Be Financially Athletic: How to Recognize and Do the Right Deal

From the Desk of Scott Crawford
Partner & Head of New Business Development

Let’s talk about staying “financially athletic.” For many leaders, stepping into the role of strategic dealmaker can feel daunting. It involves balancing risk with opportunity, driving growth while preserving capital, and keeping eyes on the long-term game. But just like a high-performance athlete, a financially athletic professional remains flexible, disciplined, and prepared for unexpected turns. My goal here is to share insights on how to stay fit in the financial world so that when the right deal comes along, you’re ready to take it on without missing a beat.

I’ve spent my career working with organizations that needed strategic guidance at pivotal moments. My role has often been similar to that of a coach—training businesses to sharpen their financial muscles. It’s one thing to have an idea for growth; it’s another to cultivate agility, discipline, and long-term vision. That’s what being financially athletic is all about.

Below, I’ll walk you through principles of financial agility and how to spot high-value opportunities that drive sustainable growth for your company. We’ll look at key indicators that reveal a promising deal, and I’ll share some common pitfalls that can sideline even the most experienced executives.

Financial Agility: What It Really Means

“Agility” is a term thrown around often in business, but there’s a deeper significance when it comes to finance. A financially agile organization can shift its focus when necessary, quickly analyze opportunities, and make decisions based on solid data rather than guesswork. It’s not just about being quick on your feet; it’s about being smart and prepared.

1. Discipline:
   A disciplined approach to cash flow management is the foundation of financial agility. Strong processes for forecasting, budgeting, and resource allocation will keep you in top shape. Without discipline, organizations can burn through capital chasing short-lived trends.

2. Flexibility:
   Markets change, even sometimes overnight. Companies that thrive are those that adapt to evolving conditions without losing their strategic core. That flexibility is rooted in a thorough understanding of financial metrics and performance indicators, which inform whether to pivot, expand, or hold tight for a season.

3. Preparation:
   A financially athletic business doesn’t wait until the last minute to shore up finances. It builds robust financial systems well before a crunch point. Processes for evaluating ROI, debt servicing capacity, and operating costs should be in place. This preparation helps you seize an opportunity quickly instead of fumbling through last-minute spreadsheets and frantic phone calls with investors.

Those three concepts—discipline, flexibility, and preparation—tie directly to how well you’ll recognize, pursue, and close on the right deal. And that leads us to the topic at hand: identifying deals that align with your goals and acting on them in a strategic way.

Recognizing a Good Deal: Metrics, Market Intel, and Gut Instinct

When it comes to deal-making, it’s tempting to chase the next shiny object. However, that approach is risky and often leads to wasted capital and resources. Being financially athletic means having a framework that helps you quickly analyze whether a deal is worth pursuing. That framework includes:

1. Key Metrics (KPIs):
   You need to know your organization’s vital signs. Whether you’re considering a partnership, investment, acquisition, or something else, you need data-driven insights to guide your thinking. Look at profitability, margins, cost of capital, current market share, and projective growth. If a deal doesn’t move the needle on these key metrics, or if it puts them in jeopardy, it might be wise to reconsider.

2. Market Intelligence:
   A great deal aligns not just with your internal numbers but also with external market trends. Conducting thorough research on market size, competitive landscape, and consumer behavior will shape your perspective. If the deal doesn’t match broader market movements, you may want to walk away or negotiate more favorable terms.

3. Your Gut Instinct:
   Don’t discount the power of intuition. After analyzing the data, ask yourself if it feels right from a cultural, operational, and strategic standpoint. Sometimes, deals look perfect on paper but don’t sit well with the team or the direction of the organization. Trusting that sixth sense—backed by facts, of course—can be the difference between a blockbuster move and a burdensome distraction.

What might this look like in practice? Imagine a scenario in which you’re offered a chance to merge with a fast-growing competitor. The numbers are compelling, the market is hot, but during discussions, you notice a clash in corporate values. The culture of the other business might threaten the very essence of your organization. That’s a red flag that can overshadow positive ROI projections. Being financially athletic means spotting that sign and assessing whether the potential upside truly outshines the risk of cultural discord.

If it doesn’t, it’s time to pass.

Training for Success: Building a Team Around You

No athlete becomes a champion without the right team, and no deal gets done by a single individual. If you want to remain agile and open to high-value opportunities, assemble a solid group of experts who have proven results that you can trust. That might include:

1. Fractional CFO Support:
   Hiring a fractional CFO can be a game-changer for many organizations. You gain access to a senior finance professional who can guide strategic decisions without the overhead of a full-time executive. Fractional CFOs typically bring experience across multiple industries and growth phases, giving you a well-rounded perspective on risk management, deal structure, and capital strategy.

2. Attorneys & Accountants:
   Skilled legal and accounting professionals do more than just handle paperwork. They spot hidden liabilities, advise on deal structure, and provide clarity on compliance obligations. Make certain you’re bringing them into the conversation early, not as an afterthought. Surprises around contracts or tax implications can derail a deal if discovered at the eleventh hour.

3. Board & Advisors:
   An external board or advisory group can offer a wider lens. These individuals often have a depth of experience that can spotlight unseen risks or opportunities. They’re there to challenge assumptions and keep you accountable.

Building this team is just as critical as the deal itself. A financially athletic leader doesn’t try to muscle through negotiations alone. You want experts to inform your strategy, vet potential partnerships, and guide you through complex transactions. That collaborative approach is how you strengthen your position and shape outcomes that genuinely move the needle.

