Your ability to handle awkward conversations makes all the difference—in both your personal and professional life.
Important conversations often involve some level of discomfort.
Whether it’s asking someone out, bringing up an issue with a spouse, friend, or family member, or negotiating in a professional context, awkwardness is part of the game.
These moments test your ability to be confident, persuade others, and to hold your frame when the stakes feel high.
A lot of us want to learn how to be less awkward in these situations.
This is where sales comes in.
Specifically, the lessons you learn from selling.
I’ve taught more than 100 coaches and consultants the sales techniques I’ve used to make millions.
They discover that sales not only helps them make money but also develops their social skills, builds confidence, and fosters empathy for others—all of which carry over into areas outside of business.
In this post, I’ll break down three sales techniques and show you how applying these principles can help you be less awkward and more confident in your everyday conversations.
By the end, you’ll be better equipped to get what you want through clear, self-assured, and honest communication.
1. Ask for what you want
Let’s start with the part of a sales call that makes people the most uncomfortable: the end, when you have to ask for money.
Asking for money on a sales call feels awkward if you’re not used to doing it.
Receiving large amounts of money can feel awkward, too, especially if you’re used to getting paid less than what you’re worth (most people are).
Many people feel guilty and ashamed about getting what they truly want.
They don’t feel worthy of having it. They feel like they’re taking from the other person when, in reality, they are simply exchanging value for money.
I’ve had clients who will not make the pitch or ask for money at all because some part of them doesn’t feel ready.
If I’m working with newer entrepreneurs, making a proper pitch and having the confidence to ask for money is one of the first things we have to fix because they will miss out on sales until that problem is addressed.
In the beginning, they’re hesitant.
They’ll tiptoe around the pitch instead of making an enthusiastic ask. They’ll trail off. There’s no structure to what they say, and no clear invitation to buy.
They will make vague and timid suggestions like, “Well, if you’d maybe like to work together, here are some options…”
That kind of pitch doesn’t work. It reeks of insecurity. In any conversation, especially in awkward conversations, whoever seems more sure of themselves tends to dictate how the conversation will go.
We’re all subconsciously testing each other’s frames to see who’s worth trusting and who isn’t. Certainty or conviction is one of the clues people look for when deciding who to follow, trust, and buy from.
If you want to close clients, you have to not only ask for the sale. You have to ask in a confident and coherent way.
Here’s an example of how I pitch my clients (and how I teach my clients to pitch), using a structure we outline inside the program:
First, we’re going to get clear on your offer. We’ll help you figure out exactly what you’re selling. Something that solves a specific problem, speaks to a specific person, and is positioned so buyers see the value right away. By the end of this phase, you’ll know who your offer is for, what to say to sell it, and how to show up with confidence. Next, we’ll validate the offer by helping you sign your first three clients. We’ll do this using our outreach and engagement strategies so you can prove people want what you’re selling. This gives you real-world feedback, client testimonials, and the confidence that your business isn’t just an idea. It’s real, and it works. Once your offer is proven, we’ll help you scale. We’ll install the Words to Dollars system in your business. This includes word-for-word DM scripts, high-converting sales call scripts, and simple daily content plans. You’ll build a process that brings in new leads and converts them into clients consistently, without guessing. You and I will work together for six months to get this result. There are two investment options. You can either do $1,200 per month or $6,000 paid in full. So what do you say? Are you ready to get started?”“Here’s how it works.
Now compare that to the vague, soft approach I mentioned earlier. The difference is night and day.
✅ Clarity vs. vagueness: The confident pitch clearly outlines the offer, the process, and the outcome. The vague version leaves the other person guessing what you actually do and how you can help.
✅ Confidence vs. hesitation: The structured pitch shows how much you believe in the value of the offer. The soft version shows uncertainty about the value of your offer. If you don’t think the offer is valuable, why would they?
✅ Leadership vs. being passive: The clear pitch guides the prospect to a decision by giving clear next steps. The unclear pitch puts the emotional burden on them to figure everything out on their own.
Apply this sales principle to a real-life scenario
Imagine you meet someone and want to ask them out. Which approach works better?
or “Hey, I really enjoyed talking to you. I’d love to take you out. When are you free this week?”“Um, well, would you maybe want to hang out sometime?”
