Why Finance Roles Require Reinvention

Ashley Reid
The Ready
Published in
9 min readFeb 12, 2024

From a finance pro who is ready for change.

Original image: Alisha Lochtefeld

I can’t tell you how many times I’ve heard this joke: “Don’t make her mad; she controls the money.” So often, people holding roles in finance and accounting (from staff accountants to CFOs) are generalized by reductive caricatures like:

  1. The “Number Cruncher,” laser-focused on analysis and lacking broader business acumen
  2. The “Bean Counter,” obsessed with cost-cutting measures that don’t consider an organization’s long-term goals
  3. The “Hammer,” too focused on compliance and control, often limiting the flexibility and creativity of other departments
  4. The “Rule Follower,” married to rules without exercising independent judgment

Sound familiar, finance friends?

Let’s face it, we can have a bad rap in organizations — and I think it’s partly our fault. Why? Because we’ve thrived in risk-intolerant environments where, not all the time but pretty often, we’ve never needed to ask for permission. We create the rules; we organize and maintain all financial data; we enforce the guidelines and guardrails; and we demand or expect personal involvement in every decision regarding money. But this level of grippy management comes with a different consequence: exhaustion. And no wonder. Finance roles can be remarkably stressful, with higher and higher rates of burnout. (For example, a DataRails study of SEC filings by 2,056 of the biggest US-listed companies reveals the average CFO tenure is only 3.51 years, underscoring how hard it can be to do the job sustainably.)

But if you’re like me, you too might struggle with this daily reality: toggling between being bothered by non-stop questions about all things money-related and being angry when someone makes a call without my input. Precision is crucial in financial decisions; if something goes sideways, it’s all eyes on the CFO. It’s easy to feel like there’s always something new to worry about — and not mess up. So, finance professionals walk this line: Be part of the team and answer for everything.

I now realize the usual finance rules don’t let us walk this line in a way that also makes our companies better. When we confine finance to a conventional, risk-averse mold, are we really fostering strategic environments? Is the traditional power dynamic inherent in these roles contributing to innovation and efficiency or holding organizations back? If we feel trapped, it’s because we are — and it’s time to either shake things up or stay stuck.

The Centralized CFO

My finance journey began in banking. But it wasn’t long before I realized that path wasn’t aligned with deeper aspirations to contribute to a greater good. I revisited my passions, searching for my ikigai, a Japanese concept combining what you love, what you’re good at, what the world needs, and what you can be paid for.

This led me to a role as the accounting manager for a local arts organization. There, I found both professional success and personal satisfaction, contributing financial expertise to an organization enriching the community through dance. For 12 years, I honed my career in the non-profit space, working with the arts, food access, sustainability, and public media. My experience is proof of finance’s evolving landscape, where success is increasingly measured not just in profits and power, but also in positive human impact.

But despite the creative missions of these spaces, I was still mostly incentivized to assert power over the companies I worked for. In non-profits, where money can be tight, being in charge of finances was a big deal, because I had a say in where the money went. Also, finance folks ensure an organization follows all financial regulations. That responsibility begets the authority to set the standards in most financial matters — another way we find ourselves in positions of control.

When we confine finance to its conventional, risk-averse mold, are we really fostering strategic environments? Is the traditional power dynamic inherent in these roles contributing to innovation or holding organizations back?

Ultimately, working in that way left me siloed; the confines of the finance roles, even in mission-driven environments, still felt too rigid and I wanted to be involved in impactful activities. I was pulled into the process space rather than the people space over and over again. I felt hemmed in by the traditional trappings and expectations of my role.

Realizing the limitations of traditional finance roles even in mission-driven organizations, I began seeing the need for the role itself to evolve beyond compliance and cost management. Finance roles need to be strategic partners within an organization and become key players in decision-making. This evolution wasn’t about changing job descriptions, but rather about redefining how finance contributes to a given mission and helps pave the way for a more resilient, financially healthy organization.

Perhaps more important, what others expected of finance professionals also needed to transform. So I began to develop and take on the identities of different finance archetypes like:

  • The “Creator” finds associations between seemingly unrelated things and can combine two or more existing concepts. For example, implementing a comprehensive data collection strategy and gathering success stories to enhance corporate donation strategy.
  • The “Teacher” uses data to develop teams capable of making the best decisions and to help leverage the power of self-direction. For example, establishing clear expense tolerance ranges, so project teams can make informed, independent spending decisions at speed.
  • The “Generator” creates integrated technical and social systems. For example, introducing a resource allocation framework that enables cross-functional budget planning that meets both team and company strategy needs.

The Decentralized CFO

When I joined The Ready 10 months ago, I was hired into the first-ever fully dedicated finance role. The Ready is a self-managing company; rather than relying on a hierarchical structure, we function in self-managing teams. It’s a highly decentralized environment — and that’s exactly what drew me to the company. I found that working in this way enabled greater transparency, greater flexibility, and, most enticing, freedom from sole responsibility — from the burden of making every financial-based decision.

