Challenges in Finance Upskilling Today

While the benefits of finance training are clear, many organizations encounter significant challenges when trying to upskill their workforce in financial competencies. In today’s fast-changing business environment, closing the finance skills gap is not as simple as scheduling a few workshops. Learning & Development and corporate training buyers must navigate a range of obstacles – from motivational issues to structural barriers – that can hinder finance upskilling initiatives. Recognizing these challenges is the first step to overcoming them.

1. The Finance Skills Gap and Talent Shortage

One major challenge is the widening finance talent gap. The demand for finance skills is rising faster than the supply of talent. Many companies report difficulty finding candidates with the right mix of financial expertise and business acumen. In a recent survey, 77% of CFOs said they lack skilled finance staff on their teams[4], and 84% of CFOs find it hard to find the right people for key finance jobs. Several factors drive this shortage:

The pipeline of new finance professionals is shrinking in some areas. Fewer students are choosing accounting and finance majors than in past decades, meaning fewer qualified graduates entering the field.
Experienced baby boomers in finance roles are retiring in large numbers (one report noted over 75% of CPAs are nearing retirement age), leading to a loss of expertise.
As finance functions evolve (with more focus on analytics, strategy, and automation), the skill profile needed is broader than before. It’s challenging to find individuals who possess deep financial knowledge and data science or IT skills, for example.
The rise of new fields like FinTech and digital finance creates competition for talent; startups and tech firms lure financial analysts away from traditional companies.

This talent crunch puts pressure on organizations to upskill existing employees to fill the gap. However, doing so is not trivial – it requires identifying the right people to train and giving them sufficient learning opportunities before the talent shortfall impacts business. Many finance leaders now view upskilling as urgent: 73% of finance leaders say upskilling their staff is key to leveraging automation and meeting future needs[4].

2. Rapid Change in Financial Tools and Regulations

Finance professionals face a moving target when it comes to required knowledge. The tools, technologies, and regulations in finance are changing at an unprecedented pace:

Digital Disruption: Automation, AI, and advanced analytics are transforming finance roles. Tasks that were manual (like invoice processing or data consolidation) are getting automated. This means finance teams need to develop new skills – from interpreting data outputs to leveraging AI-driven insights. It’s estimated that by 2030, nearly 38% of finance tasks will be automated (up from 21% now). Upskilling is required so that employees can work alongside these technologies (for instance, using analytics software, understanding algorithm-driven forecasts, or managing Robotic Process Automation in accounting).
New Financial Systems: Companies frequently update or switch their ERP (Enterprise Resource Planning) and financial software. Each new system implementation (say moving to a cloud-based financial platform) comes with a learning curve. If training isn’t timely and effective, employees might under-utilize powerful features or even make errors using unfamiliar interfaces.
Evolving Regulations and Standards: Finance and accounting rules don’t stand still. Changes in tax laws, introduction of new accounting standards (like updates to revenue recognition or lease accounting rules), and heightened compliance requirements (anti-money laundering, data privacy in financial records, ESG reporting, etc.) mean finance staff and business leaders must continuously learn to stay compliant. A major challenge is simply keeping up with what needs to be learned, as regulatory changes can be frequent and complex.
Globalization: Many companies operate across borders, which introduces complexity in currency management, international accounting standards, and cross-cultural financial practices. Upskilling might be needed in areas like foreign exchange risk management or international financial reporting standards (IFRS).

The pace of change can overwhelm employees. If training isn’t delivered proactively, staff may fall behind. Yet scheduling frequent training updates (for every new software feature or regulatory tweak) can be logistically difficult. Companies struggle to maintain a “continuous learning” model versus a one-and-done training approach, but continuous learning is exactly what’s needed.

3. Time Constraints and Workload Pressures

Ask any team slated for training what their biggest challenge is, and you’ll likely hear: “We’re too busy.” In the finance world, certain periods (month-end or quarter-end closing, annual budgeting season, audit time) are notoriously busy. Releasing staff for training during these times is often seen as impossible. Even outside of peak periods, finance and operational teams often run lean, so backfilling duties while someone is in training is a hurdle.

A study by SHRM found that the number one barrier to employee upskilling is lack of time to pursue training, closely followed by other priorities taking precedence. In practice, this means:

Managers may be reluctant to send their people to multi-day training programs for fear of falling behind on work.
Employees may resist or procrastinate on online training modules if they feel swamped with “real work.” They might skip optional training or multitask during sessions, reducing effectiveness.
Even when training is mandatory, if not properly timed, it can cause stress. Imagine asking the finance team to complete a training course in late December when year-end closes are happening – the uptake and engagement will likely be low.

4. Limited Budget and Resources for L&D

Finance training, like any specialized training, requires investment. Some companies face budget constraints that limit how much they can spend on upskilling programs, external courses, or training tools. Ironically, during economic downturns or cost-cutting phases, training budgets are often among the first to be trimmed – just when financial acumen might be most needed to navigate challenges.

Beyond money, there’s sometimes a lack of in-house expertise to deliver finance training. Smaller organizations might not have a dedicated training department or finance educators. They have to rely on finding the right external provider or online program, which can be an intimidating task (“Where do we find a training that truly fits our industry and needs?”). The absence of curated, high-quality training resources can delay upskilling efforts.

5. Variable Base Knowledge and the One-Size-Fits-All Pitfall

Employees come to finance training with vastly different backgrounds. In a single company, you might have:

Non-financial managers who haven’t looked at a financial statement since college (or ever).
Junior finance staff with a couple of years of experience and some formal accounting education.
Senior finance professionals with deep expertise in certain areas but perhaps gaps in others (e.g., a veteran accountant who hasn’t been exposed much to data analytics tools).

