It feels like we are bombarded with stories about how the cultural differences between generations (Boomers, Xs, Millenials, Zs).
Our team is lucky to interact with sellers from across all generations. Through those experiences, we have gotten to see where the stereotypes fit and where myths are rampant.
While there are certainly nuances between sellers of different age cohorts, we are seeing that salespeople share a lot of things in common. You don’t necessarily need a separate playbook for all the different groups on your team to be able to drive engagement and strong performance.
Here are some tried and true ways to drive alignment and results with salespeople at all stages of their careers, across all kinds of industries:
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Salespeople want to learn from each other
This is true whether they’re 25 or 55. While their styles may differ, every rep values peer insight. That’s why we encourage clients to create more intentional spaces for salespeople to connect such as peer roundtables, collaborative team meetings, even structured call reviews. These kinds of collaboration isn’t just “nice to have,” they build confidence, spark new ideas, and create shared language across generations.
The key is to make it feel reciprocal for all of the reps involved, not just “the veterans teaching the rookies.” This creates an open exchange of what’s working in real time.
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They want their voice to be heard
Salespeople are closest to the customer. They know what’s resonating and what’s falling flat. Yet too often, their insights don’t make it into leadership conversations. If you want stronger engagement, you must create a feedback loop with your frontlines.
Ask what’s getting in their way and involve them in shaping product rollouts or messaging tweaks. When sellers see that their input is taken seriously, their buy-in goes up rapidly.
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They respond to evidence, not just enthusiasm
It’s easy to kick off a new initiative with energy and ambition. But excitement alone doesn’t move the sales team. Before they buy in, reps want to know it actually works. That doesn’t mean you need mountains of data. A single proof point can shift perspective: a quick story from a peer, a client win, or even a few early results from the field. No matter what generation they’re from, sellers don’t want to be sold on hope. They want evidence they can trust. They’re not signing up to experiment with their customers.
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Keep it simple
Salespeople, by nature, are focused on outcomes. They don’t have time to sift through decks or dig through dense emails. If you want their attention, earn it with clarity. Use simple concepts, memorable phrases, and clean visuals so that your sales people, regardless of their age, can earn clarity. If they can’t explain your message back to a customer in 30 seconds, it’s probably too complicated.
At the end of the day, generational differences matter but not as much as some think. Salespeople want to succeed, they want to be heard, supported, and equipped. If you can build a culture that does those things well, it’ll resonate with every generation on your team.
And you might be surprised by how much they learn from each other in the process.
