Managing Millennial Sales Reps Without Getting More Gray Hair

By Tom Silk

 I have to admit, I never thought I’d be “the old guy.” But as I became the manager of an inside sales team made up of twenty-somethings, I began to feel some frustration. I would hold meetings and see my Millennial employees looking down at their phones, or calling in from home because they decided they’d be more productive that way.

At first, I found myself wanting to shake my fist and mumble, “In my day …!” Then I realized something: They were taking notes on their phones, and they actually did get work done from home. Slowly, I started to see that the differences in the way they work are not all bad.

In fact, many of them are positive for the future of work culture.

Change Of Pace

Like many others my age (let’s just say quickly approaching 40), I grew up with the generation before me setting the example of showing up early and staying late, regardless of the productivity of those hours. I learned that was how you showed commitment, desire and ability. Once I began to manage others, I adopted those values as a part of my managerial style, but it didn’t take long for me to realize that wasn’t going to work. Today’s twenty-somethings are not following the same path as prior generations.

The easy thing to do is to assume they’re lazy, spoiled or not invested in their jobs. That’s what I did at first; I got angry and questioned the values of an entire generation.

It took a while to realize that some of the ideals that they hold might be superior to those of the generation that had set an example for me. Balancing quality of life against production probably leads to better value and performance than simply being able to say, “I worked 50 hours this week.” We’re in business to get results, not to accumulate hours in an office chair. Employees who can get their goals accomplished more quickly and have more personal time will be more rested and energized to go back at it the next day, or the next week.

3 Ways to Interact Effectively

Incentivizing, communicating with and training with Millennials isn’t difficult, it’s just a little different.

Incentives: Because this generation is so focused on quality of life, the best thing you can do is give them more time to enjoy it. Allow them to have flexibility in their schedules if they are producing the numbers you are looking for. As far as rewards go, this generation is much less focused on “stuff” or trophy value. A recent Wall St. Journal article talked about the fact that Millennials are less into luxury items, like new TVs or designer bags, and instead prefer experiences, like travel or a nice dinner out. They are also much more practical than you’d think — many of them have massive student loans to pay off and will appreciate a grocery gift card or a good old cash bonus, despite what the incentive industry reports in most surveys.

Communications: As for communicating with Millennials, I was brought up to believe that conversations, especially those between a manager and an employee, were best had in person. As I’ve adapted to my younger team members, I’ve embraced texting as a way to get simple points across. It’s not only efficient, it shows your team that you are willing to embrace modern communication methods and interact with them in a way that is most comfortable for them.

Training: This is one area where some old rules still apply. Training a Millennial employee on a product or process is not that much different than it was 20 years ago for other generations, except that the mediums have changed. Now classroom learning has been replaced with on-demand, mobile-based training. This generation doesn’t need any help in using technology to learn; where they do need help is in their interactions with older generations. Some of them have a hard time understanding that if you’re selling to a 60-year old manager of an agricultural business, text messaging might not be the best way to reach out to them. Basically, as a manager I try to teach them empathy. Just because you live through your iPhone does not mean everyone who is trying to communicate with you does the same.

Millennials are not the weird, exotic breed of worker they have been portrayed as in the media. Like every generation before them, they have been shaped by the society and times in which they have grown up. Some of the ways that they prefer to work and communicate seem foreign to us older folks, but it doesn’t mean they’re wrong. In fact, next time you’re thinking about taking the later train so you can have another meeting, send a quick text and head out the door to see your family instead. You might find yourself adopting some of these “annoying” Millennial habits after all. 

Tom Silk is executive vice president of WorkStride. He joined the company as its first salesperson in 2000 and proved instrumental in WorkStride’s early success, bringing on customers such as Pepsico, Samsung and Verizon Wireless as the company built up its recognition and incentive software offering.  In 2004, Tom was promoted to, heading up a nationwide partner network and taking over digital marketing activities, vice president of sales and marketing for the company.