In a 21st century where technology continues to break down the barriers of distance & time, it’s becoming ironically difficult to develop old school sales skills with younger personnel. While there is little debate younger workers are more adapt at fusing modern tools to everyday work tasks the reality of our changing times has forced sales departments to place greater focus on the development of rapport building and other sales skills, we used to take for granted.

While social media promised to usher in an era of a more connected humanity, the reality is that Facebook, Twitter, Instagram, TikTok and other platforms are largely “me driven.” Users engage in an ever-competitive contest to gain likes, retweets and exposure for their personal brands to gain clout, whether the rewards are financial or simply vanity-driven. Modern debates on politics are less about finding solutions to our problems but rather how one’s stance on issues reflects on them as individuals. It is more important to be “on the right side of history” than improving the lives of those we claim to champion.

Technology has had a profound impact on the sales process as well. On the plus side, innovation has made it possible to reach target audiences in ways thought unimaginable 20 years ago and, in many cases, we can guide customers from our offerings to the online shopping cart without ever having to interact with another human being. Even when interaction is required, sales funnels & email segmentation make it possible to automate a very complex sales cycle without the need of anyone picking up the phone to move the process along.

This is all well and good for certain brands & models, but most businesses today still require personal interaction and sales professionals to guide prospects through a myriad of options, overcome objections and ultimately close deals. I regularly speak with business owners & entrepreneurs who cite one of their biggest challenges is developing interpersonal rapport & sales skills with their 20-something employees.

sales skills
Despite being constantly glued to our phones, the 3-hour phone call is a thing of the past

For those of us from the “Glengarry Glen Ross” generation, building rapport on the phone was a sales skill we developed during adolescence, when we would spend hours on end courting the object of our affections. Younger professionals came of age in an era where texts, memes and videos became the preferred mode of communication. This has certain advantages, as they tend to be more expeditious and less long-winded than we are but comes with the drawback of having developed intuitive listening skills and the ability to gauge tone and engage prospects via conversation.

In addition, workers who are under 40 are less likely to have gone door-to-door as youngsters selling little league raffle-tickets, newspaper subscriptions and the like which help groom sales skills. In a time of “stranger-danger” even a good portion of Girl Scout Cookies sales efforts are organized by well-meaning but often over-zealous parents.

“Sales is about relationship-management, people management and problem solving,according to serial entrepreneur Gerry Pond. Pond believes universities needs to fill the gaps that a change a culture has helped create. Just as professional careers such as accounting, law & medicine require secondary education so too will future sales organization need young professionals who obtain detailed instruction in the art of sales.

Jamie Scarborough, co-founder of Sales Talent Agency agrees, “young people have got the potential to be great employees in a sales capacity, but they’re not coming out of school completely job-ready.” Irrespective of one’s career choices, Scarborough points out, harnessing a student’s sales skills will benefit young professionals as they enter the work force and begin selling themselves in interviews and promote ideas and initiatives within the workplace.


While we wait for academia to implement much-needed salesmanship to its curriculums, sales organizations must be proactive in training & developing younger sales staff to harness skills we use to take for granted. Below are a but a few key sales skills to focus on that can help even novice sales professionals begin to improve on their ability to connect with prospects and build sustainable relationships.

Ask Questions

In the 2005 smash-hit “The 40 Year-Old Virgin” Seth Rogen’s character, Cal, reveals to a hapless Steve Carell that the key to gaining a woman’s interest is to get them to talk about themselves by asking probing questions. This not only provides for a hilarious scene as Andy (Carell) begins to gain confidence in his pursuit of love but serves as an excellent example of how timid sales professionals can break the ice with a prospect and help develop rapport which can lead to a long-term business relationship.

As Cal points out, people love to talk about themselves. This same principle applies to the sales process as well. One of the campaigns my company, Stafftronix Virtual Assistants, provided for a client was appointment setting services targeting retail business owners. This was a very competitive market in which business owners were regularly bombarded with sales calls & walk-ins from my client’s competitors.

At some stage we adapted more of a “just ask questions” approach in our telemarketing pitch and immediately began seeing increased results. Rather than give the typical “we can save you money” approach we began the conversation by asking probing questions which not only helped us determine if a prospect was adequately qualified, but got the merchant talking about their business, their goals and dreams and this helped us psychologically position them to envision the benefits of the offerings we were presenting.

Listen & Learn
sales skills
Sometimes the best way to sell is to shut up & listen

I often tell salespeople that the greatest tool they possess is not their gift for gab, but their ears. Asking probing questions is a great way to break down resistance and build rapport, but the key is to listen to the answers given. A prospect will often tell you everything you need to know about how to close them if you’re listening intently.

Far too many sales professionals are so focused on their presentation, potential objections and rebuttals that they fail to adequately listen to problems and concerns of their target audience. If you’re involved in a solution-based sale, you can’t provide a solution if you don’t understand the problems your prospect is facing. Listening is a key sales skill to develop with your teams.


Now that questions have been asked and answers have been listened to, its important your sales teams can provide tangible examples of how your company has assisted customers who’ve had similar experiences. This is a sales skill I believe younger workers are better positioned from a cultural perspective to excel in. In a modern society that places such a high value on social awareness, today’s 20-somethings are well-versed in the language of empathy and can use this in their sales approach.

Make sure you prepare your people not only with rebuttals to common objections but with examples of how your company’s products & services have helped your customers overcome problems common to your target audience. By showing how they’ve helped others in a similar situation, your salespeople can establish themselves as a champion to your prospects.

Confidence & Competence

Building rapport with prospective clients is not simply about being likeable, but a sales skill that gains the confidence of your audience. As a sales leader your job is as much about “selling” your team on this as it is a training exercise. If your younger employees buy into your company’s ability to solve customers’ problems, they will gain confidence which is infectious.

This has always been the case but even more important with a generation of young professionals desperately searching for something to believe in. Making the World a Better Place is more than just a mantra, it’s taken on an almost religious tone with many twentysomethings. But once the hubris of the student-activist comes to realize all the world’s ills aren’t solved at the ballot box or some magical policy initiative, that same passion can be transferred to your products and services. While they may not be saving all of mankind, your employees can turn a sales skill into a matter of personal pride in having a positive impact on the people they speak to & deal with every day.


There is no denying that with each generation mankind gains knowledge, makes enhancements, and stands on the shoulders of our forbearers to move humanity to even greater heights. Today’s younger professionals understand and utilize technology in ways that will forever change how the marketplace operates. That said, there are still tried & true methods of salesmanship that are relevant today as they were in the marketplaces of ancient Rome. It is the duty of the sales leader to find ways in which a younger generation can harness old-school methods to build their sales skills and bring success to themselves and your organization.

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