The Only 9 Things You Need to Know About Selling

Being a great salesperson isn't about gimmicks or systems. Here are the nine essential do's and don't's to help your pitch.

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By Steve Tobak • Feb 21, 2014


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If somebody told me years ago that a future generation of would-be entrepreneurs would learn how to sell from a bunch of writers, researchers, and consultants who've never sold a product or managed a sales force in their lives, I wouldn't have believed it.

And yet, here we are. The blogosphere and bookstores are full of content from what I can only describe as self-serving shysters with a cool gimmick and an inspirational story to sucker small business owners into coughing up their hard-earned money.

Luckily, I'm not one of them. You can tell because my hand isn't in your pocket. More importantly, I cut my teeth as a sales engineer in a highly competitive industry and ended up running sales and marketing for several high-tech companies.

And while no article – or book, for that matter – can really teach you how to be a great salesperson, I can definitely share some interesting and counter-intuitive insights that took me a while to figure out, starting with the do's and don't's of delivering a sales pitch:

Selling is a marathon, not a sprint. Selling is a process – an often long and arduous one. The bigger the deal, the longer it takes and the more hoops you have to jump through. On the plus side, you'll have more time to build a solid foundation for an enduring relationship. If you want to be the last one standing at the end, don't push too hard in the beginning.

Related: Want to Be Successful? Learn How to Manage.

You're always selling. Whether you're pitching a new concept to investors, a potential partner to join you, or your board on a risky strategy, you're more or less always selling something. And if you're not aware of that, you're not going to do the right thing to ensure your best chance of success. Truth is, even sales people spend more time selling their own company than their customers.

Make "yes" the logical and emotional choice. Selling is a skill set. Granted, a transaction does eventually take place, but the vast majority of the time, you're cultivating a relationship, listening to determine your customer's needs, or building a case for an investment of time and resources or a leap of faith. If you do it right, saying "yes" becomes the logical and emotional choice.

Be sure there's a real opportunity. Cold calling isn't synonymous with wasting your and everybody else's time. Cold calling is when you believe there is a real opportunity and this is your first unsolicited contact with a company or individual. Once you've identified the right person and that there is at least a possible fit, then go for it. Otherwise, you'll come across like a dummy, waste precious time, and maybe even burn bridges or harm your reputation.

Related: The Secret to Prioritizing Your Time

Know whom you're talking to. Try not to get too far along without knowing whom you're meeting with, what their role is, what motivates them, and how to approach them. Do what you can to learn in advance what they're doing and what they might be looking for. That way you can come up with a strategy that makes sense. There are ways to do that and adjust your plan on the fly, but that comes with experience.

Don't try too hard to relate personally. This is probably the biggest mistake small business people make. Sure, you want to build a relationship, but if you try to get too personal too quick, you risk appearing too eager, invading their personal space, or turning the other person off. Instead, pay attention and react to their cues, tone, and body language.

Don't show off how smart you are. I've been guilty of this myself, but not intentionally. Oftentimes, in a transparent attempt to relate and maybe indicate we know what others are talking about, we come off like know-it-alls who love to fill the air with the sound of our own voice. The truth is the customer doesn't care one bit about what you know. He just wants to know if you've got a solution to his problem. So listen.

Give a little, get a little. Selling is a game of give and take. If you do it right, you give a little, get a little, and repeat the process over and over. For example, after providing a general outline of your product, you might ask them to tell you about their product or company so you can determine if there's a fit. If, on the other hand, you spill your guts all at once and they say "not interested," you've provided a ton of information, gotten nothing in return, and possibly missed an opportunity to offer a customized solution.

Never rehearse. There are several reasons for that, but the most important one is that it's harder to think on your feet and adapt to new information. Instead, the rule you should always follow is to simply know your material cold, know as much about who you're pitching as you can, come up with a reasonable plan, and then ask lots of questions, listen for answers, and adjust as needed. Trust your gut.

No matter what happens, remember this: You'll make lots of mistakes but you'll get better in time. Most people think I'm a natural-born salesperson, but nothing could be further from the truth. Just listen and learn … from the right people.

Related: The 7 Easiest Ways to Insult Important People

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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