Leading Sales Across Generations – Boomers to Millennials to Gen Z and Back.

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Leading Sales Across Generations – Boomers to Millennials to Gen Z and Back.

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Are you responsible to sell across the five generations active in our workforce today? Surprising to some, nearly every professional has some sales responsibility, from selling themselves, to selling project ideas, and of course to include those who occupy full time sales positions. It is important to keep in mind that a one size fits all model created by a boomer without consideration for gen Z buyers will struggle just like a smartphone app developed by gen Z may not be ever be downloaded by a traditional.


I don’t want to confuse medium with message, brand promise with value proposition, or the nature of transactional sales as compared to consultative sales. What I am offering are three general characteristics to keep in mind when reaching across any of the five active workforce generations.

Anticipate conditions of satisfaction: To suggest you “put yourself in their shoes” may seem to be over simplifying things, but that should probably be one of your first objectives. Assuming what you are selling reaches across all generations, consider what differences will exist and what will reduce concerns or refusals. Make every attempt to view your product or service through their lens. Think gen Z selling a tablet computer to a just retired traditional.

Understand relationship parameters: Connecting with the customer and building relationships will vary. Gen Z may be thrilled to explore communicating through a follow-up text message while earlier generations may believe in eye-to-eye, face-to-face, handshakes and hard copy signatures. Always consider every customer touch point from brick and mortar buildings, to websites, to personal interactions. The value of touch points are critical, a gen Z will expect to see your website on mobile, while a traditional may expect a personal visit. Build the relationship their way, not yours.

Never waste their time: What constitutes a waste of time? It may depend on the generation. A meeting with a traditional that incorporates background and theory of the goods and services (which takes more time) may feel like a very appropriate and well invested use of time. On the other hand a 30 second elevator pitch may be all a millennial or gen Z needs to hear. This doesn’t suggest who is correct or who makes better decisions but it does suggest there are differences. Seek commonalities by considering how time is valued across the generational continuum.

A boomers satisfaction in an automobile purchase may be very different from gen Z. A real estate (home) purchase by traditionals may be very different as compared to millennials. Methods for consultative sales versus transactional sales should be carefully considered and will definitely impact your approach. Mediums, branding, and value propositions also need careful consideration and if you’re spanning all generations be sure to seek commonalities not just develop a focus on differences.

As with everything related to selling, communicating, or working across the generations there are variances in personal style regardless of the generation and in many cases there are variances from day-to-day, or even across weeks or months since schedules, job pressures, and even amounts of sleep may condition both personal and professional interactions.


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 DennisEGilbert.com or by calling +1 646.546.5553.

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February 9, 2016at 8:35 am

Hi Dennis!

I’m curious, which generation does your research and experience find to be most positive and most negative regarding their approach to life.

Thanks in advance,


    February 9, 2016at 9:01 am

    I’m not sure if there is one. I say that because there are so many factors that go into being positive or negative. You could argue that an unemployed boomer may express negativity about finding reasonable employment, but you could make that same argument about a millennial or gen Z who has a lot of college debt and is also seeking employment. Of course employment or lack of is just an example. Regarding life, other personal or professional setbacks may influence the mindset of any generation. Do you have a generation in mind?

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