Joel Schwiebert on Strategic Thinking for Growth
Craig and Jason are licensed P&C agency owners, co-authors of Million-Dollar Agency, creators of the trademarked Telefunnel, hosts of The Insurance Dudes podcast, and speakers.
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Build strategically by working on the business not just in it, applying second-order thinking to every decision, treating failure as diagnostic information, and competing on client experience instead of price. The best system beats the best salesperson every time.
Build a strategically different agency with four mental models: work on the business in addition to in it, apply second-order thinking before any major decision, treat every failure as diagnostic information about a false assumption, and compete on client experience rather than price. Joel Schwiebert built his agency on exactly that stack.
His perspective comes from deep operational experience filtered through a genuinely strategic intelligence. He's not just sharing what worked for him, he's sharing frameworks that apply broadly, regardless of market, carrier, or team size. The tactical layer follows the strategic frameworks below.
What mental models separate Joel Schwiebert's strategic thinking?
Joel's first big contribution to this conversation is the distinction between working in the industry and working on understanding the industry. Most agents are head-down in their day-to-day operations, which is necessary but not sufficient for building something genuinely exceptional. The ones who build at the highest level also carve out time to study the game from above: what trends are reshaping the competitive landscape, what consumer behaviors are shifting, what technologies are becoming foundational, and what the top 1% of agencies are doing differently.
This kind of meta-awareness doesn't mean ignoring the operational realities of running a business. It means adding a layer of strategic observation that allows you to anticipate changes rather than just react to them. Joel talks about specific practices he uses to maintain this perspective, the inputs he consumes, the conversations he prioritizes, the questions he asks when he's talking to peers who are building at a level above his own.
The second mental model worth internalizing from Joel is what he calls the "second-order thinking" approach to agency decisions. Most agents think in straight lines: if I buy more leads, I'll have more prospects, and I'll write more policies. Joel thinks about the consequences of consequences: if I hire a team to process my leads faster, what happens to my culture? If I expand into commercial lines, how does that change my carrier relationships and my required expertise? If I automate my follow-up sequence, what's the impact on the personal touch that drives my referral rate? The agents who think one step ahead compete well. The ones who think two steps ahead build something durable.
The third model is his approach to failure. Joel's relationship with setbacks is not what you'd expect from someone who has achieved a high level of success. He's genuinely curious about failure, specifically, what it reveals about the assumptions he was operating with. Every significant failure is, in his framework, a diagnostic. Something he believed to be true was actually false, and the failure exposed it. That framing transforms failure from a source of shame into a source of information, which fundamentally changes how you approach risk.
What does Joel believe about insurance that most agents don't?
The agency with the best processes beats the agency with the best salespeople. This is a counterintuitive position in an industry that glorifies individual sales performance. Joel's argument is that a great salesperson without great systems will outperform the market individually but hit a ceiling fast. A great system with good salespeople can scale indefinitely. The goal is not to hire the best closers, it's to build the machine that makes average closers excellent and excellent closers extraordinary.
Your competitive advantage is almost always your client experience, not your price. Price shopping is a reality in insurance, but it's not the whole story. Agents who compete on price are in a race to the bottom. Agents who compete on experience, responsiveness, clarity, advocacy, reliability, build books of business that don't leave when someone finds a lower rate. The experience is the moat.
The network you build now is the revenue source you'll rely on in five years. Joel is emphatic about this. The relationships he's investing in today, with other agents, with referral partners, with industry mentors, are the infrastructure for opportunities he can't yet see. The agents who treat networking as an occasional activity rather than a strategic priority consistently find themselves without options when they need them most.
Growth requires discomfort, and your job is to get comfortable with that. Joel talks candidly about the periods of his career when growth required making decisions before he felt ready, investing before he felt profitable, and leading a team when he still wasn't sure what he was doing. The waiting-until-ready approach doesn't produce growth, it produces stagnation that's comfortable enough to feel like safety.
How do I spend one strategic hour on my agency this week?
Before you move to the tactical layer, take one hour this week and think strategically, not tactically, about your agency. Not "what do I need to do this week" but "where is this business in three years if I make the right decisions?" What's the most important thing you could build, hire, or stop doing that would change the trajectory? Write it down.
Then identify one assumption you're operating with that you've never actually tested. It might be about your market, your clients, your lead sources, or your team. Design a small experiment to test it. Joel's framework turns those assumptions into hypotheses, and hypotheses can be validated or disproven. Both outcomes are useful.
Why does strategic thinking create the foundation for tactical excellence?
