Can Millennials Sell To Boomers?

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Can Millennials Sell To Boomers?

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The easy answer is, yes. The harder answer is that selling across the generations may require a certain amount of interpersonal finesse. Many people quickly recognize that there are some differences when selling across the generations and some will quickly jump on the idea that the use of (or lack of use of) technology is a big reason for gaps between earlier generations and later generations. Perhaps technology is a barrier, but even the rival political baby boomers, Hillary Clinton, and Donald J. Trump, tweet.

business woman with her staff in background at office

So what works best? The psychographics associated with any generation can certainly keep the best of the best on their toes, but here are five tips that will help millennials reach across the generational framework when selling to boomers.

  1. Eliminate hoops. Most buyers don’t like jumping through hoops and the boomer generation will quickly get frustrated with any hoops they are expected to jump through. Technology is big for this; things like automated telephone systems, website pop-ups, and multiple log-ins for information are a definite turn off. Most boomers are also not inspired by the mobile phone app craze.
  2. Social proof is not a big factor. Depending on what you are selling, social proof may not be all that important to a boomer. While there is a trend towards seeking information and reviews on-line before making buying decisions, the boomer generation will often resort to old school word of mouth when considering their final buying choice.
  3. Place experience over technology. Millennials and generation 9/11 (Gen Z, iGen) will likely have the most interest in technology oriented solutions while boomers are going to feel more comfortable with what has proven itself in the past. Boomers don’t necessarily want new, they want tested, proven, and trusted. For this reason, talking their language instead of forcing yours will yield the best results.
  4. Believe in what you are selling. This is universal for selling to any generation, including your own. When you are passionate and truly believe in what you are selling others feel it, and for you, it may feel like you aren’t selling at all.
  5. Don’t give up quickly. Boomers have a soft spot for demonstrated effort. Of course, that doesn’t mean they like being pestered, but being appropriately persistent can be a plus. Remember that some stereotypes exist throughout the generations that the more recent generations don’t work hard or value hard work. Be resilient to impress the boomer.

Lastly, remember that many factors go into conditioning the values and beliefs of any generation, including things like rural versus urban living, espoused parental values, and geographic location. Not every person in any generation will fit the generalized values and beliefs the experts often describe, but popular wisdom supports the notion that many do.

Consider these tips and watch your sales to boomers, boom!


Dennis E. Gilbert is a business consultant, speaker, and coach that specializes in helping businesses and individuals accelerate their leadership, their team, and their success. He is the author of the newly released book, Forgotten Respect, Navigating A Multigenerational Workforce. Reach him through his website at or by calling +1 646.546.5553.

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January 28, 2016at 11:23 am

Hi Dennis!

It sure would be nice if you said the ages of the generations with their name.

That would help a boomer like myself learn and remember this material.

Much Appreciated!

Very interesting material.

Is there a one size fits all recommendation (rule of thumb) for interacting successfully across the generation ?


    January 28, 2016at 12:11 pm

    Hi – the generations framework is able to be clicked on in the text. It is a hyperlink. Does that help? Here is the link:


      January 28, 2016at 12:31 pm

      Nope, rather clearly and easily see it in the message.
      Don’t like hoops 🙂
      Thanks anyway.

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