4 Reasons Your Sales Conversations Are Totally Awkward (and How to Make Them Painless)

There are so many reasons we avoid sales conversations. The toe-curling awkward silences, the crippling fear of rejection, and that inevitable moment you have to start selling. Urgh.

For many people new to sales, getting on the phone to sell is just too much. So we opt for other less fear-inducing options like sending emails or LinkedIn messages. Crossing our fingers, toes and (any other bits that will cross) that a sale comes through.

It’s fine to use other methods to sell but in our experience, nothing beats a sales call for:

  • building rapport and trust
  • checking the client is the right fit
  • speeding up the sales process.

How can we stop dreading and start loving sales conversations?

Let’s dig into the four most common fears around sales conversations. Here’s what we hear time and time again from our clients who are new to sales:

  1. I don’t want to sound pushy or salesy
  2. I don’t know how and when to start talking about pricing
  3. What if they say no? What do I do then?
  4. I don’t know how to close the conversation (and the sale)

These are all totally legitimate fears. But they can be overcome. Here’s why many people find them challenging and my tips on how to make your sales conversations un-awkward.

Reason #1. I don’t want to sound pushy or salesy

Your sales conversation is going well, you’re building rapport, discovering their problems and even getting a few laughs. Once you’ve painted yourself a full enough picture of what their problem is and you’ve decided that they’re the right kind of client for you, it’s time to move the conversation to the sales part.

This is where it often gets awkward. Fast.

For people new to sales, the thought of “salesy” selling that pushes the customer into something they might not want to do, just doesn’t sit right. It’s definitely not what you signed up for when you started your business.

The good news is there are definitely ways to sell without sounding pushy or salesy. Here are a couple of steps to make it seem more like a natural conversation rather than “selling”.

Step 1: Use a bridging sentence
Move the conversation along to the sales part with a simple bridging sentence like this:

“Thanks so much for that info, from what you’ve told me it sounds like I can definitely help.”

Step 2: Repeat back the issues they’ve raised
Re-iterate what you found out in the first part of your conversation to show that you’ve heard their problems and understand them.

“What I’m hearing is that you understand a digital campaign is probably the right thing for your business just now, but you’re looking for some guarantees and a really clear outline of what you will get in return for the money you spend”

Step 3: Show how you’ve solved the problem for another client
Lots of business owners find it hard to talk about themselves and how great they are. So rather than directly bragging about how wonderful YOU are, talk about what you’ve done for other clients.

 “We’ve had a client recently who was also a [type of company] and was struggling to [problem they have]. 

Our [offering] has really helped them overcome this. Does that sound like something you’d be interested in?”

Here’s an example
“We’ve had a client recently who was also a small consulting company and was struggling to get a consistent flow of leads. Our easy-to-follow sales strategy has really helped them overcome this. Does that sound like something you’d be interested in?”

As you can see it’s selling, but it’s not pushy. Download a FREE printable script and create your own non-salesy sales pitch.

sales pitch script

Reason #2. I don’t know how and when to start talking about pricing

Once you’ve understood their problems and showed how you can solve them, most people will now ask you to send a proposal. It’s tempting to do this (and avoid the dreaded money talk), but what often happens when we do this is the client decides you’re too expensive and then dodges your follow-up calls or emails.

By talking about pricing in a sales conversation, you have the chance to address any objections they might have (read more about handling sales objections here).

Talking about pricing in a sales conversation means you’ll have a quicker and less wasteful sales process. Here’s what I say when someone asks me to send them a proposal:

“What might be better is if we just chat through the process of onboarding and pricing and then if you’ve got any questions around that I can just answer them straight away.”

If they then say “no way, that’s too much” you haven’t wasted time putting together a proposal for the wrong client. Your proposal should really just be a confirmation of what you’ve already discussed, a mechanism to close the sale.

Set out a pricing strategy before the conversation
When you’re starting out in business, it’s really easy to undervalue your time or product. When someone says “how much is it?” what you hear is “are you worth it?” There’s a lot of feelings wrapped up in those unspoken messages, and for business owners it often feels very personal.

Think hard about your value and set out a clear pricing strategy. Make sure these are written down and in front of you when you’re having your sales conversation.

The way you talk about pricing has a big impact on how it’s received. If you’re super unsure about your pricing, you’re sending the message that your price is negotiable. Be firm and confident by having a clear idea of your value from the start.