Pitfalls That Can Derail Good Intentions

I’ve seen quite a few deals that should have been winners in my day, but ended up hitting major snags. Here are some pitfalls that can cause trouble:

1. Short-Term Thinking:
   Some organizations chase deals for a quick payoff, forgetting about the long-term picture. While short-term wins can look appealing, a lack of forward-thinking often results in integration challenges or missed future opportunities. Keep your strategic vision at the forefront.

2. Over-leveraging:
   Taking on debt can be part of a healthy deal structure, but it becomes toxic if it crushes cash flow. Overleveraging is like an athlete running an ultramarathon without training. It leads to burnout. Make sure your financial model can sustain the added leverage.

3. Cultural Mismatch:
   As mentioned earlier, if a deal makes sense financially but the cultures don’t align, you could face operational headaches. Culture clashes can strain management and destroy productivity for all involved. Factor cultural alignment into your due diligence.

4. Ignoring The Hidden Costs:
   Everyone knows the basic acquisition costs, but hidden expenses like technology integration, employee turnover, regulatory hurdles, and supply chain realignments can sneak up on you. A thorough due diligence process is crucial. Break down every potential cost before finalizing terms and be very clear on where everything aligns.

5. Failure to Integrate:
   A merger or acquisition isn’t complete once the ink dries and handshakes are passed out. Integration—aligning systems, processes, and teams—requires real effort. If you neglect this step, you’ll lose synergies that are critical to your ROI.

Avoiding these pitfalls comes down to one word: alignment. Alignment with your goals, your culture, and your capacity to handle the challenges that come with growth. When everything lines up, your organization moves forward with both energy and stability.

The Right Way to Act on Opportunity

Spotting a good deal is half the battle, while executing it the right way is the other half. If you want to close the best deals and drive meaningful growth, consider the following steps:

1. Plan & Prepare:
   Before you even see an opportunity, have your financial house in order. That means up-to-date financial statements, clear cash flow visibility, and a robust forecasting model. Prepare draft deal structures that can be adapted quickly.

2. Build Relationships:
   Deals rarely land out of the blue. They often emerge from a strong network of industry contacts, advisors, and even competitors who respect you. Cultivate genuine relationships and keep in touch with your circle. Opportunities often surface in these interactions when trust is already established through previous experiences.

3. Stay Objective:
   Even if you feel excitement about a potential acquisition or partnership, keep emotion in check. Let data guide you and allow your advisors to challenge your assumptions. If the numbers or intangible factors don’t add up, it might not be the right moment.

4. Negotiate with Confidence:
   Financial agility allows you to negotiate from a position of strength. You know your numbers, you know your limits, and you can walk away if the deal doesn’t match your requirements. Confidence in your own position is a powerful bargaining chip.

5. Execute Thoughtfully:
   Once you’ve decided to move forward, approach closing and integration with the same discipline you used to evaluate the deal. Craft a detailed plan for merging teams and systems (if it’s an acquisition) or aligning responsibilities (in a partnership). Good communication is crucial here because people need to know what’s happening, why it’s happening, and how their roles might change moving forward.

When you bring clarity and discipline to each of these steps, the process becomes smoother and sets the stage for true success. Every business leader wants to look back on a completed deal and see it as a milestone that sparked the next wave of growth, not just another transition that added complexity.

Momentum: Creating a Cycle of Continuous Growth

Executing a successful deal isn’t the end of the story. It’s the start of a new chapter, and that chapter should be about creating momentum for future opportunities. Think of each deal as a launch pad to:

• Refine Your Model:
  Every completed deal provides fresh data and learnings. Use that information to refine your forecasting and risk assessment processes, so you’re even stronger for the next opportunity.

• Boost Your Reputation:
  A well-executed deal raises your profile. People talk. Reputation for strategic, successful deal-making leads to more inbound possibilities. This is where you gain the “athlete’s edge”—over time, you become known as someone who can consistently identify and close valuable deals.

• Invest in Innovation:
  Growth from a deal often frees up resources for the next big push. Invest in your team, technology, and research to keep your competitive edge sharp. That cycle of investment is how you stay agile in a rapidly changing market.

• Sustain a Winning Culture:
  Culture is the heartbeat of every business. If you align your deals with your mission and values, your team will feel ownership and excitement. That momentum generates loyalty, boosts productivity, and draws in top talent from everywhere.

At Preferred CFO, we believe the best deals are those that spark a cycle of sustainable growth. Strategy isn’t just about looking at the next quarter; it’s about keeping an eye on the next several years. Being financially athletic means you’re always training, always looking ahead, and always in a position to capitalize on opportunities that fit your strategic goals.

Final Thoughts

“Financially athletic” is more than just a turn of phrase. It’s a way of approaching your organization’s future with a blend of discipline, flexibility, and foresight. By understanding the key principles—recognizing real opportunities, building a strong team, and avoiding common missteps—you equip your business to thrive. Deals are inherently risky, but they don’t have to be paralyzing. With the right groundwork and a consistent game plan, you can adapt quickly, strike at the opportune moment, and lock in a path toward sustainable growth.

At Preferred CFO, we see clients transform from being reactive to proactive, from being strapped by cash flow constraints to dynamically investing in strategic opportunities. These transformations don’t happen by accident; they’re the result of focused, disciplined action. If you’re looking to reach that same level of financial agility, I invite you to visit Preferred CFO and attend the upcoming webinar. We’ll dive even deeper into building a lean and powerful financial foundation.

Opportunities are out there, waiting. The question is whether you have the agility to spot them, the wisdom to choose the right ones, and the discipline to close them.

With the right mindset and the right advisors, you’re on your way to achieving lasting success.

— Scott Crawford
Partner & Head of New Business Development, Preferred CFO

(Interested in learning more? Connect with me on LinkedIn or at the button below and let’s talk about how your business can benefit from a proactive financial strategy.)