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Collaborative Selling, Part VI

Best Practices for Ensuring Selling Success Across Generations

By Theresa Caragol, Achieve Unite Founder & CEO


Darn Millennials, they're changing everything! If you're a Baby Boomer or a Gen Xer, you've probably said this a time of two out of frustration. If you're a Millennial, you've probably said this out of admiration for your fellow Millennials. The truth is, you're all right. It's the reality of the multi-generational world in which we live – and work – together.

In this post, we explore the dynamics of building trust across generations and recommend three best practices to maximize your success. We hope that you find it enlightening and maybe, just maybe, help the different generations across your workplace understand and work better with each other and with customers.

Jim Schwartz, Sr Director, Global Channel Programs, Sungard AS

• • •

Selling success hinges on understanding who your customers are, and today more than ever before, this means building trust across generations. Not only does today's IT workforce comprise the widest age range of workers ever seen before, but dynamics have also shifted as Millennials represent an increasingly larger portion of the industry.

In fact, according to CompTIA research, Millennials will dominate the workforce, accounting for 52% of target customers by 2022. These changes in workforce composition affect collaborative selling strategies, necessitating a review of communication mediums, communication styles and personal motivators to ensure we continue to deliver dynamic, customized solutions for our customers (see chart).

Today's IT Workforce
Generation Level of Tech Knowledge Communication Preference
Baby Boomers 4% use the latest technology* Face to Face or Email
Generation X 21% use the latest technology* Text or IM
Millennials 30% use cutting-edge technology* Social Media
*According to 2017 CompTIA study.

3 Best Practices to Model with Your Customers


Collaborative selling rests on developing trust and synergy across generations. We find these 3 best practices particularly helpful:

  1. Understand their personal values and drivers: When building relationships, it's a good practice to ask open-ended questions to get the conversation going. As you do this, you should seek to understand their business objectives as well as their personal objectives. Doing so will help you understand their personal values, which, in turn, will set the stage for your communication. For instance, if you know you're working with a Millennial who is saving to take a European tour with their friends, helping them make more money so they can take that trip will be powerful. On the other hand, if you're dealing with a Gen-Xer with small children at home, you might want to limit communication on nights and weekends.

  2. Establish Your Personal Brand: In addition to understanding one's personal motivation, you should also establish your own personal brand. According to Karen Leland, author of The Brand Mapping Strategy, "A strong personal brand goes beyond what's seen and said on the surface to a deep expression of values, purpose and contribution – all backed up by action." No matter how you're communicating, you should be authentic to your brand and be professional. This will ensure that your message is received in a positive way by any generation.

  3. Use the Appropriate Communication Medium: Developing multi-generational communication techniques will also help you with your customer communications. For instance, don't rely only on email for customer communications. If you solely communicate on email, you may miss non-verbal communication queues that might lead to miscommunication. It would be a wise idea to ask your customers their preferred mode of communication. You should also consider replying to communications they initiate with the same medium. So, if they call you with a question, don't email them back with the response. They could perceive this as a lack of respect. Also, as you craft your messages, be cognizant of your level of formality and style of communicating. It's a wise idea to observe your customer's level of formality and communication style and try to mirror that.
Ultimately, understanding the generational dynamics in the workforces will enable you to more successfully connect with anyone. By leveraging your personal brand, you will convey authenticity and professionalism. Using your insights into generational preferences and proactive communication skills will enable you to choose the right communication mediums, messages and styles to connect with your customers in a meaningful way.





Theresa Caragol is founder and CEO of TCC, LLC, and Achieve Unite, a strategic advisory firm that provides business acceleration services to global enterprise. She has more than 20 years' experience in building and managing multi-million-dollar indirect channel teams and strategic alliance business and programs from inception to sales success. Prior to founding TCC, Theresa held senior executive roles at Extreme Networks, Ciena and Nortel.

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