How to Teach a Millennial the Art of Selling

September 25, 2018

How to Teach a Millennial the Art of Selling

Editor’s Note: This guest post was contributed by Sean Bisceglia, Operating Partner, Sterling Partner’s Education Opportunity Fund.


We have all heard about how Millennials communicate. The new generation of digital natives tends to rely on text messaging with a vocabulary of shorthand — IDK, LOL, BTW. Anyone with kids knows the drill.

They also use social media such as Snapchat and Instagram to make their communication an even more exaggerated version of shorthand. And many of them have moved beyond email. It’s common to read articles about how this generation has fostered a new kind of communication in the workplace, which is more digital and less face-to-face.

But the unanswered question remains: how does this style of communication hold up in the world of sales, which depends so much on interpersonal relationships and the soft skills that make that possible? After all, people buy from people.

Millennials are truly at the starting gate when it comes to this critical business discipline. But they’re fast learners and adapt easily. With practice, they can master the nuances of one-to-one persuasion.

Teaching Millennials the soft skills of selling

It’s one thing to be brilliant with technology — and there are jobs for that. But it’s a whole other dynamic, when it comes to developing the soft skills required to nurture a lead, get a prospect to agree to that first call and then stand before a client and make a convincing sale. That requires persistence, the ability to listen and a deft touch in both written and spoken communications.

A typical sale doesn’t close quickly; often it’s the result of a relationship that evolves over time. Whether it’s technology solutions, machinery, coaching or real estate, the sales cycle is lengthy — often 6 to 12 months or longer — and requires a strategy, persistence and lots of personal engagement.

Overcoming an age and experience gap

Think about it, the audience could be a product manager, a category manager or a C-level executive. Those in a position to buy and make a decision are typically older and more experienced. This can create a communication style gap. The buying group will have a decade or more of professional experience and often come from an educational background focused on the liberal arts, where writing and communication skills were stressed.

On the opposite side of the table sits a 20-something who may expect to communicate via text or some live-onscreen app such as Zoom, ReadyTalk or Join.me. Millennials are learning that the selling cycle, which research says requires up to 13 touch points, also demands a nuanced set of skills that are new to this digital generation.

In other words, technology alone can be too easy to disregard. How many times a day do working people simply trash solicitation emails? Even if the email makes it past spam, it’s an interruption that gets pushed away. Personal engagement is the mission.

So it takes a combination of emails, networking, and phone calls to turn a lead into a conversation and ultimately into a person-to-person presentation that results in a sale. It’s strategic. It’s time consuming. And it requires training.

Sales training is coming back with corporate universities. Many corporations like Boeing, Allstate, Apple, and others are investing in corporate universities — a powerful tool for employee retention. It just makes sense when you consider that 25% of Millennials have worked at five or more organizations, and 60% have worked at two to four. An investment in sales training can pay for itself, because it kills two birds with one stone. You cut down on recruiting expenses, while providing the training in soft skills people need to close a deal.

There is no shortcut to effective selling. It’s about building relationships over an extended period of time. If corporate universities can teach these essential soft skills, they’ll reap the benefit in higher revenues.

Four key pointers on transforming Millennials into sales people

  1. Drop the stereotypes about Millennials; they can learn to sell. We’ve all heard the clichés. They need safe spaces and a trophy for showing up, They insist on work-life balance, and they lack discipline. But from my experience, training young sales professionals, there are as many Type-A personalities in this group as there are in any. Establish a process that identifies the most motivated candidates.
  2. Help them understand it’s a persistence game. Forty percent of sales people say prospecting is the most challenging part of their job. Make sure Millennials in training know it’s a marathon, not a sprint.
  3. Train them to engage in conversation. Selling is more about one-on-one communication than it is about digital messaging. Sales statistics say it takes 18 calls to actually connect with a buyer — and this is a 2018 data point. Millennials will welcome the challenge to amp up their verbal skills. Conversation leads to conversion.
  4. Stress the importance of vocal communication. Only 24% of emails are opened. A follow-up phone call is essential since email solicitations often go to spam.



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