When you want to be great at something, the best place to start is by learning from people who have already achieved greatness. Having the chance to talk with Bill Benjamin allowed me to gain insights as to what it takes to be great in sales. The discussion I had with him is what gave me the opportunity to write this article, and many of the examples and ideas are a collection of both of our experiences.

Sales not for Selling

How many of you have heard “It doesn’t matter what you do, you still have to sell?” I know I have heard that line countless times, mainly, because it’s true. Think about it. Whether you are pitching a product to a client, an idea to your boss, a concept to your class, or even yourself to a potential employer, you are always selling!

You’re probably sitting there saying, “I already knew that,” or “Okay, that makes sense.,” Regardless of what your response is, there is a bigger problem; this is where the conversation ends for most people. And unless you have been working in sales for quite a while, you may not even know what that means or what goes into selling; you may think you know, but you aren’t exactly sure.

So let’s start having this conversation, what goes into not just being mediocre at selling, but what goes into being great at selling?

Before we begin, I want to make something very clear. Acquiring these skills does not happen overnight. Many self-help articles and books make you feel like you are so far behind and will never be able to catch up; if you are young, ambitious, and impatient (like I am) or feel like you needed these skills and tools five minutes ago, take a deep breath, relax, and be patient. These skills will come in time. Heck, you may already be doing some of them and not even know it!

Know what you’re selling

Bill referred to this as “the price of doing business,” and he is right. You can’t sell something if you don’t know the in’s and out’s of what it is that you are selling. This doesn’t mean you need to know absolutely everything, which brings to me to an important point: don’t make things up; your integrity is all that you have. If you don’t know something, admit it, “I don’t know the answer to that, but I will find it and let you know as soon as I do,” is acceptable. Overall, it’s absolutely imperative that you know what it is you’re selling. If you are selling yourself, know what you’re good at; if you are selling software, know what makes yours different or more relevant than the competition’s.

Know your audience

If you have a good understanding of who your audience is, then you will have a great advantage in being able to tailor your message in the right way. A few questions you might ask yourself are:

  • What does my audience value? (i.e. Hard work, family, innovation, cost, etc.)
  • Does my audience like? (interaction or a formal presentation)
  • What keeps my audience up at night?
  • What does my audience do for fun?
  • Why is my audience here?

These are just a few things to get your mind going. As you work through these questions, you will begin to develop a set of your own questions that will help you tailor your message to your audiences.

But what if you have never met them? What if you don’t know the first thing about them? Obviously, this situation is not ideal but do as much “homework” as you can. I’ve even gone as far as calling an individual’s assistant and asking questions about them so that I can get to know him/her better. Sometimes you will have to think outside the box on this one.


Relationships are probably one of the most ambiguous things in business, especially when you are starting out. What does it mean to have a relationship with someone? Do I have to be their best friend? Do I have to be able to carry on long conversations with people? Or is it just being their acquaintance and doing the job they hired me for?

Let’s think about some of the best relationships that you have ever had. What made them great? Likely, in some form or another, it was that the person took time to listen to you, and genuinely cared about you and the problems you may be facing. So when you are looking to start a new relationship, whether it is in business or in your personal life, ask yourself, “What would show me that someone else really cares about me, and how can I show this person that I really care?”

“When I walk into a client’s office, I am very aware of my surroundings,” says Bill, “I look for things that could be potential connections. For instance, if I see of picture of them with their kids, I can use that to relate to them and build a deeper connection.”

When it comes to business, it isn’t absolutely imperative that you are best friends with your clients or audience, but you do need to be adaptable and find different ways to connect with them. If you are able to do so, it will be an enormous advantage to you, your work, and your level of happiness. I do have one hint, and most of you may already know this, but people love to talk about themselves, so ask questions. Be interested, not interesting.

Reframing a problem and providing a solution

Have you ever convinced someone of something? It could be anything–from convincing your parents to let your best friend stay the night on a school night when you were a kid to convincing your boss on a process improvement that could save the company millions of dollars. If you are saying, “Yes! I have done that!” then you are already on the right track. The question is … How do you do this sustainably?

One of the best ways to do it I found in a book called The Challenger Sale by Matthew Dixon and Brent Adamson. The process they described in the book (which I recommend checking out) takes the audience on a ride that reveals to them a problem that they never even knew existed, shows them how critical that problem is, and then breaks it down into more human-like, relatable pieces. This could be a little uncomfortable; Think about it;, you are showing people a huge problem that they never even knew they had. How would you respond? But this is where it gets good for you. If you can show them that the problem has the ability to be fixed, and that you have a plan that is going to make their life easier through the entire process, then you are, both, deepening the relationship and getting closer to making the sale.

This is a great framework for a successful sales pitch. If you can take your audience through these different stages and make your way to your solution, you will be moving in the right direction. This is one of the key pieces that will take you from a “regular old sales rep”, to a partner in their business.

Success vs. Failure

What’s the biggest difference between sales people who achieve success and those who fail? While many different factors apply, Bill says the biggest one of them all is “resilience.” The more time you spend selling, the more you will quickly realize that it’s not all rainbows and butterflies. Sales will take you on a roller coaster of a ride, where one day you will sit back and say to yourself, “I think I have this job down.” And the very next day you will arrive home thinking, “What happened today? I don’t know if I will ever be successful at this.”

“This is where the difference lies: Can you get up the next day and say, ‘Yeah, yesterday wasn’t my day, but today is a new day, and I am going to give it everything that I have?’ If not, maybe sales is not the right profession for you,” says Bill.

But like I said, no matter what you do, you’re going to be selling.

I would like to thank Bill for giving me the opportunity to write this article. It was very eye opening and a great way to reflect on my experiences thus far.

A bit about Giovanni:

Giovanni Roberto currently works as a Sales Development Representative for Whirlpool Corporation in the Greater Denver Area. Aiming to fulfill his passion, he is also a co-founder of DESIGNEDtoLEAD, the first ever leadership development conference at his alma mater, Western Michigan University. While attending WMU he earned a BA in Business Management with a minor in Philosophy with Applied Ethics.

Everyone at IHHP would like to congratulate Giovanni on the birth of his son Cooper. Very cute baby!