If you've ever thought, “I hate sales,” or “Why does every sales conversation feel so awkward?” you're not alone.
This is one of the most common things clients say when they first come to work with me. They're talented, experienced, and genuinely care about the people they serve. Yet the moment a conversation shifts toward the possibility of working together, something changes.
They second-guess themselves.
They over-explain.
They talk too much.
Or they avoid the conversation altogether.
After decades of observing thousands of sales conversations, here's what I've learned:
Sales don't feel awkward because you're bad at sales. Sales feel awkward because something in the conversation creates discomfort, either for you, for the other person, or for both of you.
The good news is that awkwardness isn't a personality trait. It's a signal. When you understand what's creating it, you can change the conversation.
Why Do So Many People Hate Sales?
When people tell me they hate sales, I don't believe they actually hate selling.
What they hate is how selling has been modeled for them.
Many of us have experienced sales conversations where someone tried to convince us, pressured us to decide before we were ready, or made us feel like saying “no” wasn't acceptable.
These experiences leave an impression.
Without realizing it, we begin to believe that selling requires becoming someone we don't want to be.
So we avoid making offers.
We hesitate to follow up.
We soften our language until the other person isn't even sure we're inviting them to work with us.
Ironically, trying not to sound “salesy” often makes a sales conversation feel even more uncomfortable.
The Real Reason Sales Conversations Feel Awkward
Here's something I've observed over and over again.
Most awkward sales conversations have very little to do with the words being used.
They have everything to do with where the seller places their attention.
When your attention is on yourself, questions start running through your mind:
- What if they say no?
- What if they think I'm too expensive?
- What if I sound pushy?
- What if I mess this up?
The conversation becomes about protecting yourself from rejection.
The moment your attention shifts inward, it's difficult to stay fully present with the other person.
That's when conversations begin to feel forced.
Rapport Comes Before Trust
One of the biggest misconceptions in sales is that trust comes first.
In my experience, rapport comes first.
Rapport is created when the other person feels seen, heard, and respected.
It happens because you're paying attention to them.
You're noticing how they communicate.
You're listening for what's important to them.
You're responding to their cues instead of following a script.
Rapport is never about pretending to be someone you're not.
It's about making it easier for the other person to be in conversation with you.
When rapport is present, the conversation becomes more natural.
When rapport is missing, even the best sales technique feels awkward.
Why Trying to Convince Someone Never Works
One of the quickest ways to create resistance is trying to convince someone.
Here's why.
The moment people feel you're trying to change their mind, they naturally begin protecting their current thinking.
It's simply human behavior.
Nobody enjoys feeling judged or feeling like they're have to defend their decision.
The harder someone pushes, the stronger the other person often resists.
That's why relationship-based selling isn't about convincing anyone.
It's about creating a conversation where people have enough information, enough clarity, and enough safety to decide what's right for them.
Notice the difference.
One approach tries to control the outcome.
The other respects the buyer's ability to make their own decision.
Only one of those builds long-term relationships.
The Hidden Cause of Feeling “Salesy”
When someone says, “I don't want to sound salesy,” I usually hear something underneath that statement.
They're worried about making the other person uncomfortable.
This is actually a beautiful instinct.
It means you care about the relationship.
The challenge is that many business owners respond by avoiding the conversation altogether.
They don't make a clear invitation.
They don't ask (Invite) the prospect to move forward.
They leave the conversation hoping the prospect will somehow figure out the next step.
That isn't relationship-based selling.
It's unclear communication.
People appreciate clarity.
They appreciate knowing what their options are.
Offering someone an opportunity to work with you isn't pressure.
It's an invitation.
And invitations are easy to decline.
What Relationship-Based Selling Looks Like
Relationship-based selling begins with one simple belief:
The conversation is about the buyer, not the seller.
Instead of focusing on what you want to say next, become curious.
Ask thoughtful questions.
Listen longer than feels comfortable.
Notice patterns.
Reflect back what you hear.
Guide the conversation with genuine interest instead of an agenda.
When people feel understood, they naturally become more open.
Not because they've been persuaded.
Because they feel respected.
Relationship-based selling isn't just a philosophy. It's a repeatable process.
Over the years, I've developed a framework that guides people through each stage of a sales conversation so they always know what comes next. When you understand the structure behind the conversation, selling feels more natural because you're no longer guessing your way through it.
A Simple Shift That Changes Everything
The next time you find yourself feeling awkward during a sales conversation, pause and ask yourself one question:
Where is my attention right now?
When your attention is on your own fear of rejection, gently bring it back to the person in front of you.
Become curious about their experience.
What are they trying to accomplish?
What's getting in their way?
What would success look like for them?
These questions naturally create better conversations.
Better conversations create stronger relationships.
And stronger relationships lead to more yeses.
Not because you convinced anyone.
Because you created a conversation where the right decision became easier to make.
Final Thoughts
Sales conversations don't have to feel awkward.
When you stop trying to perform and start focusing on the person in front of you, everything changes.
You ask better questions.
You build rapport.
You communicate with confidence.
Most importantly, you create a conversation where both people feel respected, regardless of the outcome.
That's what relationship-based selling is all about.
It's not about saying the perfect thing.
It's about creating the kind of conversation where people feel comfortable deciding whether working together is the right next step.
If sales have felt awkward in the past, don't assume that's just the way selling is.
Sometimes the smallest shift in where you place your attention changes the entire conversation.