4 Steps Entrepreneurs Need to Take to Get Comfortable Selling If you find yourself fearing that next sales call, meeting or pitch, follow these tips

By Michael Luchies

Opinions expressed by Entrepreneur contributors are their own.


Of all the things an entrepreneur can be afraid of, there aren't many that rank higher than the fear of selling. It's a fear I know all too well.

While some believe the fear of failure is the biggest barrier to success, I'm not afraid to fail. In fact, as the founder of content-marketing company Treprep I sometimes dive head first into failure by presenting unique content ideas to clients and working on new business ideas long before they are fully formed.

But, the physical process of establishing and presenting a price and asking for a sale was harder than anything else I've done as an entrepreneur or within the startup world. It seems completely irrational, and I know it was, but selling situations caused my palms to sweat, my heart to race and led to many missed opportunities. But I needed to get over this fear, otherwise I would not survive and need to get a "real" job.

Related: Dealstorming Will Help You Sell More

If you find yourself similarly fearing that next sales call, whether it's for a job or your own venture, take these four steps.

1. Confirm your passion and commitment.

We all have doubts from time to time, but there's a big difference between not being passionate and committed to what you're doing, and simply going through a tough time. Before you can address any fear of sales, you need to address your commitment. If you're not passionate or committed to your current venture, it's very likely that this "fear" is disinterest or being uncomfortable in the business more than fear of the act of selling. Ask yourself the following question: Does my passion and interest for this business outweigh my fear of selling?

I asked myself this question, and it confirmed that my interest in the business was greater than my fear of selling. If your fear of selling outweighs the passion and interest you have in your business, it's probably not the right fit.

2. Make a decision.

Rosa Parks once famously said, "I have learned over the years that when one's mind is made up, this diminishes fear; knowing what must be done does away with fear."

I made up my mind that I was going to make my business work, which requires selling. Being intentional about it is an extremely easy step, but the slight shift in mindset can help take doubts and thoughts of failure out of the picture. It no longer becomes an option or something you're okay with or without; success now becomes a decision you've decided to make.

Related: We Are All Salespeople. Use These 3 Techniques to Become a Better One.

3. Find available channels that play to your strengths.

When people think of selling, they often envision a tense sales meeting in a barren office setting or ugly conference room pitching to people that aren't interested in what you have to say. It doesn't have to be this way. Figure out what approach and environment works best for you and use it.

As a former manager for a fundraising-dependent nonprofit, networking became a skill and something I came to enjoy. I started reaching out to my connections and asking them how I could help their business and if there were any introductions I could make for them. I ended the call with "Is there anyone you know who could use my help with content marketing?" Just a few calls into this strategy, I got a lead that resulted in one of my biggest clients that I have now been working with for the past eight months.

4. Set firm 'this or that' goals.

I will either achieve this, or do that. For me, the "this" was to double my current level of sales. The "that" was to give up my business and search for jobs. My family would eat whether my business worked out or if I got a 9-to-5 job. But, my disinterest and disgust for normal corporate work, along with my passion for what I'm doing, drove me to accomplish the "this" goal I had set, which was to double my monthly service commitments. They have now tripled, and this wouldn't have been possible for me without taking these four steps.

Related: 3 Steps to Qualify a Sales Lead

While I'm far from "cured" and selling still makes me anxious, I've been able to minimize its impact on my entrepreneurial aspirations. By following these steps, you too can give yourself a realistic shot at succeeding regardless of your fear of selling.

Michael Luchies

Founder of TrepRep

Michael Luchies is the founder of content strategy and creation company TrepRep, a business that works with small businesses and entrepreneurs to expand their personal and business brands through storytelling. Michael is an author, TEDx alum, public speaker and enjoys helping other entrepreneurs grow their business. 

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