How to Turn Embarrassing Moments into Trust Builders

“I missed a major deadline. The client wasn’t happy. The team looked at me differently.” That’s what a young manager confessed to me over coffee. He’d led a key project that flopped — and suddenly, the trust he’d built with his team and boss felt like it evaporated overnight. He said something that stuck with me: “It’s like I went from promising leader to liability… in one mistake.” That’s the scary part about leadership when you’re early in your career. So, what do you do after the fall? Here’s what I told him: 1. Manage expectations like your credibility depends on it (because it does). You already owned the mistake. Good. But now, over-communicate. Set crystal-clear expectations for your next project: ↳ What’s the exact deliverable? ↳ Who are you building it for? ↳ When is each piece due? ↳ How will you keep stakeholders in the loop? Ambiguity is where mistakes breed. Clarity is where trust rebuilds. 2. Under-promise. Over-deliver. Tempted to prove yourself with a moonshot? Don’t. It backfires more often than not. Instead: ↳ Set realistic targets. ↳ Build in buffers. ↳ Deliver slightly more than what was promised. It’s not flashy, but it works. 3. Win small. Win fast. Credibility doesn’t return all at once. You earn it inch by inch. Focus on quick, visible wins that move the project forward and help the team, not just your image. Examples: ↳ Found a process gap? Propose a fix. ↳ Need support? Make a solid business case for additional resources. ↳ Don’t wait till the final deadline — share milestones early. Momentum builds belief. 4. Reassess. Periodically. Finished your comeback project? Great. But rebuilding trust = consistency over time. ↳ Every 2–3 months, ask: ↳ Am I gaining back confidence from stakeholders? ↳ Are my deliverables exceeding expectations? Do I feel like I trust myself again? If the answers aren’t clear — maybe it’s not just you. Some environments don’t allow for second chances. If that’s the case, find one that does. The truth is: Credibility is hard to earn. Harder to regain. But absolutely possible — if you approach it with humility, clarity, and strategy. We’ve all dropped the ball at some point. The question is: What do you do after the bounce? — PS: I write about leadership, trust, and growing through setbacks every week. #leadership #careeradvice #trust #growthmindset #youngprofessionals

In which of these 2 scenarios, will a sales rep sell more blenders? a) She nails the demo, flawlessly blending a smoothie in front of potential customers b) Same exact pitch, but when she pours the smoothie, she spills it all over the table Dr. Richard Wiseman conducted this exact study. More people bought the blender when she made an absolute mess. This phenomenon is called the "other shoe effect." The underlying principle: We instinctively know people aren’t perfect. So when someone appears too polished in high-stakes moments—job interviews, pitches, first dates—part of our brain asks: “What are they hiding? When does the other shoe drop?” The longer someone appears flawless, the more suspicious we get. This creates a dangerous cycle: • You try to appear perfect in the first impression • The other person's brain gets increasingly distracted wondering about your hidden flaws • When your imperfection finally shows (and it will), it hits much harder than if you'd acknowledged it upfront I learned this the hard way. When I first wrote Captivate, I tried to sound like an academic. My editor called it out: “This doesn’t sound like you.” So I rewrote the intro to be me, very me in a vulnerable way: “Hi, I’m Vanessa. I’m a recovering awkward person.” That vulnerability built instant trust. By dropping my shoe early, I built trust immediately and let readers know they were in good company. This is also how I introduce myself in conversations, and I have noticed everyone laughs and relaxes when I say it. There are a couple situations where you can actively use this effect: • Job interviews: After sharing your strengths, say "One area I’m still growing in is public speaking—which is why this role excites me." • Investor pitches: After a strong open, confess: "One challenge we’re still working through is [X], and here’s how we’re tackling it." • Team meetings: Proactively raise project risks, then offer a solution. Don’t let others discover it first. Rules to remember: • Choose authentic vulnerabilities, not fake ones • Drop your shoe AFTER establishing competence, not before • Pair vulnerability with accountability - show how you're addressing it Remember: The goal isn't to appear perfect. It's to appear trustworthy. And trustworthy people acknowledge their imperfections before others have to discover them.

