Connections to Experts: Connecting Generations in Business

Article by:
Staff EO Global
EO Global

One of the most important parts of running a business is effectively managing various generations of employees. This is especially true when working with today’s youth, which require a unique set of skills. Octane sat down with generational thought leader Jason Dorsey—the Gen Y Guy®—to discuss how to manage Gen Yers (people born between 1977 and 1995) and build generational bridges.

What insights can you offer those who are struggling to connect generations for business growth?
JD: The biggest insight for entrepreneurs is that the generational divide they’re experiencing is a perfect opportunity to beat the competition. Gen Yers, also known as “Millennials,” are flooding the workplace and the marketplace— and it’s only going to get worse. This new generation brings a completely different view that is confounding the best executives and salespeople. The opportunity for entrepreneurs is to adapt to make the most of Gen Y before the competition does.

What are some secrets to managing Gen Yers?
JD: To make the most of Gen Y employees and help them overcome their sense of entitlement, there are some tactics that work like magic. For starters, be candid with Gen Y prospects about the day-to-day responsibilities of the job they seek. Entitled Gen Yers often have a rose-colored view of employment; show them that they have a big future in your company, but that it comes with mastering each position. Many Gen Yers think that within a week’s time they’re ready for a promotion simply because they can do the job. Set the expectation around mastering the position and calibrate their expectations around effort, not just a weekly calendar. Finally, create a mini-talent-development program. This could be a quarterly project or meeting. Gen Yers will think that they have the talent needed and will step up their performance in order to prove themselves right.

What are some common mistakes you’ve seen entrepreneurs make when it comes to managing Gen Y employees?
JD: The biggest mistake entrepreneurs make with Gen Y employees is assuming that they know more than they do. This comes from the fact that other generations started working at a much younger age than Gen Y. The best thing you can do to solve this problem is to provide specific examples of the performance that you expect. Start by making a list of the 10 things new hires do that absolutely annoy you and waste your time. Then make an example of each that is scalable, such as a photo for dress code and a video for customer service. These should become part of your orientation program. The result is that the Gen Y new hires learn faster, you save time because you’re no longer hand holding and you can immediately hold them accountable. Everybody wins!

If you could give our members one piece of advice when it comes to building generational bridges in business, what would it be?
JD: Make the first day of employment with your company unforgettable. Gen Yers decide on their very first day whether or not they can stay long-term. Here are three more ideas: Have someone about the same age as the new hire welcome them and give them a tour. These peer-to-peer tours always lead to more significant first-day questions than a tour from a boss or non-peer. Also, when the Gen Yer arrives at work, present them with a tiny box. They open this tiny box in front of you and find inside six pre-printed, temporary business cards with their name already on it. This gives you, as their boss, complete permission to say, “Welcome to the team. You now represent us just as we now represent you.” Who is the first person a Gen Yer is going to give their business card to? Their mom! And many of them will give it to her when she picks them up from work!

An acclaimed speaker, bestselling author and generational thought leader, Jason Dorsey has delivered 2,000 speeches around the world, including many for EO events. He’s also a Gen Y entrepreneur who texts his mom every day. Watch him in action at

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