Notice the difference between these two as well.
✅ Directness vs. uncertainty: A confident ask like “I’d love to take you out, when are you free this week?” shows clear intent. The vague version, “Would you maybe want to hang out sometime?” leaves the other person unsure of what you actually want. Is it a date? Are you wanting to hang out as just friends? It’s unclear and lukewarm, which lowers the odds of getting what you really want, a date.
✅ Attraction vs. hesitation: Confidence is attractive. It’s a more powerful attraction tool than looks or money. Direct communication conveys this self-assuredness.
In a way, being clear and direct about what you want shows vulnerability. Being clear means you’re risking rejection because you’re putting yourself out there without hedging. Confidence is nothing more than the ability to push your chips in the middle of the table and see what happens.
Timid language reads as insecurity, which makes you seem less desirable even if you are a good catch.
✅ Initiative vs. indecision: A confident approach takes the lead and moves things forward. A passive one puts the other person in the awkward position of figuring out if they should make the first move, which puts unnecessary pressure on someone who just met you.
In both sales and dating, doing things the right way requires courage. Both might feel awkward at the moment. But one of them signals confidence and clarity. The other doesn’t.
This is the heart of it.
When you learn to ask for what you want with confidence, even when it feels awkward, you dramatically increase your odds of getting it. And—bonus—you become much less awkward in the process.
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2. Challenge beliefs (the right way)
Sales calls can turn into awkward conversations because, often, to make the sale, you might have to challenge your prospect’s beliefs in order for them to see a new perspective to influence their behavior.
Here is a classic example from prospects I’ve dealt with.
I work with skilled professionals who want to take their existing skills and use them to build online businesses. They tend to be quite smart, which can be a double-edged sword.
Their intelligence causes them to overthink. They spend too much time weighing different options. Often, they will tell me they’ve spent months or years thinking about their business idea but never got it off the ground.
The call goes smoothly in the beginning. We discuss their problems, desired goals, and roadblocks. I walk them through the ideas I have for how to fix the bottlenecks and describe the roadmap we’d use to help them land clients.
Everything is smooth sailing until—you guessed it—the part where I ask for money.
Almost always, you will get one of these default responses:
- “I need time to think about it.”
- “I can’t afford it/it’s too expensive.”
- “I’m too busy/I don’t have enough time in the day.”
There’s a saying in sales: Prospects aren’t liars, but they will be dishonest with you. Usually, the first objection they give isn’t the real one.
The real objections are typically:
- I don’t fully trust you to help me get the result.
- I don’t fully trust myself to get the result.
- I’ve been burned in the past, and I don’t want that to happen again.
Bottom line → if they could look into a crystal ball and see themselves getting the result in the future, they would buy.
Objection handling is a topic deserving of a full post, but I’ll give you an example of one I like to use. It may cause a bit of an awkward conversation, but it does get them to change their perspective.
I hear the “I need to think about it” objection more than any other.
The prospect feels like the process is happening too fast, and they’re using “I need to think about it” as a stall tactic.
It’s their pattern after all: constantly stalling, procrastinating, and being indecisive when it comes to moving forward in this area of their life.
I offer them reframes that challenge their beliefs. Here are three different examples:
You’ve probably read posts about it, maybe even talked to friends about it, and now you’re here because something in you knows it’s time to actually do something. So no, this isn’t rushed. This is you finally facing the thing that’s been slowing you down. And the only real question is whether you’re ready to move forward.” “You’ve just spent the past half hour telling me how you’ve struggled with overthinking things and procrastinating in the past. Do you really think it makes sense to try to solve your problem with the very thing that’s causing it?” “You don’t need more time to make a decision. You need more information. And since I created this program, I’m your best source of information. What can I clarify for you to help you make a decision today?”“I get it. I know it feels like this is happening fast, but truth be told, it isn’t. You’ve been thinking about making this decision for a long time already. Maybe not this exact call, but the problem we’re talking about? It’s been on your mind. You’ve gone back and forth with it.
All of these reframes, usually formed in questions, open a door where they can acknowledge the flaws in their logic while giving them room to save face at the same time.
Use reframes for real-life resistance
You don’t have to be selling something to run into resistance. Any time you care about someone and want to help them grow, you’ll eventually hit a moment where their beliefs don’t align with their actions. The best way to support them is to help them change their perspective by subtly challenging their beliefs.
