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5 Secrets to More Confident & Generous Selling

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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Content Systems
Content Strategy
Sales Funnels
5 Secrets to More Confident & Generous Selling

Can you remember your first sales call?

The feeling you had when you saw the request come through in your inbox? Whether you had it automated through a calendar booking tool, received a contact form through your website or had a more informal arrangement.

I’d bet you felt your nerves rumbling.

I know I did. Nervous they’d asked a question I didn’t know the right answer to. Worried I’d come off as too pushy. Scared to be rejected and feel like a total loser.

More than anything, I went into that first call feeling like I had to prove myself and that it’d be a hard sell. And honestly, that feeling hasn’t 100% gone away either.

What I hear most often, especially from fellow female entrepreneurs, about sales is that:

  • They feel a lack of confidence in themselves (not usually in their solutions)
  • They don’t want to feel pushy or salesly
  • They’re scared of being seen as having an agenda the whole time #awkward
  • It makes them think of sleazy, used cars salesmen in bad suits saying and doing anything to get the sale (no, thank you!)

But there’s a simple shift that can make sales feel so much better. Like by selling – you’re actually being generous, caring and serving your audience.

For myself, that shift came in the form being fully committed to my mission statement:

Radically serving others is at the centre of all the free content I create, all the programs I put out and all the services I offer.

It’s the gut check I filter every new thing through before deciding whether to do it or not.

It’s the pump-up song I repeat before going into a sales conversation or kicking off a launch.

It’s the pick-me-up for when I start tail spinning and get lost in a mountain of to-dos.

Here are the 5 secrets to transforming how you feel about selling

1) Reframe your offers, content and packages as being of radical service

Exactly like my mission statement suggests, start seeing your offerings as you being of service for the greatest good instead of a burden to those who need what you offer.

When you’re focused primarily on helping others through any type of work you do (free, paid and premium), it’s hard to feel icky about wanting people to sign up for them.

2) Let your content do the lead generation and some of the selling for you

Next week’s post will be all about selling through your content but by strategically using content – you can actually do a whole lot of selling without a whole lot of selling. Mmmkay?

It’s all about using your content to attract and validate potential customers, nurturing those budding relationships and then making an offer. Using a value-led content strategy has been a key piece in releasing all the pressure that comes with thoughts like I have to book 10 consult calls this week to meet my goals!??

3) Reframe the “pitch” as an invitation

Take the pressure off by not thinking of the moment when you switch from chatting about a potential project to that make-or-break-it moment where you ask for the sale.

That isn’t helpful.

Think of it as an invitation. I think you’d be great for x [your offer]. I’d love to work with you to get you [the benefit they want most & that you can deliver on].

Then stop. Take a breath and embrace the silence that’ll give them a chance to speak.

If it’s not a great fit for them, great. You’ve (a) gotten practice with asking, (b) left room for the people who you can really serve with this offer, and (c) lost absolutely nothing from asking.

A rejection to a pitch feels like a letdown. But a rejection to an invite feels like a rain check. It isn’t personal.

4) Focus on your delivery

An amazing and generous sales strategy? Focus on delivering an incredible experience with your service or product.

The best marketing is actually free marketing.

It’s the word of mouth that your insanely happy customers use to tell everyone they know about how awesome you are. You can’t buy that kind of advertising.

Nibble on this stat – A 2016 Nielsen Study found that 80% of people seek recommendations before buying anything.

So once you have the sale, go above and beyond to deliver a sweet experience from start to finish. This doesn’t mean you’ll have to kill yourself to do it either, a little extra attention and care go a long way.

5) Build a network … generously

You know that stat you nibbled on above? Yeah, that one (“A 2016 Nielsen Study found that 80% of people seek recommendations before buying anything.”)

Well, it goes without saying that building a network builds up your referral potential.

But don’t go into it with that agenda – it’s too much pressure on yourself, will prevent you from making real connections and there’s a much more effective way to go about it.

Nervous about networking?

I love this little nugget I heard in a mastermind session and then tracked it down as being from Dale Carnegie’s book Win Friends and Influence People: “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”

It’s so true. Approach business (and all) friendships by thinking about how you can be interested in and support them. Reina, my partner in the Selling with Generosity campaign lives by this business growth philosophy through her signature social glue method.

So struggling with sales? Just focus on these 5 core principals of generous selling –


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