How to Conquer Your Fear of Selling

In my experience, most solopreneurs have a discomfort with sales that is holding them back. That’s putting it mildly. This discomfort ranges from slight uneasiness to a paralyzing fear of selling, and everything in between.

What’s worse, fear of selling is why a lot of solopreneurs throw in the towel and give up their dreams to return to the grind of earning a paycheck. Even if it means they have to take a job they don’t really want. (If you’re like me, the thought of having to go earn a paycheck is about as appealing as swimming in a shark tank!) But don’t freak out. That doesn’t have to be your story.

One of the reasons it’s a challenge to master sales skills is because of the deeply rooted fear and psychological resistance that many of us have. It comes from our culture, it comes from stereotypes that are reinforced online, in the media, and in the movies. It comes from bad experiences we have all had at some point with a self-centered, unethical, and/or poorly trained salesperson.

But guess what? We also get triggered around sales from of our own lack of self worth, our fear that we’re not good enough, and our complex and often dysfunctional relationship with money. If you’re not comfortable with sales, you may be repelled with anyone selling anything to you. Even if they are doing it in an authentic and ethical way. And whether or not you’re aware of your reaction. If you find yourself easily triggered by any kind of selling ask yourself, how is that playing out in your business?

The reason most sales trainings aren’t effective is because they are too short, too focused on strategy and tactics, and completely overlook the giant elephant in the room: your fears, your emotional triggers, and your psychological aversion to the concept of sales. Your mindset is where all that fear and emotion lives. It’s your lifetime of self worth issues. It’s all the negative associations you have about sales. (I had a truckload.) All those fears and negative associations with sales are like a big destructive bomb, sending out waves of emotional shrapnel into your business and obliterating your bottom line.

In order to truly master sales and empower yourself to enroll clients with confidence, you have to be willing to unravel your fears, face your self worth issues, and heal your relationship with money. It’s not something that happens overnight, and it’s not always easy. But if you’re willing to do it, you’ll experience a true transformation that will free you of your fears and open you up to unlimited financial success. Then, and only then, will you be able to sell (and serve!) with confidence.

Below are five mindset shifts you can make to begin your journey of sales mastery.


#1: Serve, don’t sell.

I don’t mean to imply that you get to skip the step of selling in your business. You don’t. But if you show up in service during your enrollment conversations, you’ll get better results every time. Here are some questions to ask yourself that will help you shift into service.

  • What can you do to serve the best interests of each prospect you talk to?
  • What value can you provide during this conversation?
  • How can you make this conversation a win-win, even if they don’t decide to work with you?

If you can find a way to make the conversation worth their time regardless of whether they hire you, that is showing up in true service. Bonus: when you focus on providing value, you’ll be less likely to come across as too pushy or overly persuasive.

#2: Listen more than you talk.

Listening is about focusing your presence and attention on the best interests of the person you’re talking to. Stay out of your head. Don’t skim through your mind calculating the perfect thing to say next. This is common, especially if you’re new to selling and worried about your “script” and how to control the conversation.

Listening is easier when you ask great questions that will not only help guide the conversation, but give you something engaging to listen to! It only takes a few thoughtful questions to learn about your customer, what they want, and whether you’re the right person to provide it to them. Ask great questions and train yourself to be a good listener. When you get in the habit of being present vs. being in your head and following a script, you’ll feel more confident and build more trust with your potential clients.

#3: Let go of the outcome

It is so, so important to learn to let go of the outcome of your sales conversations. It will be difficult to show up in service or listen with full presence if you’re overly fixated on closing the sale. Obviously, you wouldn’t be in an enrollment conversation if you weren’t interested in working with this potential client. But if you want it too much, and allow that energy to bleed into the conversation, you’ll come across as overeager and sales-y, even if you say all the right things.

Letting go of the outcome means checking your emotional baggage at the door before every enrollment conversation. Whether you really need the cash flow from this sale, or you’re just super excited to work with this particular person, you need to let all of those emotions go before every sales appointment. If you don’t, you run the risk of repelling the client with the emotions and energy of what YOU want. It can be subtle, but your customers will sense it. And it will kill the sale every time.

I recommend taking a moment to get grounded, let go of your attachment to the sale, and set an intention to serve in your highest capacity before each discovery session or consultation (depending on what you call them in your business). This will allow you to excel at steps #1 and #2, above. It will help you build more trust, and guide the client through the decision-making process from a place of genuine support, and totally separate from what you want – which is to close the sale. It’s simply amazing how this one shift can improve your results.

#4: Stand in your value

This is a critical mindset shift that can have a huge impact on your sales results. (And everything else in your business.) If you don’t believe in the value of the work you do, your clients won’t believe it either. The more closely your business is tied to you and your personal brand, the more challenging this can be…and the more important it is.

Your self worth will always be closely tied to your ability to succeed in business, especially if you are a solopreneur with a personal brand. That’s why being an entrepreneur requires so much personal growth. Standing fully in your value, especially if you’re new to business, probably isn’t going to happen overnight. But it’s important that you make the time to build your confidence and your belief in yourself.

In the short-term, use your grounding practice to help you stand in your value during each discovery session. (Power poses and affirmations can also be great short-term, immediate ways to tap into your value before you make a sales call.)

In the long-term, there’s no substitute for a good coach or mentor to help you stand in your value at each stage, and in every area, of growing your business. (If you know you want help with that, let’s chat.)

#5: Make an offer, not an ask

This is a simple framework that in itself can be a game-changer. I was at a business training recently where the presenter was talking about sales. “You have the make the ask,” he told a room full of coaches. I disagree with that. Making the ask is about what you want, not what the customer wants. Asking for something fills YOUR need. And that fundamentally goes against the mindset of authentic selling and the other principles outlined above.

Instead of making the ask, make an offer. The energy of offering is about extending an invitation. It’s focused more on what the customer wants, and less on what you want. “You have this challenge? I offer you this solution.” That’s so different from asking for the sale, asking for their money, asking for their trust. (And if you have to ask for their trust by the end of the conversation, it means you didn’t earn it!)

If you truly embrace the energy of offering vs. asking, it will also help you avoid coming across as pushy, sales-y, and all the things we have learned to dislike about traditional, old-school selling.

So now you know five sales superpowers that will help you get beyond your fear of selling, enroll more clients, and ultimately serve more clients. Oh, and it will help you create cash flow in your business. In case you’re into that. (If you’re not, you’re reading the wrong blog!)

Use these five mindset shifts together and you’ll start to see your results change…and watch out, you might actually start to enjoy selling! That is my hope and dream for you.

Excited about these tips but know you need more than a blog post to put them into practice?

You’re right, it will take more than reading this blog post to transform your sales skills. The good news is there are a few spots left for my SuperPower Intensive: Client Enrollment Camp. In this 6-week program you’ll learn these 5 strategies and more…and by the end you’ll know everything you ever need to know to enroll clients with confidence and grace. Grab your spot ASAP – program starts May 1!