Why Leaders Need to Vulnerably Open Up About Failure

Failure is almost always spoken about in the past tense. That creates an artificial safety net. There isn’t true vulnerability in that. Love this article (“Opening Up About Startup Failures and Vulnerability”) in “First Round” that goes into it. Read on.

Leaders, entrepreneurs, founders and others many times open up and share their failures ONLY after they are successful. But does that really help others who are in the midst of struggling? Founder Jeff Wald shares what it means to get raw and vulnerable about failure in the “present tense.“

CHALLENGE #1: GETTING VULNERABLE BY MAKING IT PERSONAL

Failure’s become trendy. We live in a culture of innovation and pushing envelopes, which requires failure,” Wald says. “But I’d draw a distinction between failure and vulnerability. We’ve confused the idea of putting failure out into the market as making yourself vulnerable, when it isn’t. Talking about how your startup didn’t work or how your product fell flat isn’t the same as digging into how that made you feel or how you failed specifically as a leader — there’s a degree of separation there. You actually need to put yourself out there.”

Here’s the difference between talking about failure and getting truly vulnerable: Vulnerability is necessarily personal while failure is not. Don’t conflate the two.

Sharing tales of startup failures, market defeats and company losses is not necessarily an exercise in true vulnerability, especially when there’s a safety net of follow-on success to fall back on. “I only got comfortable mentioning Spinback after there was a successful end to that story, when there was no downside for me,” he says. “Given where I am now, everyone automatically views the failure as a stepping stone to that success. So even though I’m more forthcoming about it, talking about the company going under doesn’t really make me vulnerable. It’s an abstract layer, a discussion in which I’m still shielded. Talking about the depression that went along with it and the inability to cope with the failure — that’s a little bit more down the road of vulnerability.”

FAILURE AS A TEACHER: TACTICS FOR EXTRACTING THE LESSONS

Failure has been an invaluable teacher for Wald, but only because he put in the time to excavate its lessons. “Failure can be something that happens to you, or it can be something you learn from. But that doesn’t happen through osmosis, it takes a lot of concentrated effort and dedication to unearth the takeaways,” he says.

For Wald, moving past the notion that his failure defined him ultimately required professional help. And something he’d once scoffed at — working with a coach. When first approached with the idea, he wasn’t too receptive. “One of the WorkMarket board members took me on a walk and said, ‘We think you need to get a coach’ and I said, ‘I think you need a coach,’” Wald says. The board member, however, made it clear that the suggestion wasn’t optional. 

“At the time I was more focused on proving that I was right as opposed to being effective. I was very emotional and volatile. There were board meetings where I would sit in the corner with my arms crossed, hoodie up, and not say anything,” he says. “There were other times where I threw things — sometimes tables and chairs. I was an asshole. I wasn’t giving off the impression that I could provide the leadership that a growing and transforming company needs.”

Wald reluctantly went through the process of finding a coach, determined to do the bare minimum to satisfy his board and nothing more. “I certainly planned to blow it off,” he says. But just as Wald needed to connect with fellow founders to get a better context for his work, it took a coach who had a similar career path, and thus more relevant context, to realize how helpful an outside perspective could be. “I met with people that had clinical backgrounds in coaching, but I knew from my own makeup that I needed somebody that had sat in my chair before. I was introduced to someone who had been incredibly successful in the startup world first and then went back to become a coach.”

https://firstround.com/review/founder-exposed-opening-up-about-startup-failures-and-vulnerability/

Example of Great, Inspiring Company Values by CEO of Twilio

Excellent post on creating great company values (versus lame ones) & challenges behind “living them” by the Twilio CEO. Encourage you to check out the article below.

“CULTURE is a word that Silicon Valley and startups everywhere toss around all the time,” says Lawson. “What does it really mean and how does it relate to VALUES? What I landed on is that culture is living your values.

Values are written words, and your culture is how you actually live those written words.”

“Our values are in motion, specifically through a three-stage lifecycle that gets us to the next stage of growth. First, we articulate our values, then live them and finally, test them.”

Love these two values the most (see the picture below): 

1) “Empower Others: Make Heroes. Unleash the greatness of others inside and outside the company.”

2) “No Shenanigans: Be thoughtful. Always deal in an honest, direct, and transparent way.”

Values are for guiding behaviors and helping people make decisions that everyone will support and feel proud about.  

Values are really really hard to get right and usually take iteration. But it’s worth investing in because the positive/negative consequences are massive. 

https://firstround.com/review/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have/

Social Wealth Book Review on Building Great Business Relationships [From Amazon]

“This book is one of the best-kept secrets I’ve come across in a REALLY long time! There is are so many tips for conversations and networking skills in today’s society. If you can master what Jason talks about in this book, you’ll definitely build long-term wealth! Many other reviewers have compared this to “How to Win Friends & Influence People” and I cannot agree more. Buy two copies and give one to someone in your network.”

It’s always great to read a review from someone you don’t know about the positive impact Social Wealth had on them. I’ve been fortunate to have more than 125+ five-star reviews on the book. If you are looking to build deeper, more meaningful business relationships (either in your company or through business networking), you may want to consider checking it out. It works for introverts and shy people just as well as extroverts.

Best Things in the Workplace Are Free – Connection

“Best Things in Life Are Free.” That’s the classic song in MadMen when Burt Cooper dies. It’s signifies the #1 asset and “secret sauce” that leaders typically overlook. 

People value and are starving for true connection, complete trust, & teamwork with people who deeply care. 

It’s that emotional bond that enables us to accomplish and create the seemingly impossible. 

It’s also what brings the very best out of us individually and collectively. 

People after the fact point to success as the stock price, profit, sales, etc. But that completely misses the mark. That’s the effect, not the cause. 

The gold is in first creating the unbreakable foundation for “the together team.” It’s not to get distracted by process, strategy, etc. Because then leaders make lack of time excuses why they built the foundation on sand. We know what happens over time when they do (and the huge financial cost and emotional turmoil for poor teamwork).

Coco Chanel said, “The best things in life are free. The second-best things are very, very expensive.”

When leaders and managers behaviors and actions prioritize the business over the team, it requires them to pay a very expensive price. 

Here’s the video from MadMen that’s worth a watch: https://lnkd.in/e8gD2HF

Dilemma of Choosing Profits over Principles

One of the most difficult decisions leaders and managers have to make is choosing principles (and values) over profits. 

It’s rarely an easy choice nor is it black/white. 

Lately, I’ve encountered several client situations where this choice had to be made over the past two weeks

1) The top salesperson didn’t feel like they had to follow the same rules as others. They were putting the company at risk with their actions. The challenge was the individual was bringing in a significant amount of revenue and had excellent relationships with clients. It came down to the company making a decision on money versus behavior. 

2) Leader in the company treated a large team pretty poorly. But they were getting excellent KPIs and results. The leader didn’t want to change so the company was at a crossroads on what to do.

It may seem clear cut on what to do, but consider this. First, companies have duties to pay employees (who have families), serve their customers and other obligations. Second, principles are not always valued/shared unanimously. The definitions, understandings, and lines aren’t always clear. 

But prioritizing profits can lead a company, executives, and managers to forget, push aside or change their principles. Those choices lead to negative and very expensive consequences.

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