Olsen on Sales: Confident & Caring

What is the demeanor of the Master Seller? If we ask 100 salespeople what kind of seller they are, 99.9% will respond, “I am a relationship seller,” but 80% of them won’t know what kind of relationship they are attempting to develop with their customers or how to do it.

Many sellers try to be as agreeable as possible and hope the customer likes them best. Others are only interested in getting the order. On the surface it appears that the first strategy is the best, but both strategies are flawed and lead to poor treatment by customers and poor results for the salespeople who employ them.

Obsequious sellers send the message they are not experts. This cloying approach puts off buyers because it’s obvious they aren’t being sincere. They are just boot lickers hoping for the best. Do some buyers want a master/servant relationship with salespeople? Yes. But they are a small percentage of the total and are not the strongest buyers.

Great buyers want strong, confident money-making partner relationships with the salespeople they work with. “If two people agree on everything, one of them isn’t necessary,” observed Churchill. Great buyers feel the same way.

The best approach is a mix of confidence and caring.

How to Project Confidence

The Master Seller is prepared for all questions and objections they will face on every call. They anticipate their customers’ needs and trepidations before they make the call so they can stay calm, cool, and clear-headed.


  • Speak in the calm lower register. We all have an upper and lower register—no need to fake or force it.
  • Use clear, easy to understand, declarative sentences.
  • Smile—whether live or on the phone. Act like we are enjoying ourselves.
  • Humor. A little levity here and there shows confidence.
  • Positively Assumptive. Master Sellers project the attitude of the possible.
  • Ask for the order in a natural, relaxed way.

Opposite of Confident:

  • Interruptions.
  • Beat-around-the-bush-itis. Adding extra words while trying to get to the point makes buyers uneasy.
  • Verbal tics—double words, (“good, good,” “okay, okay”), um, uhs, ya knows, likes.

How to Project Caring

Journeyman salespeople listen to the Master Seller and ask, “How do they get away with that? I could never talk to my customers like that.” The reason the Master Seller can speak to their customers with some push-back is because their customers know they are coming from a place of caring, not need or greed.


  • Work harder for the customer. It is hard to say no to a salesperson who is outworking the competition. The Master Seller knows that one of the best ways to stand out—and show we care, is to bring more value.
  • On missed orders instead of saying, “Well what are you buying?” the Master Seller gets curious about the order they just missed asking probing questions before moving on to the next item to offer.
  • The Follow-Up Question. When the customer is talking most sellers are thinking about what they are going to say – because they are winging it, thinking on the fly. The Master Seller already knows what they are going to say, so while the customer is talking they are thinking about an interested and interesting follow-up question. This creates conversational flow and rapport.


  • Lazy, non-value, boring sales calls. “Whaddya need today?” insults buyers and reeks of laziness and non-caring.
  • Offering one item only.
  • When the customer says no, immediately asking, “Well, what are you buying?” instead of drilling down and asking about the product we offered to set up the next call.
  • Never asking or following up on personal questions.

Seller: “What did you do this weekend?”

Buyer: “Spent some time with my family.”

Seller: “Great. Anyway, I’ve got a deal on…”

  • Not asking for the order. Not asking for the business sends the message we don’t want it.

A mix of confidence and caring creates trusting partnership relationships that are profitable for buyer and seller.


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