What Makes a Sales Conversation Feel Awkward and How to Fix It

Sales is happening all day, every day… whether you like it or not.

Getting your partner on board. Getting your kids to listen. Asking for your money back on something you forgot to cancel.

And then… you go to talk about your own services
and suddenly it feels awkward.

In this episode, we unpack why sales conversations can feel uncomfortable even when you know you’re good at what you do and how that awkwardness has very little to do with your ability and everything to do with what’s happening underneath.

Using a real life story, grounded insights from behavioural psychology, and ideas from Thinking, Fast and Slow by Daniel Kahneman, this is a powerful reframe of what’s really going on in those moments and how to shift it. 

In this episode we cover:
• Why sales conversations feel awkward even for capable professionals
• The moment your energy shifts and what’s actually happening there
• Why over explaining, rushing, or softening your price isn’t random
• The real role of emotion in decision making
• Why connection matters more than information in sales
• How self protection shows up in conversations without you realising
• The link between visibility, rejection, and discomfort
• Why silence in a conversation can feel so hard to hold
• The difference between performing and leading in sales
• How confidence in sales is built over time, not overnight

Key insights:
• People make emotional decisions first and justify them logically
• Awkwardness often comes from self protection, not lack of skill
• Connection creates safety and safety drives decisions
• Over talking and under pricing are often signs of discomfort
• Sales becomes easier when you see it as leadership, not pressure

🎧 Listen now wherever you get your podcasts
https://www.sharonfrancisco.com/podcast

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Questions for the podcast? hello@sharonfrancisco.com

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👉  Also: The Entrepreneurial Bookkeeper — grow your business without sacrificing your health: sharonfrancisco.com/program

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Have a question for the podcast? Email hello@sharonfrancisco.com

