How May Times Should you Follow Up?

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?

Don’t Let Technology Make you Lazy

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.

People Aren’t Waiting Around to Buy From You

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.

Learn from 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.

Have a Set Schedule for Personal Follow-up

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.

Insurance

Solving Insurance Back Office Bottlenecks: How Automation and Compliance Tools Empower Agencies and MGAs

The insurance industry is undergoing a quiet transformation. While headlines often focus on the flashy front-end tools and direct-to-consumer disruption, the real revolution is happening behind the scenes — in the back office. From agency onboarding delays to outdated compliance workflows and manual licensing tasks, these friction points cost MGAs, carriers, and agencies valuable time, revenue, and relationships.

Read More »
Employee

Why Employee Ownership is the Key to Sustainable Agency Growth and Talent Retention

In an increasingly competitive commercial insurance landscape, agency owners are struggling to find long-term solutions for succession planning, talent retention, and business perpetuation. Many have considered private equity sales, others offer limited equity to top producers—but a growing number are discovering a more powerful alternative: the Employee Stock Ownership Plan (ESOP).

Read More »
Sales

How to Reverse Engineer Your Sales Funnel and Crush Your Q4 Insurance Production Goals

As we enter the fourth quarter, many commercial insurance producers begin to panic. Whether you’re behind on your goals or just trying to hit that final sprint, the Q4 crunch is real. But the producers who consistently win don’t treat Q4 as a Hail Mary. They plan with precision, reverse engineer their goals, and execute with ruthless consistency.

In this post, we’ll break down how you can reverse engineer your sales funnel, identify your revenue gaps, and finish the year stronger than you started. Whether you’re writing workers’ comp or cyber liability, these strategies apply across all middle market verticals.

Read More »
wholesale

Mastering Wholesale Partnerships: Submission Strategies, Underwriter Relationships, and Technology Tools for Middle-Market Success

In today’s competitive insurance marketplace, middle-market agencies must leverage every available advantage to win and retain business. One of the most underutilized yet powerful resources at an agent’s disposal is the wholesale market. By establishing strong partnerships with wholesalers, agents can access capacity, expertise, and proprietary programs that are often unavailable through direct channels. However, success in the wholesale arena requires more than simply submitting risks and hoping for the best.

Read More »

Responses

Killing Commercial Login