You can only watch so many sales training videos before you just have to get out and do it yourself.
I’m guilty of it, too. I’ve put in hours watching Grant Cardone, Jordan Belfort, Alex Hormozi, and plenty of other salespeople. I’ve learned frameworks, techniques, psychology, and different ways to approach a sales conversation.
But the reality is: you can’t learn to ride a bike if you never get on it, and you can’t learn to golf if you never swing the club.
Some days the ball lands in the woods. Some days it goes straight into the hole. But you have to go to the driving range and actually swing the club if you want to get better.
Sales works the same way.
You can watch all the sales training you want, but eventually you have to pick up the phone, send the email, have the conversation, and figure out what happens.
That’s where the learning starts.
The Art: Stop Scripting, Start Having Conversations
I was training some of my coworkers on B2B outbound outreach recently, and I noticed a high level of reluctance.
There were a lot of questions.
“What if I do this wrong?”
“What if they get annoyed?”
“What if they ask me something I don’t know?”
I understood the hesitation because that’s where I was when I started, too.
When you’re new to sales, it can feel like there’s a perfect thing you’re supposed to say. You imagine that experienced salespeople have some secret script in their head that tells them exactly what to say in every situation.
I don’t think that’s how good salespeople operate.
I’m not a fan of rigid scripts. Once you start reading from a page, you can sound like a salesperson instead of just sounding like a person.
People can tell.
Nobody wants their time wasted by someone pushing a product. But if your intent is genuinely focused on solving a problem and being helpful, sales stops feeling like a dirty word.
The goal isn’t to have the perfect pitch.
The goal is to have a conversation.
Create a Clear Reason for Reaching Out
If the reason you’re calling isn’t immediately obvious, create one.
Look at your current successful customers. What do they have in common? What problems did they have before they became customers? Are there other companies that look similar?
That gives you a reason to reach out.
Instead of:
“Hey, I’m calling from XYZ Company. I wanted to see if you have any interest in our services.”
You can make the conversation about them:
“Hey, you look a lot like a customer we’ve worked with in the past. They were running into [specific problem]. Are you experiencing something similar? If so, would you be open to hearing how we helped them solve it?”
Now there’s a reason for the call.
Maybe they have the problem. Maybe they don’t. Maybe they’re interested. Maybe they’re not.
That’s fine.
You’re trying to find out.
And I think that’s a much easier way to approach outbound than worrying about memorizing the perfect script.
Focus on Diagnosis Over Pitching
The more I do sales, the more I think good sales is mostly about asking good questions.
The best salespeople aren’t necessarily the people who can give the most impressive pitch. They’re the people who understand their industry well enough to recognize problems and ask the right questions.
It’s like being a doctor.
A doctor doesn’t walk into the room and immediately tell you what medicine you need. They ask questions first.
What’s wrong?
How long has it been happening?
What have you tried?
What’s causing the problem?
They’re diagnosing before they prescribe. Sales works the same way.
You want to understand what’s actually happening before you start explaining why your product or service is the answer.
Does the problem exist?
How big is it?
What is it costing them?
Have they tried to solve it before?
Why hasn’t it been solved?
Can you actually help?
Sometimes the answer is no.
Maybe there isn’t a problem.
Maybe it’s not important enough to solve.
Maybe they’re happy with what they’re doing.
Maybe you’re simply not a fit. That’s okay. Not every conversation needs to turn into a deal.
The better your questions are, the better you’ll become at figuring out where there’s a real opportunity.
Navigate the Gatekeeper Naturally and Kindly
Cold calling also means you’re not always going to get the person you want on the first try.
Sometimes you get the front desk.
Sometimes you get an assistant.
Sometimes you get someone who has no idea what’s going on.
I don’t think you need to treat these people like an obstacle you have to defeat.
Just have a conversation with them.
For example:
Call 1:
“Hey Susie, I’m trying to reach the person who handles [X]. Who would that be?”
Maybe Susie tells you it’s Dan.
Now you have a name.
Call 2:
“Hey Susie, is Dan available?”
That’s it.
You’re not trying to trick anybody.
You’re just figuring out who you need to talk to and how to reach them.
The more comfortable you get having these conversations, the less complicated outbound starts to feel.
The Math: Understanding Your Sales Funnel
There’s an art to sales, but there’s also a math side.
You can be great at having conversations, asking questions, and diagnosing problems, but you still need enough opportunities to create enough business.
Your close rate will vary depending on your industry, offer, sales process, and skill level. But let’s use 30% as a simple example.
100 Discovery Calls × 30% Close Rate = 30 Closed Clients
If your average contract value is $1,000, those 30 customers represent $30,000 in revenue.
Now you can work backward from your goal.
If you need $30,000 in revenue, maybe 100 opportunities gets you there.
If you need $60,000, maybe you need 200.
Of course, real sales funnels aren’t this clean. Your close rate can change, deals can have different values, and not every “opportunity” is equal.
But the basic math still matters.
It gives you something to work with.
Control the Input
This is where I think sales gets interesting.
You can’t control whether someone buys from you.
You can control how many people you reach out to.
You can control how many conversations you have.
You can control how many discovery calls you schedule.
You can control how consistently you follow up.
Your close rate is a reflection of your current sales skills and process. You should absolutely work on improving it.
But if you’re at a 30% close rate, the easiest thing to change tomorrow isn’t necessarily getting yourself to 40%.
It might just be creating more opportunities.
If you’re only having 10 conversations, try having 20.
If you’re scheduling five discovery calls, try to schedule 10.
If you aren’t doing enough outbound, do more.
This is why sales is both an art and a math problem.
The art is having better conversations.
The math is creating enough conversations for those conversations to eventually turn into business.
You need both.
You Still Have to Get on the Bike
I think this is the part that’s easy to forget.
You can spend a lot of time learning about sales.
You can listen to the sales gurus.
You can read books, listen to podcasts, study psychology, learn closing frameworks, and build the perfect CRM.
All of that can help.
But eventually, you have to make the call.
You’re going to have bad conversations.
You’re going to say the wrong thing.
Someone is going to hang up.
Someone is going to tell you they’re not interested.
You’re probably going to annoy somebody.
And sometimes you’re going to have a great conversation that turns into a great customer.
That’s how you build the skill.
You don’t learn to golf by watching someone else swing the club, but it helps after you’ve tried it.
You don’t learn how to ride a bike by watching someone else ride one.
And you don’t learn sales by watching someone else sell.
At some point, you have to get on the bike.