But I was also met with a sense of uncertainty. Finance, even in a less bureaucratic system, was still a concept that felt both fragile and rigid. In our self-managed system, the absence of traditional structures can create a sense of vulnerability and inflexibility in areas that require precision and utmost clarity, like finance. And while The Ready has been successful, we’re not immune to larger economic forces and other cultural shifts ushered in by the pandemic. So the environment I entered was one of decreasing profit margins and disruptive cost-cutting conversations. We couldn’t skip past feelings of scarcity.

Suddenly, I found myself facing the very tasks I had sought to escape. It became clear that relying on the tools I had used before couldn’t be the sole solution. I’d seen firsthand how falling back on traditional moves might lead to a more profitable company; but they could also burn me out and chafe against The Ready’s principles.

I started reflecting on the essence of my role. I found myself navigating my instincts, discerning which to follow and which to challenge. It was a balancing act, learning to channel the beneficial while steering clear of the detrimental. It was important to handle things carefully, without trying to control everything too much. I had to be patient and think deeply about how to help the company stay on track, while also staying true to our bedrock principles. Luckily, I had a surprising blueprint to help navigate this dichotomy.

In her book, Radical Acceptance, Tara Brach tells a story about a group of highly-trained pilots in the 1950s who were given a mission to fly at altitudes higher than ever before attempted. When the first few pilots reached the target altitude, they experienced their planes spinning and tumbling out of control. The pilots would frantically respond, applying correction after correction — but the more they manipulated the controls, the worse it got and they’d plunge to their deaths.

This occurred several times until one pilot was knocked unconscious during a mission. The plane tumbled for seven miles until it re-entered a safe altitude and standard navigation strategies could be implemented. At that time, the pilot came to and was able to land safely. He inadvertently discovered that the only lifesaving response in that moment was to do nothing.

It’s common to push harder when things feel chaotic, because that’s what feels safer. When we find our organizations in situations we can’t control, we frantically try to over-manage. The tendency is particularly resonant with folks in finance, who often find themselves in high-stakes environments. Over-managing might look like scrutinizing every line item in a budget or engaging in unnecessary financial reporting to exert influence over day-to-day decisions. Especially during a crisis, we might insist on constant updates or additional approvals for routine expenses, inadvertently impeding the organization’s ability to respond to rapidly changing situations.

The instinct to exert greater control is similar to the pilots’ initial reactions. But this approach often leads to unintentional territory, where the more we tighten our grip, the more tumultuous things become. In such high-pressure roles, learning to step back and assess the situation with a calm mind can be crucial. It’s about understanding that sometimes the most effective action is thoughtful inaction, allowing a system’s mechanisms to do what they were built to do and for a clearer view of the financial picture to emerge.

If we focused more on effective system design that could adapt to change, could we reduce the need to constantly manage the control panel? If finance professionals didn’t have to spend all their time micromanaging million dollar budgets and exhaustive financial analyses, where else could they focus their expertise?

Finding Finance’s Third Way

If we want to help our organizations move toward lasting resilience, we must let go of the power inherent (and inherited) in our roles; we must transform our knowledge into more than just authority and conformity. The problem I see with the current state of the finance profession is that it can’t just be one or the other; antiquated binaries of centralized versus decentralized, authoritative versus laissez faire, and bureaucracy versus chaos are holding us back. There is a new paradigm between these extremes.

Sometimes, the most effective action is thoughtful inaction, allowing a system’s mechanisms to do what they were built to do.

I’ve been experimenting with this third way in my new role and there are two things I now know for sure.

  1. Number crunching and bean counting can be superpowers if we see them through the lens of powerful data. Those skills can enable predictive insights, risk management, resource optimization, transparency, empowered decision-making, and collaborative innovation, all of which are crucial for an organization’s success and sustainability. The person who holds all the data should not have unchallenged authority regarding what to do with that information. True financial power lies in the sense-making and sharing of data with peers, so financial decisions can be made at the edges, collaboratively with those closest to the work.
  2. Both the “Hammer” and the “Rule Follower” have an ability and opportunity to help design and organize around the data. At The Ready, I’m surrounded by talented org designers. It’s important I be one, too. Using the wealth of knowledge around processes, systems, and compliance, my job is to create enabling constraints, a.k.a. defined parameters that empower and guide individuals or teams to make decisions autonomously, that distribute decision-making authority to the edges and don’t negatively impact financial health at the center.

This new Creative, Educative, and Generative finance person does not completely leave behind the foundational skills of the historic archetypes. Instead, we need to flip them upside down. Doing so will help us let go of power for the sake of power and live into the real purpose of the role.

The Ready is a future-of-work consultancy and transformation partner. We help some of the world’s largest, oldest, and most inspiring organizations remove bureaucracy and adapt to the complex world in which we live. Learn more by subscribing to our podcast and newsletter, checking out our book, or reaching out to have a conversation about how we can help your organization evolve ways of working better suited to your reality.

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