What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

I’m not sure if you noticed this, but there is a massive gap between what salespeople and leaders know and what they actually do.

I’ve written 18 books and trained hundreds of thousands of salespeople. I can’t tell you how many times someone comes up to me and says, “Jeb, I read Fanatical Prospecting. Great book. But that stuff doesn’t work for me.” Or they’ll say, “I tried that objection handling technique you taught, but it didn’t work, so I went back to what I was doing before.”

Here’s what they don’t understand: The problem isn’t the technique. The problem is that they gave up too soon. The brutal truth is that most people fail to implement what they learn. 

The Skate Park Lesson

A couple of weeks ago, I was traveling for business, working with one of my clients’ sales teams. One afternoon, I decided I needed some exercise, so I went for a walk. Along the way, I came across a skate park where kids were riding their skateboards and doing tricks.

There was a bench nearby, so I sat down to watch for a while.

Close to me was a group of young guys, probably 13 or 14 years old. They were huddled around a phone watching a YouTube video of someone doing a particular trick on their skateboard. They watched it, talked about it, and then one of them threw his skateboard down and attempted the trick.

He immediately fell off and failed.

The next kid tried, and he failed.

Then the next one and the next one. All of them failed to do the trick. 

So what did they do? They went back and watched the YouTube video again. Then they threw down their boards and crashed and burned, but this time, slightly less dramatically than the first time.

They repeated this process over and over. Watch the video. Try the trick. Fail. Watch again. Try again. Fail a little less badly. Until finally, one of them nailed it.

When he landed the trick, they all erupted. Clapping, fist pumping, and cheering. And once one kid got it, the rest of them started getting it too. They practiced until they had the trick nailed down, then went back to YouTube to find another trick to learn.

At that point, I got up and headed back to my hotel. But as I was walking, I couldn’t stop thinking about what I’d just witnessed.

Too Often, We Give Up too Soon

How often do we do the exact opposite in business and sales? We read a book, watch a video, listen to a podcast. We hear about a technique or concept that sounds really good. And we think, “Yeah, I’m going to try that.”

So we give it one shot. Maybe two if we’re feeling ambitious. And when it doesn’t work perfectly the first time, we say, “Well, this doesn’t work for me,” and we give up and never try it again.

Or worse, we read the book, feel really good about the concept, then put the book down and never even attempt it at all because we’ve already convinced ourselves it wouldn’t work for us before we even tried.

But here’s the thing: Those kids at the skate park didn’t look at that trick and say, “This looks hard, it probably won’t work for me.” They looked at it and said, “We’re going to figure this out.” They understood something that most adults have forgotten: Just because you read about something or see someone else do it, doesn’t mean you’re going to master it on the first try.

The Homemade Yogurt Failure Paradigm 

As I was walking back from the skate park, this lesson reminded me of something that had happened to me over the holidays.

I’d seen something in my news feed about making homemade yogurt. It looked interesting, so I bought some milk, studied the recipe, and made an attempt.

And I failed. My concoction didn’t turn into yogurt at all. My immediate reaction was, “Well, this isn’t going to work; it must be a bad recipe.” I gave up after one failed attempt.

But after watching those kids at the skatepark, I realized the giving-up-too-soon trap I’d fallen into. So when I got home from my trip, I went back, reread the recipe, walked back through my steps to figure out what went wrong, and tried again. This time it worked, and I actually made yogurt.

The recipe wasn’t the problem. My execution was the problem. And I only figured that out by trying again.

The Human Overconfidence Fallacy 

Here’s the lesson: We are all susceptible to this human fallacy of believing that we can read something, watch something, or hear something once and then immediately do it perfectly.

When it doesn’t work the first time (or even the second time), we conclude that the technique is flawed, or it won’t work for us, or our situation is unique and different.

But the truth is, we gave up too soon, before we gave the technique a fair shot. That’s just being human. We’re wired for overconfidence, instant gratification, and immediate results. When we don’t get them, we move on.

Why This Matters in Sales 

Let me bring this back to sales, because this pattern will absolutely kill your results.

You read a book on prospecting, learn a new cold calling technique, watch a sales training video on objection handling, or attend a conference or training and learn new ideas.

