Episode January 19, 2026 14 min 27s

Where Confidence Comes From and Why it Matters in Sales (Money Monday)

Have you ever gone into a closing meeting, a sales presentation, or even a prospecting call with total confidence? That mindset and feeling that everything’s going to go your way, that nothing can go wrong, that you’re absolutely going to win?

I’ve been there. I know you have too. It’s one of the greatest feelings ever.

But let’s juxtapose that against going into a meeting feeling insecure, where your focus is on everything that could go wrong versus everything that could go right. And then, as soon as something does go wrong, everything starts to spiral downward.

There is absolutely nothing that can make or break a deal like confidence.

In this Sales Gravy podcast episode, we’re going to explore exactly where confidence comes from, why it matters so much in sales, and most importantly, what you can do to build the unshakeable confidence that closes deals.

The Insecurity Death Spiral

Recently, I learned a profound lesson about confidence.

I was invited to play golf with a group of businesspeople in Florida. Beautiful day, sunshine, great course. It should have been perfect.

Except I’m not a very good golfer. And these guys? They were good. Really good. The kind of golfers who carry single-digit handicaps and talk about their swing plane like it’s a science project.

So I’m standing on the first tee, watching them stripe their drives straight down the middle, and I can feel it happening. That little voice in my head starts whispering: “You don’t belong here. You’re going to embarrass yourself. Everyone’s going to see how bad you are.”

I started strong enough. Made it through the first couple of holes without humiliating myself. But then I hit a bad shot. Then another. And instead of shaking it off like I normally would, I started fixating on those bad shots.

That’s when the downward spiral began.

Every swing became an exercise in anxiety. I was so focused on not messing up that I couldn’t help but mess up. My mechanics fell apart. My rhythm disappeared.

By the end of the round, I had played one of the worst games of golf in my life. Not because I suddenly forgot how to swing a club, but because I let insecurity take over.

Now, I managed to keep a smile on my face. We were playing golf in the Florida sunshine, after all. But inside, I was frustrated because I knew what had happened. I let my insecurity about being the weakest player in the group sabotage my entire game.

And here’s what hit me on the plane home: That’s exactly what I see happen in sales all the time. One moment of uncertainty, one unexpected challenge, and suddenly, a salesperson who is perfectly capable starts spiraling. Their confidence evaporates. And with it goes their ability to perform.

Why Confidence Matters in Sales

In sales, there is nothing that sells like confidence. Nothing.

Buyers lean into confidence. They’re attracted to it. They trust it. And because of emotional contagion—your ability to transfer your emotions to another person—you basically take your confidence and hand it to the buyer, who then gains more confidence in you.

Think about it. When you walk into a meeting radiating confidence, the buyer thinks, “This person knows what they’re doing. They believe in what they’re selling. I can trust them.”

But when you walk in feeling insecure, the buyer picks up on that too. They start thinking, “Why is this person nervous? What aren’t they telling me? Maybe this isn’t the right solution.”

In sales, because we can’t always control the playing field and because we don’t always feel like we should be where we are—especially when we’re dealing with the C-suite or high-level decision makers, when we’re in super competitive situations, or when we don’t really know what we’re talking about—one thing that goes wrong can create a cascade of other problems, creating a downward insecurity spiral that is real and deadly.

The Ultimate Source of Confidence

So the question is: Where does confidence come from? Where do you get it?

Well, confidence by its very nature comes from the inside. It’s a mindset. It’s something that you believe, just like insecurity is a mindset that comes from the inside.

Confidence is mostly created by certainty.

When you feel certain that you can control the outcome, you feel more confident.
When you’re in situations that feel familiar, or you’re talking about a product, your service, or some part of your offering that you totally understand, you feel more confident.
When you’ve executed the sales process perfectly and built deep relationships with your customers, you feel more confident that they’re going to buy from you.
When you’ve practiced your presentation multiple times and know it by rote, you feel more confident.

By the way, the same thing works in reverse. Uncertainty begets insecurity.

When you walk into a situation, and you feel uncertain—and this happens to a lot of brand-new salespeople who don’t know what to say or feel like they don’t really understand the product offering, their industry, or their customer’s business—it creates a level of insecurity.

So the answer, if we want to be more confident, is to create more certainty.

Certainty Creates Confidence

Let me give you an example from my horrible, awful, terrible round of golf.

In the middle of that terrible round, I got desperate for anything that would give me confidence. So I started playing entire holes with my 7-iron because that was the one club I felt I was certain I could hit.

Except for putting, I would hit the 7-iron off the tee, on the fairway, and chip with it around the green. 150 yards at a time with my 7-iron, I could make it go straight down the fairway and hit the green.

That certainty in that particular club helped me feel more confident, and my game actually improved when I stuck with what I knew worked.

Now, in sales like golf, there is nothing you can be 100% certain about, simply because there are too many variables. We’re dealing with human beings, nasty competitors, and a shifting landscape. Even in accounts that are in our pipeline, things are always changing.

So for us as sales professionals, there’s no absolute certainty. But there are ways you can boost certainty in order to gain more confidence.