Designing a training program that is neither too basic for some nor too advanced for others is a balancing act. A common challenge is that generic training ends up missing the mark for many participants. If it’s too elementary, the knowledgeable folks disengage; if it’s too technical, the novices get lost. Tailoring content by skill level is ideal but can increase costs and complexity.

Additionally, different roles need different emphases. A sales manager might need a focus on understanding profit margins and pricing, whereas an HR manager might need training on reading financial reports to justify HR investments. A one-size-fits-all finance workshop could end up being only partially relevant to each, diluting its impact. Without careful needs assessment and customization (which itself is a challenge to execute), training may not fully resonate, reducing enthusiasm for future upskilling.

6. Engagement and Perceived Relevance

Let’s face it: not everyone finds finance concepts thrilling. There can be a psychological barrier – finance is sometimes seen as dry, difficult, or only for “numbers people.” This can lead to low enthusiasm or even anxiety around attending finance training. If learners are not engaged, the upskilling effort won’t stick.

Challenges here include:

Overcoming Fear/Intimidation: Employees who do not work with numbers regularly may feel intimidated by terms like “discounted cash flow” or “EBITDA.” This can make them avoid training or only half-participate.
Making Training Interactive: Traditional lecture-style training with dense PowerPoint slides of figures might cause eyes to glaze over. But developing interactive and gamified finance training requires creativity and possibly external expertise. (For example, gamification of possible scenarios might work well for topics like cybersecurity in finance or fraud prevention.)
Demonstrating Immediate Value: Busy professionals want to know, “What’s in it for me right now if I invest time in this training?” If the payoff seems abstract or long-term, they may not fully commit. It’s a challenge to design upskilling such that learners leave each session with something they can use the next day. For example, teaching a manager how to quickly calculate break-even for her product line so she can apply it in the next pricing discussion – that creates a sense of immediate relevance.

7. Measuring and Proving Training Effectiveness (The Evaluation Challenge)

Even when training is delivered, many organizations struggle to measure whether the upskilling actually worked (this will be discussed in depth in Blog 5). If stakeholders don’t see clear evidence of impact, they might be hesitant to continue or expand finance training programs, creating a vicious cycle where challenges remain unaddressed.

For instance, if a company trains 100 employees in finance basics but doesn’t track any metrics, executives might later question, “Did we actually get better outcomes? Was this worth it?” Without measurement, even successful upskilling can be underappreciated, jeopardizing future support and funding.

Overcoming the Challenges: Toward Solutions

Despite these challenges, organizations are finding ways to push forward on finance upskilling:

Executive Sponsorship: Securing buy-in from top leadership (CFO, CEO) helps create a culture that prioritizes training. When senior leaders champion upskilling and even participate in kick-offs or share personal finance knowledge, it underscores the importance. It also helps in getting the necessary resources allocated.
Protected Learning Time: A best practice is to carve out dedicated time for training, treating it like any important project. Some companies, for example, declare “learning afternoons” once a month where meetings are banned and teams focus on development. Others align training schedules with lighter work periods (like right after quarter-end, not during crunch time). Management must actively help employees balance workload so they can focus on learning without guilt.
Customized Learning Paths: Rather than a single program for all, progressive organizations assess skill levels and segment their audience. They might offer a basic finance 101 for non-finance folks, an intermediate course on strategic finance for mid-level managers, and advanced analytics training for finance specialists. This ensures relevance and maintains engagement. It leverages the idea of personalized learning paths, which can be supported by technology (learning platforms can often adapt to a learner’s pace and level).
Blended and Flexible Learning: To address time and engagement issues, many opt for blended learning – a mix of short e-learning modules, live workshops, and on-the-job projects. Microlearning (bite-sized lessons) can be slotted into busy schedules more easily than day-long classes. For instance, employees might complete a 10-minute interactive module on reading an income statement during a coffee break, then later attend a brief live session to discuss how it applies to their department’s budget. This flexibility helps integrate training into daily work life.
Mentoring and Peer Support: Some companies are pairing less experienced employees with finance mentors (either within the finance department or trained “finance champions” in each function). This on-the-job guidance helps reinforce training and encourages a culture of asking questions. It also addresses fear by giving learners a go-to person for “dumb” questions in a safe setting.
Showcasing Quick Wins: To maintain momentum, it’s effective to quickly highlight any improvements from upskilling. If, say, after a training, one team discovered a way to save \$50k by cutting a redundant expense, share that story internally. It proves the value of training and motivates others. It creates a positive feedback loop: training → result → recognition → more enthusiasm for training.

Staying the Course

Upskilling in finance is undoubtedly challenging, but the cost of not doing it is even greater. A 66% majority of financial organizations say skills shortages are the primary barrier to transformation – which means companies that fail to address this will struggle to innovate and compete. On the other hand, those that tackle these challenges head-on often find that their efforts pay off. Many firms are already investing heavily in reskilling; 87% of finance employers plan to prioritize reskilling programs to build future-ready teams.

By understanding the common challenges – from time and budget constraints to keeping learners engaged – L&D professionals and business leaders can design smarter interventions. It may require creativity and persistence: reworking training schedules, getting leadership to model the importance of learning, and using new tools to make training enjoyable. The path to a financially savvy workforce is not without hurdles, but with commitment and the right strategies, organizations can overcome these barriers.

Need help overcoming training challenges? The Training Marketplace is here to support. We can connect you with finance training experts who understand your industry’s unique constraints and can tailor solutions that fit your schedule and budget. From bite-sized e-learning to immersive workshops, our network of providers offers flexible options to integrate finance upskilling into even the busiest environments. Don’t let challenges stop your team’s growth – let us help you find a way forward and turn finance training roadblocks into stepping stones for success.