Insights from Chief Mastermind Jack Kelly

Yesterday, I had lunch with an impressive young enterprise sales professional. He joined his new company last May and has already sold an account worth over $4 million to his new company. They are a startup in the financial services software business… not an easy market to break into.

He is very entrepreneurial and asks great questions (one big reason he is successful). He listens intently and offers smart and insightful input to the conversation. He mentioned how challenging it is to sell into the industry and how excruciatingly long the sales cycles are for what he does. He then asked me a simple, yet very challenging, question:

“What can I do to shorten the sales cycle?”
The Power of Leveling Up

The idea of leveling up may seem counter-intuitive to many sales professionals. When I say: “level up” I am talking about your relationships with your potential buyers.

Sales professionals who are great at getting in the door often position themselves as subservient to their potential client. They are so happy to be invited to the dance, they willingly sacrifice just about every ounce of self-dignity just to stay there. As a sales leader, how can you tell this is happening?

  1. They have multiple appointments with no progress
  2. Their discovery is poor and without complete documentation
  3. There are multiple changes and versions of the “final” proposal
  4. The deal hangs forever in the pipeline without any definitive timeline to close

Sound familiar? It is a disease that is rampant. The good news is it can be turned around easily.

Develop Peer-to-Peer Relationships

Once you have the interest of a buyer, your sales professionals need to gain agreement on a couple of things:

  1. The buyer has a genuine need for and is interested in your solution.
  2. They will choose your company’s solution if you satisfy their requirements.
  3. The organization has the budget to purchase your solution.
  4. The buyer is willing to go through a thorough buying process

Before you say, “That is what we do on every opportunity,” ask yourself, do they really? Does your sales team really ask these questions or do they assume the answers to these questions based on a “less direct” method?

Question #3 is hardly ever asked, and if it is, it is squishy. And, has your team ever asked question #4? Showing prospects how to buy effectively provides them a huge service, ensures your company can deliver on your promises and speeds up their sales decision-making cycles.

What is most important about asking these simple questions – CONFIDENTLY – is that your sales professional is letting the prospect know they are not a “lowly” sales rep just trying to make a buck. They are establishing themselves as a peer to the buyer. In order to come to the right solution for the prospect, your team needs to have a frank, peer-to-peer relationship with the prospect built on mutual respect for each other as professionals.

By “leveling up” your team’s relationship with their prospects, you will speed up your sales cycles, increase profitability and create higher satisfaction for every new customer.

Mastermind Insights