Coaching Your Team for Leadership: Tony Proctor’s Blueprint for Developing the Next Generation in Accounting Firms

At WorkflowCon 2025, Tony Proctor, EA, brought the room to life with a practical, high-energy guide to coaching team members for leadership in accounting and bookkeeping firms. Drawing from nearly two decades of firm ownership and another decade in IT management, Proctor challenged leaders to step beyond firefighting and daily routines, making the deliberate shift from problem-solving experts to true enablers.

His session was filled with personal stories, relatable humor, and frameworks designed to help every attendee multiply their firm’s capacity and prepare for a stronger, more resilient future.

Recognizing the Real Barriers to Team Growth in Accounting Firms

Many accounting and bookkeeping firms reach a plateau because their teams are stuck in a cycle that limits growth. Tony Proctor began his WorkflowCon session by shining a light on the real obstacles that keep firms from reaching their potential. He explained that the challenges are rarely about technical ability or hiring the “perfect” new staff member. Instead, the roadblocks are usually rooted in the daily habits and mindsets of leaders and teams alike.

First, Proctor pointed out that most firms run at a frantic pace, with everyone focused on immediate deadlines, urgent client requests, and putting out fires. This reactive environment leaves little room for intentional development. He observed, “Everybody’s busy, but not everybody is growing. Not everyone is developing.” When leaders and team members are stuck in survival mode, the focus shifts to checking boxes and completing tasks, not learning, problem-solving, or preparing for bigger roles.
Another barrier is the unspoken assumption that leadership and growth just happen with tenure or technical expertise. Proctor cautioned that this belief leads to underinvestment in people. “If you wait for leaders to emerge naturally, you’ll wait forever,” he warned. Without a plan to coach, challenge, and empower team members, firms end up with a shallow bench, too few people ready to step up when needed.

Communication patterns also play a big role. In many firms, team members look to partners or managers for all the answers, creating a culture of dependency. Proctor explained that when leaders always solve problems themselves, they unintentionally train their teams to stay passive. “If I’m the one always fixing things, my team never gets to build their own confidence or skills,” he said.

Using the Skill-Will Matrix to Tailor Your Coaching Approach

A highlight of the session was Proctor’s walkthrough of the skill-will matrix, a simple but powerful tool for understanding team dynamics. He broke down the four quadrants:

• High Skill, High Will: These “dream team” members are self-motivated and capable. Proctor recommended stretching them with special projects, leadership opportunities, and peer coaching assignments to keep them growing.
• High Skill, Low Will: These individuals are talented but disengaged, often due to burnout or boredom. The solution is not more pressure, but honest conversations and motivation. Proctor suggested checking in about life outside of work to uncover what might be holding them back.
• Low Skill, High Will: These enthusiastic but green team members need training, shadowing, and patience. With the right support, they can become future stars.
• Low Skill, Low Will: These are the toughest cases. Proctor advised setting clear expectations, providing honest feedback, and having the courage to make tough decisions if engagement and performance do not improve.

By identifying where each team member falls on this matrix, leaders can better match their coaching style to the individual’s needs, rather than applying a one-size-fits-all approach.

Moving from Expert to Enabler: The Mindset Shift for Modern Firm Leaders

One of the most critical transformations for any firm leader is learning to let go of the expert identity and step into the role of an enabler.

Tony Proctor challenged attendees to look at how much of their day is spent solving problems versus coaching their team to do the same. In traditional accounting cultures, leaders are often expected to be the go-to resource, providing quick answers and technical fixes for every challenge that arises. While this can feel productive and even gratifying in the short term, it ultimately limits both the firm and the individuals within it.

Proctor explained that when leaders stay in the expert seat, they unintentionally create a dependency loop. Team members learn to bring every issue to the boss, rather than building their own critical thinking and confidence. This approach may keep work moving, but it also creates a bottleneck, with leaders stretched thin and the firm unable to scale. “As an expert, I’m solving all the problems,” Proctor said. “But as an enabler, I start to ask thoughtful questions and provide the opportunity for thinking.”
Making the shift to enabler means getting comfortable with not always having the answer. Instead, leaders create space for others to problem-solve, guiding their team through questions such as, “What do you think we should do?” or “If I weren’t here, what would you try?” Proctor shared that this style of coaching not only helps individuals grow, but also surfaces creative solutions leaders might never have considered.

This new mindset also invites more engagement and accountability. When team members are given ownership of solutions, they are more likely to take initiative and less likely to wait for permission. Over time, this approach builds a culture of trust, shared responsibility, and continuous improvement.

The 10-80-10 Model

Delegation is often misunderstood in accounting firms. Many leaders assume that handing off a task is enough to develop their team. In reality, true leadership is built through intentional delegation, a process that empowers, educates, and builds confidence, rather than simply shifting workload. Tony Proctor introduced the ten-eighty-ten model as a practical roadmap for delegation that strengthens leadership at every level of the firm.

In the first 10%, the leader’s responsibility is to provide clear context and direction. This means setting expectations about the goal, defining what success looks like, clarifying any boundaries or constraints, and communicating timelines. Proctor stressed that this initial investment sets the stage for success: “You can’t just say, ‘Take this and run with it.’ You have to be clear about the outcome you want, what’s at stake, and what resources are available.” Leaders who skip this phase often find tasks bouncing back unfinished or off track, leading to frustration on both sides.

The 80% in the middle is where real development happens. Here, the team member owns the work. They decide how to approach the task, make decisions, handle unexpected issues, and manage their time. Proctor pointed out that this is the zone where growth occurs, mistakes are made, questions arise, and creative solutions are born. Leaders must resist the urge to micromanage or jump in at the first sign of trouble. Instead, they should be available for support, but allow their team to experience the challenge and satisfaction of finding their own way.

Finally, the 10% is when the leader steps back in, not to redo the work, but to review, provide feedback, and help close the loop. Proctor explained that this is the moment for coaching and reflection: “The final ten is where you help connect the dots, reinforce what went well, and talk through what could be better next time.” This phase is also where leaders can recognize effort, celebrate wins, and make learning visible to the whole team.

When used consistently, the ten-eighty-ten model turns every delegated task into a leadership-building experience. Over time, team members grow more independent, confident, and able to take on larger projects without constant oversight. Leaders, in turn, are freed to focus on strategy and growth instead of daily firefighting.

Wrapping Up

The heart of Tony Proctor’s message is that leadership isn’t reserved for a select few but a skill that can be cultivated throughout your entire team. Real progress happens when firm owners are willing to step back, trust their people, and invest in everyday moments of coaching. When leaders make room for real ownership, they build a foundation that outlasts any single busy season. In the end, the firms that thrive will be those where everyone feels invited to lead, not just follow.