5 Steps to Conquering Your Fear of Selling

Chris Grouchy
8 min readJun 2, 2016

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www.chrisgrouchy.com

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” — Tim Ferriss

… Cold calls count as uncomfortable conversations, right?

Conversational boredom usually sets in when the person sitting across from you starts the discussion with the following sentence, “Selling is everything.”

Spare me the cliché.

Yet, it’s hard to argue their point. Persuasion is a vital condition to professional and personal achievement.

Despite the ubiquitous need for sales skills, people are told too often that they should be selling themselves more. Most of us don’t take the advice.

Fear prevents us from selling ourselves.

For many, the fear of selling can be so paralyzing that most people would rather not try and settle on becoming investment bankers instead.

Most of our fears are innate. We have been hardwired with many fears since we were children. Fears induced by the thought of selling are no exception. On your first day of school, you were told that failure is unacceptable. We played by the rules to avoid disappointing our teachers, peers, and parents.

Consequently, it should be no surprise when we later realize that our fears are usually baseless. This is not to say that fear is unproductive — it’s just exaggerated and, fortunately, conquerable.

I don’t blame you for being scared to sell yourself.

But the spoils of opportunity are endless for those who can manage their fears associated with selling.

This is not a post written in an effort to convince you to enter a career in sales or to teach you the intricacies involved in the psychology of persuasion.

I’m going to openly discuss your fear of selling so that you can confidently channel your inner Wolf.

Let’s take a look at the three most common fears associated with selling.

1. Fear of Initiating Cold Inbound (Email or Calling)

Many of my classmates from university who became investment bankers immediately out of school to delay their dreams of becoming an entrepreneur are worse-off than you’d think.

One day, after they finally quit their jobs to start a business, they will wake up, walk over to their desk, and just stare at the phone. Minutes and then hours will pass. They know what they must do; but they are scared.

They are scared to pick up the phone and cold call.

Yet, how else are your leads going to know who you are?

2. Fear of Rejection

This one explains itself. In sales, you are going to get kicked in the face a lot.

Are your excited about that?

3. Fear of Losing the Deal

Sales processes can be long and draining. Prospects will naturally pull themselves out of the funnel at varying stages. Investing time and energy into a prospect only to find out that the deal won’t close becomes a sunk cost. If only you had known that they were going to buy from your competitor before you called them, you wouldn’t have bothered trying.

It’s easy to think that it’s your fault when the deal doesn’t work out. There are millions of activities vying for your time and attention during a workday. Why spend your time on a prospect that may not convert to a customer?

Are you fearful?

Sales fear is real. We mustn’t let our fears conquer us.

That’s why I’ve curated five practices that will enable you to make your fear a source of motivation to sell better. Let’s dive into these practices.

1. Manage your fear by flipping your perspective

You never really lose your fear of selling. You just learn how to manage it.

Top sales people deliberately look at their failures as opportunities to identify and learn from their preventable mistakes. They also see their tribulations as opportunities in which they will benefit.

This practice was famously executed by Thomas Edison when a chemical fire destroyed his entire empire. As he was watching the fire burn his life’s work to the ground, he was making plans to rebuild his business. Upon execution of his plans, his his new empire was even more successful than his previous one.

People in the business of selling are really are no different. They must manage obstacles and the fear of anticipating them.

I implore you to flip your perspective by conducting a pre- and post-mortem process of each sales attempt.

Flip your perspective by asking the following questions:

· How will I benefit from what I am about to do?

· What were the preventable mistakes I made during the sales process?

· What can I learn from this experience?

· How can I benefit from this failure tomorrow?

In addition to flipping your perspective, learn to manage your fear by saying, “Who cares?”

Stop overthinking it. Execution is the best cure to the intoxication of fear.

2. Long benefits; short features.

My sales mentor used to tell me to stop preaching features. He was right.

Your prospects already know what your product does. And if they don’t, why would you explain to them something they can read off of your website? You are wasting their time otherwise unless they directly ask you about them.

Give them benefits that are tailored to the stones in their shoes.

Why does this matter when it comes to conquering sales fear? There are two reasons.

The first is that focusing on benefits in sales makes the psychology of the seller about helping the buyer capture value. The second reason is that if and when a prospect rejects you, it is ultimately their loss for missing out on the benefits they would have accumulated otherwise.

