The Insecurity Death Spiral

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.

Four Ways to Create Certainty and Boost Confidence

1. Invest in Yourself Through Education

If you get insecure when you’re talking about things in your industry or about your product that you don’t understand, then go educate yourself.

Take the time to learn. Take classes. Go to your LMS and take e-learning. Read everything about your product. Become an expert—not just in your product, but in your industry.

Also, learn about business. The more you can educate yourself about business, the more you gain business acumen, which makes you feel more confident in conversations with executives.

When you know your stuff cold, understand your product inside and out, and can speak intelligently about your industry and your customer’s business challenges, uncertainty evaporates, and with it, goes insecurity.

2. Plan Every Single Call

Winging it is wickedly stupid on sales calls because when you wing it, you create uncertainty.

So sit down and think about every single call.

• What am I going to do?
• What questions am I going to ask?
• What’s my objective for being there?
• What am I going to close for at the end (targeted next step)?

Build a plan, write it down, and review it in advance of your meeting. Planning creates certainty.

3. Murder Board Your Big Meetings

Along with planning comes the concept of murder boarding, red teaming, or scenario playing. Murder boarding creates certainty around handling the unexpected.

Especially in large presentations and closing calls, you need to start pulling the thread on everything that could possibly go wrong. Every objection you could get. Every pushback. Every hard question.

Think about the different stakeholders who are going to be around the table, and the types of questions they’re going to ask, and the potential things they may say. Then find somebody on your team or somebody in your household to role-play all those scenarios with.

I’ve found that nothing gives me more confidence in big sales meetings than murder boarding. Because when I get into those situations—especially with objections or negotiations that can be super intimidating—the more I role-play those things, the better I am at them and the easier they are to deal with. In fact, they’re far less difficult in real life than they were in the role-playing.

4. Keep a Full Pipeline

This is powerful: There’s nothing that makes you more confident than being able to sell like you don’t have to sell.

When you are fanatical about prospecting and build a full pipeline, it gives you lots of options. You know you can walk away from anything. You’re detached from the outcome.

When it doesn’t make a difference if you win or lose, you gain immense confidence, which is why a full pipeline is the ultimate confidence builder.

With Confidence, Mindset Matters

When it comes to confidence, mindset matters. If you are obsessed with how you might fail or what you might do wrong, there’s a tendency to get the thing you’re focused on. It’s called target obsession. Whatever we focus on, we tend to attract and move toward. So be careful what you’re focused on.

One of the things I do—and I know this is kind of weird, but it works—is before I walk into a sales meeting, I look into the mirror and tell myself, “I’m a great salesperson.”

I actually say the words out loud. It’s a little bit cheesy. But by saying those words, changing my body language, pushing my shoulders up, my chin out—the power pose, as some would say—that actually begins to change my mindset and makes me feel more confident.

Add to that eating well, getting plenty of sleep (sleep really does wonders for your confidence), exercising, and making sure, before you go into a big presentation, that you’re not going in on an empty stomach.

How to Overcome Insecurity in the Moment

I sell every single day, and I’ve been doing this for 30 years. I know what it’s like to walk into a meeting with a prospect or customer and feel insecure. It happens to me still. But here’s the thing: I’m very careful not to let people see me sweat because insecurity and sales make a poor mixture.

Because emotions are contagious and people have a tendency to respond in kind, I want to avoid transferring my insecurity to them, causing them to feel uncertain about me. So I’m very careful with my body language, eye contact, voice inflection, and how fast I speak.

One tactic I use when I feel insecure is to slow down, pause, and ask a question. This gives me a moment to regain my composure and manage my body language.

Build Confidence with Knowledge, Planning, Practice, and Pipeline

Confidence isn’t something you’re born with. It’s something you build through preparation, knowledge, practice, and a full pipeline.

The good news is that all of these things are within your control. You can choose to educate yourself, to plan, practice, and prospect.

Here’s what I want you to do this week:

First, identify your gaps. Where do you feel uncertain in your sales process? Is it product knowledge? Industry knowledge? Objection handling? Closing? Write it down.

Second, create a learning plan. For each gap you identified, create a specific plan to fill it. What books will you read? What training will you take? Who will you shadow or learn from?

Third, plan your next three calls. Don’t wing another call this week. Sit down and plan your next three sales conversations. Write out your objectives, your questions, and your close.

Fourth, murder board your biggest opportunity. If you’ve got a major presentation or closing call coming up, spend an hour this week role-playing every possible scenario with a colleague.

Fifth, evaluate your pipeline. Is it full enough that you can sell without desperation? If not, block time this week for serious prospecting.

This is how you build the kind of unshakeable confidence that buyers respond to, competitors fear, and that feels so good.

And remember, when it’s time to go home, and you’re tired and worn out, always stop and make one more call. Because that one more call gives you the confidence that you can walk in any door, anytime, stand toe to toe with any buyer, and have a winning sales conversation.

Over a million sales professionals and sales teams have become more confident prospectors with the Fanatical Prospecting system. Learn more here.