Over the years, I’ve embarrassed myself a LOT. I’ve blurted out the wrong thing at the wrong time, revealed my own ignorance and poor judgment, and put my foot in my mouth more times than I can count. I basically have a 3rd degree black belt in making a fool of myself. And I’ll be honest: I’ve winced, cringed and stayed up at night replaying my most epic faux pas, just like every other human being on earth. (No, but really, WHY did I write Libby Walker that note in sixth grade? Of COURSE she was gonna show the whole school!) Embarrassment is real. And it can be devastating. But over the years, I’ve learned that there’s only one way to cope with this complicated emotion: You have to own it. You have to talk about it. And then you have to laugh about it. Laughter is the only foolproof strategy I’ve found for cutting through the shroud of shame and self-loathing that falls around you when you make a fool of yourself. Why? Because laughing at yourself — even just being willing to laugh at yourself — creates a healthy buffer between you and the embarrassing event. It says: I don’t take myself too seriously, I’m not trying to protect my weaknesses too much, and I’m willing to celebrate these ridiculous parts of my personality. It drags the facts you’d rather hide into the open, and shines a light on them in a way that’s strangely healing. Which is why talking about embarrassment is also such a powerful technique for storytelling and relationship-building. It humanizes us. It makes us available to other people. It invites them to locate those same aspects of themselves in us, which is a massive relief and honestly super fun. Rapport, empathy, (true) confidence, trust — they all follow from that vulnerability. So if you’re struggling to work through some embarrassment, big or small, start by asking yourself: What quality or feeling am I trying to hide by tucking this experience away? Who can I share this story with in a way that’s safe? And once you open up about your embarrassing moment… What experience of yourself do you have? What are you now in touch with? And what did opening up do to your relationship with that person? If you want to hear how this idea played out in a listener’s life… Check out episode #971, where we took some of our listeners’ most embarrassing stories and shared some of our own. The one theme they all had in common was how powerful it is to laugh about what happened. That laughter was the flame that burned up their shame, and converted it into relief, healing, joy, entertainment and connection. Have you found this principle to be true in your world? Struggling to make use of it? Hit the comments and tell me about it. I’m all ears! Oh and Libby, if you're reading this, we’re cool. Promise.

I rebuilt my life by taking advantage of one principle Gary Vee taught me at one of my lowest moments. It's called Stage Theory, and here's how it works: Most entrepreneurs think they need perfect content to build their brand. But the opposite is true. When I shared my worst moments, people connected with me more than ever before. People learned from my mistakes, watched me grow, and we started to build trust. Here's the problem: People sit on content goldmines and life lessons and simply let them die. Every conversation you have has something that could change someone's life. Every client call. Every commute thought. Every moment with your kids. The cost of not capturing these is letting your thoughts die with you. I use Stage Theory to turn my daily life into a content machine: 1. CAPTURE your real moments Record everything for 30 days. When something hits you strongly - love it or hate it - capture a 30-second note. 2. MODIFY for each platform One recording becomes 10 pieces of content. LinkedIn post, Twitter thread, Instagram story, YouTube short. 3. AMPLIFY through your network When people ask, "How can I help you?" say: "Share my content with 3 people who need to hear this." Most people say "I don't know" because they haven't thought about it. Word-of-mouth beats advertising every time. 4. PERPETUATE with search Build a library so deep people can't escape your rabbit hole. If someone watches 5 of your videos, the algorithm serves them 50 more. Your content library has 3 ingredients: your skills, your knowledge, your opinions. Mix these in every piece. You know you're doing this right when people either love you or hate you. The people who don't care? We don't want them anyway.

As a founder or leader, you’ll face many curveballs—some you can anticipate, others, not so much. You are responsible for your team’s successes and mistakes. During the good times? Absolutely. During the bad times? Even more so. Recently, I had one of the most humbling experiences of my career. We made a mistake with a client—yes, I’m owning it—and I heard about it. Loud and clear. No matter how seasoned you are, hearing that your team dropped the ball is tough. And apologizing for it is even tougher. Imagine being told, “I made the biggest mistake working with you” or “Do you even know what you’re doing? You’re running a mess—shut it down!” It stings, especially when it comes from someone you know personally—a former classmate or an old friend. But here’s what I’ve learnt from my mentors and advisors: Own the mistake. Swallow your pride. Apologize. And then get to work on fixing it. Because fixing what went wrong is what earns trust. Think about it—Amazon messes up orders too, but what do they do? They make it right. And by doing so, they turn a mistake into a reason for you to trust them more. So, when things go wrong, don’t shy away from saying sorry. Just focus on making it right. Got any experiences to share that I can learn from? 😊 #lifelessons #entrepreneurship #womanownedbusiness