And if it doesn’t work out, the failure cannot be entirely on you. You were only trying to be helpful.

3. Practice your self-talk through affirmations.

When things go south, what to do you say about yourself inside your head?

For most people, our brain’s default dialogue is typically the sound of negative, self-defeating thoughts. It’s easy to blame ourselves or others when the plans we created go to shit. You have to own it.

That’s why I recommend implementing a strict daily affirmations ritual. Folks like Oprah Winfrey, Tony Robbins, and Will Smith have used the power of affirmations and visualization to enable their own success.

The process is simple. Rewire your brain’s default state to one of intention and not reaction.

Get out a scrap piece of paper. Write down the following and fill in the blanks:

I, [my full name], am [first quality I wish to develop], [second quality I wish to develop], and [third quality I wish to develop]. I will achieve [attainable goal in the near future] by [concrete action that the goal depends on].

Example:

I, Jane Doe, am persistent, confident, and resilient. I will achieve 110% of my sales quota by December 2017 by conducting 200 cold calls every day.

The power of repetition multiplies the impact of affirmations when the statements are repeated various times in a day or session. Try writing the same statement on paper 15 times in the morning. Then throw out the paper and start again the next day.

Affirmations are powerful tools because they are the fuel behind self-belief.

And in the face of constant rejection, such as that which is experienced in entrepreneurship and sales, that fuel is what keeps the motor running.

Will Smith once said, “In my mind, I’ve always been an A-list Hollywood superstar. Y’all just didn’t know yet.”

4. Quantify your contributions.

Measure and track what you do during a day.

In sales, success is an objective reality. And your fear is a seductive and dangerous vacation from this reality.

While your CRM system will track conversations, pipeline metrics, and the details of your closed deals, you can create a personal spreadsheet that measures efforts taken in minutes.

There are two steps to enabling your productivity through quantification.

Step one: Determine your progress metrics and set minimums for each of them.

For example:

200 MIN. # OF COLD CALLS / DAY

200 MIN. # OF COLD EMAILS / DAY

50 MIN. # OF LEADS CONVERTED TO PROSPECTS / DAY

40 MIN. # OF PRODUCT DEMOS / WEEK

10 MIN. # OF DEALS CLOSED / WEEK

5 MIN. # OF CUSTOMER LOVE LETTERS RECEIVED / MONTH

This will require trial and error to get the mix right.

And you should ask your sales manager if there are any progress metrics that you should be measuring. These aren’t vanity metrics because they are intentionally designed to guide you to quota attainment.

Why minimums? The alternatives are flawed.

Maximum values (such as 300 maximum calls per day) are a binary state of success. You either hit the maximum or you didn’t. There’s no motivation to exceed them.

Range values (such as 200–300 cold calls per day) blur the state of success. If you surpass the minimum value but didn’t hit the maximum, you’re stuck in the middle.

Minimum allocations on progress metrics set the bar, and it’s up to you to determine how high you will jump over it. The upside for success can be unlimited.

Step two in this process is to track it all in Google Sheets or some other fancy spreadsheet. Just do it.

5. Celebrate incremental wins during the process.

Sales is about winning, yes. But in order to conquer your fear of selling, you must also genuinely look forward to the process of winning.

Enjoying the process of winning is all about recognizing and celebrating progress and incremental wins.

This revolutionary concept was coined as the Progress Principle by Teresa Amabile and Steven J. Kramer. The utility of the Progress Principle can be understood by the following quote, “Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work.” [1]

Track your minimums and do something fun after you’ve hit them.

Go for a walk, workout, or a coffee. Be mindful not to exaggerate the degree of progress by rewarding yourself a preposterously large reward. Ensure that the achievement and celebratory activity are proportional.

For example, going out for a night on the town because you conducted 200 cold calls is probably not the most productive celebration of progress. Save that activity for when you hit 200% of your annual quota.

The point in celebrating progress is so that we displace fear with anticipation. Doing so will unlock positive forms of extrinsic motivation.

[1] https://hbr.org/2011/05/the-power-of-small-wins

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Chris Grouchy

Co-founder, Convictional.com — a platform that enables B2B commerce. Reader. Amateur Stoic. Not entirely grouchy, I promise.