Then you try it. Maybe it feels awkward, or the prospect reacts differently than you expected. Maybe you stumble over the words, or you get shut down and rejected. So you conclude it doesn’t work, and you go back to what you were doing before, which, by the way, wasn’t working either. That’s why you were looking for something new in the first place.

Here’s what you’re missing: Sales is and always has been a numbers game. Statistics and the law of averages matter. Even the best techniques don’t work 100% of the time. You have to use them enough times to see the patterns and to understand what’s working and what needs adjustment.

The Iteration Process

Those kids at the skate park weren’t just repeating the same failed attempt over and over. They were iterating.

They’d try the trick, fail, and then make a small adjustment. They’d watch the video again, notice something they missed the first time, and then talk to each other about what went wrong and what to try differently.

That’s the process: Try, fail, learn, adjust, try again.

But most people skip the “learn and adjust” part. They just try, fail, and quit.

Let me give you a sales example. Say you’re trying a new prospecting email template. You send it to ten prospects and get no responses. The try-fail-quit people conclude the template doesn’t work. But a try-fail-learn-adjust-try again high performer would ask: 

• Did I send it to the right prospects? 
• Was my subject line compelling? 
• Was the timing right? 
• Did my call to action make sense? 
• Should I test a different version?

They’d iterate and test different variables until they figured out what worked. That’s what separates top performers from everyone else. They don’t give up after one attempt. Instead, they iterate until they succeed.

The Success Leaves Clues Principle

Here’s something else those kids understood: If someone else is doing something successfully, that means it’s possible.

When they watched that YouTube video, they didn’t say, “Well, that guy is just naturally talented.” They said, “If he can do it, we can figure out how to do it too.”

This is the “success leaves clues” principle. If someone else is making something work, that’s proof it can work. Your job is to master their patterns and believe that you can make it work too.

When you read a book like Fanatical Prospecting, and you see examples of people who built massive pipelines using these techniques, that’s not fiction. Those are real people who learned how to execute these strategies.

When you watch a training video and see someone handle an objection smoothly, that’s not magic. It is someone who practiced that response dozens or hundreds of times until it became natural.

The clues and evidence are there. The only question is: Are you willing to put in the practice and endure the failures until you get there yourself?

The Practice Paradox

Here’s the paradox that trips people up: The techniques that work best often feel the most awkward at first. That’s because they’re different from what you’ve been doing, and anything different feels uncomfortable.

For example, when I teach salespeople to slow down and use silence in negotiations, they hate it. It feels unnatural. They want to fill the silence with words. But the ones who push through that discomfort and practice using silence close bigger deals at better margins.

When I teach salespeople to ask for referrals using a specific framework, they feel like they’re being pushy or scripted. But the ones who practice the framework until it becomes conversational generate more referrals than they ever thought possible.

The discomfort is temporary. The results are permanent. But you have to get through the discomfort in order to get to the results.

5 Keys to Mastering New Sales Skills

So, how do you actually implement what you learn? Here’s what I recommend:

• First, commit to practicing any new technique at least twenty times before you decide if it works. Not once. Not twice. Twenty times minimum. That’s how long it takes to get past the awkwardness and start seeing results.
• Second, track your results. Don’t rely on your feelings about whether something is working. Write down what happened each time you tried the technique. Look for patterns and notice what’s improving.
• Third, iterate. If something isn’t working after multiple attempts, don’t just abandon it. Adjust it. What needs to change? What variable can you test differently?
• Fourth, find someone who’s making it work and learn from them. If you’re struggling with a technique that others are using successfully, reach out to them. Ask questions. Watch how they do it.
• Fifth, be patient with yourself. You’re not going to master anything instantly. Give yourself permission to be bad at something new while you’re trying to master it.

Your Homework this Week

Here’s what I want you to do this week: Pick one technique you learned recently – from a book, a podcast, a training – and commit to trying it at least twenty times this week. Track what happens each time. Notice what’s working and what’s not, make small adjustments, and keep at it.

Because here’s the truth: The techniques work. But you must put in the work before they will work for you.  

Those kids at the skate park didn’t give up after the first fall. They kept going until they nailed the trick. That’s what separates winners from everyone else. Not talent, luck, or some magical gift. Just the willingness to try, fail, learn, adjust, and try again until you get it right.

And remember, when it’s time to go home, make one more call. Because that one more call is one more rep, one more attempt to get better, and one more step toward mastering your craft.

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