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Accounting Firm Upskilling Considerations checklist

Hiring new talent isn’t the only way to strengthen and enhance your team. Often, the potential of your existing staff goes untapped—and these are people who already know your clients, your culture, and your systems. Upskilling offers a strategic way to grow that talent, boost retention, and close skills gaps without the cost and risk of a new hire.

This checklist is designed to help accounting firms thoughtfully approach upskilling, from identifying the right candidates to tracking success—so you can build a stronger, more adaptable team from the inside out.

1. Gauge Employee Interest & Willingness

Why it matters: Upskilling only works when employees are genuinely interested and have the bandwidth to grow. Pushing training onto someone who isn’t ready—or doesn’t see the value—can backfire. Start by gauging interest through conversations, surveys, or performance check-ins.

Considerations

Have we asked employees which areas they’re interested in developing?

Do they show curiosity or initiative in their current role?

Have we clearly communicated the time commitment and expectations?

Is there a safe way for employees to decline or delay upskilling without penalty?

2. Identify Ideal Candidates for Upskilling

Why it matters: Not everyone is in the right stage of their career—or life—for growth. The goal is to invest in team members who are both ready and likely to thrive in more advanced roles or services. Look for people who already show signs of leadership, adaptability, or ambition.

Considerations:

Does this employee demonstrate consistent performance and reliability?

Are they open to change, learning, and feedback?

Do they show signs of hitting a ceiling in their current role?

Have they taken initiative to improve processes, serve clients better, or help colleagues?

3. Align Skill Development With Firm Goals

Why it matters: Upskilling should tie directly to your firm's strategic objectives. Whether you're expanding CAS, adopting new tech, or trying to retain clients with higher-touch services, the skills you invest in should support that growth.

Considerations:

Are we prioritizing skills that align with our service roadmap (e.g., forecasting, advisory, automation)?

Will this reduce our need to hire externally or rely on contractors?

      
Can we measure ROI on this training, such as improved margins or retention?

4. Plan the Learning Journey

Why it matters: A scattered or unclear learning process leads to frustration. Upskilling must be structured—whether formal training, shadowing, certifications, or mini-projects—and should include checkpoints to build confidence and accountability.

Considerations:

Have we mapped a clear development path with milestones?

Is there a variety of formats (online, in-person, peer learning) to match learning styles?

Can we relieve some workload while someone is actively training?

Are we using microlearning to keep progress steady and manageable?

5. Communicate the Opportunity Clearly

Why it matters: Employees need to understand the why behind the upskilling effort, along with what’s expected and how they’ll be supported. Framing it as a partnership—not an obligation—builds trust and motivation.

Considerations:

Have we clearly explained how this benefits both the firm and the employee?

Is the opportunity framed as a career-building step, not just extra work?

      
Have we outlined what success looks like and what support is in place?

6. Reward & Retain After Mastery

Why it matters: Upskilling is only worth the investment if it leads to retention and utilization. Employees who grow and stay should feel valued, recognized, and challenged. Without follow-through, you risk losing your most capable talent to competitors.

Considerations:

Is there a defined next step—role, title, project, or leadership opportunity—once skills are demonstrated?

Are there compensation or bonus structures tied to skill mastery?

Do we have a way to recognize new skills publicly or internally?

Are we involving newly skilled team members in mentorship or cross-training?

7. Avoid Burnout or Resentment

Why it matters: Growth shouldn’t feel like punishment. If employees are overloaded while trying to learn new skills, the process can backfire—leading to frustration, mistakes, or burnout. Balance is key to making the experience positive and sustainable.

Considerations:

Are we adjusting workloads to accommodate the time needed for training?

Have we communicated that upskilling is an opportunity, not a requirement?

      
Do we have regular check-ins to make sure no one feels overwhelmed or taken advantage of?

8. Track Success & Adjust

Why it matters: Just like any initiative, your upskilling strategy should be evaluated and refined over time. What worked for one team member might not work for another. Tracking results helps you improve future training, prove ROI, and justify ongoing investment.

Considerations:

Are we tracking metrics tied to upskilling, like productivity, retention, or client satisfaction?

Are we collecting feedback from participants about the learning experience?

      
Do we have a process to adjust or tailor future learning paths?

If soft skills are an area you'd like to upskill your teams on, a good place to start is our Soft Skills video series. Absolutely free!

 It provides the basics for different soft skills, helping to build a basis for learning more.

Access them here!