generations in business

Unlocking the Secrets: How to Effectively Engage and Sell to Five Distinct Generations

Posted in: Hiring Salespeople

Discovering the right salesperson for your business can be challenging. It’s essential to consider your company’s sales culture and the type of salesperson you need, such as a Hunter, SDR/BDR, Channel Manager, Account Manager, or Farmer. However, it’s crucial to recognize that selling to different generations requires various approaches.

For the first time in history, five very different generational types are working – and each wants to be sold differently.

Bridging the Generational Gap


Everyone’s living longer, and many senior executives in their 70s and 80s have no interest in going out to pasture and retiring. They’ve got their hands firmly on the reins of their company or department and won’t make room for the people behind them.
Traditionals like to be sold by face time. And we don’t mean Apple FaceTime. We mean face-to-face business. They want to be taken out for steaks and drinks. They want to play golf with you and be treated as loyal and valuable customers. If you’ve got many of these customers, an essential sales skill set will be the ability to play golf with a low handicap.


We’re all tired of hearing about this over-indulged group. But many are now CEOs, CSOs, or at least one step away (if the Traditionals ever retire). Boomers will communicate and do business on an old, 20th-century device called the telephone. They’ll even do video conferencing. They think they’re hip and efficient and won’t kill an entire day playing golf just to win a sale possibly.


The first generation that’s reasonably comfortable with technology. They’re the people who installed and ran many of the software platforms the business runs on. But they’re very used to what they’re used to, which is first-generation tech. Microsoft Office. Outlook. Dropbox. They email with attachments. HUGE attachments. They were the leading edge that was fast becoming the trailing end.

Millennials (GenY)

The first genuinely high-tech generation. And they’re a bit like their grandparents (Boomers) because they want to be indulged and catered to. But their platform of choice is texting. Along with all its cousins: Twitter. Instagram. YouTube and the like.


Born just at the turn of the century, this generation grew up with iPhones in their elementary school backpacks and gaming devices in the back seat. They assume a confident, know-it-all attitude and are contemptuous of first-gen tech users. They don’t have home phones. They don’t have cable TV (and increasingly don’t even own one). They may not have a direct office extension. They don’t own a desktop computer. And all their software lives in the cloud. They pretend to know what they’re doing, but they’re secretly insecure because, while they understand tech intuitively, they were never taught how business works. So they make it up as they go along.

As outlined above, crafting Sales Strategies for a Five-Generation Workforce in the Modern Era has unique challenges. The Traditional generation prefers face-to-face interaction and golf outings. At the same time, Boomers are comfortable with phone calls and video conferencing. GenX gravitates toward first-generation technology, Millennials love texting and social media, and GenZ lives in the cloud and prefers intuitive tech, yet they must learn how the business operates.
Remember all these details when hiring and assembling your sales team so that your team can match Hunters, SDRs/BDRs, Channel Managers, Account Managers, and Farmers to generational prospects that are a good fit generationally and culturally.
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