How to Actually Sell: 5 Tips to Close More Deals
Let’s be real—no one wakes up in the morning excited to talk to a salesperson. No one’s sitting around thinking, "You know what would make my day? A cold call from a sales guy who wants me to change the way I do things."
So, if you’re having a conversation with a prospect, it’s because something is bugging them enough that they’re willing to endure talking to you. And your job? Find out what that thing is.
But too often, sales reps rush straight into the demo. They’re comfortable showing off the product, explaining how it works, and throwing in a bunch of features. And then, they wonder why the deal goes dark.
Let’s talk about why that happens—and how to fix it.
Step 1: Determine the real ‘pain’ and why they want to explore a potential solution
This is the golden rule of outbound sales:
If someone who didn’t ask to be sold to is willing to take a meeting, there is something in their world that sucks more than dealing with a salesperson.
Your job is to uncover what that is. And no, they won’t just tell you. You have to ask the right questions and dig into their world.
Example:
Instead of jumping straight into the demo, say:
“Hey, I know you’ve already got a system in place. Sounds like things are headed in the right direction. So tell me—why take this call with me? What’s missing from what you have today?”
Or, if they give a generic answer ("We’re always looking at new tech."), don’t just accept that—press further.
“Okay, cool. What’s great about your current setup? And what’s… not so great?”
This is where you start uncovering the real pain points.
Step 2: Don’t discuss scope until you’ve confirmed the fit
A classic mistake? Asking technical and buying process questions before you’ve even confirmed they want your solution.
Too many sales reps jump into questions like:
“If we did a pilot, would you guys handle the install yourselves or would you need outside help?”
“Do you have internal resources dedicated to implementation?”
But here’s the problem: The prospect isn’t even sure if they want to buy yet.
And now, instead of getting excited about the solution, they’re thinking: "Oh man, this sounds like a lot of work."
What should you do instead?
Hold off on scoping and implementation questions until they’re sold on the value.
First, confirm the gaps in their system. Then, later, they’ll care about the setup.
Think of it like dating—don’t talk about wedding plans on the first date.
Step 3: Customize the demo to solve their pain
Another mistake: Giving a generic demo instead of tailoring it to what they care about.
If a prospect mentions a specific pain point, that’s your cue.
Instead of running through all the cool things your product does, go straight to the feature that solves that exact problem.
“You mentioned manual tracking is a pain. Let’s start with how we make that ridiculously easy.”
Walk through the feature. Show how it solves the issue. Then ask:
“Does this address what you were hoping for?”
Why is this important? Because you want confirmation throughout the demo that you’re on the right track. If they say, “Eh, not really,” then guess what? You just saved yourself from a dead deal later.
Step 4: Ask the ‘Dumb’ Questions
A lot of sales reps hesitate to ask deeper questions because they’re worried about looking uninformed. But here’s the truth:
Your prospect will always know more about their business than you do. But you will always know more about your product than they do.
That’s why you need to ask until you actually understand their pain. Even if it feels dumb.
“Hey, I might be way off here, but can you walk me through what that process actually looks like?”
Most prospects don’t even realize how bad their current system is until you start peeling back the layers.
Step 5: If They Go Dark, Give Them an Easy Way Out (or Back In)
So, you sent a follow-up email. No response. You called. Nothing.
Now what? Don’t just keep hammering them. Give them space to disengage without feeling pressured—or re-engage on their own terms.
Try something like this:
“Hey [Name], just following up on my last email. I want to be mindful that I reached out to you proactively—this wasn’t something you were actively shopping for. I’d love to work around your timeline—let me know when it makes sense to reconnect.”
This does two things:
It gives them an out if they’re not interested (so they don’t ghost you).
It signals that you’re not just a pushy salesperson—you’re someone who respects their priorities.
Final Thoughts: Sales Is Just Smart Listening
At the end of the day, sales isn’t about running a great demo. It’s about listening for cues, identifying problems, and guiding them toward a solution.
So, next time you’re on a call, keep this in mind:
Step 1: Find out why they’re talking to you.
Step 2: Don’t jump into the technical weeds too early.
Step 3: Customize your demo based on their pain points.
Step 4: Ask “dumb” questions to get to the real issue.
Step 5: If they go dark, give them space instead of chasing.
Do this, and your deals won’t just move forward—they’ll move forward with momentum.
And if you’re struggling to put this into action? Do a roleplay. Seriously. Say it out loud. Get the reps in. That’s how you actually absorb this stuff.
Now go sell something.