One unexpected challenge I faced during my first 90 days as CFO was aligning legacy financial processes with rapidly evolving business needs. The company was scaling quickly, but many reporting systems and approval workflows were outdated, leading to delays in decision-making and occasional misalignment between departments. To overcome this, I prioritized a comprehensive audit of all financial processes, identifying bottlenecks and areas where automation or simplification could have the biggest impact. I implemented streamlined reporting dashboards and introduced a few key automation tools for expense approvals and cash flow tracking. Equally important, I held cross-functional workshops to ensure that finance was fully aligned with operations, sales, and strategy teams, so that everyone understood the new processes and their role in them. My advice to new CFOs is to expect process friction early and treat it as an opportunity. Focus on quickly understanding where inefficiencies exist, engage other departments collaboratively, and use technology to accelerate decision-making. Preparing for both operational alignment and cultural buy-in will make your first 90 days far more effective and set a foundation for scalable financial management.

When I was working with different startups and across various teams, one unexpected challenge I often observed in the first 90 days of a CFO stepping in was how differently people understood "the numbers." Sales, product, and finance would each have their own version of revenue, margin, or burn rate, and everyone believed their version was the right one. I recall one situation where two leaders debated runway figures that were both technically correct, but based on completely different assumptions, creating unnecessary tension in a strategy meeting. What worked best in those cases was building a shared financial glossary and aligning everyone around a single source of truth. Once teams had the same definitions and access to consistent data, decision-making became faster and far less contentious. My advice to new CFOs is to prepare for this hidden challenge of translation and alignment. Before diving into advanced models or forecasts, make sure the fundamentals are clearly defined and agreed upon. It's a simple step, but it prevents a lot of confusion and wasted energy later on.

When I first stepped into the role of CFO in my own company, I thought the biggest challenges would be technical—cash flow modeling, reporting, investor relations. I was prepared for spreadsheets and forecasts. What I wasn't prepared for was how much of the role depended on communication and trust. In those first 90 days, one of the hardest lessons I learned was that numbers don't speak for themselves. I vividly remember presenting an early financial report to my leadership team, packed with detailed analysis I thought would impress. Instead, I was met with blank stares. It wasn't that the numbers weren't accurate—it was that I hadn't translated them into a story the team could understand and act on. That realization hit me hard. I had always prided myself on being detail-oriented, but in that moment, I realized my job wasn't just to crunch the numbers—it was to connect the dots between the numbers and the business strategy. To overcome this, I shifted my approach. Instead of leading with charts, I started framing every financial discussion around two questions: "What does this mean for us right now?" and "What do we need to do next?" I also began having more one-on-one conversations with department heads, not just to share insights, but to understand their challenges. That context helped me present financials in a way that resonated, because I could link the numbers directly to their goals. The advice I'd give new CFOs is this: don't underestimate the human side of the role. Technical skills are a given, but your ability to communicate financial insight in plain language and build trust across the organization is what makes the difference. The first 90 days aren't just about proving you can handle the numbers—they're about proving you can be a partner in decision-making. For me, that was the unexpected challenge, but also the most valuable growth point. Once I embraced it, the role felt less like managing finances and more like shaping the future of the business.

One unexpected challenge I faced during my first 90 days as a CFO was uncovering significant gaps in the accuracy and availability of financial data. This issue wasn't obvious on the surface but became clear as I dug into reporting and cash flow patterns. These data gaps hindered timely decision-making and risk management. To overcome this, I prioritized implementing more reliable financial systems and processes, strengthening controls and improving data transparency across departments. I also focused heavily on building trust through open communication with stakeholders to align on financial realities and priorities. My advice to new CFOs is to invest time early in thoroughly understanding data quality and company culture. Don't rush into changes without this foundation, and proactively build relationships that facilitate honesty and collaboration. This groundwork is essential for long-term success.

One unexpected challenge I faced in my first 90 days was realizing how quickly liquidity can tighten when multiple large loans fund at the same time. We had several bridge loans, each over $5M, close within days of each other while our warehouse lines were already stretched. I had to move fastnegotiating an emergency credit facility while also building out better daily cash flow forecasting to avoid repeat surprises. Looking back, strengthening short-term liquidity planning early would have saved us a few frantic days. My advice for new CFOs is simple: don't just rely on standard modelsstress test your cash flow for the worst-case timing overlaps and have backup funding options pre-positioned.

One surprise that emerged during my first 90 days as president of an out-of-home advertising company was realizing how much time I spent building trust in the numbers themselves. This was not the same as just producing a financial statement; moving from operational responsibilities to CFO was more about building confidence that others would believe in the numbers. Early on, I began to see differences in the predicted revenue for the field sales team in our CRM compared with how the financial models were loading the numbers. That difference led to reluctance in decision-making. I addressed this by reconciling the data sources and creating one single forecasting process that the sales and financial functions could use and trust. For new CFOs, my message is straightforward: be prepared to spend as much time on systems and alignment as you do on strategy. People won't act on numbers until they trust them, and creating that trust is as important as managing cash flow.

As a business owner in a field like this, a major unexpected challenge in our first 90 days was the high turnover of our new hires. They were incredibly talented, but they were leaving. We couldn't figure out why. We thought we had a great program and a good team, but something was still missing. I realized we weren't preparing people for the emotional weight of this work. We were so focused on training them clinically—how to file paperwork, how to run a session—that we weren't talking about the burnout, the stress, or the emotional toll of dealing with trauma every single day. They were hitting a wall that we never prepared them for. We completely changed our onboarding. On the first day, we're honest about the challenges. We share stories about the difficult days, not just the good ones. We also put a system in place for every new hire to have a dedicated peer mentor. This person's only job is to check in on them, grab coffee with them, and be a resource for the emotional side of the job. The turnover dropped significantly. The new hires who stay are more resilient and feel a sense of community from the very beginning. The most valuable thing I learned in our first 90 days wasn't about the business; it was about the people. Your business is only as strong as the people who run it. The most valuable thing you can do in your first 90 days is not just to hire great people, but to support them.

While I'm not a CFO, as the director of marketing and operations, I'm fully responsible for the financial health of my departments. In my first 90 days, I faced a completely unexpected challenge: we were doing great in sales, but our cash flow was a mess. We were bringing in a ton of revenue, but all of our cash was tied up in inventory, and we were falling behind on payments to suppliers. It felt like we were succeeding and failing at the same time. The way I overcame it was by building a new, immediate communication system between our sales and operations teams. In the past, the sales team would celebrate a big order, but they weren't thinking about the cash needed to fulfill it or the payment terms. We created a simple rule: a big sale isn't a success until the cash is in the bank. Our sales team couldn't just close an order; they had to confirm the payment terms and logistics with the operations team first. This forced them to think about cash flow in a way they never had before. From an operations standpoint, we started creating a simple, daily report that showed not just sales but also outstanding invoices and cash on hand. This forced me to look at the money in real-time, not just at the end of the month. It was a simple change, but it was a game-changer. We went from being a reactive company to a proactive one. We could now make smarter decisions about when to run a promotion and when to invest in new inventory. My advice for other directors is to not just focus on the top-line revenue. Your most important job is to manage the cash flow. Your financial well-being is a direct result of the decisions your team makes every single day. If you don't have a real-time understanding of your cash flow, your business will fail even if you're a sales powerhouse.