Most of us have marketing automations, drip email campaigns and all kinds of things to stay in touch with our prospects. But the real question I have for you today is, how many times should you personally follow up?
In today’s age of technology, it is so easy to get lazy. A lot of the time, we think that we want our CRM system to do all of the automation and communicate with everybody and follow up on our behalf. But the real question is, how many times should you personally follow up with a prospect before throwing your hands up and giving up? The answer to that’s straightforward. You follow-up until you get the order!
I mean, let’s face it, it’s not that difficult to plan appointments around a red hot prospect. If somebody is worth your time to do a marketing drop to the very first time, they’re still worth your time when you follow them up the second time.
Nobody is going to buy from you just because you walked in the door. I hate to break it to you people, but you don’t have a bunch of prospects sitting there waiting with their checkbook in hand saying, “Hey David, thank you so much. We’ve been sitting here waiting to write you a large check to purchase insurance and risk management services from your firm.”
It just doesn’t happen that way. You have to follow up with people methodically, and you have to make yourself relevant. Think of your outside sales job as if you were running a route. Some of the best salespeople I’ve ever encountered in my life were when I was in the grocery industry. And I use the example of the bread guy.
The bread guy is the first guy there every day. He’s there at five o’clock in the morning, if not earlier, and he makes sure that you never run out of bread. Your bread rack is neatly organized and clean, his labels are facing out, his price tags are visible and he doesn’t allow all of the garbage that people throw into the bread rack to stay in his section at all.
So, when the bread man used to come to me and say, “Mr. Carothers, can I please have an off-shelf display this weekend? I know the company does not authorize it, but I’m in here every morning for you. I make sure your bread rack is full and clean so your customers can always have the most variety to pick from when they shop in your store.” My answer was yes.
It wasn’t because he came in one morning at five o’clock in the morning to make sure that I knew he was there. It was because he was there every single day, and his product area was always perfect. I think producers can learn a lot from the bread man. We believe we are going to walk in and close a piece of business just because we walked in the door when really what we need to do is remain relevant.
If you have somebody that seems like they’re interested, follow up with them two weeks later. Schedule more marketing drops around that location so that you can drop back by and take them something relevant based on your previous conversation. It might be a box of Girl Scout cookies. It could be their coffee order. It doesn’t matter. The only thing you want to do is stay in front of them because what will happen is them seeing you becomes a habit, and then they want to buy.
You’re never going to be there to take the order if you’re one and done. You’re never going to get the order if you wait for your phone to ring, or you wait for an email to come in. You have to go in there, and you have to ask for the order, and you can only do that if you’re physically present and relevant. If you can figure out how to stay connected by following up with prospects the appropriate number of times, you’re going to kill it in commercial insurance.
In the ever-evolving world of commercial insurance, marketing has become a critical lever for growth. Yet most agencies still struggle to understand what’s actually working. From websites that generate leads with no attribution to CRM systems that silo vital data, insurance agencies are often flying blind.
If you’re a commercial insurance producer trying to grow in the middle market, you’re probably aware that the old-school prospecting methods—cold calling hundreds of businesses, dropping off trinkets, hoping someone is “coming up on renewal”—are no longer enough. In today’s competitive environment, success isn’t about how many people you reach. It’s about reaching the right people at the right time with the right message.
Too many agents stop learning once they’ve earned their license. The bare minimum—meeting continuing education requirements—is not enough in today’s climate. Producers often resort to online forums, asking where they can complete CE hours “as quickly as possible.” This mindset directly impacts their ability to communicate complex subjects like reinsurance or risk modeling to clients in an understandable way. As a result, they struggle to retain accounts and close new business in an increasingly competitive market.
The problem? Too many producers are pitching too soon, to the wrong people, with nothing more than a quote to offer. This article walks through how to close more business by positioning yourself as a trusted advisor, selling Total Cost of Risk (TCOR) outcomes, and using a structured approach to differentiate at every stage of the sales process.
In the modern commercial insurance landscape, trust is no longer built solely through in-person meetings, networking events, or polished brochures. It’s earned digitally—often before a prospect ever takes your call. As sales dynamics shift and competition tightens, the producers who will thrive are those who understand one thing: educational content is the new handshake.
Most commercial insurance producers think of referral networks as an afterthought—something that might generate a lead or two if they attend enough events, shake enough hands, or stay active in their BNI chapter. But the producers who consistently dominate the middle market think differently. They treat referral networks like revenue engines, built with the same discipline as a sales pipeline, and they use those relationships not only to generate appointments but to recruit the next generation of elite producers.
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