Transcript

SPEAKER_00 0:02

Hello and welcome back to the Sharon Francisco show. Today we are going to be talking about sales, my very favorite subject. I say that with a giggle because I know it's not many people's favorite subject. And the reason why it's my favorite subject is because most people I speak with really struggle with the word sales. I remember years ago I was um I was teaching my program and I asked the people in the group to describe what they think of salespeople. And one lady said, pon scum. And I was thinking, oh, goodness gracious. If we think salespeople are sponsor, and I think there's probably all variations of that word in a lot of our minds at the moment, and when we think about salespeople. And if we think about salespeople like that, and we have to sell in business because every person in the world is in sales, right? And I'm going to explain that in a minute. But specifically in business, if we think something like pon scum is what salespeople are, how are we going to sell without feeling like pon scum or pushy or sales ill, whatever the word is that you might have for salespeople? So today it's my goal to help you uh understand that salespeople aren't pon scum and neither are you. So sales is happening every day, like I said before, whether we like it or not. So getting your partner to watch the kind of movie that you want at the pictures is at the pictures, that makes me sound old, doesn't it? At the movies, is sales. If you're going up with a group of people and you're going out to see a movie and you want to see a particular movie and you're putting your bid in to see yours, that's sales. Getting your children to listen to you, that's sales. Maybe even asking for your money back after like a trial period, you know how it goes over the seven days or whatever it is. And they say, sorry, you've got over the seven days. It's sales to get your money back. I'm going through that particular thing right at the moment. So that's sales to learn how to get your money back if it's gone over the trial period or whatever it might be. And of course, as I said before, in business, we're selling our services all the time. And yet the moment we have to do this in our business, it suddenly feels a bit awkward, or we can feel like pond scum. So I wanted to talk about something today that almost every business owner experiences at some point. And that's where sales conversations can feel awkward. We get to that stage where it's the price reveal, as we say, and it can feel a little bit awkward. So that's why I've just decided to chat about today, because I've had a lot of people try to sell to me lately. And because it's something I'm totally fascinated in with, and what I notice is like the different styles of salespeople. So that's why I wanted to share this with you in hope that you kind of understand a little bit about your sales style and how you can get a better outcome with having that, without having that awkward feeling. We had a professional many years ago, uh, a solicitor, that I wanted to engage in, a solicitor for doing some routine wills. It was many years ago, and I Googled different solicitors to do our wills. And this particular person said that she prided herself on coming to us rather than we having to go into the city and find a park and and take time out of our day. And I thought, you know what? And she was a woman, and I thought, you know what, that fits perfectly with what I want. I want to work with uh a woman solicitor, and I, you know, it's just convenient that she's going to come to us, which was fantastic. And I thought, yay, that's gonna work for me. And better still, that she's a female, which is fantastic, in a typically male-dominated profession. So it was a no-brainer, and her website looked really warm and friendly and it ticked all the boxes. So I thought, yep, she's my woman. Then she came to the door, and it was the most awkward experience that I've ever felt. We really awkwardly shook hands. Um, we invited her in. We offered her a drink, to which she said no, and she very quickly sat down at our table. We didn't invite her to sit down at the table, which is again a bit awkward, but whatever. Um, you've got to remember that I'm guessing that this person was very nervous. So we sat down very quickly to make her feel okay. So we were trying to comfort her in her awkwardness of sitting down straight away. She very quickly opened her laptop to get to business. Now, what that did was put a barrier between us and her, that laptop being up. And yes, she needed a laptop, but not just yet. She needed to make the connection first before she opened her laptop and got to business. So opening that laptop put a barrier between us and her, and it also got her to straight away get into business. There was no rapport built, there was no drink uh preparing or anything. We were sitting there getting straight into business with this woman we've never met to talk about some really personal will discussions are not easy. They're they're very personal discussions. And it felt super, super awkward to the point where my husband told me later that within the first five minutes to 10 minutes, he was ready to wrap up the whole meeting and say, Look, I don't think this is for us. That's how awkward it felt. And we kind of pursued with it and and it and the meeting unfolded. So I'm not sure what that feeling was, but it was really strange. And we both talked about it a lot later, not only with each other, but with our friends and family. So we know this doesn't happen to us all the time, but it's kind of enough for us to notice, especially when we're the ones doing the selling. That moment where we're explaining what we do, and suddenly we feel that energy change. Now, what I want you to think about before I continue on is if you're selling a service, it's like a general service that you're very comfortable selling and that is usually taken up pretty quickly. I don't want you to think about this in this circumstance. I want you to think about a service that would possibly push you a little bit. So if you normally say charge, you know,$150 an hour for your service and for your regular service, but you might have a service that's triple that. And you don't have many of that, you don't offer that very often because it's so much more expensive and not everyone takes it up. I want you to think about that because the service that you sell naturally and easily, you're going to feel really comfortable about selling and it's not going to be a stretch, or you're not going to seek out training or information on how to be better at that because it comes easily to you. So think about that service or that thing that you sell that's not as easy to sell when I go through this today. So think about when you're explaining what that, what you're doing, what you do for that, and suddenly the energy shifts. So you know that the ordinary service that you sell is$150 and you're about to sell a service for$500 an hour. You might start talking a little bit faster. You might add a little bit more detail than necessary because you're a little bit nervous that you're about to talk about something that's so expensive compared to what you're usually selling. And you might soften your price a little bit before you've even said it properly, before you've even explained what you do properly. You might think, well, I'd just soften that a little bit because it sounds a bit too expensive to say that. And after