A Primer on Post-Screw Up Emails

As a keynote speaker on the topic of Courageous Leadership, every news day is full of delicious speech fodder for me. Leaders, leadership (and the lack thereof) are all over the news. The Brits have their royals, we have endless hours of suspense-filled dramas brought to us by people in leadership positions both large and small.

Some days, I don’t even have to go looking for cautionary tales. I sit down with my morning Nespresso, swipe open my phone, and find – to my delight – a long-winded email from a well-paid corporate CEO. 

On a recent morning much like the one described above, I was struck by the contrast between the emails from two, high profile company CEOs. Both companies had erred. Both were blasted by the media. But one grew stronger from his mistake. The other? He set me up with enough content for at least 413 different leadership exercises. Maybe more.

Admitting mistakes is the secret to leadership success

As leaders, we make mistakes. Some of us make them so spectacularly we become playthings for the media. Like hapless feathers on a stick we get batted around by journalists until they’re distracted by another toy and saunter off sans remorse. In the end, the details of our mistakes don’t really matter much. What matters is the recovery, which gets less media coverage but pays off in the long run.

Recovery is magical when it comes to building customer and investor loyalty. For example, if a company serves us perfectly every time, we become loyal customers. But if they screw up and then recover with generosity and grace, our trust grows, we become more loyal, maybe even advocates who bring in more customers. 

The same is true for leaders. As leaders, our mistakes can be blessings but only if we handle the recovery well.

In recovery mode, motivational platitudes can come off as insincere

Last month, the new CEO of Peloton (let’s call him Barry) sent an internal email immediately after laying off 2,800 employees in which he:

  • strung together every platitude, metaphor, maxim, and aphorism known to humankind; 
  • assured readers that the ousted CEO (John) would still be very involved; and 
  • threw out a to-do list of “go get ’em” affirmations that enabled recipients to come to their own individual conclusions about what will be happening next. 

As a former financial head, Barry is not new to leadership but he is new to the top role. I honestly think he was trying his best in that email. Pouring his heart out with all the authenticity he could muster. He probably has that list taped to his Peloton screen. He probably dictated the email to Siri while on an endurance ride. 

Here’s the thing. While relying on well-worn maxims might feel good in the moment, they are actually a defense mechanism some leaders use to protect themselves from further admonishment. Even though it’s hard to do, successful recovery from a gaffe requires us to be our most true selves. To speak in our own words, from the heart.

As the social media comments revealed, many readers of Barry’s words could feel his defensiveness and were left wondering what to do with all those maxims when the email ended. 

That failed recovery was Barry’s gift to us. His email offers clear examples of missed leadership opportunities. Not the least of which is, never give the microphone to the money guy.

It’s better to imagine yourself sitting down for a heartfelt conversation

In other news, electric car startup Rivian’s CEO (aka RJ) also sent out a mea culpa this month. His email had a very different effect. His words formed an organized, clear, honest, heartfelt, and well-written message admitting the company’s recent retroactive price increase was wrong, that it broke the trust pre-order customers had in the company. 

As a founder of Rivian, RJ has a natural advantage when it comes to owning up to mistakes. He feels a personal connection to his investors, which is what pre-order customers are. He handled his recovery well and a good number of the people who had canceled their orders – or were considering canceling – changed their minds as a result of RJ’s response. We can learn a lot from his recovery, as well as from the company’s original misstep.

With these two CEO missives in mind, here are 4 tips for having top-down courageous conversations via email. Whether we’re writing the email ourselves or trying to parse the meaning behind one we received, here’s how to tell the great leaders from the ones who have more to learn.

4 Tips for Owning Up to Leadership Gaffes with Courage and Grace


Have a personal conversation

While we may be writing an email to an entire organization, our words are being consumed by individuals, one at a time. So we need to write as though we are speaking to just one person. Because the most productive and useful conversations are honest, down-to-earth, and one-on-one.

In RJ’s email to Rivian’s pre-order customers, he opens with “Hello Everyone” and then proceeds to write a clear, specific email that feels like a personal conversation. He doesn’t tell us he’s being real, he demonstrates it with his actions.

In contrast, Barry’s email to Peloton employees hides behind a string of cliches and aphorisms—so many that it almost feels computer generated. He uses I-me-my a lot, which comes off as defensive. When he shifts into we-us-our, he keeps things broad and vague. 

Take full responsibility

As handsomely-paid leaders, it’s our job to take responsibility when things go awry, even if there are others who share in the blame. 

RJ opened with a clear explanation of the mistake Rivian made and apologized as though the decision had been his and his alone. 

Barry opened with an Academy Awards-style list of thank yous to people who “don’t know me from Adam,” embarrassing self-promotion, and a vague allusion to an “inconvenient” truth (that 2,800 families had lost their livelihood because “the math didn’t work otherwise”). 

Offer a more than fair solution

Fix it. After identifying the mistake and taking responsibility, courageous leaders offer a solution to the problem that is more than fair. If it’s a dirty hotel room, we thoroughly clean the room and comp a nice dinner as well. More than fair is how we keep loyal employees, customers, and shareholders loyal.

RJ was more than fair. He told customers Rivian would honor the original price for pre-orders, even though it will cost the company dearly. He put long-term customers ahead of short-term shareholder profits, which was generous, and those customers responded by not canceling their Rivian orders. 

So what’s the problem at Peloton that their fearless new leader was hired to fix? The media are blaming the company’s failings on the grandiosity and blind optimism of the ousted co-founder and CEO, John Foley. But they are the company’s failings, not just John’s. 

When we accept a leadership role in a new company, we acquire the company’s mistakes as well as their glories. As new leaders, it is our responsibility to acknowledge, take on, and fix the problems that our predecessors left behind.

Instead of “I’m here for the comeback story,” which echoes the very grandiosity for which his predecessor is being excoriated, Barry could have said, “We screwed up. We’re never going to make that mistake again. And here’s what we’ve changed to ensure a better outcome … .” 

Commit to following up 

Follow through is not just a golf metaphor, it’s what makes a relationship a relationship. As leaders, we inspire loyalty from our team members, internal customers, and external customers by consistently being there. 

One rousing speech (or email) doesn’t build loyalty. Repeatedly showing up and demonstrating that you are personally committed to the health and wellbeing of the relationship does.  

In his sign off, RJ demonstrated that he had been and would continue to be in touch with his customers. “Thank you for the personal notes and discussions I had with so many of you,” he said. Even those who didn’t talk with him personally felt the love. 

Barry’s sign off? “I promise the journey won’t be dull.” Indeed!

Right now, at Cindy Solomon & Associates, we are deep diving into the leadership skills needed to pull off deft and powerful recoveries, in both company-wide emails and in private. If you’re a leader who struggles with how to recover from missteps (or you’ve got a  leader who could benefit from a little guidance), visit cindysolomon.com to purchase a webinar, workshop, or keynote. 

Thanks for reading and have a great week! 

Signature of Cindy Solomon, Courageous Leadership expert and keynote speaker

Cindy Solomon is CEO of the Courageous Leadership Institute, a thriving leadership and customer experience training organization with access to up-to-the-minute insights on how today’s most innovative corporations are defining the future of leadership. Learn more at www.CourageousLeadershipInstitute.com.

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