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.
Influence is one of the most powerful tools we have in business, leadership, and personal life. Used well, it inspires people, builds trust, and creates ethical results. Used poorly, it can slide into manipulation and self-interest.
Reinvention is one of the most powerful themes in the insurance industry. Some of the best commercial producers in the country did not grow up wanting to sell insurance. They did not study risk management in college. They did not come from an agency family. They found this industry after they tried something else. They found it after life pushed them toward a career where performance, autonomy, and mindset determine the outcome.
The most successful producers in the middle market did not get there because they quoted faster, smiled bigger, or knew how to talk longer. They got there because they learned how to differentiate themselves so clearly that prospects had no choice but to see them as trusted advisors. They learned to operate like businesspeople first and insurance technicians second. They learned how to tie operational mechanics to insurance outcomes. They learned how to control their time, their pipeline, and their future.
In commercial insurance, the most dangerous threats to your book of business aren’t always visible on the loss runs. One of the most overlooked vulnerabilities for middle market producers is ignoring the personal lines needs of their business owner and executive clients.
The commercial insurance industry is one of the few professions where someone can enter with no experience, no connections, and no background in risk management and still build a long, lucrative career. But success is never automatic. It requires hunger, humility, curiosity, and the willingness to keep showing up even when the process feels overwhelming. That is why the story of Pam Seidler has already started making waves among new and aspiring commercial producers.
In an industry where tradition often outweighs innovation, artificial intelligence and automation are slowly but steadily reshaping how independent insurance agencies operate. The push toward smarter, more efficient workflows is no longer a matter of if—but when. While many agencies are still evaluating how AI fits into their operations, early adopters are already reaping the benefits of streamlined submissions, faster processing, and actionable data insights.
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