Rolling out new technology in a traditional industry like insurance isn't just hard, it's often met with outright resistance. Managers fear replacement. Veteran agents refuse to engage. Top performers see no value in changing what already works for them.
We sat down with Bryan Dinklenburg, Director of Operations at L&T Agency Group Inc, who successfully rolled out AI coaching tools across his insurance team. With 19 years of property and casualty insurance experience, Bryan knows the industry's challenges inside and out. He advocates for a collaborative culture of continuous training, tailored to each agent's needs.
In this article, we'll break down exactly how Bryan overcame resistance, got buy-in from every level, and created a training culture that drives real results.
Before diving into solutions, let's be honest about what Bryan was up against. The insurance industry faces a massive AI adoption problem that goes far beyond the technology itself.
Managers think they'll be replaced. The fear is real. When you introduce AI coaching, the first thought that runs through a manager's mind is often, "Are they trying to phase me out?" This anxiety creates immediate resistance, even if it's not openly expressed.
Veteran agents refuse to engage. When you've been successfully selling insurance for 15 or 20 years, why would you need an AI tool? These experienced sales reps have built their careers on relationships and proven methods. To them, AI feels like a solution to a problem they don't have.
Top performers see no value. Your best agents are already crushing their quotas. They're making great money and earning recognition. From their perspective, AI coaching is something for underperformers—not for them.
The result of all this resistance? Teams stay stuck in old habits while competition gains ground. The gap between top performers and low performers keeps widening. Sound familiar?
Bryan faced all of these challenges head-on. But instead of forcing change, he built a playbook that transformed skeptics into advocates.
Bryan's first breakthrough came from reframing how everyone thought about AI in sales enablement. As he puts it:
"Tools like AI could never replace the human element. What they allow my leaders to do is SCALE their efforts."
This is the fundamental shift that makes everything else possible. AI doesn't replace managers—it multiplies their impact.
Think about the math. Instead of conducting one role-play per week with each agent, sales reps can now practice multiple times on their own schedule. Instead of managers spending hours listening to 500 calls to identify coaching opportunities, they can review trends and scoring patterns in minutes.
What does this mean practically? Managers get 5 hours back per week. Time they can spend on strategic coaching, relationship building, and high-value activities that actually require human judgment and emotional intelligence.
But knowing this intellectually and getting your team to embrace it are two very different things. That's where Bryan's six-step playbook comes in.
Bryan's first rule is simple but often ignored: involve your frontline leaders from day one.
Top-down dictatorial mandates don't work. They breed resentment and passive resistance. Instead, Bryan made his managers partners in the process.
He gave them a voice in selecting the tool, ownership of the rollout plan, and input on how it would fit their existing workflow. As Bryan says, "People want to feel appreciated and heard."
Why this matters: When leaders help build the process, they champion it. They become advocates rather than obstacles. They see it as "our solution" instead of "management's latest initiative."
How to do this in practice:
This collaborative approach transforms your biggest potential resisters into your strongest supporters.
This is where many AI rollouts fail. Companies focus on organizational benefits—efficiency gains, better data, improved performance metrics. But individuals don't care about that. They care about what's in it for them.
Bryan made the value proposition crystal clear and personal.
For agents: "If I could help you increase your policy volume by 2-3%, that's an extra $6,000 in your pocket each month."
For managers: "Instead of listening to 500 calls, review trends in 10 minutes. Get 5 hours back per week."
Notice the specificity. He didn't say "improve performance" or "save time." He quantified exactly what success looks like in terms each group cares about.
For sales reps, it's about their commission checks. For managers, it's about reclaiming their time and reducing tedious tasks. Make it about THEM, not about the tool.
This personal value proposition is what gets people to actually try the technology instead of just nodding along in meetings and then ignoring it.
Here's where Bryan's strategy gets really smart. He didn't mandate usage. He didn't start with struggling agents who might skew results. And he didn't pressure top performers who were already resistant.
Instead, he created an experiment. Bryan asked for 5-6 volunteers and focused on mid-tier performers—agents who were doing okay but had clear room for growth.
Why mid-performers? They're motivated to improve but not demoralized. They're open to new approaches because they know their current methods aren't getting them to the top. And critically, their improvements are more noticeable and attributable.
Bryan tracked their progress closely. And the results came faster than expected.
