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Converging Generations in Your Sales Team

Updated: Jun 13, 2023

Published on September 14, 2022


Recently I found myself in a small group of business leaders who confided in me that they were having trouble relating to some of the younger generation members on their sales teams. They were acknowledging that the values within their diverse teams simply weren’t aligned like they once were.


There was no question that they saw the unique value the new generations brought to their companies. These top executives diagnosed the problem being... ‘THEMSELVES’ and their own struggle to learn how to effectively lead the convergence of multi-generations in their organizations.


Exploring this further with my Fractional Sales Leader colleagues across North America, we found this struggle broadly effecting seasoned sales leaders. Collectively, we captured our learnings around how to navigate the fact that varying age groups naturally have different work styles and intrinsic motivators.


Multi-Generations Impact to Business


Looking back through the ages, not being able to relate to a younger generation is not new. The difference today is that we are living through a rare time in history where age diversity is at its most prevalent. The exciting part about that is that many are sitting on the opportunity of a lifetime as a team leader.


We can view differing social group characteristics as powerful clues by not putting any of the generations ‘in a box’. Therefore, it’s important to know the years when each generation begins and ends. It should be noted that studies have proven that you can be born within three years on either side of the beginning or ending of a generation and have characteristics of the generation before or after.




Sales Transparency Evolution


One of the biggest business changes in the last two decades has been the introduction of systems and tools providing transparency to business workings like never before. In the world of sales, this translates into greater accountability through metric-driven performance indicators.


If you haven’t established this level of visibility yet, gain helpful guidance from my previous article, Does Your Sales Dashboard Provide Powerful Insight?.


In the past, it was common for a sales team to have that one “untouchable” salesperson in their ranks. You know the one. They landed a few large customers many years ago and have been consumed in account management activities on these profitable accounts ever since, doing little-to-no new business development.


This was an accepted practice in many businesses for a long time. But, as owners and sales leaders gain more visibility into the everyday actions of their sellers, expectations for ongoing sales contribution have increased. Some salespeople chafe at that level of oversight, but most understand it is the new way of doing business given how it has proven to achieve stronger results.


Sales activity transparency for most in the younger generation has been an easy concept to embrace because they are coming from an upbringing where social media transparency is a way of life. They are used to being “an open book” and tend to easily adapt to the objective of capturing sales activity real-time as they navigate their day.


After all, most professionals born in the mid-1990s and after function almost entirely paperless in their personal lives.


In fact, they seem rather baffled by their more seasoned colleagues who seem to “want” all that paper by doing things like collecting a receipt after they buy a cup of coffee or printing a bill they paid online.


Our younger generate is agile and travels light!


Best Practices Come in All Forms


One of the most impactful things I have experienced as a sales leader is the outcomes that come from the convergence of bringing diverse people together. In this case, we’re focusing on diversity as it relates to multi-generations.


However, rich learning only happens when a leader cultivates and fosters an environment of best practice sharing. Team members need to be open to recognizing that ‘best practices’ don’t require decades of experience to develop. There is value in the fresh thinking of our younger generation and the different ways they communicate in our society.


I’ve seen both ends of the spectrum experiment with the other’s sales best practices. For example… Gen Z’ers schmoozing on a golf course to win business. I’ve had Boomer's text with a new lead until they converted into a prospect who was ready to sit-down and discuss a new opportunity.


As leaders, our job is to find a way to relate to our team members as individuals, discover what motivates them to perform, and arm them with methods that can help them succeed.


I’ve also seen some fulfil the stereotypes that accompany each generation. But – not in a negative way!


Things like Millennials adopting to technology at an accelerated speed and realizing early success by ramping up quickly.


Gen Zers breaking down doors with unique social media tactics and establishing trusting relationship faster than most.


Boomers landing big deals by leveraging their wealth of industry experience to understand ‘the real’ concerns of their customers.


Each of these groups have valuable ideas and approaches that can be showcased and taught to others on the sales team.


Shift in Intrinsic Motivators


If you find yourself having a hard time understanding how younger generation professionals are approaching their work, let’s look at what truly drives their actions. Starting with money - a primary motivator for salespeople of all ages.


Younger generations tend to be savvier in conducting compensation research online and through their social communities. They also don’t tend to approach a new position with the thought that they’ll do everything in their power to make this a long-term stay.


The younger professional has been groomed for quick gratification and is hungry to be compensated based on their performance. I’m not suggesting you must pay the maximum salary listed in an online survey, but you do need to understand the candidate is probably looking through this lens.


The strong performers that are geared for sales are not going to stick around for average pay, so you need to get creative. Such as…

  • Reward hard work with mini promotions and title changes

  • Additional time off

  • Provide full or hybrid remote work options

  • Offer unique benefits that are high impact


Provide the job that treats its employees so well they have no reason to look for better opportunities elsewhere.


Sales performance requirements haven’t changed from generation-to-generation but the value drivers that motivate performance have.

Our younger generation has a stronger commitment to finding work that provides them a healthy work-life balance. That means you will find fewer people willing to put in extra hours. Or if they are willing, they expect more than just a thank you. They expect the extra work will be rewarded in some way such as the examples I referenced above.


Embrace the Differences


Ultimately, I have found that leading people hasn’t changed. You need to have goals and a plan to help your team achieve them. The key to coaching for success is understanding the seller’s motivations and what drives them to do better, no matter who you have working with you.


If you haven’t already, it’s time to move past the out-of-touch avocado toast type commentary relating to the different habits and styles of our young people.


Instead, we need to invest all our energy in tapping into the unique talents of all the members on our teams to find ways to coach them to their full potential. Even more, we can unlock something really special when we successfully converge the generations within our teams.


Take my Sales Leadership Assessment at no charge to gain visibility into how your skills rank in 10 high-impact areas. This self-serve tool was custom developed to help you improve!



If you’d like to discuss assessing your sales team in more detail or chat about the improvement you’re looking for in your business, contact us at info@sxwisconsin.com or fill out our Contact Us form.


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We are part of a national group of Senior Sales Leaders who collaborate to share insights like the examples shown in this article. We formed because of our shared passion to help business leaders exponentially grow their revenue.

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