The Three Biggest Struggles Young Insurance Advisors Face (and How to Get Past Them)

In a previous blog post, I went through the five tips beginning insurance and financial advisors needed to know when starting in the industry (check it out here). I got a lot of positive feedback to this article and had a few conversations with advisors who were just starting out. One really interesting discussion was with a young individual insurance advisor named Matt, who asked what the biggest struggles financial advisors faced when starting. It was a great question, so I decided to dig in.

As always, I turned to the braintrust I’ve developed over the last year or so of topnotch insurance advisors and financial planners who have successfully built impressive practices. What I wanted to understand was what struggles they had faced when starting up and what they had learned through them. The answers were fascinating, and I’d like to share them below.

Struggle #1: Being Okay With Being Uncomfortable

I once had a mentor who told me that whenever he had to make a life decision between two options, he went with the one that scared him the most. He argued that only during moments of discomfort that was growth truly possible. This resonated with me quite strongly (I’m pretty sure my entire career to date has been inspired by this idea).

Seasoned, successful advisors, when asked about the early struggles of being new to the industry, had similar beliefs. They talked about how uncomfortable they were starting off and what a struggle it was to get used to being uncomfortable! But they also believed that tackling this discomfort head-on was a huge part of what made them successful. Like my mentor, one advisor I talked to claimed that whenever an opportunity for discomfort presented itself to her, she jumped into it with both feet.

So what’s so uncomfortable about being an advisor in the early stages of your career? Well, sort of everything. Think about what your job fundamentally is. You need to meet new people and, within a conversation, try to convince them to give you the time of day to buy something from you. Moreover, insurance is often sold cold. Whether you’re at a networking event, hitting the phones, or knocking on doors, you’re often trying to turn a stranger into a prospect on the spot. This is the sort of industry that means you need to develop a very thick skin. Especially when you’re often reaching out to people who don’t want to be disturbed. Ever call someone when they’ve just sat down for dinner after a long day of work? Eeek!

In other words, you have to learn how to be uncomfortable!

Unfortunately, many young advisors draw the wrong lessons from this. They get swatted on the nose one too many times and, instead of toughening up, they decide to try a lower-stress approach to prospecting. Maybe they send out mass emails instead – after all, a “take me off your list” email response is much less anxiety-provoking than being shouted at over the phone. Or they partner with a lead gen service that does online marketing and feeds them clients, never allowing them to wholly own the client relationship. The problem is, while many of these channels may be productive, they are almost certainly less productive than the direct outbound approach. Being an advisor is all about building relationships, and good advisors realize that this starts from the prospecting stage.

In other words, one of the biggest challenges for young advisors is understanding that it’s not only okay to be uncomfortable, it’s downright encouraged. As one advisor told me, if a young advisor isn’t willing to train themselves out of their comfort zone, they shouldn’t be in the insurance business. They’ll just find themselves doing below average and earning in the bottom quartile of the profession.

So how do you become better at being uncomfortable?

To quote Nike, “just do it.” No, seriously, it’s really just that. Think of anything that you started which scared you the first time you did it, whether it was going to an acting class, going to the gym, your first day backpacking on your own, whatever. How did you get over your fear? You kept going and kept doing it. Over time, the fear was replaced with comfort.

Prospecting is very similar. The first 100 cold calls you make will be ordeals. The next 500 will be uncomfortable. The next 10,000 will be doable in your sleep. But the only way to get to that point is to do those calls. It’s to get hung up on and cursed out by strangers. It’s to put yourself out there and see that even after the most brutal phone interactions, you’re still in one piece. And then do it again and again and again, day in, day out. Eventually, it becomes old hat. Bad calls no longer faze you, good calls become more consistent, and now your business is starting to grow. The same can be said about networking events or door-to-door sales. Both require an initial period of discomfort that you have to muddle through.

Notice that the best way to get over the fear is to do it regularly over a long period of time, not to try to blitz through it quickly. You can do 200 calls over Monday and Tuesday, but if you don’t do another call until the next Monday, expect to be feel almost as nervous that following Monday morning. Instead, if you did 200 calls from Monday to Friday (i.e., 40 calls per day), you’d feel much better on the phone the following Monday.

Overall, then, you must be consistent and driven to put yourself into situations you don’t find comfortable. And when you start finding them comfortable? It’s time to turn to the next thing that frightens you and devote yourself to that as well.

Struggle #2: Not Knowing What To Focus On With Your Prospects

I still remember the first time I met with a company on my own as a venture capital associate. I was very green at the time. I had sat through a few sessions with my boss doing the same thing, collecting the information he needed to make a decision, and it had seemed so effortless. And then I did my first one on my own, and halfway through the conversation, I realized that I had no idea what to ask next. The company was interesting, but I didn’t know if it was venture capital interesting, or just interesting to me as a lover of startups. What I lacked was the intuition, developed through hundreds of meetings, to determine what made a good investment and what didn’t. As a mentor once told me: “During the first six months of venture capital, you love everything. During the next six months, you hate everything. Then you start to balance out.”

