The Zenefits of Admitting You Messed Up

Andy Raskin
Firm Narrative
4 min readMar 16, 2016

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Wading through Business Insider’s account of the Zenefits fiasco, I was reminded of a counterintuitive truth about brand storytelling:

The most effective business stories start with how you messed up.

In my Storytelling for Success workshops, I try to bring this point home with the following exercise:

  1. Think of an adjective that you want others to associate with you (“trustworthy”, “honest”, etc.)
  2. Next, write about a time when you acted in the opposite way, and it led you to a bad outcome. (In other words, if your adjective was “trustworthy,” a time you betrayed trust and came to regret it; for “honesty”, a time you lied.)
  3. Finally, reflect on what you learned, and how you now act differently as a result.

Here’s a story shared by one workshop participant— a man who works as a recruiter:

In my line of work, it’s important to constantly check in with promising job candidates. But I used to be lax on that, and one day, I paid the price.

I hadn’t checked in with a candidate whom my client was actively considering, and when the client made an offer, the candidate told me he had already accepted elsewhere. As a result, I had the hugely embarrassing task of informing my client that her top choice wasn’t actually available.

My client was so angry (she and her team would have to deliberate all over again) — and the bawling out I received so harsh — that I’m now maniacal about keeping in close contact with my candidates. Basically, I vowed never again to let my clients suffer those kinds of surprises.

If you were hiring a contract recruiter and it came down to this guy and someone who simply said, “I’m trustworthy,” you’d pick this guy, right?

The secret to building trust: Opening up about “dumbass” moments

In his book What Great Salespeople Do: The Science of Selling Through Emotional Connection and the Power of Story, sales trainer Michael Bosworth calls these narratives “Who I am” stories, because they offer a credible account of how you acquired the values you hold dear.

According to Bosworth,“Who I am” stories are critical for building trust and connection with people who don’t know you well — in sales conversations, job interviews, etc. — and nearly always contain what he calls a “dumbass moment”:

Remember, no one connects with perfection. Portray yourself as human, vulnerable, and flawed like the rest of us. The character (you) should be someone the listener can relate to and sympathize with, someone who is not immune to having a “dumbass moment” now and then.

The Zenefits debacle as effective brand storytelling

Bosworth posits a brand version of the “Who I am” story that he calls the “Who I represent” story. Here, the company (or its leaders) stand in as the main character who goes through some sort of transformation.

In this light, the Zenefits saga is a well-structured “Who I represent” story. Specifically, here’s why:

1. They shared specifics about how they messed up

Improperly licensed salespeople. Frequent alcohol-drenched celebrations of sales milestones. Condoms in the hallways. People inside and outside the company now have pretty vivid pictures in their minds about what the world of Zenefits used to be like.

2. They named an enemy

Fairly or not, Zenefits pinned responsibility for the past on founding CEO Parker Conrad, and his dismissal symbolized a break with the way things were. That’s not to say your enemy has to be an individual: It could be a way of thinking or an organizational mindset that led to problems. However, by making Conrad the enemy, Zenefits gave its audience — reporters, bloggers, etc. — an easy way to understand the story, and they ate it up. Whereas Conrad’s predictions about Zenefits hitting $100 million in sales could have been praised as motivational leadership, most writers tagged him a liar.

3. They have started to share evidence of reflection and transformation

New Zenefits CEO David Sacks has publicly shared some evidence that things are changing, including new licensing controls, corporate policies, and staff changes. To be sure, he’ll have to share a lot more than that to keep the story credible, but I wouldn’t be surprised to hear that Zenefits has already gained some trust among customers, employees, investors, and partners.

It will feel wrong, but try sharing your own dumbass moments

Of course, Zenefits was forced to tell their story, because word of such monumental failures would have gotten out sooner or later. But everyone— and every brand — can benefit by sharing similar, if not so over-the-top tales.

The next time you’re building a sales pitch, a case study, or your own bio, consider revealing a dumbass moment of your own— and how you’re different now. It will feel like the wrong thing to do, I guarantee it. But if you do it well, you’ll find others not only trusting you, but also sharing their own not-so-proud moments right back at you.

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Andy Raskin
Firm Narrative

Helping leaders tell strategic stories. Ex @skype @mashery @timeinc http://andyraskin.com