Coach Craig Keeping It Kosher: What Real Coaching Looks Like in an Insurance Agency

There is a version of coaching that happens in insurance agencies that is really just management with a warmer tone. The manager calls it a coaching session. They sit down with the agent, go through the performance numbers, identify the gaps, tell the agent what they need to do differently, and end the meeting with some encouragement. The agent leaves with action items they may or may not execute. The manager feels like they did coaching. The agent feels like they got managed.

Jason Feltman's observation about Craig Pretzinger as a coach, and what makes Craig effective in this role, is that the sessions look different. The distinction matters because the outcomes are different, and if you're running an agency and trying to develop your team, understanding the difference is worth your attention.

What Coaching Is Not

Coaching is not telling someone what to do. That's directing. It's a legitimate leadership function, sometimes the most effective thing is a clear, direct instruction, but it is not coaching. The confusion between the two is where most agency coaching programs fail. The principal knows what needs to change. They tell the agent what to change. They call it coaching. The agent may change the behavior. But the understanding of why the behavior matters, and the internal ownership of the improvement, usually doesn't develop. The next time a similar situation comes up, the agent waits to be told again.

Coaching is not cheerleading. A lot of what gets called coaching in sales organizations is motivational support, encouragement, energy, reminders of what's possible. That has value. It is not coaching. Coaching requires an honest look at current performance, which is a different kind of conversation than "you can do this."

Coaching is not performance management. If an agent is underperforming, there's a time for a direct conversation about standards and consequences. That conversation is important and necessary. It is also not coaching. Conflating them confuses both the coach and the agent about what the session is for.

What Craig's Coaching Actually Looks Like

The Craig coaching session that Jason describes has a specific structure. It starts not with the numbers but with the agent's own perception of their performance. "What do you think is going well?" "Where do you feel stuck?" "What's one thing you'd do differently if you could replay this week?" These questions are not rhetorical warmups. They are the actual beginning of the diagnostic.

The reason this matters is that the agent's self-assessment tells Craig far more than the performance data alone. An agent who knows exactly what's getting in their way is ready for a different kind of conversation than an agent who thinks they're performing fine when the numbers say otherwise. The self-perception gap is often the most important coaching target, and you can only find it by asking.

From the self-assessment, the coaching conversation moves to exploration. Not prescription. Craig's coaching questions are designed to help the agent arrive at insights rather than to transmit Craig's insights to the agent. "What do you think happened in that conversation?" "If you imagine a version of that call that went really well, what would it have looked like?" "What do you need to change to move from where you are to where you want to be?" These questions put the agent in a problem-solving posture rather than a receiving posture. The solutions that come from the agent's own thinking are the ones they'll actually implement.

The Kosher Framework

Keeping it kosher, in this context, means maintaining the integrity of the coaching relationship, specifically, being honest even when honesty is uncomfortable, and staying genuinely focused on the agent's development rather than the principal's performance goals. These two things are usually aligned. But when they diverge, when the honest coaching conversation points toward something the principal doesn't want to hear about their operation, keeping it kosher means having the conversation anyway.

Craig's coaching works because agents trust that the sessions are genuinely about them. Not about hitting a number by the end of the month. Not about the principal looking good. About the agent getting better at the work they're trying to do. That trust is not given automatically. It's built through consistent behavior over time, through coaching sessions where the honest feedback actually helps, where the agent's perspective is genuinely heard, where the relationship feels like development rather than performance management with a coaching vocabulary.

What This Means for Your Agency

Evaluate your current coaching practice against one specific test: at the end of a coaching session, can the agent articulate, in their own words, one specific thing they are going to do differently and why they believe it will make a difference? If the answer is typically yes, you're probably coaching. If the answer is typically "I told them to improve their close rate," you're probably managing.

The goal of coaching is the agent's insight, not your instruction. Restructure your sessions around questions that produce insight, and watch what happens to both performance and retention.

The Bottom Line

Coach Craig keeps it kosher because the coaching relationship only works when it's genuine. Real coaching produces agents who understand their own performance and own their development rather than waiting for direction. Building that kind of coaching culture inside an agency is one of the highest-leverage investments a principal can make, and it requires a completely different approach than the management session that gets called coaching.

---

Catch the full conversation:

• Listen on Spotify
• Listen on Apple Podcasts
• Watch on YouTube

About Jason Feltman: Jason Feltman is co-host of The Insurance Dudes podcast and co-author of The Million Dollar Agency. He runs a high-volume independent insurance agency and is known for making the business of insurance both practical and genuinely entertaining.

Level up your agency:

• The Million Dollar Agency Book
• Join Agent Elite on Skool
• Book a Free Strategy Call
• TheIDudes.com