Bridging the Training Gap

May 28, 2025

Casey Maughan

Like many in the financial services industry, I never planned on ending up here. Early in my career, I discovered my love for sales, but didn’t love the environment or product I was selling. Eventually, I found myself working for a multiline agent, focusing on growing the agency’s sales. I loved having control over my time, engaging in meaningful conversations and building relationships.

Soon after that, I received a fantastic offer to join a team of driven financial service professionals. There was just one catch: I needed to get my securities licenses before I could start. If this took longer than two months, I’d be expected to attend the company’s new three-month, in-person training program, which wasn’t appealing to me in the slightest. I felt I already knew what I needed to know and do, thanks to my excellent district manager, who also thought I was beyond the training level offered. So, I rushed through my exams and started just in time to avoid the training program.

I now lead our agent training programs . . .

I’ve thought about that experience a lot. What was it about the training program that was so unappealing to me as a new agent? Why did my district manager feel like I was beyond the skillset of the training? And why did the home office invest in the training program to begin with?

The main issue was the perceived gap between the home office training and what I actually needed to succeed as an agent. Whether this gap was real or not, the perception of it created a divide. By not addressing that gap, we can drive a wedge into organizational cultures, making it challenging to develop the demanding skillset needed for success in the financial services industry. This confuses the agent, frustrates the company and can be a waste of time and money.

To address this, I’ve found that there are a few consistent steps that will help bridge the gap:

  1. Establish clear goals
  2. Encourage transparent communication
  3. Adapt and evolve

Let’s look at them in turn.

Clear goals

Organizations that have goals established, clearly defined and widely adopted have a leg up. Often in the financial services world, we use contests to define some of these goals. I’ve seen instances where the home office was using contests as quick-hit solutions to address lagging production. The field initially responded to these, but they were so frequent that, in time, the agents would joke about the “contest of the month.”

In another instance, there was a long-lasting and well-established contest in place. The home office eventually took aspects of it for granted and stopped emphasizing and rewarding it. The agents who earned it felt at best ignored and at worst disrespected because they’d worked hard to achieve this. Renewed efforts to make sure that the award was properly promoted and recognized helped clarify the importance of the goals they were achieving. A clear and effective goal is one that is understood and reinforced by the whole organization.

Transparent communication

When teams have transparent communication, they need to have thick skin. They need to be ready to hear the good and the bad. The most important step we’ve taken to make sure our training was relevant was interviewing our field leaders to understand precisely what training is needed and when.

Their feedback was a gift, and they were able to tell us key details that have shaped decisions we’ve made on every aspect of our training—from the content we train, to when we hold it, to what time of day we start and how we reinforce the training. This feedback has created clarity into the great things happening in our training sessions and the resulting successes in the field. There is a definite difference between empty feedback and genuine feedback, and getting genuine feedback is a process worth investing in.

Adapt and evolve

It’s often said that you never arrive, which is paramount to adapting and evolving. We continue these interviews with our field leaders to maintain open feedback loops and listening posts, ensuring we provide effective learning experiences. We measure the performance of our agents and do our best to monitor the escalating changes in the insurance markets. Updates to training used to be predictable, annual events, but now the needs of the field adjust quickly, and we need to consistently ensure our training meets those needs.

Staying curious and constantly asking “How can this be better?” will always be beneficial. A good motto to adopt might be “Training is never done,” because the second we think it’s completed, we begin to drive a wedge between the program and the field.

At this stage, we’ve aligned our field leadership and agent training teams well enough that if there’s a miss, neither side is too proud to acknowledge it. It’s possible that we might miss the mark on the training side, but it’s also possible that we could miss the mark on the hire. This collaborative approach helps us continuously improve and adapt our training programs to meet the real needs of our agents. Getting there is a process, not an event. But if you can learn to love the process, then the process will love you back.

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