Sales and the Fear of Failure



Last week was a memorable one. I gave a talk on scaling sales development at Sales Hacker and got an incredible lead from a person in the audience. Then the group I started back in August, the NYC Enterprise Sales Meetup, not only surpassed 900 members but also had its highest turnout ever with over 100 sales closers in attendance. But it was one conversation in particular during the meetup that stood out.

As I was waiting to speak to one of our speakers after the panel concluded, I struck up some small talk with the person next to me. I thought it was a good opportunity to ask what brought her to the meetup. She mentioned that she was somewhat new to sales and saw the meetup as a good place to listen and learn. Then unprompted, she added this;

“And what I really like about the meetup, is you can admit failure and it’s okay.”

I am paraphrasing slightly, but it really hit deep because she said in one short sentence what I have poorly attempted to articulate over the past several months about our growing community. The meetup is a place where salespeople can talk about, admit to, and learn from failure.

If you live in the tech startup world, talking about failure is nothing new. There are even entire conferences dedicated to the topic of failure. In fact, failure is deemed laudable and a virtue, the badge of honor that shows you tried where many others refused to tread. That is not to say winning is not better, just that failure is in itself nothing to fear. It is the way we learn, build from, and forge ahead.

Sales is funny profession though when it comes to failure. If you are in sales, you are experiencing mounds of failure on a daily basis. Every time you send an email, pick up the phone, or walk up to a stranger, you are facing failure. But failure is not laudable or worthy of praise in our profession. No one talks about their greatest failures, there are no President’s Clubs for failing to make quota, and management has no patience for why your big deal does not close when you said it would. We simply have no tolerance for failure in sales. Ask any VP of Sales what the reward is for failing to make the quarterly numbers. Yet in a profession seeped in failure, we do not let the word pass our lips.

We need to start talking about failure. One of the reasons I started the meetup was that I felt that as a profession, we were not being served with helpful outlets to learn and share sales knowledge. The world of sales has radically changed in only a few short years, yet the way many of us are selling is quite frankly outdated. If we are afraid to talk about what does not work and why we experience failure, then we perpetuate the low state of sales awareness in our industry to the detriment of our profession and our careers.

Let’s be honest though, it is not easy to talk about. It is painful and embarrassing. In a field where winning is everything, fueled by comp plans and greed and ambition, we could all benefit from raising the bar on our sales awareness and capabilities. We need to adapt to a new world where the sales experience has become ever more critical in forging deals, but requires an even higher level of expertise. That means we have a lot to learn and it starts with overcoming our own hesitance to talk about failure. I invite you to join us for our next event on “Negotiating the Enterprise Deal” and let’s begin the process of learning as the lever to discuss our failures, improve our skills, up the ante on our results, and slay those quotas!



Reprinted by permission.

Image credit: CC by PJ Johnson

About the author: Mark Birch

Mark is an early stage technology investor and entrepreneur based in NYC. Through Birch Ventures, he works with a portfolio of early stage B2B SaaS technology startups providing both capital and guidance in the areas of marketing, sales, strategic planning and funding.

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