The 5-Step Process to Overcoming Your Selling Fears

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Bill Caskey
Bill Caskey


It’s a storyline that plays out every day in the sales profession:

  • A salesperson fails to meet his or her goals. 
  • A perennial high-achiever suddenly hits a plateau.
  • A new seller is reluctant to make calls or take the actions necessary for success. 
  • A seasoned vet hits the wall and everything they touch turns to sh*t.

Deep feelings of inadequacy are at the heart of these problems.

If you think inadequacy isn’t costing your company money, think again. After coaching and training sales teams for 25 years, I can tell you -- it’s huge.

Imagine you have 25 salespeople of varying performance. You look at the bottom 50% and start measuring them more closely or decide they need training.

You send them to a one-day seminar, thinking that will make a dent. It doesn’t.

A year later, you send the low achievers to another one. Usually these one-day sessions make a slight difference, but the success is short-lived. You haven't worked on the real problem. You’ve worked on a symptom.

The Origins of Inadequacy

Feelings of inadequacy begin early: We get cut from the sports or academic team we really wanted to make, our parents inadvertently made us feel insufficient in some way, a teacher failed to recognize our talent or belittled us in public for our inadequacies, and so on.

To cope, we adopt a persona. C.G. Jung defined this as a “mask or façade presented to satisfy the demands of the situation that does not represent an individual’s personality.”

For example, if a salesperson is deeply hurt, he may outwardly adopt a commanding and powerful persona.

Do this for 10 years, and we achieve at sub-optimum levels. Do this for a lifetime and we begin counting the days to retirement.

The 5-Step Process to Resolving Inadequacy 

Here are five steps that you can take with your team -- or with yourself -- to begin to isolate the real issue. If you're a spreadsheet type, then create a five-column scorecard. Each step below is its own column.

Step 1: Identify the Pressure

No one wants to admit they have fears. Having done more than 5,000 trainings, I can tell you that we are all suspicious when someone asks, “Where do you experience fear?”

But what we can admit is where we feel pressure. Make a list of those places in the sales cycle where you feel the most pressure. That’s Column 1.

Is it during the prospecting phase? Is it when money is brought up? Is it when you find you’re competing against another vendor? Is it when your prospect objects to your proposal? Is it when you lose a sale that you thought was yours?

Step 2: Link the Pressure with the Fear

Column 2 is for linking the pressure with the underlying fear. If you feel pressure, fear lurks in the background. The more honest we can be with ourselves, the more likely it is that we will heal ourselves.

Step 3: Do a Reality Check

In Column 3, ask yourself, “How real is this fear?” Meaning, is the fear likely to come to fruition? Ask yourself, “What could happen to me if I fail?”

Going through this reality check typically shows you that your deepest fears are illusions.

Step 4: Purposefully Reframe Each Pressure or Fear

Take each Pressure or Fear and reframe it. For instance, if calling is your pressure point, look at it through a new lens. It’s not an opportunity for rejection -- it’s an opportunity to help clients identify a serious problem and solve it. If they are unwilling to share their problems with you, you can’t help them -- and you must move on. Their loss, not yours.

Once you purposely reframe, no longer will you feel pressure.

Step 5: Pay Continuous Attention to Triggers

If you reinforce this exercise, you will catch yourself going down the dark hole of inadequacy. Notice the triggers. When you get that feeling of hesitation or pressure, recognize that you just aren’t thinking about it in the right way. It might take 3-5 seconds. But it happens quickly.

You might need some props on your journey to reframe. Going back to the previous example, put a sign on your desk that reads: “Every Call I Make Is An Opportunity To Help Someone Solve A Huge Problem.” Or my favorite: “Some Will. Some Won’t. They All Might. Next.”

I want you to succeed wildly in your business life. You have unique gifts that need to be expressed in the market. But you won’t be able to communicate those gifts if you’re hiding behind a persona. And you can’t shed the persona if you don’t address the illusion of inadequacy.

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