Phil Geldart on Building a Coaching Culture for Insurance Agency Leadership Development — Part 2
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A single great training experience can shift a producer's mindset for weeks. A coaching culture shifts their trajectory for years. Phil Geldart's first conversation, on experiential learning and the mechanics of skill-building, laid the foundation. Part 1 is here. This second conversation addresses the harder problem: how do you build the organizational culture and leadership capacity that makes learning continuous rather than episodic?
The answer, it turns out, has less to do with training programs than with how managers see their job, and whether the agency owner has invested in developing those managers as coaches.
What a Coaching Culture Actually Requires
Most organizations confuse a coaching culture with a culture that has coaching. A coaching culture isn't defined by whether coaching happens occasionally, it's defined by whether the instinct to develop people is built into every leader's daily behavior, and whether that instinct is supported by the systems and incentives of the organization.
Phil is direct about what's required: leaders in a coaching culture need to be skilled in a specific set of behaviors that don't come naturally to most high-performing operators. They need to ask questions more than they give answers. They need to sit with a team member's struggle rather than rescuing them from it. They need to believe that the discomfort of learning is productive and not a management failure. And they need to give feedback that's specific, timely, and grounded in observable behavior, not "you need to be more confident" but "I noticed that when the prospect raised a price objection, you reduced your quote before exploring their actual concern."
This is a fundamentally different skill set from what got most agency managers where they are. The skills that make a great producer, drive, competitiveness, the ability to handle rejection, a strong personal sales style, can actually be liabilities in a coaching role. Great coaches aren't the ones who know best how to do the thing. They're the ones who know best how to help someone else figure out how to do the thing. That distinction matters enormously.
Phil's framework for developing coaching capacity in managers starts with two shifts. First, from answer-giving to question-asking: every time a manager's instinct is to solve the producer's problem, they practice asking a question instead. "What have you tried?" "What's your read on why that prospect went cold?" "What would you do differently if you were making that call again?" These questions are uncomfortable for managers who are used to being the expert in the room, and that discomfort is the point. It builds a different kind of muscle.
Second, from event-based feedback to continuous observation. Feedback that comes once a quarter, or only when something goes wrong, is almost useless for behavior change. Phil's model has managers giving specific, behavioral feedback multiple times per week, ideally within minutes or hours of the observed behavior. Not evaluative feedback, "that was good" or "that was bad", but descriptive and curious feedback: "I noticed you asked three questions before proposing a solution. What made you take that approach?" That kind of feedback is also a teaching tool, it makes the producer's own behavior visible to them in a way that accelerates self-awareness and intentional adjustment.
Building Systems That Reinforce the Culture
The leadership behaviors Phil describes don't sustain themselves without organizational support. Agency owners who want to build coaching cultures need to align their systems and incentives with the values they're trying to embed, because culture does what it's rewarded for, not what it's told to value.
The most important system shift is making manager development a measured expectation, not an assumed outcome. If managers are evaluated only on their team's production numbers, the rational response is to do whatever produces short-term results, which is usually doing the selling themselves rather than coaching the producer to improve. Add coaching behaviors to the manager's evaluation: are they conducting weekly one-on-ones? Are their direct reports improving over time? Are they giving documented behavioral feedback? When you measure it, you create the incentive to do it.
Peer learning is one of the highest-leverage and lowest-cost tools Phil endorses. In a coaching culture, producers aren't just learning from managers, they're learning from each other. That requires deliberate structure: regular sales calls where producers share what's working and what isn't, peer shadowing arrangements, and team debriefs where wins are analyzed as carefully as losses. The knowledge in a high-performing agency usually lives in the heads of the top three producers. A coaching culture gets that knowledge into the system where everyone can access it.
Psychological safety is the environment in which all of this works. If producers fear judgment for admitting what they don't know, they'll perform competence rather than developing it. If managers fear looking weak by asking their team for feedback, they'll manage from authority rather than trust. Phil is explicit: the signal that leadership sends about its own willingness to be vulnerable and continue learning sets the ceiling on how much everyone else will grow.
What This Means for Your Agency
Identify your most experienced manager and have an honest conversation about how they currently approach one-on-ones with their producers. Are those conversations primarily administrative, reviewing numbers, resolving issues, or are they primarily developmental? If it's the former, that manager may have excellent operational instincts and underdeveloped coaching skills. That's not a performance problem, it's a development gap that can be closed with intention and practice.
As an owner, consider building one peer learning structure into your team's weekly rhythm. It doesn't require a big production. A 30-minute call where two producers share one win and one challenge each, and the group discusses both, creates a learning feedback loop that compounds over time. The structure is almost irrelevant, the habit of honest reflection and shared learning is everything.
The Bottom Line
Phil Geldart's coaching culture framework is ultimately about one thing: creating an organization that gets better at the speed of experience rather than the speed of formal training. When every manager is a coach and every experience is a learning opportunity, the agency compounds in ways that no single training program can replicate. Build the culture. Develop the coaches. Make learning the daily default, and watch the long-run results separate you from every agency still relying on the annual product training event.
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Phil Geldart is a leadership development expert and founder of an organizational learning firm focused on building coaching cultures across complex industries.
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