Within weeks, policy volume jumped 3-5% among the pilot group. One agent actually DOUBLED their production. And here's the kicker—top performers started asking to join.
This is the power of proof points. When your mid-tier agents start outperforming veterans, everyone takes notice. Let early wins create FOMO (fear of missing out). Suddenly, AI coaching isn't something management is forcing—it's something people want access to.
One of the fastest ways to kill AI adoption is through privacy paranoia. If your team doesn't understand what's being recorded, who can access it, and how it's being used, they'll assume the worst.
Bryan addressed this head-on by answering key questions publicly before rollout:
No surprises equals no paranoia equals higher adoption. When people understand the rules, they can focus on using the tool rather than worrying about how it might be used against them.
Pro tip: Put this in writing. Create a simple one-page document that outlines your AI coaching policy. Share it openly. Reference it often. Make it clear that you're committed to transparency.
This step is about changing the fundamental mindset around learning and development in your organization.
Bryan put it this way: "Process over outcome. If you've got a consistent, repeatable, strong process, you're going to succeed."
Old mindset: Training is an event we do once—maybe during onboarding or at annual sales kickoffs.
New mindset: Learning is part of who we are. It's continuous, expected, and celebrated.
Here's how to make this shift practical:
Celebrate effort, not just results. Recognize the agent who completed 10 AI roleplays this week, even if their numbers didn't jump yet.
Make practice expected, not optional. Build it into your weekly rhythms. "Thursday mornings, we practice objection handling with our AI sales coach."
Focus on leveling up one skill at a time. Don't try to fix everything at once. This month, we're working on discovery questions. Next month, we'll tackle closing techniques.
When training becomes normalized rather than exceptional, resistance drops dramatically. It's no longer "extra work"—it's just how you do business.
Bryan didn't wait for perfect results or massive transformations. He celebrated incremental progress loudly and often.
A 2% improvement in policy volume? Celebrated. An agent moving from 40 to 50 policies per month? That's a team-wide announcement. Managers saving 5 hours per week? Worth recognizing publicly.
As Bryan explains: "If I can take somebody from 40 policies to 50, that's a 25% increase. That's meaningful."
He's right. A 25% increase in productivity for a mid-tier performer can have significant impact on team results. But more importantly, it shows everyone else what's possible.
How to share wins effectively:
Make wins visible and adoption becomes contagious. People want to be part of success stories, not left out of them.
Before we wrap up, Bryan shares one crucial reminder that every leader needs to hear:
"AI gives you CONTENT. But not CONTEXT."
You still need human intelligence and emotional intelligence. You still need manager judgment, personal connection, and cultural understanding. The AI sales coach can tell you what was said in a call and flag potential issues. But it takes a human manager to understand why it matters for that specific agent in their unique situation.
Know what the tool is. Know what it isn't. Use it to amplify humans, not replace them.
This mindset protects you from over-relying on AI while ensuring you're getting maximum value from it. The technology provides data and scalable practice opportunities. Humans provide wisdom, empathy, and strategic direction.
Rolling out AI coaching in a traditional industry like insurance doesn't have to be a battle. Bryan Dinklenburg's playbook proves that with the right approach, you can transform skeptics into champions and deliver measurable results quickly.
The six-step framework is straightforward: co-create with frontline leaders to build ownership, sell the personal upside to make it relevant, start with volunteers and mid-performers to build proof points, set clear guardrails to eliminate paranoia, normalize your training culture to make practice expected, and share wins often to make adoption contagious.
Remember that AI doesn't replace the human element, it multiplies the impact of your best managers. It gives them back time, provides scalable coaching, and helps level up your entire team. When you frame it as a multiplier rather than a replacement, everything changes.
In this episode of SellMeThisPen Podcast, we dive deep into the practical challenges of rolling out AI coaching tools in the insurance industry. Bryan shares the exact strategies he used to overcome resistance from managers and veteran agents, turn mid-performers into champions, and build a training culture that drives measurable results. He breaks down the six-step playbook that transformed skeptics into advocates and delivered meaningful improvements in policy volume within weeks.
Bryan Dinklenburg is the Director of Operations at L&T Agency Group Inc with 19 years of property and casualty insurance experience. He's passionate about building collaborative cultures of continuous training tailored to each agent's needs. Bryan successfully rolled out AI coaching across his team and now shares the playbook that actually worked in a traditional, relationship-driven industry.