“Can I ask…what do you think is actually keeping you from making a move? Is it that you don’t have a plan, or are you afraid the plan won’t work?” Or maybe your kid wants to quit something again, guitar, karate, a sport. You’ve seen the pattern before. Instead of a lecture, you pause and ask: “Do you want to quit because you really don’t enjoy it, or because it’s getting hard and you’re not sure you’re good at it yet?” In a leadership context, imagine a talented team member dragging their feet on a project they said they wanted to own. Rather than push, you get curious: “You’ve got the skills to do this. What’s making you hesitate right now? Is there a part you’re not sure about?”Take a friend who’s been talking about quitting their job for years. They’re clearly unhappy, say they want to go freelance, and talk about “figuring things out.” But nothing changes. You might ask:
When you meet people where they are and ask the question that helps them hear their own hesitation out loud, you give them a chance to break their own pattern.
Whether you’re trying to close a client, coach a team, or love someone well, finding a way to help them break their patterns with empathy makes a potentially awkward conversation way less awkward.
3. Stay grounded even when you’re screaming inside
There’s no way around it: Sales calls are, by definition, awkward conversations full of awkward moments.
I’ve been on sales calls where the person I’m talking to might take multiple minutes to mull things over in their head before they reply.
As the salesperson, sitting through that tension projects confidence. Trying to fill the void too early reeks of insecurity.
I remember one time I was on a call with a guy for nearly two hours. I must have handled a dozen objections. After each one, there would be these super long pauses. He’d look up to the corner of the room, trying to avoid eye contact while he was thinking. He’d sigh.
And I just sat there, cool as a cucumber.
Or so he thought. Inside, I was feeling tense too, thinking to myself, “My goodness…can this guy just make a decision?” But I didn’t show it.
When others are indecisive or skeptical of your value, the interaction feels awkward because their doubts hurt your ego.
Let’s say you’re deep into the conversation, and suddenly the prospect says something like, “How do I know this will work?” or “Have you actually done this yourself?” or “Why should I trust you over someone else?”
It’s not just about the offer anymore. It’s about you.
This is where a lot of people shrink. They get defensive. They start trying to qualify themselves to the prospect, which is a huge, huge no-no.
The right way to handle this pushback is to stay calm, stay grounded, and meet it without flinching. They’re looking to see if you need validation to feed your ego. If you show them you don’t, they’ll trust you more.
When someone asks me why they should choose me over someone else, I ask them:
“Well, what was it about me that made you want to speak with me in the first place?”
I let them fill in all the reasons why I’m amazing, and then I just say:
“OK, let’s go with that as the answer,” with a grin and a chuckle.
People test your boundaries to see if you’re strong. If you pass their tests, they are more likely to do what you want.
Remain unfazed in everyday situations
Say you ask someone out, and they’re taking just a bit too long to respond with their answer. Don’t try to fill the void and buckle “well, um, it’s OK if you don’t want to.” Nope, hold tight and be grounded.
You might have your credibility questioned in a job interview. Instead of giving a supplicating type of answer, give a grounded one that demonstrates your competence and value in a non-needy way.
Stop avoiding tough conversations you need to have with a friend or family member just because it will be a bit awkward or maybe even seriously tense. If the conversation needs to happen, then make it happen. But do it with empathy, care, and also firmness at the same time.
Related:
Sales is the ultimate training ground for awkward conversations
If you can get good at sales, life in general just opens up to you. If it were up to me, I would make it mandatory for everyone to have at least one sales role in their life because it teaches you so much.
Not just how to handle an awkward conversation, but also a ton of valuable life skills like confronting your own insecurities, being okay with receiving what you deserve, leadership, and learning how to coach others.
You, as a human being, are in a metaphorical awkward conversation with life itself. You’re trying to ask for what you want, you get resistance, you fumble opportunities, you bounce back, and—if you’re willing to embrace uncertainty long enough—you tend to get what you want.
I tell all of my clients that business is one of the most spiritual realms they’ll ever enter. Some of them shrug it off until they go through it, and then they come back to me saying, “I get it now.”
Business, especially sales, is a crash course in understanding human nature. If you get good at it, you get good at pretty much everything else by default.
