Better Understanding Generations To Enhance Sales
Oscar Toledo
May 2017

It was only a few minutes before the client seminar began, and as my team prepared to present I noticed something I had not seen in my 18 years in the business. I have done a number of client seminars throughout the years and have experienced strong success with them. Because where else can you get 25 clients/prospects in one place and commit to a meeting with you at the same time?

So, what was this new vision at my event? In the door walked a young prospect in his early 20s. When we advertised the event, we were very specific in the age demographic we targeted; it was baby boomers. But here is a 20-something walking in and sitting down. I asked myself if he was going to be a distraction. The answer panned out quickly.  Yes, he was a distraction.

He was actually responding to the questions being asked by the speaker and I was impressed with his answers. It turned out he was a teacher in the local school district and he was interested in life insurance. And not just term insurance, but it was an indexed universal life policy. It’s at that moment a light bulb went off! I need to be more open-minded about Millennials.

Am I asking you to make Millennials your primary market? Absolutely not!

I’m asking you to accept the fact that our market space continues to evolve. The better you understand that different generations have very distinct views about products, politics, religion, careers, and just about everything else, the more successful you will become. 

Here is some insight that may help you prepare to understand and better relate to different generations—the Matures, Baby Boomers, Generation X and the Millennials.

First, it’s important to understand a customer’s decision to buy is usually about 85 percent emotional and 15 percent rational.1   There is no question that the more we can connect to the prospect, the greater our success. The two qualities that stand out in order to have this connection are likability and respect. Respect can be built by knowing our business—a strong understanding of the products and industry. Likability can be more elusive. It’s one of those things that seem to be there with some and not with others. It’s this sense of likability that would make the prospect’s shoulders drop during the initial appointment.

Other times, however, it seems more difficult and this happens most often with customers who are of different ages and backgrounds than our own. As a young insurance agent in his 30s, who also happens to be a minority, I had to demonstrate my knowledge of the industry (respect) and I had to figure a way to connect with them quickly (likability). One of the methods I found most useful is understanding the generation I’m speaking to and learning to speak their language. I want to connect with all my prospects, regardless of age. You see, I understand it is human nature to sell and communicate based on our own perspectives. However, the type of planning I have done for my family may not align with yours. 

Especially when I come from a different background. It’s best to understand how customers’ backgrounds affect their buying preferences and not to assume all customers prefer to buy the same way I do.

Occasionally during the sales process I show my clients my personal policies, which consist of life insurance and an annuity. I do this to show them my belief in the products. But when I’m asked which one I own and if it’s available to them, I remind them not all circumstances are the same. 

Beware: Sales techniques that are effective for one generation may come off as “pushy” for another. Generational differences are more significant in marketing and selling now than at any other time in our history. For one thing there are currently more generations alive and active than ever before, as modern medicine and affluence have produced a revolution in longevity.

Let’s break each generation into sections and point out some quick tips on how to best work with them in general:

Matures, born before 1946
The Matures are really a composite generation of several groups, all born before the end of World War II. This includes the Veterans, also known as the G.I. Generation (born before 1925) and the Silent Generation (born between 1925 and 1945).

Baby Boomers, born 1946-1964
They get their name from the remarkable “boom” in the birthrate following World War II. As this exceptionally large generation has moved through each life stage, it has reshaped ideas about youth, education, work and aging.

Selling Tips:

  • Show your credentials.
  • Be part of their team.
  • Be optimistic.
  • Customize their solution.
  • Clearly explain your solutions and do it in person.

Generation X, born 1965-1979
In 2017, the start of Gen X is turning 52 and needs to be fully focused on creating a retirement plan. They were originally known as the “Baby Bust” due to the decline in birth rates that resulted from birth control’s wide availability during the 1960s. Gen Xers grew up with less economic and family security than the Boomers, often in households with divorced or two working parents. The advent of the personal computer and Internet during their youth made them the first tech-savvy generation.

Selling Tips:

  • Be quick and efficient.
  • Share everything. Don’t hide anything.
  • Educate them and offer options so they can decide.
  • Target both genders. Many Gen X women are in the workplace and are just as involved in money-making decisions as their spouses.
  • Show concrete benefits—they are pragmatic and want facts.
  • Trust is a must—they want to know you care about them and their personal and financial well-being, so showing your sincerity, commitment and compassion are important.

