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4 Abilities of the Most Effective Saleperson with Whom I’ve Ever Worked

How does the best salesperson I know separate himself from all the salespeople I’ve met in my career?

Besides selling Goosebump novels and candy to kids on the playground in 3rd grade, the only real sales experience I have is selling Cutco knives. But as a Product Marketer, I work very closely with our entire sales team. From market definition and customer segmentation to crafting product pitches that align with customer needs, much of the marketing that falls under my jurisdiction depends on close collaboration with sales. I’ve seen the messages and processes click with some sales reps, and I’ve seen others reps fail to recognize the message, as well as fail to utilize assets and environments around them to successfully find more opportunities and close more business. The more salespeople I get to work with, the more I have recognized how a salesperson separates from the pack.

Let’s assume everyone has the same access to product information: the same quality-level of prospects, the same sales tools and enablement assets, the same level of caffeination–the set of salespeople are on a level playing field. What separates a salesperson from the pack? Not just barely beat a few reps in their monthly quota. Continuously blow all other reps out of the water.

If you aren’t the lead dog the view moves but never changes.

I currently work with one salesperson that can do 3 things extremely well that propel him beyond others and make him an essential part to not only our monthly-recurring-revenue, but also to our marketing, product, and executive team.


His personality helps him across the board. He alters his mentality and pitch quickly upon meeting a person on the phone, and tailors his call-to-actions appropriately to that person. He is transparent. He tells them, “Hey, I am a sales guy. But I am also a specialist and if you have this specific problem then I know I can help you.” The response to this “I’m a sales guy” openness is incredible. It is refreshing. It cuts through the bullshit. Prospects respond with, “Ok. Well then, let’s have it.” It eliminates any suspicion of sleaziness–a problem that has infected the sales population and in many ways has spoiled the career brand–unfortunately “SALES” is considered a dirty word. It also saves an inordinate amount of time. He eliminates the time wasted in ‘sales skirting’ by quickly qualifying a business as a serious prospect or not. If they are not qualified, he says “nice to meet you, and if your need changes or our offering expands then I hope we can reconnect.” Next prospect please. Smart people can efficiently get to ‘yes’ or ‘no’ and professionally say farewell.

Disarming must happen at the beginning of the call. The goal is to make it clear that there is a sale to be made while making the prospect feel comfortable in that sales situation.

Other disarming tactics

“I’m going to turn my hat backwards for this one.”

“Let me step out of the office for this call.”

In-your-face honesty.

Acknowledging truths–prior actions taken.

Refer to regional idioms.

Match tone & pitch of other person.

Active listening. Referencing things they’ve said already.

Combat Objections

His deep knowledge of the space allows him to answer almost any question a prospect may have about the space, the product, or a competitor. And almost every prospect objects to something. To this sales rep, a combative question is not a challenge, but an immediate ‘qualifying’ characteristic that offers a perfect opportunity for a counter. If a prospect asks a prudent question about a value proposition, or how a product or service differs from another, then he or she has previous exposure to the topic and has likely been involved in a similar buying decision. Prospects ask difficult questions because they…

  1. Have been targeted and pitched to by other competitors (for a reason)

  2. Are already paying customers of one of your competitors

  3. Research market options prior to connecting with your sales rep

These prospects understand your product and your space; their questions reveal their knowledge, and a smart sales rep uses their objections to determine their likelihood to buy. Like my effective salesperson, you still must know every competitor, your differentiators, and why those will be be more effective or cost efficient.

The last combative skill this rep has acquired is the ability to determine competitors and ‘complimenters’. Lots of prospects claim, “I don’t need you, I already use Worse Option Inc.” Many sales people lack the ability to match the puzzle pieces due to insufficient knowledge of not only your direct market but all those ‘Olympic Rings’ that interlock your market with others. To excel beyond other reps, this person doesn’t just know Market A–he knows Market A and B and can sell a solution that equals C.

In a recent article by the #1 Sales Influencer, Anthony Iannarino exposes the defective side effects drawing the “bright line between us and them” and offers a method to avoid aggressive competitor conversations. “By so aggressively making your case, your prospective client may feel the need to defend our competitor.” Here’s an alternate route:

  • Know whether your prospect is a current client of one of your competitors

  • Avoid initiating explicit attacks against a competitor

  • Compliment your competitor on their differentiators

    • Example: our rep says, “Insideview is a great lead generation tool for finding decision makers within enterprise companies.”

  • Transition with “We do a few things differently that have helped our clients do X and Y.”

  • Ask questions about their needs and ‘ideal world’


His training, coupled with his personality/attitude, empowers him to turn behaviors or current processes of a prospect into challenging questions. He doesn’t look to agree. He looks to make a prospect say, “I’ve never thought of it that way before.” Or “Hm. Maybe you’re right.”


“(Challengers have) a deep understanding of the customer’s business and use that understanding to push the customer’s thinking and teach them something new about how their company can compete more effectively.”

Much of his initial conversation is occupied with “Why?” and “How are you currently…” and “What makes you do/think that….” What he, and many other innovative sales professionals, have found through the concept of the ‘Challenger Sale’ is that most prospects make decisions and take actions without justification or objective knowledge. They make decisions based on what they’ve done, have been told to do, or due to lack of exposure to other options. While most sales people focus on building customer relationships, the best sales people push customers’ thinking, introduce new solutions to their problems and illuminate problems customers overlook.

Challengers do the 3.5 T’s:

  1. Teach

  2. Tailor

  3. Take control while using constructive 3.5) Tension.

For the quick and dirty, Matt Heinz explains this further on his blog: “The Challenger Sale in less than 10 Minutes.”

Hard work

I’ve seen new sales reps work hard to learn the market and our product, understand and observe this ‘golden’ rep’s methodology and tactics, and work with pipelines filled with opportunities. And I’ve seen a few of those sales reps fail, either moving positions within the company or moving onto new companies/careers. My main pieces of advice to reps who are not as good as this sales professional–work harder. He doesn’t just work 9 to 5. He doesn’t come to work with low energy. He doesn’t only interact with sales–he interacts with everyone in the company to extend his knowledge.

Collaborating with other organizations in the company has not only made him a better salesperson, but a trusted advisor to our product and marketing team. If he believes there is an opportunity in a new vertical, then marketing will create assets and campaigns to help him penetrate that market. If he gives product feedback it is because he has diligently recorded patterns in prospect and customer feedback. This feedback allows our sales management team pinpoint potential lost revenue numbers due to the absence of specific product offerings.

What’s his reward for this extra effort if it is not direct reflected in commission or a bumped base salary?

A better, fuller pipeline. First pick at verticals. Freedom to work from home. Authority to become an internal sales trainer. New product features that allow him to go back to previously disqualified leads and close.

Have a sense of purpose like this salesperson and you will succeed.

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