You don’t find confidence, you build it

In today’s edition, we’re digging into sales confidence. Most people think confidence is something you either have or don’t. But here’s the truth: confidence is a skill. It’s built through preparation, practice, and proof. I’ll share a simple story that shows why confidence grows after the action, not before, and break down 3 practical ways you can start selling with more confidence today.

Hello Reader,

Think back to your first day at a new job.

Remember that feeling?
Uncertain. A little out of place. Questioning if you belonged.

You might have been struggling to fit in or find the confidence.

But here’s the thing, you didn’t quit.
You showed up.
You kept learning.
You stacked small wins.

And over time, confidence came.

This is how it works in sales, too.

Confidence isn’t something you stumble upon.
It’s something you build.

One of the biggest mistakes I see salespeople make is waiting to feel confident before they pick up the phone, send that email, or walk into that meeting. They hesitate. They procrastinate. They think, “Once I feel more confident, I’ll start.”

But confidence doesn’t come before the action. It comes after.

When you consistently show up, get the reps in, and stack small wins, your confidence grows naturally. You can’t shortcut that process. But you can make it easier.

Let’s break down 3 simple ways to start selling with more confidence, even if you don’t feel ready.

1. Prepare like a pro
Nothing builds confidence faster than knowing your stuff.

Confidence isn’t about hype. It’s about certainty.

When you know your product inside out, when you understand your prospect’s world, and when you have your key questions and opening lines ready, you remove 80% of the fear.

So before every call or meeting:

Research your prospect’s company, their challenges, and recent wins.
Write down 3–5 strong questions that show you’ve done your homework.
Practice your opening line until you can say it calmly and naturally.

Prepared people don’t panic. They perform.

2. Celebrate the small wins
Confidence isn’t built in leaps. It’s built in layers.

When you obsess over just closing deals, you miss all the small wins that build momentum:

Booking a meeting? That’s a win.
Getting a prospect to say, “That’s interesting”? That’s a win.
Completing your outreach block for the day? That’s a win.

Track these. Log them. Talk about them.
It keeps you moving forward when the big wins feel far away.

Momentum creates confidence.
So stack the small wins, and the big ones will follow.

3. Build a feedback loop
Confidence grows when you can see your progress.

One of the best things you can do is record your calls (with permission) and review them.

Where did you sound confident?
Where did you hesitate?
What would you change next time?

This isn’t about beating yourself up. It’s about coaching yourself forward.

The faster you close the gap between each attempt and each improvement, the faster your confidence will grow.

Feedback is a hidden superpower; use it.

And if you’re wondering why or how this works, here’s why:

Confidence comes from action. You can’t think your way into it; you have to work your way into it.
Repetition builds comfort. The more you practice, the more your brain says, “I’ve been here before.”
Focused preparation removes uncertainty. You fear what you don’t know. Practice and preparation will build familiarity and shrink that fear.
Small wins compound. Confidence isn’t built by winning one huge deal. It’s built by winning often.

So remember: Stop waiting to feel confident. Start earning it.

It’s like your first day on the job, you’ll feel awkward at first. But if you show up consistently, you’ll soon become the one others look to for confidence.

Wishing you a confident week ahead,

James