This was a second common struggle that seasoned advisors spoke about. The problem was simply that neophyte insurance and financial advisors didn’t know what they were looking out for when talking to prospective clients. In the early days, it’s really hard to get the right information or even know what the right questions to ask are. A junior advisor may focus on the right key information necessary to generate policy pricing for a client, but completely fail to convince a prospect that these policies will solve a specific pain point because they simply don’t know that pain exists. Or they may receive an “it’s fine” response to existing policies and give up, not knowing how to dig in on what issues a client may actually have that they could service or address appropriately.

It’s not that young advisors aren’t listening, it’s that they just don’t recognize what they should be listening for.

So how do you figure out what to focus on?

Well, there’s a few things you can do. First, this is why I previously talked about targeting a specific niche when starting out in the insurance industry. It helps you really understand the troubles that your clients are having, because many of these troubles are both industry-specific and widespread across an industry. It’s way easier to really learn the customs, norms, and issues of one industry, instead of trying to learn them for many industries.

A second tip is to engage in active listening. Ask open ended questions and really LISTEN to the responses. Often, instead of investing the time in really listening to the prospect, junior advisors rush to make the sale instead. This is problematic, because it often leads to missing an opportunity where you could really add value to your client’s life. You must go into every conversation ready to listen to the problem before you decide you know what the solution is. It’s the old adage: “when all you have is a hammer, everything looks like a nail.” You need to avoid that. Instead, you want to spend more time just asking questions and really trying to drill down to the root issues a prospect may be having. Think about selling later.

At Finaeo, we ask our sales development reps to do something similar. When they come across an advisor who is using a competitive product they haven’t seen before, we tell them to forget trying to sell the advisor on Finaeo. Instead, we want our salespeople to do market research with the advisor and learn everything they can about the competitive product. What happens is that they start to dig into it and, before you know it, the advisor is telling them his or her biggest issues with the competitor. And if Finaeo solves that issue, our rep is one step closer to creating another happy client. The exact same is true for insurance prospects – many times, they have real pain points a young advisor could solve. But if you don’t actively listen, you’ll never find out.

Young advisors should also focus on taking down good notes while listening. Do this either during the meeting or, if you have a good memory, right when it ends. The goal is to have something to analyze. Whether you win or lose the prospect, analyze the notes. Try to look for patterns amongst clients. Are there certain questions you ask which really warm them up to you and get a good conversation flowing? Are there problems you’ve seen across the board that you can figure out a solution to for the next time? Be very analytical and organized about the process and pretty quickly you’ll have a solid set of questions and discussion pieces that you know to focus on.

Struggle #3: Not Enough Touch-Points to Maintain Relationships After the Close

Recently, I talked to a CEO at a company which deals directly with life insurance advisors. He had recently purchased a study by LIMRA that stated the average client will go through seven life insurance policies with SIX different advisors through their lifetime. Think about that: you go through all the work of winning a client, and said client will, on average, only stay with you 16.67% of the time. But this isn’t the client’s fault. This is the fault of advisors who don’t understand that insurance shouldn’t be treated as a one-and-done situation. Really good insurance advisors invest heavily in their relationships after the close.

One of the guys on our team currently has a term 10 life insurance policy. Because he’s in the space, he knows all the particularities of his product and he recently discovered that his term 10 can be converted to a term 20 product for a few extra dollars per month. To him, that’s a no-brainer. He wants the extra ten years of coverage and is willing to pay the few dollars more per month. Meanwhile, the advisor who sold him his term 10 policy has yet to contact him about this conversion potential. So what we have here is a situation where someone is more than happy to pay more every month, and stick around for longer with his current advisor, but the advisor isn’t proactively courting him for business. And in individual benefits, this is commonplace. The struggle that young advisors face is finding the right balance of touch-points to maintain relationships with existing clients. After all, converting a new prospect into a client is almost always harder than up-selling an existing client.=

So what touch-points should you focus on?

Unfortunately, there’s no one-size-fits-all response to this question. However, there are a few tricks to help you out. First off, remember important dates – policy anniversaries, birthdays, Christmas, these are all great moments to make a quick phone call and check up on the client. See how things are going. Figure out if any life events have taken place that have created a new pain or a new need.

Likewise, use other tools to keep track of important dates and product information about your clients. For example, Finaeo helps individual insurance advisors keep track of  conversion limitations and expirations, as well as end-of-level periods. It also helps keep track of birthdays and annual renewal dates so you stay informed. All of a sudden, when a client turns 45, you know and are prompted to approach them about other insurance products such as long term care. Or adding them on Facebook can let you keep tabs on important life events like a new child, new house, or new job.

In the end, it’s all about process. Whether you use technology or stick to pen & paper, you need to set up a cadence of touch-points and stick to it. The number of newer insurance advisors who tell me they need to be doing annual reviews but don’t is staggering. The struggle of maintaining clients is real and it plagues young advisors, but it is also an incredible opportunity to build long-lasting relationships that will last for decades. Great advisors do this, and young advisors should as well.


For this week, I’d like you to pick one business task that makes you uncomfortable but would be very valuable for growing your book. Schedule working on it for the entire week, one hour per day. See how it feels to challenge yourself towards doing something you dislike! See what business value you can gain from it. And consider whether it was as bad to do on Friday as it was on Monday. Let me know your thoughts!