Suck at Selling? 7 Tips to Grow Your Confidence and Make The Sale

You’re five seconds away from stepping into a meeting that could make or break your business. You’ve got your best pantsuit on, your hair is perfectly done, and your favorite shade of lipstick sits boldly on your lips.

On the outside, you’re the face of confidence. But on the inside, you’re a hot mess of fear and the increasing urge to bolt the other way.

Whether you’re a shoe designer hoping to sell your wares to a large retailer or a tech startup looking to land your next round of funding, chances are you didn’t become an entrepreneur for the business of it. You got into it because you had an idea and you wanted to see it through.

As you know by now, as soon as you become a business owner, you’ve got to wear all the hats. Not just the one you want to. And that means handling everything from product/service production to the nitty gritty sales and marketing - that is, until you can hire help. Even then, sales will always be a part of your job description.

But what if your palms get clammy and you freeze up at just the prospect of having to step into the shoes of a saleswoman? Here are 6 tips you can use to grow your confidence and, ultimately, make the sale that will grow your business to the next level.

1. Change Your Mindset Around Selling

Whenever we think of a salesperson, we usually imagine that slimy used car salesman at the sketchy shop down the road. We think of someone who clings onto you and won’t let go until you hand over the cash - even if you don’t want to buy.

We become so scared of this perception that we hesitate to sell ourselves even just a little bit. Instead, we take the side of relationship-builder, not daring to ask for a sale for fear we might look like that multi-level marketing representative who won’t leave you alone about that damn weight loss kit.

Because we’re so afraid, we don‘t make the ask. And that doesn’t make us great salespeople - it makes us look weak.

So how do you ask someone to buy something from you without seeming pushy or overwhelming?

As long as you truly believe in what your business has to offer (and we’re assuming you do) and you know your product/service will solve your prospect’s problem, you’re not pushing anything on them they don’t want; you’re helping someone in need.

Once you reframe your mindset around what you’re selling, you can start to feel a little better about the whole process.

2. Own Your Strengths

You are incredible.

We’re not just saying that to make you feel good. We’re saying that because we truly believe it.

You have done something millions of other people cannot do. You took what you know and love and turned it into something that actually makes money.

You get out of bed every single morning and battle the messiness of entrepreneurship - all while balancing everything else life has to offer. You’re growing something incredible out of nothing. And that’s something to be proud of.

Because you’re reading this right now, we know you have a slew of strengths at your helm. Maybe you’re a fantastic writer. Or you’re great at communicating your needs to your team. Or perhaps you’re talented at managing all the projects that come your way.

Take a moment to write down a list of your strengths - both hard and soft. Keep that list by you at all times, and especially before you’re about to walk into a sales situation. Remind yourself that you’re a total badass and you can do this.

3. Ignore Your Imposter

From the moment you land the opportunity to pitch yourself to the moment you stand in front of your audience, there’s a little voice in the back of your head that whispers, “who are you to do this? Isn’t there someone else much more qualified/experienced/stronger/etc.?”

That voice is a little shit. Ignore it.

If you have a working human conscience, you probably experience a little thing called imposter syndrome from time to time. This is where your brain - isn’t it so convincing? - tries to convince you that you can’t do this. It fights to tear you down and keep you from going after incredible opportunities.

You’re not the only one who struggles. Everyone from Sheryl Sandberg to the people on our team deals with imposter syndrome on a daily basis.

So the next time your inner imposter tries to convince you to run and hide, move beyond it with these steps:

  1. Recognize it for what it is: it’s just your fear speaking up and trying to protect you. Follow Marie Kondo and say, “thank you, I’ve got this,” and put it aside

  2. Take a deep breath and remind yourself, “I am enough.”

  3. Make a list of proof points; awards you’ve won, clients you’ve satisfied, anything that proves you do, in fact, are the only one for the job

  4. Take another deep breath and remind yourself, “I am enough.”

Because you are.

4. Do Your Research

The best way to prepare for any meeting - especially in a sales situation - is to arm yourself with as much knowledge as possible about the prospect.

When you’ve done your research, you can speak directly to your audience’s pain points. You can answer their objections before they even come up. You can take control of the situation and show you’re the solution to their problems.

If you don’t understand your audience, their market, and how your solution specifically fits with their individual needs, you’re not going to make the sale.

Risk comes from not knowing what you’re doing.
— Warren Buffet

So where do you begin? HubSpot has a great article including 18 sources you can find information on your prospects. A few of our favorites include:

  • LinkedIn - Dissect their and their company’s profile. Find out if you have anything in common to latch onto

  • Google - You can find everything from their social media profiles to articles they’ve been mentioned in and even podcasts they’ve been interviewed on.

  • Blogs - Read both articles your prospect has written (if any) and articles they’re likely to read

  • Their Website - Dive into their website and find out as much as possible about them, their company, and ways you can fit in

5. Challenge Your Buyer

A post shared by Dee Mullin (@dee__mullin) on

When it comes to sales, recent research revealed by Brent Adamson and Matthew Dixon in The Challenger Sale shows there are five types of sales representatives:

  1. The Hard Worker

  2. The Lone Wolf

  3. The Relationship Builder

  4. The Problem Solver

  5. The Challenger

Many people instinctively believe The Relationship Builder is the most successful type of salesperson. After all, who wouldn’t be charmed by someone who remembers our kid’s names and our birthdays?

Yet, research reveals the Relationship Builder is not only not the most successful - they’re the least. The most successful type of salesperson is The Challenger.

What does The Challenger do? Well, for the full picture, I recommend you pick up the book here (or read this summary).

But as a quick review: The Challenger opens their audience up into a new view of the world, has a strong understanding of their customer’s business, and pushes them in the right direction.

In other words, stop focusing on building those relationships and instead focus on improving your customer’s lives.

6. Clarify Your Message

Whether you’re selling your product/services through your website or in a face-to-face meeting, your audience won’t buy unless they understand what you do and how it benefits them.

When people ask what you do, what do you say?

Do you circle around the answer with a soft response like, “Oh, I sometimes help people with a website when they ask me to, but I just do it once in a while.”

Or do you say something like, “I help interior designers land clients by designing websites that attracts clients within 8 seconds”?

If your message isn’t clear, people won’t buy from you. It’s that simple.

Clarify both your website and your pitch by making sure you answer these six crucial questions:

  1. Can you solve my problem?

  2. What makes you qualified to solve it?

  3. Can you prove it?

  4. What can I expect from working with you? How does it benefit me?

  5. What makes you different from your competition?

  6. How do I work with you?

7. Make The Ask

The last, and most important, piece to making the sale is just asking for it.

A sales pitch without a call-to-action is like a house without a roof. It might look pretty and have everything you’d ever want inside, but if there’s no roof, no one’s going to be living in it.

Once you’re done making your case, tell people exactly what their next step should be. Here are a few examples:

  • Buy now

  • Contact us

  • Schedule a consultation

  • Get your quote

People don’t take action if you don’t ask. So increase your chances of success and ask them to do it.

And It’s not slimy if you’re helping them solve a real problem.


Your website is your company’s biggest salesperson. It should work 24/7 to attract visitors, convert leads, and grow your business.

But if your message isn’t clear, you don’t understand your audience, or you’re not making the ask, your website is more like an expensive postcard that might look pretty but doesn’t actually do anything to increase your revenue.

Make your website work for you by driving leads and growing sales. Schedule a free consultation to find out how we can take what you have and turn it into your biggest revenue driver.