You’ve booked an appointment. Awesome. Great job. Now, what are you going to do? That’s what today’s article is about. Let me give you five things you need to know how to do before you go into an appointment.
The very first thing you want to do when you get your appointment planned is to make sure that you get there early. Now I know it seems like it’s probably common sense, and you probably think that it has something to do with just giving a first impression, but that’s not true. Yeah, that’s great. And it’s certainly something you want to do, but at the end of the day what you want to do is make sure that you have plenty of time to do recon in the lobby of this prospect. The longer you can be in the lobby without it being weird that you’re just sort of hanging out there all day, the better off it’s going to be because you’re going to learn about how this company promotes themself. What they think is important in terms of their value. You can see their mission statement. You could see a safety policy statement, And you can see all of the accolades and awards that they have brought in over the years. A secondary benefit of this is you can engage in conversation with the person that’s there at the reception desk because you want this person to be your ally going forward. The more you can learn about them, the better off you’re going to be because it will break the ice every single time you go in to meet with this future client.
The second thing you want to do is you want to make sure you take time to build rapport on the front end. You should have researched this person you’re meeting with and be able to have common ground before you ever walk in the front door. You should have things that the two of you can talk about that have absolutely nothing at all to do with business or the task at hand. But keep in mind there’s a delicate balance of what’s enough and what’s too much. You don’t want to put yourself in a position where this person is twiddling their thumbs, tired of small talk, and ready to get down to brass tacks.
The number three thing you need to do is you need to make sure you ask educated, open-ended questions. Educated open-ended questions are an excellent way for you to talk a little and listen a lot. You need to make sure that your prospect knows that you understand their business, but you want to understand them. There’s a difference between understanding an industry and understanding a specific company. You can demonstrate industry knowledge through your questioning, but you only understand a particular company through listening. Make sure that you are asking open-ended questions that you have planned, and you will learn way more than you ever thought possible.
Number four, you want to make sure you let them know you understood what they said. Ask great follow up questions that you have created on the fly. Now I’m not saying you have to make these things up that second. I want you to think about what the possible answers would be and come up with those questions for follow-up before you go into the meeting and then pick which ones you want to use. By demonstrating that you understand how they answered the question and asking an insightful follow-up question, you only build more credibility. How do you prepare for this? Well, truthfully, think about how an attorney might go about preparing for a deposition. If you’ve ever been through a deposition before, you know that they have a series of questions that they ask. After each of those is a series of follow-up questions, they have anticipated asking based on what your answer may be. Do the same thing. Anticipate what their response may be, have the follow-up questions, and roll with it. You will have credibility from that prospect at that point.
Number five and the most important, in my opinion, is book the next appointment. I never leave a meeting without booking the follow-up appointment. It takes all of the animosity out of the process. Don’t worry about getting them on the phone, or whether they’re going to respond to your email. Book the next appointment before you leave the meeting you’re on. If you do that, you will win more than you will lose.
These are five great tools for you to use when you go to a prospect meeting. If you do all five of these things, you are going to kill it in commercial insurance.
Until next time: Kill or get killed!
For years, commercial insurance producers could survive by being good enough across a wide range of industries. They could write a little construction, a little manufacturing, a little hospitality, and a little habitational business and still build a respectable book.
The commercial insurance industry is in the middle of a quiet evolution.
While most conversations still revolve around premiums, deductibles, limits, and carrier appetite, a different category of risk transfer has been gaining traction beneath the surface—parametric insurance. It is not new, but it is finally becoming accessible, relevant, and actionable for middle market producers who are willing to think differently about risk.
In a recent episode of the Power Producers Podcast, I sat down with Brian Thompson from Descartes Underwriting to unpack what parametric insurance actually is, what it is not, and why producers who ignore it may be leaving their clients—and themselves—exposed.
This article breaks that conversation down into practical, producer-friendly language and shows how parametric insurance fits into modern middle market risk management.
The last several years have reshaped the landscape of property insurance across the country. While most national carriers have retreated from coastal states, wildfire zones, and other catastrophe-exposed regions, a handful of disciplined players have taken the opposite path—leaning into difficult markets with a strategic, data-driven approach.
For most entrepreneurs, the decision to start a business is rooted in the promise of freedom. Freedom from a boss, freedom to control income, and freedom to build something meaningful. Yet for many business owners, particularly in service-based industries and middle-market companies, that freedom slowly erodes. What begins as ownership eventually turns into obligation, where the business demands constant attention and the owner becomes the single point of failure.
The insurance industry is full of shortcuts. Some producers look for ways to streamline the quoting process, others avoid hard conversations with clients, and many rely on endorsements or extensions because they are “easier” than diving into the details. Nowhere is this more dangerous than in the world of cyber insurance.
Too many agents assume that a cyber endorsement on a BOP or commercial package policy is “good enough.” It isn’t. In fact, treating a BOP cyber extension as a replacement for a standalone cyber policy leaves clients dangerously exposed, puts producers at risk of losing accounts, and opens the door to costly errors and omissions (E&O) claims.
Cyber threats evolve faster than any other area of risk, and endorsements simply can’t keep up. If producers want to protect their clients and themselves, it’s time to understand why standalone cyber insurance is non-negotiable.
In the middle market, producers don’t lose because the competition has better pricing.
They lose because the competition understands people better—their motivations, their fears, their priorities, and what makes them say yes.
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