How We Turned Failures into Big Wins by Creating a Culture of Transparency


Failure in sales is real.

  • Calling a customer by the wrong name.
  • Forgetting who you’re calling.
  • Having that pitch, you’ve practiced for so long, fall flat.

It happens to all of us.

As salespeople, we have dozens of scenarios that we can bucket into the failed calls category. They’re embarrassing, and most of the time, we just want to sweep them under the rug.

However, I’ve found there’s immense value in embracing these moments and sharing them with others — regardless of how much it makes you cringe.

I’m going to show you how creating a culture of transparency and celebrating our failures transformed our sales team and brought huge success to our entire org.

Celebrate the failures

Here at Lucidchart, my team of enterprise sales reps has a weekly ritual called Fo’Real Fridays, and it’s all about celebrating and learning from our failures.

It started about a year ago when I asked my team to share their most embarrassing fails of the week. I had a trophy and a $25 gift card for the team member voted as having the “biggest jackass” moment.

Were they a bit hesitant at first?

Sure — no one likes to flaunt their failures.

But did we all laugh until we cried? Yes!

And we’ve kept the tradition going ever since.

While humor is often just what we need at the end of a long week, these sessions provide far more than just a good laugh. They’ve helped our team develop a culture of vulnerability, iterate and innovate faster, and accept failure as a valuable part of the process.

Creating the Culture

Let’s dive deeper into how we created this culture of transparency and the benefits we saw from it.

Create a culture of vulnerability

This tradition has brought our team closer than ever before. There’s something about creating a safe space where we can truly be open and vulnerable with each other that breaks down barriers and takes team bonding to a completely new level.

And opening up doesn’t have to come with a funny anecdote. Sometimes it’s just about being honest and real. As Brené Brown says:

“Vulnerability is not weakness; it’s our greatest measure of courage. People who wade into discomfort and vulnerability and tell the truth about their stories are the real badasses.

At the beginning of the pandemic situation, as our team transitioned to working from home, one of our most seasoned sales reps used our weekly session to open up about his current struggles.

He discussed how COVID-19 had derailed his goals and plans for the year and disrupted many different areas of life. But he taught a very timely lesson — we can’t control our quota, our pipeline, or how customers will react, but we can control what we say and how we act on every single call.

The response from the team was immediate. Everyone thanked him for being so real and began surfacing their own struggles in turn. It was an impromptu moment, and I don’t think we knew just how badly we all needed it until it happened.

It helped us cope with the new normal.

This culture of vulnerability has allowed us to maintain that closeness and personal connection, even as we rapidly grow.

And these team-building moments have only become more crucial during today’s remote work environment when we can’t rely on watercooler talk or ping-pong games to foster those relationships.

Vulnerability encourages empathy, trust, inclusivity, engagement, and problem-solving among teams, regardless of whether you’re sitting next to each other on the sales floor or scattered across the globe.

Iterate and innovate faster

In general, the bigger your team gets, the slower some things start to move. But these meetings encourage iteration and innovation, so success doesn’t slow.

Because, the more we learn from each other’s failures, the faster we understand how to avoid those same mistakes and how to react in similar situations.

As a team, we’re all experiencing different scenarios at different times, and Fo’Real Fridays is a natural venue for surfacing them.

One team member sharing their story can help the remaining 21 develop muscle memory on how to effectively react in those situations.

The trick is that these meetings don’t focus on the failed or successful outcomes — they focus on how we got there and what we can do differently next time.

As these meetings have evolved, I’ve turned ownership over to individual reps. They are the ones in the trenches, so they know what is most relevant and what the greater group needs to hear.

We pick a topic to focus our discussion around, such as a certain competitor, a specific product, or a new sales motion. Team members share their experiences, and then we have a discussion about best practices. Reps ask for advice on how to approach certain situations, and instead of only getting a manager’s perspective, they get real-time feedback from fellow reps.

This format allows us to identify things that aren’t working and iterate on them more quickly. We think outside the box and get creative with solutions.

According to Brown, “Vulnerability is the birthplace of innovation, creativity, and change.” And we have seen that in action every Friday.

Realize failure is part of the process

We have big goals for our team. We want to be a world-class sales team, and we have ever-increasing revenue goals. And sometimes that can feel like a lot for reps in the day-to-day grind.

Fo’Real Fridays help us realize that we all mess up, and that’s okay. It’s helped our team become okay with admitting failures, however big or small.

Regardless of whether you’re a tenured rep with experience at top tech companies or still breaking into the sales space, we all have our moments. It’s about continuous learning and progression, and those failures are just stepping stones towards that goal.

In fact, Brown encourages accepting and embracing the concept of failure because it is “a natural part of the path of progress.

As a result, we’re better able to reverse our mindset about failure and see that every time we fall and get back up, we are that much closer to succeeding.

Start Your Own Fo’Real Fridays

Since we started Fo’Real Fridays, we’ve never learned more and never laughed harder, but most importantly, we’ve never been closer.

And in today’s volatile world, that has never been more important.

Spin up a version that makes sense for your team to develop a culture, innovation, and mindset that will help your team adapt and succeed in today’s sales environment.

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