Building Executive Authenticity Through Failure Stories

Early in my career, when I shared the story of a workshop that completely bombed (an email announcing layoffs arrived in everyone's inbox during day 1 lunch of a two-day program -- and I had no idea how to handle this), three women immediately reached out to share their own "disaster" stories. We realized we'd all been carrying shame about normal learning experiences while watching men turn similar setbacks into compelling leadership narratives about risk-taking and resilience. The conversation that we had was more valuable than any success story I could have shared. As women, we are stuck in a double-bind: we are less likely to share our successes AND we are less likely to share our failures. Today, I'm talking about the latter. Sharing failure stories normalizes setbacks as part of growth rather than evidence of inadequacy. When we women are vulnerable about their struggles and what they learned, it creates permission for others to reframe their own experiences. This collective storytelling helps distinguish between individual challenges and systemic issues that affect many women similarly. Men more readily share and learn from failures, often turning them into evidence of their willingness to take risks and push boundaries. Women, knowing our failures are judged more harshly, tend to hide them or frame them as personal shortcomings. This creates isolation around experiences that are actually quite common and entirely normal parts of professional development. Open discussion about setbacks establishes the expectation that failing is not only normal but necessary for success. It builds connection and community among women who might otherwise feel alone in their struggles. When we reframe failures as data and learning experiences rather than shameful secrets, we reduce their power to limit our future risk-taking and ambition. Here are a few tips for sharing and learning from failure stories: • Practice talking about setbacks as learning experiences rather than personal inadequacies • Share what you learned and how you've applied those lessons, not just what went wrong • Seek out other women's failure stories to normalize your own experiences • Look for patterns in women's challenges that suggest systemic rather than individual issues (and then stop seeing systemic challenges as personal failures!) • Create safe spaces for honest conversation about struggles and setbacks • Celebrate recovery and growth as much as initial success • Use failure stories to build connection and mentorship relationships with other women We are not the sum of our failures, but some of our failures make us more relatable, realistic, and ready for our successes. So let's not keep them to ourselves. #WomensERG #DEIB #failure

My Gen Z staff texted me at 10:47pm. "You're the only boss I've had who admits when they're wrong." That shouldn't be revolutionary. But apparently it is. Last month, I made a call that cost us a client. Wrong approach. Wrong timing. Wrong everything. In the meeting, I owned it: "I screwed up. Here's what I missed. Here's what we're changing." The room went silent. Then something unexpected happened: → My team started sharing their own mistakes → We problem-solved together instead of finger-pointing → Everyone left energized instead of demoralized Here's what most leaders get wrong: They think admitting mistakes shows weakness. They think perfection earns respect. They think vulnerability kills authority. Truth is: Your team already knows when you mess up. Pretending otherwise just makes you look delusional. What actually builds loyalty: • Owning your failures publicly • Asking "what can we learn?" • Showing you're human too • Creating psychological safety I've failed the bar exam 3 times. Built a 7-figure firm anyway. Still make mistakes weekly. The difference? I talk about them. Leadership isn't about being perfect. It's about being real. P.S. When's the last time your boss admitted they were wrong? 👇 P.P.S. Join 405+ professionals building authentic leadership in our community → see featured section

Museums don’t exist to glorify perfection; they preserve history. Leadership works the same way. The best leaders aren’t flawless; they curate and apply the lessons their failures taught them. Think about your own career. Perhaps you hired the wrong person, allowed emotions to interfere with effective decision-making, or mishandled a difficult conversation. At the time, those failures felt like wounds—painful and raw. However, with time, those wounds became scars. And scars are the artifacts in your “museum of failures”. They don’t hurt anymore; instead, they remind you of what you endured, what you learned, and how you grew. The leaders we admire most often have the most artifacts in their failure museums. They’ve tried, failed, adjusted, and tried again. Their strength doesn’t come from avoiding mistakes; it comes from learning quickly and putting those scars on display so others can learn, too. Here’s a simple exercise: - Take inventory of your failures. - Reframe them as failure artifacts. These experiences are proof of your resilience. - Share those stories with your team, because scars inspire more trust than perfection ever could. When fear or doubt shows up, step into your failure museum. Look around. Each artifact is proof that you’ve already overcome hard things, and you can do it again.

