Great Salespeople Fail Often. — You Should Fail More!

Becoming a Better Sales Rep — Post #34


When you think of successful people, you always think of their successes. It makes total sense: Successful people do have successes; otherwise, they wouldn’t be successful. — Sorry, I just enjoyed using five variations of the word “success.”

But people barely ever look at all the failures these people went through on their way to becoming successful.

So, this post is about getting a better understanding for why failure is normal; and why it’s crucial to your success.

So, embrace it!

Photo by Jonas Denil on Unsplash

A Few Anecdotes on Failure.

I like data and facts, but stories just resonate better. So, let’s take a look at a few examples of benefits of failure that might surprise you.

  1. The Serial Entrepreneurs: I really liked something Jeremy Stoppelman, co-founder of Yelp, said in this episode of the How I Built This Podcast with Guy Raz: “Nobody wants to be a serial entrepreneur because it means you failed many times.” However, this is what it takes to be a successful entrepreneur. Entrepreneurship in itself is often defined by doing something regardless of the resources that are available to you. You’re doing new things that many people have never done before. So, when I hear people tell me that they want to earn more experience before they start their companies, I oftentimes disagree with them. Yeah, sure, get your degree, work for one or two years. There’s certainly some value in this. But, doing a master’s degree in entrepreneurship or earning five years of experience to then do something that this all about trial and error? What do you expect to learn about something unconventional when you’re just doing conventional things. So, coming back to Stoppelman’s comment: there’s a reason that entrepreneurs only become successful after having failed over and over and over again. And the reasons are endless. Sometimes they fail because their idea wasn’t good, sometimes the co-founders don’t get along that well, sometimes they lack organizational skills. But, whatever it is, great entrepreneurs learn out of their mistakes and don’t make the same mistakes again. However, without having made those mistakes, they would’ve never gotten anywhere.
  2. Medical Doctors: Sure, doctors usually are pretty quick about helping you with a broken bone or the common cold, but once things get complicated, doctors also don’t have the answers. They just have two things: experience and options. And, based on their experience, they start trying their options. And, when they run out of options, they try to come up with you new options. But medical school isn’t about here is problem A, and here is solution A that goes along with it. It’s more about understanding the human body and then figuring out how to ask the right questions and test the right things. So, if well-respected professionals such as medical doctors need to fail over and over again to find ways to help someone cure or live with a terrible disease, why do you think that you as a salesperson need to do everything right the first time?
  3. World-Class Athletes: The media loves their stories. And, interestingly, the story that a world-class tennis player has been on the tennis court when they were 4 years old or that they have been playing with a racket before they could walk is something that we immediately interpret as being amazing. There’s this entire narrative around people only being able to be world-class if they start out super early. However, a friend of mine who is an anthropologist and psychologist told me that there’s a much more interesting phenomenon. Yes, many great athletes have started out in their field when they were super young but the top 10% to 20% of world-class athletes usually started in their field at a later stage of their childhood. And, it makes sense. How high are the chances that you excel at the first thing you try? Think about it, only in the Olympics, there are 42 disciplines. And, they’re vastly different. Someone who’s good at swimming might not be the best runner. So, the athletes that are truly the best of the best are usually the ones who try different disciplines while they’re young and stick with the one that they enjoy the most.

So, these examples are not that different from your sales work. You can’t expect to know it all from the beginning, just like an entrepreneur, you need to try things out to find the way that works for you. Every lead is different, just like every case a doctor is looking at. So, you need to try different approaches with different people. And, every sales strategy’s got its benefits and flaws. So just like young athletes, you must try different ones and fail with some of them to discover the ones that truly work.

Photo by Grant Ritchie on Unsplash

The Benefits of Failure.

So, the examples above were rather specific. Let’s take a look at how failure can positively impact your sales work.

  1. Increasing Effectiveness: You can’t know what works unless you try it. And you can’t know what works better if you only stick to an old routine. This is why startups do have chances at beating large corporations. They just constantly try new ways of doing things until they stumble upon a way that’s superior to the one that’s common practice. And, as things change over time, startups might get beaten in the future. We all heard the phrase: “never change a running system.” However, people who believe in this forget that, in the real world, the circumstances around the running system always change.
  2. Increasing Efficiency: Sure, making the same mistakes over and over again will cost you valuable resources. But making a mistake once or twice in exchange for discovering something new that’ll make your sales work go through the roof is absolutely worth it. On top, not being afraid of failure will help you avoid procrastinating on a deadline. Because oftentimes, we just don’t wanna do things because we don’t want to fail. But as long as we don’t try it, we won’t know the outcome.
  3. Keeping You Humble: In an earlier blog post, I mentioned the Dunin-Kruger Effect. In a nutshell, it describes the phenomenon that people who know little about something oftentimes feel overconfident in their knowledge and vice versa. The more you know, the more aware you become about how little you actually know; so you end up feeling relatively dumber. So, by trying things out and making mistakes, you actually become aware of your own limitations which will automatically humble you. And, the days of the overconfident car salesman are over. The world of sales is looking for driven individuals who want to create value for their customers. So, being humble is an asset.
  4. Keeping You Connected: We all fail. We just rarely promote those parts. So, you don’t see it on someone’s LinkedIn. I don’t have a section that shows that I have failed both my interviews at McKinsey and The Boston Consulting Group. But you see that I made it into Harvard. You get what I mean. The interesting thing tho is that once you start being open about your failures, other people open up as well. And it creates this amazing feeling of connectedness. It just feels good that one is not alone in their mistakes.

So, rather than being afraid of failure, embrace it, accept it. Make it part of your work and learn from it to become a better sales professional!

So, Get Out of Your Comfort Zone and Give Resonaid a Try.

Resonaid is a tool that writes personalized messages for your sales outreach. It identifies unique and personal hooks that you can use to send out messages that are customized for every single lead. It literally takes all the work away from doing outreach. So, rather than spending 5 hours reaching out, it’ll only take you some 30 minutes.

Make sure to give it a try, if you haven’t already!

Access Resonaid via the Chrome Web Store.

Resonaid is a tool that helps sales professionals with writing personalized messages for their sales outreach.

We recently released the first version of our product as a Chrome extension in the Chrome Web Store.

As we just went live this summer, you can currently test Resonaid for free and get large discounts by being an early user.

About the Author.

Teddy Lange is a co-founder at Resonaid and is responsible for business development and customer experience. Before joining Resonaid, he’s been a Sales Rep and Junior Sales Manager, and co-founded various companies. He’s currently finishing his graduate degree in Public Policy with a focus on communication at Harvard University. Feel free to reach out to him at



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