Joel Schwiebert thinks bigger than most agents, and that thinking is what makes his operational choices more strategic. The strategic frameworks are the lens; what follows is where those frameworks become specific tactics you can implement this week.
Turn strategic thinking into measurable agency results with five practices: log every significant decision (reasoning, expected outcome, 90-day review), build a clarity stack so the team operates without constant intervention, vet every tool against the underlying process, hire for upward trajectory not current skill, and block one strategic hour weekly.
The gap between knowing and doing is where most agency growth plans die. Here's how Joel bridges it.
How does Joel translate strategy into daily agency execution?
Joel's approach to strategy implementation starts with a practice he calls "decision logging", writing down the significant decisions he makes, the reasoning behind them, and the expected outcome. Six months later, he reviews these entries. The feedback loop this creates is remarkably powerful: he can see exactly which of his assumptions were correct, which were wrong, and how his thinking has evolved. Most agents make decisions by instinct and then wonder why the same mistakes recur. Joel creates the documentation that allows him to learn from his own history.
His team management approach is similarly systematic. He's built what he describes as a "clarity stack", a set of documents and processes that ensure every team member knows exactly what they're supposed to be doing, why it matters, and how success will be measured. This isn't a thick policy manual nobody reads. It's a lean set of living documents that he reviews and updates quarterly, and that his team genuinely uses as reference. The result is an operation that requires less intervention from him, not because he's hands-off, but because the structure does the management.
On the technology side, Joel has been more deliberate than most about adopting tools that reduce friction rather than tools that are impressive on a demo. His CRM, his communication platform, and his reporting tools were all chosen because they integrate cleanly, produce actionable data, and can be operated by his team without constant troubleshooting. Every technology decision went through the same filter: does this make my team more productive or does it make them manage more tools?
What are Joel's most valuable tactical insights for agency owners?
The weekly strategic hour is non-negotiable. Every week, Joel blocks one hour that is exclusively for strategic thinking, not problem-solving, not planning, not reviewing numbers. Just thinking about where the agency is going and whether the current activities are aligned with that destination. Most agency owners operate 100% in reaction mode. This one hour of proactive thinking pays dividends that are difficult to quantify but impossible to ignore.
Hiring for trajectory, not just current performance. Joel's hiring framework weights future potential heavily alongside current skill. He's looking for people who are on an upward curve, who have demonstrated growth in past roles, who are hungry to develop, and who show evidence of self-directed learning. A candidate with great current skills but a flat growth trajectory will be a liability within two years. A candidate with good current skills and a steep growth curve will be an asset that compounds.
The best agency owners are students of persuasion. Joel reads broadly about communication, influence, and human behavior, not just insurance-specific content. He's found that the concepts from negotiation, behavioral economics, and communication science translate directly to how he trains his agents and structures his client interactions. The best sales conversations in any industry apply the same principles. Understanding those principles at a fundamental level makes you a better teacher and a better practitioner.
Process before technology. Every time Joel considers implementing a new technology, his first question is whether the underlying process is clean. Technology applied to a broken process produces faster broken results. Technology applied to a solid, documented process produces leverage. He won't implement a new tool until he can write down, in plain language, what the tool is replacing and why the current process it's supporting is worth automating.
Revenue diversification is underrated in P&C. Joel has thought carefully about the revenue mix in his agency, not just which products, but which client types and which lead sources. Concentration risk is real in insurance. An agency that depends on one lead vendor for 80% of its volume, or on one major commercial account for 40% of its revenue, is fragile in ways that aren't visible until something breaks. He designs for resilience.
How do I install decision logging and a tool audit this week?
Start Joel's decision logging practice this week. Before the week is over, write down one significant decision you're facing, the decision, your reasoning, and your expected outcome. Set a calendar reminder to review it in 90 days. That's the first entry in a practice that will make you a better strategic thinker over time.
Then look at your technology stack. List every piece of software your agency uses. For each one, ask: does my team use this consistently, does it integrate with the other tools, and does it produce data I actually act on? Anything that answers "no" to two or more of those questions is a candidate for elimination. Simplicity wins. Fewer tools used well outperform many tools used poorly every time.
Why does building a thinking organization create compounding returns?
Joel Schwiebert's value is in the translation, taking genuinely sophisticated strategic thinking and making it operational. The practices and principles in both parts of this conversation are available to any agency owner willing to invest the time in building the infrastructure of a thinking organization. Start with the practices that are most foreign to your current operation. That's where the highest return is.
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