Change the scope, not the price
If your initial price is not on the mark, reduce the scope instead of the price. Have a few different value options which will allow you to up-sell or down-sell depending on their budget.

Reason #3. What if they say no? What do I do then?

So many people confuse objection for rejection. They hear “no” and think it’s the end of a sales conversation.

But objections can actually be a positive thing (shocking view, I know).

Here’s what objections can give you:

  • Market feedback: How is your offering received? Is it hitting the mark? Do people actually want to buy it?
  • Engagement: Even if it’s not entirely positive, having a conversation is real engagement, a powerful way to build rapport and trust.
  • An opportunity to respond: Your client might not have fully understood your original positioning – this is your chance to offer clarity.

First, figure out if it’s a generic objection or a specific one. Read more about generic and specific objections here.

There are a few tried and tested ways to handle objections but I find the following method works well because it highlights your expertise. It also addresses how the customer is feeling and we know that empathy is the cornerstone of good customer experience.

  1. Empathise: Understand and acknowledge what they are saying.
  2. Isolate: Is this their only objection or do they have more concerns about your product/service?
  3. Address: Figure out if they would go ahead if their objection can be resolved. There may be more than one objection so make sure you identify any more that they may be feeling.
  4. Close: Once all their objections have been addressed, then ask them again – are you happy to go ahead?

Here’s an example of a real objection I received recently:


“I’m nervous about outsourcing sales because you don’t know our business well enough”


“Yes, I totally understand, lots of our clients worried about this too, but they found our set-up process really helped them through their concerns” [Empathise]

“If I can show you how our training process solves this issue, is there anything else that is concerning you?” [Isolate]

“We offer a full set up process that includes full training – does that seem better for you?” [Address]

“Shall we get your set-up session locked in?” [Close]

Download this FREE objection handling template – it will help you outline common objections you hear and show you how to overcome them.


Reason #4. I don’t know how to close the conversation (and the sale)

Having a clear objective for your sales conversation is important. Whether that’s booking another meeting, getting verbal confirmation of a sale, or booking in an initial consultation, a sales conversation is completely pointless unless you’ve asked for what you’ve come for.

Even some of the most experienced salespeople don’t close sales conversations well. Why?

  • Self-doubt: you don’t have enough confidence to follow through to the end
  • You haven’t had the best vibe in the conversation
  • You’re freaking out and just want to get off the phone!

Here are some ideas for closing your sales conversation:

“Based on our conversation today would you be happy to go ahead?”

“So typical next steps are to book in our ‘client onboarding call’ – if you’re ready to go shall we do that?”

“I’m just managing our resources for August as it’s booking up which is great! Shall I lock you in for the 20th?”

“So the process is, I send you an invoice and once you have paid the deposit we go straight into stage 1. Shall I send you the invoice?”

“Would you prefer the contract over e-sign or a pdf version?”

“If you are keen to go ahead, we start with the invoice and then I can confirm the strategy call. Does that work for you?”

Never assume it’s a no. Sometimes I’ve had the worst calls, full of awkward moments and so many objections. But when I propose a meeting they agree straight away. It always surprises me!

Preparation is the key to sales confidence

Once you’ve done a few sales conversations you start to realise there’s a structure to them. Most of the time the flow and objections are the same. And it’s really true that practice makes perfect when it comes to sales conversations.

Here are some tips to get prepared for a sales conversation:

  • Have your scripts ready: Get your opening line and sales pitch customised and ready to go.
  • Figure out your most common objections and have responses prepared. Here’s a template to help you out.
  • Have a clear objective at the start: what is the end goal of the conversation?
  • Remind yourself it’s just another person you’re talking to. Be human!
  • Build rapport early on, it makes the sales part much less cringy.

And if you find sales calls really terrifying – pretend it’s not your product. Talking about someone else’s business is SO much easier than talking about your own.

Rather alphabetise your tax receipts than make sales calls? We can help. We help small business owners create simple sales processes and strategies so they can start having sales conversations with confidence. Find out more.

About the Author

Jenny White is the Managing Partner of True Potential Sales. After 15 years’ on the front line of sales in IT, recruitment and advertising in the UK and Australia, she decided to put her knowledge to good use and help others improve their sales processes and pipelines. Together with her business partner Chris Hull, they created True Potential Sales. They now have a team of sales people across Australia providing sales expertise and campaigns to small and medium sized businesses. Jenny lives with her husband, Tim and their two small daughters, Tessa and Nina in Helensburgh, Northern Illawarra.