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9 Confessions of a Legacy Salesperson

5 min read
Updated Aug. 10, 2021
Published Oct. 17, 2013

Legacy salespeople have given a bad rap to the sales industry. They’re notorious for using guile and trickery to sell, well…anything.

But as the internet has become a resource for customers, transparency is rapidly increasing. The snake oil salesman has seen his demise, and it’s time to learn from his mistakes.

Here are nine things salespeople have done wrong in the past:

1. Hide Price

If a salesperson is talking all about their product, it’s great features, why you should buy it, and never mentioning price, this should be a red flag. If you’re paying for a software or product, you should know exactly what it’s going to cost you.

Why it doesn’t work:

You probably want the most value for your money. This doesn’t automatically mean the most expensive solution is right for you. If a salesperson is unwilling to discuss price, it shows they’re not confident in their value. And if they’re not confident, it’s probably not right for you.

2. Think There’s Only One Decision Maker

As Steve Richard said,

“Today, there is not a single decision maker, instead decisions are based on consensus. Map their decision making process to better understand your targets.”

He’s right. Especially in big businesses, there is a cycle of people discussing every deal and passing it along. If you can learn this cycle as it pertains to businesses you work with most often, you’ll be able to figure out who the best people to talk to are.

Thinking there’s just one decision maker may leave you barking up the wrong tree, prolonging the sales cycle.

3. Think Sales Is Greater Than Marketing

It’s important not to focus solely on what you do. While sales is where the actual deals are made, marketing plays a crucial role in bringing people to your business in the first place.

It’s engagement vs. deal close.

The best strategy is to align sales and marketing. Determine what a qualified lead is in both cases, focus on sincerity, and have open lines of communication.

4. Think the Sales “Close” is the End of the Sales Process

As long as there’s an ongoing relationship, the sale never ends. It’s important to make sure your customers are delighted and create a platform that drives strong relationships and ongoing usage.

Hiring a customer success manager can help drive usage and adoption with customers long past their initial deal close.

Regardless of how it’s done, make sure customers are beyond satisfied. Seek to have them love you.

5. Think You Have to Physically Meet Someone To Close the Deal

Unless you’re selling solely to elephants- half a million dollars in one swing- you don’t always need to shake someone’s hand to close a deal.

For every one outbound sales rep being hired, there are ten inside sales reps. That’s saying a lot.

You have to be confident enough to sell over the phone, via Skype, or in person. It all comes down to your process and skills. If you lead the charge, you’ll find customers have no problem closing deals with you.

6. Don’t Understand Technology (Still Have Flip Phones)

Since most prospects are sourced online, it’s important for you to be able to understand the best ways to interact with them. Get off Internet Explorer, and realize the full potential of the internet.

Social media is your friend. Sharing your favorite blog posts, newfound sales tools, and interesting finds via Twitter, LinkedIn, and Facebook let you reach out and have a social presence. While you’re at it, start generating prospect lists using Salesloft.

Oh, and update that flip phone. You have to be able to provide quick responses to questions your prospects or users ask immediately. Putting social media, emails, and sales apps in the palm of your hand makes things easier for everyone.

7. Are Scared to Share Secrets

For a long time, people kept their best practices secret. If they have a strength or a trick, it’s theirs and theirs alone.

It might make sense, but here’s why it’s ultimately unproductive.

When everyone refuses to share, no one is learning new things. When everyone shares, information constantly flows, helping sales professionals become more well rounded, let’s them help more buyers, and improves how people view sales in general.

8. Wear Suits and Sportcoats All the Time

There’s a time and place for your suit, but it’s not every single day. Customers want to see the real you, so lighten up a bit!

With inside sales increasing at a rapid pace, the focus is on establishing trust. It’s not that how you dress doesn’t matter, it’s that the focus in sales is shifting from less about looks to more about quality.

9. Play Games and Stretch The Truth

Don’t exaggerate your solution when you’re selling. Huge claims are only exciting initially, especially when a buyer finds out they’re not true.

There’s a difference between confidence and bragging. You’ll only promote a bad image of salespeople and make future engagement more difficult

Learn more about how sales is always changing in this guest post on