How We Transformed Failure in Sales into Major Successes by Establishing a Culture of Openness

Failure in sales is real.

  • Calling the wrong name to a customer.
  • I’ve had to remind myself who I’m calling by writing it down and looking at my list of contacts.
  • It’s terrifying when you’ve practiced your pitch for so long and it doesn’t go well.

It happens to all of us.

When we have a failed call, it’s usually embarrassing and we just want to sweep them under the rug.

I’ve found that it’s important to share this failure in sales stories, even if they make you cringe.

An article in the New York Times about a woman who faced sexism when she was hired for her first job is summarized by saying “With my first salespeople, I made the mistake of constantly testing pay and commission structure.” The paraphrase says “I felt that with enough of a base pay and lucrative commissions, it would be enough motivation for them.”

I want to show you how transparency and celebrating failure in sales created a culture of success for our sales team.

Celebrate Your Failure in Sales

Every Friday, I have a ritual where my sales team sits down and talks about their failures from the week.

I had a trophy and $25 gift card for the team member voted as having the “biggest jackass” moment. This started about a year ago.

Yes, they were a little hesitant at first.

We all know that nobody likes to show off their failures.

But did we all laugh until tears streamed down our faces? Yes!

It’s been a tradition for us to do this every year.

While humor is often just what we need at the end of a long week, these sessions help our team in many ways. They’ve helped us develop vulnerability and innovation skills.

Creation of the Culture

Transparency is an important part of our culture, so let’s explore how we created it and the benefits that have come from it.

Create an environment that is receptive to vulnerability

We’ve created a space where we can be open and vulnerable with each other, which breaks down barriers. This has really bonded our team.

As Brené Brown says, it’s not always about telling a funny anecdote. Sometimes you can just be honest and real.

It is not a sign of weakness to be vulnerable. It takes courage and strength.

Our most experienced salesperson opened up during our weekly meeting about his current struggles. He went on to say that he felt like a failure, and was worried people would think less of him because he couldn’t find work.

He talked about how COVID-19 derailed his goals and plans for the year. He also discussed that we can’t control our quota, pipeline, or customer reactions but what we sayact on every single call.

The team thanked him for being so honest and they all began speaking about their own struggles with mental health. It was a spontaneous moment, but we realized how badly it needed to happen.

We have had to adjust and cope with the new normal.

Our culture of vulnerability has helped us maintain a close-knit group as we grow.

Because the work environment has changed to a more remote one, we can’t rely on watercooler talk or ping-pong games and other team building moments in order to foster relationships.

Vulnerability breeds empathy, trust, inclusivity and engagement among teams. It also encourages problem-solving.

Iterate and develop more rapidly

Success doesn’t slow as you grow, and these meetings help with that.

We learn from each other’s failure in sales, and that helps us understand how to avoid mistakes in the future.

As a team, we all experience different scenarios at different times. Fo’Real Fridays is the perfect way for us to share them with each other.

One person can help the other 21 learn how to react in a particular situation.

The meetings don’t focus on whether or not the project was successful, they learn what went wrong and how to do better next time.

As meetings have evolved, I’ve given ownership to individual reps. They know what the greater group needs and they are in the trenches so they can provide information as needed.

We often have meetings where we discuss a certain topic. For example, if our competitor is creating an ad campaign that might affect us in the marketplace, or when discussing how to handle customer objections.

This format allows us to identify what isn’t working and fix it quickly. We think outside the box for solutions.

Brown says that it is through vulnerability and openness to change that we can grow and create. And this has been true in our weekly meetings.

Recognize that failure is a necessary part of the process

We have big goals for our team. We want to be a world-class sales organization, and we are always setting new revenue goals.

Fo’Real Fridays have taught us that we mess up sometimes, but it’s okay. They’ve helped our team become more accepting of failure and be able to talk about it with each other.

Regardless of how much experience you have, we all make mistakes. It’s about continuous learning and progression to succeed.

Failure is an important part of the learning process.

In the past, we’ve been told that failure is a bad thing. But now there are more and more people who have changed their perspective on this idea of ‘failure.’ They see it as something to learn from so you can get closer to success.


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 failure in sales


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Justin McGill
About Author: Justin McGill
Justin McGill is the Founder of LeadFuze - a lead generation platform that discovers new leads for you automatically. Get 25 leads free.