Most executives are ghosts on LinkedIn. They sit on transformational AI strategies. Lead billion-dollar pivots. Navigate market disruptions that rewrite entire industries. Then they post their company's press release and wonder why nobody engages with it. Here's what my experience helping executives find their voice taught me: The barrier isn't capability. It's conditioning. These leaders can command a boardroom, inspire thousands of employees, and close nine-figure deals. But ask them to share a lesson learned? They freeze. "I don't want to seem self-promotional." "What if I say the wrong thing?" "My legal team would have a heart attack." Meanwhile, their biggest competitor's CEO just posted a vulnerable story about a failed product launch that brought in three partnerships. The executives I coach aren't lacking insights. They're drowning in them. Every day brings: Decisions that could fill a business school case study. Challenges that test everything they know. Victories that nobody hears about. But they've been trained to hide it all behind corporate polish. Here's what happens when executives finally start sharing their real experiences: → A CFO posted about a budget mistake that cost millions. Landed two board positions because they value honesty. → A founder shared why their first product failed. Their next funding round was oversubscribed. → A CEO wrote about crying in the parking lot after layoffs. Their employee engagement scores hit record highs. The magic isn't in perfection. It's in proof that you're human. Your teams already know you're not perfect. Your customers suspect it. Your competitors hope for it. When you pretend otherwise, you're not protecting your reputation. You're preventing connection. The most powerful thing you can post isn't your latest achievement. It's the lesson from your last failure. What truth are you hiding that could help someone else? #ExecutivePresence #LinkedInStrategy #Leadership

Tell me about your failures. Not your successes disguised as failures. Not your humble brags about working too hard. Your real failures. I can learn more from how you failed than all your wins combined. Last month I interviewed two VP candidates. First one listed perfect wins. No setbacks. Just victories. Second shared a painful product launch disaster. What went wrong. Why she missed it. How her team recovered. We hired the second. Your response to failure tells me everything: 💡 Do you blame others or own mistakes? 💡 Do you hide problems or address them head-on? 💡 Do you learn lessons or repeat patterns? The strongest leaders I know have spectacular failures in their past. Product launches that flopped. Teams that fell apart. Strategic bets that backfired. They talk about these openly. They analyze what went wrong. They show how they grew. Weakness isn't failure. Weakness is pretending you never fail. I don't trust leaders with perfect records. I trust leaders who turned failures into wisdom. What failure shaped you into who you are today? That story matters more than any success on your resume. #Leadership #Recruiting #InterviewTips #PersonalGrowth

When I started sharing my speaking journey publicly, everything changed. The traditional business advice says "fake it till you make it." But after working with hundreds of entrepreneurs, I've learned something counterintuitive: your biggest breakthrough comes from being transparently vulnerable about your struggles. I was on a call with a successful founder last week. When I asked if he'd spoken at conferences, he froze. "I can't even handle team meetings without sweating." When I shared my own speaking disaster story, forgetting my entire opening at a 500-person conference, something beautiful happened. He realized everyone wanted him to succeed, not fail. Here's what I learned about building in public through transparent speaking: 1. Vulnerability Broadcasting  Share your panic attacks, forgotten openings, and sweaty moments openly. Building your confidence journey in public permits others to be human. Your struggles become someone else's breakthrough story. Speaking fears are universal, your transparency breaks the shame cycle. Others see that success isn't about perfection, it's about persistence. 2. Story Stack Development  Document your 5 go-to stories for any situation and share them. Building your narrative library in public creates accountability for authenticity. Your stories become templates for other entrepreneurs to adapt. Transparency about your frameworks helps others structure their own experiences. 3. Confidence Protocol Sharing  Show your exact pre-speech routine and why it works. Building your confidence systems in public creates replicable frameworks. Your meditation, breathing, and preparation become roadmaps for others. 4. Authority Multiplier Transparency Document how one speech creates 50+ opportunities. Building your authority systems in public shows the compound effect. Your podcast invitations and connection requests become proof of concept. Transparency about speaking ROI motivates others to overcome their fears. 5. Failure Reframe Strategy Share how disasters become your best teaching moments. Building your resilience story in public transforms setbacks into comebacks. Your 15 seconds of silence become someone else's courage catalyst. Transparency about recovery shows that perfection isn't the goal. Others learn that audiences want value, not flawless delivery. This isn't just about becoming a better speaker, it's about creating beautiful, systemized, and impactful ways to share your expertise with the world. When you build your speaking journey in public, you're not just overcoming fears. You're showing other entrepreneurs that their voice matters and their message deserves to be heard. __ Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Curious how this could look inside your business? DM me ‘System’ and I’ll walk you through how we help clients make it happen. This is for high-commitment founders only.

My 10-Second Test That Predicts C-Suite Failure I've interviewed 1,000+ executives. One of my favorite questions to ask: "Tell me about a time you were wrong." The failures? They pause. Deflect. Reframe it as a "learning opportunity." The successes? They lean in and own it. Last week, a CFO candidate—great resume, stellar references—spent 3 minutes explaining how his "wrong" decision was actually everyone else's fault. Hard pass. Another candidate, less polished, immediately said: "I nearly bankrupted my division chasing a market that didn't exist. Here's what I missed..." Guess who got the job. The executives who transform companies share one trait: They're comfortable being uncomfortable with their mistakes. They admit failure and then they dissect it. Here's what I've learned: • Deflectors protect ego over results • Blamers create toxic cultures • Minimizers repeat mistakes • Owners drive real change The best leaders I know have spectacular failure stories. And they tell them without flinching. Leadership isn't about being right. It's about getting better. What's your biggest professional mistake? Can you own it?

