments face, they start to become a business partner rather than just the person controlling the budget." Glen frames it as time well spent early: understand the relationships and incentives, and the financial problems get easier to read.

Win with fundamentals, not a transformation 

The temptation in a new role is to announce a big change. The leaders we spoke to would rather you bank a few quiet, useful wins.

Glen points to working capital. "Unlocking cash already within the business often delivers faster results than seeking external funding or major cost-reduction programmes." A resolved debtor dispute, a streamlined approval, a reliable 13-week cash forecast: small things that show progress fast.

Des puts numbers on it. By day 30, a dependable 13-week cash forecast that leadership agrees on. By day 60, one painful manual step removed from the month-end cycle. By day 90, a simple monthly spend overview handed to department leaders so they stop calling finance for every minor question. He'd also write a short State of Finance memo for the CEO and board at the 90-day mark, setting out what's working, what's still fragile, what the risks are and what support the function needs.

On AI, the four are level-headed. The job in the first 90 days is to set up the processes that the tools then run inside, says Raymond, because the initial judgment is still yours. Pick one area to automate and measure the time it saves, says Ian. Forecasting, invoice review, anomaly detection, month-end close: any of them frees up hours, says Des, and the point isn't to replace judgment, but to give the finance team better information, faster.

The plan still matters 

None of this means the 30/60/90 plan is redundant. It just sits on top of a messier reality than the framework indicates. The first weeks are less about transformation and more about seeing clearly: where the basics are broken, where the numbers mislead, where spend disappears and where trust has to be earned.