Millennials, born 1980-2000
The early cusp of the Millennial generation is nearing 40 years of age! Millennials were originally known as the “Echo Boom” because they represent a surge in the number of births that came mainly as a result of the Baby Boomer generation having children of their own. The Baby Boomer and Millennial generations are the two largest generations in American history. Until the emergence of the Millennials, Baby Boomers were considered the most important demographic in commerce, marketing and sales.

Millennials have lived for most of their youth in a time of broad economic and technological expansion. Indeed, ease with technology and telecommunication is one of the hallmarks of Millennials, along with a sense of optimism and entitlement that comes from growing up in an “everybody wins” world that their very attentive parents (Baby Boomers) carefully structured and programmed.

I encourage you to watch Simon Sinek’s video on YouTube titled: “Millennials in the Workplace.” I believe you will gain good insight from this 15-minute video.

Selling Tips:

  • Tell them where to research and let them educate themselves so they can decide.
  • Stay in touch with and through technology.
  • Be a trusted resource and be yourself.
  • Don’t be pushy.
  • They’ll tell you when they’re ready to buy.

Don’t discount Millennials as a sales opportunity. They are the youngest and largest generation in the workforce. They have adopted an understanding that they need to save for retirement. Seventy-two percent of Millennial workers have started saving at the young median age of 22-years-old.2

Selling Across Generational Divides
Of course, generational biases are not ironclad and birth date does not dictate personality. The first step in applying generational tactics in selling is to learn about the generations by becoming familiar with each one’s characteristics, likes and dislikes. Once we do that, we need to understand how to sell across generational divides rather than allowing these differences to short circuit that crucial connection to provide the best service to our clients.

We need to try to understand how customers’ backgrounds affect their buying preferences. As an example, during my fact finder with a prospect I begin with questions such as:

  • Where are you from, and what was it like growing up?
  • What did you learn about money growing up?
  • What was the hardest lesson you’ve had regarding money?

I do this because the information they will share with me during the first half of the meeting will allow me the opportunity to better understand their buying preferences and, just as important, build rapport with them.

Proper Fact Finding Creates Better Understanding and Results
Fact finding is similar to an MRI health scan. It helps you dive deep into your client’s perceptions and financial make-up to better understand them, build rapport, help you understand their financial goals and start to identify how you can help them. Using a well-designed factfinder to understand your prospects and capture what is important to them is a key step in a successful sales process. 

Make the Connection, Reconnect, and Follow-Up
Listen to the needs, wants and goals of your prospects and understand that different generations and individuals have different perceptions and expectations.

Another great opportunity to get good insight is to reconnect with prospects where you didn’t initially close the sale. Give them a call back to ask for just a few minutes of their time and ask a few questions about the process and information you provided to them and sincerely ask: “Could you provide me ideas on how I could improve my process for the future? Do you have suggestions on my process that could have helped you better?” This could help you tremendously and might even open new sales opportunities for you. In addition, be sure to remember to follow-up with your clients on an ongoing basis and ask about new developments or changes in their situation. People’s lives change, parents and spouses may pass away, divorce, health issues, an inheritance, better realization of the need for long term care coverage—all these things can happen in a client’s life and new needs may appear, but they may not reach out to you unless you show an ongoing interest in them.

Consider ways you can remove the focus from your own values and perceptions in order to allow you to focus on your client’s values and perceptions. Then you can start to speak your client’s language.



  1. MarketingProfs -, last accessed 1/17/17.
  2. Transamerica Center for Retirement Studies, August 23, 2016, “Retirement Insecurity: A Multi-Generational View” -, last accessed 1/17/17.

For financial professional use only. Not for use with consumers. The information in this article is for general information only. Always follow your firm’s policies and procedures regarding review and use of third-party templates, creation and distribution of client and prospect materials, hosting of client and prospect events, offering giveaways or prizes, and your firm’s employment process.

Author's Bio
Oscar Toledo
director of sales and marketing, Partners Advantage, has spent 17 years in the insurance industry as a business consultant and in personal production. He has helped hundreds of financial professionals and agencies grow their life, annuity and linked benefits business by providing innovative sales concepts, extensive product knowledge and superior support. He has also qualified for the Million Dollar Round Table for several years as a personal producer. Toledo can be reached via phone: 888-251-5525, ext. 124. Email:

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