Bunny Hunting a Bear: Why Do Leasing Sales People Fail?

by Linda Kester

Linda Kester is a bestselling author and professional speaker with 25 years of experience in leasing sales and marketing management. As founder of the Institute of Personal Development, Kester has helped hundreds of salespeople increase their volume. Her book, 366 Marketing Tips for Equipment Leasing, has produced results for leasing companies in the U.S., UK and Australia. For more information, visit lindakester.com.



Linda Kester explains why some sales reps aren’t cut out for the equipment finance industry. She dives into some of the major weaknesses that some reps suffer from and explains that it takes grit and resilience to succeed.

Listening to James make a prospect call was like watching a bunny trying to hunt down a bear. He had no confidence. He gingerly asked questions and could not push past any resistance. He was happy to end a call. It was a waste of time for everyone involved.

Ellen would call a prospect and immediately ask “How are you today”, without listening to the answer. She’d launch into a two-minute monologue about her company. It was like the prospect was being vomited on with unwanted material. Even if the prospect was nice and provided a little bit of information she would just keep presenting feature after feature.

Scotty would call an automated attendant and hang up. Then he’d dial the same number and hang up. He did it again and again. He was just trying to increase his number of dials, without actually having to talk to someone.

Gretchen was affable, met her dial goals, went to every possible networking event but rarely got an application. She was good at making friends and lousy at generating volume.

Can you imagine if all these slipshod sales reps worked together at one company? Kind of like the island of misfit salespeople.

In their defense, they were probably never cut out for sales. I’m sure that Scotty’s gut was twisting into a giant ball every time he made a real prospect call, so he decided to avoid it. It’s natural when you are starting out in sales to get butterflies in your belly. These “reps” have more than just butterflies; they didn’t believe in their leasing company and didn’t implement basic sales skills. They got hired, so they looked like they had potential, but they failed. Costing the company time and money.

Why do leasing salespeople fail?

  • Lack of activity
    They don’t have a disciplined and scheduled time to prospect. They are reluctant to pick up the phone.
  • Lack of personality
    They can’t get the lessee’s attention, and have a hard time connecting with prospects.
  • Being too nice
    They are better at customer service than going out and generating new business.
  • Afraid to ask
    They don’t like the tension, the risk and the possible rejection that comes with sales.
  • Spending too much time calling on vendors who don’t do much leasing
    They waste their time on non-producing vendors or they call on end-users without a strategic plan, and when the lessee finally does need financing, they are nowhere to be found.
  • They get intimidated by high producing vendors
    They spend their time genuflecting in front of a prospect and hoping for business rather than having a meaningful conversation.
  • Too much time waiting
    I once worked with a sales person who told me he didn’t make prospect calls because he was waiting for his new business cards. I asked him how long he had been waiting, his response “over a year”.
  • They don’t understand the dynamics of the business
    Equipment financing is a complicated process with lots of moving parts. They don’t want to look foolish, so they don’t take action.

Top leasing sales people possess grit and resilience. They schedule time to prospect and stick to the schedule. They engage the lessee while providing value.

Reps can be trained to push back and develop their knowledge and skills; however, they have to be willing to learn. Often I walk into a sales meeting to find the attendees arms crossed in front of their bodies, they think since they’ve been in sales for a while and that they know it all. Once the training is over they are very grateful, but they came in kicking and screaming. Selling leasing and financing requires us to continually sharpen our proficiency.

Enter the discussion. Write a comment below. Do you have a story about a bad salesperson? Do you have any tips to shorten the on-boarding process?

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Terry Mulreany
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