afterwards, you might think, why did that feel so uncomfortable? So over the years, I've had my fair share of sales conversations, and I'd like to share what I've personally learned about these sales conversations. And this is not about criticizing ourselves, it's about understanding what really happens in a sales conversation. And one of the biggest insights that I've noticed is this people rarely make buying decisions purely on logic. Behavioral psychology research has shown that most decisions are first emotional, and then we justify logic afterwards. So, what does this mean? Daniel Kainman, he wrote a book uh called Fast and Slow Thinking, explains it, and I'm hoping I pronounced his name right. I probably didn't. So, Kane in this, uh it'll be in the show notes, um, his details if you want to grab that book. He explains uh how humans make intuitive emotional judgments very quickly before the rational brain steps in to explain the decision. In real life, this can look like somebody choosing, say, a bookkeeper because they have a Bass agent's license, they've been in business for 20 years, they have the experience in all the systems. But the real driver of that decision, of going ahead with that bookkeeper, is that they felt safe to open up to them. They felt understood and they felt a human connection to begin with that has nothing to do with how many years of experience they've got, their BASS agent or license or not, um, and systems or whatever it might be that's the logic side. It was the emotional side that had the connection and where they felt understood and the human connection and they felt safe opening up that actually makes the buying decision. So the left brain builds the story that makes the decision feel more sensible. Does that make sense? The left brain builds the story that, yeah, she's that they're a nice bookkeeper, they've got the bass agent license, they've been, they've got experience, they've got systems, they've got bookkeepers that have got experience and license uh the bass agent license working for them. That's the left brain justification to build the story that makes the decision feel more sensible. This is why sales conversations can feel awkward when we just focus on the information, the logic, and forget about the connection. Like my friend, the solicitor years ago, that came to the front door and it was all about the logic. She came to sit down, open up the laptop, and talk about wills. And that was that's why it felt so awkward because we're humans behind this experience. We're not just robots that need a will. So let's unpack this a little bit more. After a sales conversation, you might ask yourself, did I create space for a real conversation or did I rush into explaining my services too quick, like the solicitor that came? Did I listen intently enough, or was I already preparing my next question or point before I really listened to what they said to my last question? Did I hold the kind of calm authority, or did I start performing because I wanted approval or wanted a yes? Did I state my price clearly, or did I wrap it up in kind of a nervous justification? These questions are not about being perfect, they're about becoming more aware about how you sell. There's also strong work from Brene Brown. She's obviously the expert on vulnerabilities. So Brene Brown around vulnerability and shame, she explains that why sales can feel uncomfortable. Many capable professionals are not afraid of the mechanics of selling. They're uncomfortable with what selling may represent for them. And it may represent being more visible, it may represent being more elevated or better than what we think we are, or it may represent being told no. So to keep themselves safe, we do all these things. So unconsciously, we protect ourselves by perhaps over-talking, um, over-delivering or underpricing to protect ourselves. And from the outside, guess what? That looks like awkwardness. So from the inside, it's just self-protection. The shift starts to happen when sales bit is reframed as leadership. I'm going to say that again. The shift starts to happen when sales is reframed as leadership, slowing down, asking better questions, and allowing for silence without rushing to fill that silence. And if you know anything about me, I talk a lot about disc profiling, D-I-S-C, and I'm a high eye. So high eyes tend to fill silent spaces. High eyes struggle with silent silence. So it's been a real thing for me to learn over the years to not fill the space with me chatting, allowing the silence to be just silence. And that's not an easy thing for some people. So if you're a high out high eye out there, I hear you and I understand how tricky that can be, but it's just a skill to learn. I've had to learn that skill, and it's not been an easy one for me. To trust that connection and the clarity, trusting that connection and clarity are more powerful than pressure. Confidence in sales rarely arrives overnight, as we know. Often it begins as borrowed belief from somebody else, which is what I've done over the years. Belief in the value of the outcome that you create and from other people before full belief in your own authority can catch up. Over time, as you reflect and adjust and continue having these conversations, sales starts to feel less like something you're trying to get right and more like an natural extension of how you help people. So it's just like you catching up as you, talking about what you do, hearing what people say, and understanding that there's an energy transfer with sales. It's not just about what you logically sell and doing the laundry list of things that you sell that is sales. There's so much more to it, and there's so much more ease to it when you do it this way. And that's when the awkwardness will start to fade away when you start doing it like a more of a natural energy transfer. Not because you've memorized that better script or the right thing to say, but because you've become more grounded about who you are and the difference that your work makes, and you know that you're an authority in your industry. So you can have those conversations in a clearer, more practical and emotional way. I love this quote. Someone less qualified than you is making more money than you because they believe in themselves more. That's a gut punch, that one, isn't it? Someone less qualified than you is making more money than you because they believe in themselves more. Meaning that when you go into a sales conversation, having that self-belief and being able to have it from a leadership perspective, and knowing that you've got all your ducks in a row and that you're calm enough and open enough to have an open emotional conversation with a potential client, and that you don't have to rush to get the answer, and that you know that you're in your place when you're doing, you're in the right place when you're having that conversation. And whatever the outcome is, is okay by you. That's an energetic transfer, and that's when things start to work really nicely for you. Remember, we're all in sales every single day, even if we don't own a business, like I mentioned earlier, with even the small things like choosing a movie, getting your kids to do the things that you want them to do, like pick up their toys or whatever it might be, and the choice for dinner. If you want a particular meal or a restaurant, those sort of things are all sales. Hopefully, this has been helpful, guys, and I'll talk to you next time. Bye.