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The 7 CEO Selling Mistakes

In the beginning, the entrepreneur starts a company, and does all the selling himself. Then, as the business grows, he hires a salesperson, then a few more salespeople. This goes on for a couple of years, then he hires even more salespeople and a sales manager.

As this progression occurs, this entrepreneur, now the CEO, makes selling mistakes. All CEOs make these mistakes, even if their background was in sales before they started their company, or before they joined the corporation. There aren’t many companies run by salespeople; in my experience, CEOs usually come from engineering, finance, or operations. But even the sales-background guys and gals make these same mistakes. Avoiding these seven mistakes can save you a lot of grief.

Here they are. I’ll be stating each mistake as a belief, because it is the belief that gets the CEO in trouble. These beliefs are actually dangerous myths, myths that cost companies millions or billions of dollars every year.

1. The salesperson I’ve hired will sell the way I sell. This is the first and most serious mistake entrepreneurs make. I’ve seen this mistake kill new businesses, because the entrepreneur didn’t figure out what was going on before he ran out of startup money.

The entrepreneur who starts a company has been thinking about his idea, service, or product for years – and all of his business friends know about it by the time he starts his business. When he makes those initial sales calls, he comes in as the expert on the subject, and someone with historical credibility. This gives him an edge, the kind of edge that breathes life into a sale.

The salesperson hired by the entrepreneur has no such edge. Plus, that salesperson is usually put to work on the “cold call” customers – not the CEO’s buddies.

The CEO doesn’t expect the new salesperson to be as successful as he was, but he has no idea how unsuccessful that salesperson is going to be until the salesperson has been there a while, quietly failing. Finally it will dawn on the CEO that the salesperson is not going to do any better, unless the CEO starts helping him somehow.

If you want to avoid this happens-every-time trap, you will make cold calls yourself, before you hire someone. You’ll map out your successful sales. You’ll figure out the sales tools that are needed at each step in the buying process. By the time you hire a salesperson, you will be ready to provide him with everything he needs to succeed.

2. Salespeople are open to change. Anyone who has managed salespeople will laugh out loud at this one. While engineers are wrongfully accused of being inflexible, in fact they are most likely to be open to new ways of doing something. Next to your corporate lawyer, salespeople are the most inflexible people working inside your company.

Once a salesperson has found that a certain method works, she will determinedly continue to use that method, long after it stops working, and long after the potential customers have moved on. A simple example: Buyers are more likely to contact you via email now, than by phone. But what are most salespeople still doing? Giving their priority to phone calls, of course. Today’s most successful salespeople are fast typists and capable email composers.

You can assume that you will have to work HARD to get your salespeople to change. You can never, ever assume that they will change after you merely explain why they must change and how they must change. You will have to check up on them constantly and coach them constantly until they finally have developed a new habit. And, then you’ll have to check up on them some more, because they can easily slip back into their old ways.

3. You can “wind them up and let them run.” I always laugh when people refer to salespeople as “feet on the street.” Ha. They are not feet on the street. They are baby birds in the nest, with their beaks open, begging for more. More materials they can sell with. More reasons to call the customer back. More ideas about how to contact customers. More proof that you care about them and you are removing even the smallest barriers to the sale.

4. Salespeople can be managed the way other workers are managed. This is related to #3. Salespeople are out there, all day long, trying to get people to say “yes” when it’s so much easier for those prospects to say “no.” Salespeople hear every possible reason for saying “no,” and then they bring those reasons back into the company.

Salespeople need to know that management is listening to the troubles they’re relating. They need to know that management is receptive to resolving these issues and is actually trying to do something to eliminate them. They need to be able to go back to their customers and say, “Our managers are aware of this, and they are taking steps to solve it. The steps are…”

You must be in constant communication with your salespeople about these issues, because they are in constant communication with your customers. If you aren’t listening, aren’t receptive, aren’t making changes, and aren’t communicating – and you have to do ALL of these things – then you are forcing your salespeople to go out into the cold, ready-to-say-no world, naked and unprepared. In the absence of an answer from you, they will make up their own answers. If you overheard those answers, you’d be horrified.

5. A “one size fits all” approach to coaching will work. The basics of successful selling are well-known, and not that complex. You find the people who might be interested, or they come to you. You listen to them describe their need. You show them how your product or service can meet that need. You answer all their questions. You make it easy for them to take the next step, including getting approval from their boss, spouse, or whomever. You close the sale, and make sure they’re happy afterwards.

This basic successful selling method (very “old wine”) has been sold and resold to CEOs, for ages, as being the latest, hottest method (in a catchily buzzworded “new bottle”). CEOs fall for it because the people selling it are great pitchmen who know how to sell their new bottles.

Besides, the CEO has a BIG problem: He absolutely, positively must increase his sales. It’s pretty easy to sell water when your customer is parched. So the CEO brings in the guru, the guru does his/her thing, and the CEO thinks, “Great. Now our sales will go up.”

Sales might to up, a little, because someone stroked the salesperson. But what usually happens is sales don’t go up. Why? Because the only coaching that really works, long-term, is the type where you focus on the individual – who is doing things in a particular way – and work with them to improve their methods and behavior, over time. I wish I could tell you there was an easier way, but I can’t – because there isn’t one.

6. Salespeople know what their customers are thinking. The easiest way to disprove this myth is to ask yourself: When was the last time YOU told a salesperson what you were thinking, while he was selling to you? Right. So, while it’s important to ask your salespeople what happened – who was involved, the questions they asked, what happened next, etc. – you won’t get the truth about what their customers were really thinking until after they have purchased your product, and someone courteous and intelligent calls them and asks them.

7. The best salesperson is an aggressive salesperson. People who are, by nature, fundamentally aggressive, make terrible salespeople. They argue with customers. They interrupt them. They push when they should be listening and drawing them in. They make snide remarks. I could go on, but you get the picture – because you’ve encountered these same irritating folks when you were trying to buy something.

The best salespeople are persistent (not aggressive), and detail-oriented. They follow up every opportunity and never let anything fall through the cracks – but they are also, by nature, helpful. They are not jerks. If you had the chance to buy something from a jerk or a caring person, which person would you want to give your money to? Wouldn’t you even go out of your way to give the caring person a little extra edge? I rest my case.

You can save yourself years of grief and not-enough-sales if you avoid these most common CEO sales management mistakes.

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