Chapter 9 - Failure* Failure doesn’t always look like a collapse. Sometimes it looks like being erased. Years ago, I was leading design at a fast-growing company. Our team was doing work I was deeply proud of—bold, meaningful, considered. Fast Company spent months interviewing leadership across the company for what was meant to be a broad piece on brand and culture. But as the story evolved, it became something more specific: a feature on design, and by extension, on the team I led. They photographed me. The story was written. It was slated to run in their design issue. But someone at the top hadn’t been told. The day they found out, I was called into a closed-door meeting. No gray area. I was told I wasn’t the face of the company—and I was out. That same day, they contacted the magazine and pulled the article. Just like that, it was gone. And so was I. It was humiliating. But it wasn’t the first time I’d been let go, and it wouldn’t be the last. I’ve been fired, laid off, phased out, reorged. And each time, I walked away carrying the same question: Did the work matter if no one wanted to hear from me anymore? That’s what failure does. It shakes your sense of authorship. It leaves you standing in the wreckage of something you gave everything to, wondering if it’s even yours to remember. But here’s what I’ve learned: Failure doesn’t make you fearless. It makes you sharper. You stop making decisions for applause. You learn how to see risk coming. You learn how to work with people who can take a hit and stay focused. You stop over-explaining. You stop posturing. You get real about what it takes to do good work inside imperfect systems. Failure also doesn’t make you humble—not if you already were. What it does is rewire your instincts. You start leading differently. You become the person who stays calm when the floor drops out. You get clearer. More generous. Less interested in credit and more interested in whether the thing actually works. I’m not proud of the firings. But I’m proud of how I came back. I still take risks. Still push ideas further than I should. Still back people before the system does. And yes—sometimes that gets me in trouble. But it also gets me to the work I believe in. The kind that still wakes me up. So if you’ve failed lately, quietly or spectacularly—don’t rush to reframe it. Just carry it. See what it teaches. Let it sharpen you. You’ll come out quieter. But better. *note: not all chapters are doomsday chapters. Chapter 10, Authority, coming next. #Leadership #CareerDevelopment #PersonalGrowth #Resilience #WorkplaceCulture #Motivation #Creativity #Innovation #Mindset #Success #FailureIsFuel #CreativeLeadership #StillMaking #LearnedTheHardWay #ManifestoManifesto #WhatTheWorkTaughtMe #DesignEthics #RebuildFromHere

Many executives try to project perfection. But perfect people make me nervous. It either triggers my insecurities (because I know how imperfect I am) OR it makes me wonder what they’re hiding and why. Because, generally, perfection is unattainable for all but a few fleeting moments if at all. So the odds are, they’re not showing their scars. And EVERYONE has scars unless they’ve never tried anything hard. The leaders who earn real respect show their scars…They’re real. I once had a commanding officer ask us to get him up to speed on a weapon system we were using that he used too back when he was us. Did it crack our confidence in him? Not in the least. It just made us want to work for him even more. We knew he’d used it well when carrying it back in his day. He and our Master Chief were legends. But he had 24 hours in his day just like we did. And he was using his hours to lead us well, and make massively important decisions - instead of staying great at what he used to do. "Here's what I'm thinking, but I could be wrong." "I made that mistake before, and here's what I learned." "I don't know the answer, but let's figure it out together." “You can find out that’s gonna hurt, or you can just let me tell you about this scar right here.” This isn't weakness. It's authenticity. And authenticity is what you call vulnerability when you’re not scared anymore. If we want people to bring us problems early, we have to show them it's safe to not have all the answers. If we want innovation, we demonstrate that intelligent failure is acceptable. I tell my folks all the time “I’ll never tell you to make no mistakes. Just make new ones.” And I mean new to ALL of us. Not just themselves. How are they not going to repeat my mistakes if they don’t know about ‘em. But it’s tough for my teams, because I am a wildly aggressive failer (not failure) so they have to get pretty creative to make more mistakes faster than I do. Perfect leaders create teams that wait for permission. Authentic leaders create teams that take initiative. #leadership #authenticity #culture #teamwork #growth #vulnerability #development

The book you're afraid to write → is the one your audience needs most. That chapter on your biggest failure? It's someone else's breakthrough. I've watched brilliant executives delete their most powerful stories. The messy ones. The human ones. The real ones. Your expertise becomes most valuable when it's: → Human, not polished → Honest, not perfect → Vulnerable, not sanitized Here's what happens when experts hide behind perfection: 1️⃣ Trust Barriers ↳ Flawless experts are admired but not trusted ↳ Real stories create "I see me" moments ↳ Clients invest in humanity, not just capability 2️⃣ The Authority Paradox ↳ Your mistakes build more credibility ↳ Sharing struggles positions you as guide, not guru ↳ Authentic expertise outsells perfection 3️⃣ Impact Limitations ↳ Your battle scars are permission slips ↳ That messy framework? It saves others years ↳ Your raw story changes someone's life Don't hide your human journey ⬇️ Vulnerability connects. Perfect intimidates. Start publishing. Stop polishing. Be really YOU.