How to Build Trust by Admitting Failures

Last week, my Gen Z staff texted me at 10:47pm. "I need to talk to you about something." My heart sank. In my experience, late-night conversations that start like this end with resignations. "I've been here 1 year," he said. "And I've noticed something about you." Here it comes, I thought. The criticism. The resignation. The— "You're the only boss I've had who admits when you're wrong." Wait, what? He continued: "Remember when you insisted on that new intake system? It failed spectacularly. But instead of blaming us, you called a meeting and said 'I messed up. Let's fix this together.'" That conversation changed how I think about leadership. Here's what I've learned running a 7-figure law firm with 15+ team members: → Vulnerability creates loyalty → Admitting mistakes builds trust → "I don't know" is a complete sentence → Your team already knows you're not perfect The old Jimmy would've pretended to have all the answers. Failed the bar 3 times? Hide it. B- grades? Never mention them. Spending $five figures/month on ads that aren't working? Keep quiet. But here's the thing: My team doesn't follow me because I'm perfect. They follow me because I'm real. Last month, I made a $20K mistake. Old me would've buried it. Instead, I called an all-hands meeting: "I screwed up. Here's what happened. Here's what we're doing to fix it. Here's how we'll prevent it next time." You know what happened? Three attorneys shared their own recent mistakes. We created a new review system together. Team morale went UP, not down. The most dangerous leaders are the ones who can't say these five words: "I don't know. Help me." Your team isn't looking for perfection. They're looking for humanity. P.S. That Gen Z staff who texted me late at night? He asked for more responsibility, not to quit. He's now our intake manager. P.P.S. To every leader pretending to have it all figured out: Your team knows. They're just waiting for you to admit it.

Failing Is Good. Sharing Failure Is Great—Here’s Why (and the Difference) There’s a saying in leadership: “Fail fast, learn fast.” It’s useful, but here’s a more brutal truth I see every day as an executive coach—failing is good, but sharing your failure? That’s where greatness lives. Why? Because when you keep your setbacks to yourself, you learn and (hopefully) adapt. Good leaders do this all the time: they make mistakes, reflect quietly, and get a little bit better. But great leaders zoom out. They turn their tough moments—botched launches, missed deals, the uncomfortable conversations—into teachable stories for their teams. They debrief openly, admit what went sideways, and let others in on the real lessons. That’s not just transparency—it’s leadership with leverage. It shifts a culture from “hiding shortcomings” to “shared growth.” From my coaching chair, here’s what I see: → Teams led by “silent learners” improve slowly and in silos. → Teams led by “story-sharers” (even the humble, unpolished ones) build trust and adapt at light speed. My best work isn’t about helping leaders hide their failures. It’s helping them find language, timing, and confidence to share it: “Let’s dissect this together. Here’s what I missed, what I learned, and what I want us all to watch for next time.” The difference? Good leaders bounce back. Great leaders multiply learning. If you want to unlock not just your own growth but your entire team’s potential, start here: → Normalize quick, safe failure debriefs after every big project. → Model vulnerability. Admit you miss first. → Ask your people: “What would you do differently?”—and listen, really listen. → Set the expectation: we’re here to share learnings, not to get it perfect the first time. In leadership, it’s not how you fall that changes your culture; it's how you respond. It’s who learns—and how many—from how you get back up. Coaching can help; let's chat. Enjoy this? ♻️ Repost it to your network and follow Joshua Miller for more tips on coaching, leadership, career + mindset. #executivecoaching #leadership #professionaldevelopment #growthmindset #careeradvice #learning #success

The strongest leaders I know have one thing in common… They’re not afraid to say these three words: “I screwed up.” One of my bosses once stopped a high-stakes meeting cold with those exact words. No excuses. No deflection. Just: “I screwed up. Here’s what happened. Here’s how we’ll fix it.” In that moment, he didn’t lose the room. He earned its respect. We started bringing forward problems earlier. Solving them faster. Owning our work more fully. Because vulnerability…real, humble accountability… is a leadership multiplier. Here’s what it does: → It breaks down walls between “leadership” and “the team” → It gives others permission to own their mistakes, too → It shifts people from fear-based compliance to trust-based commitment The irony? Leaders who try to look bulletproof often come off as insecure. Want to lead like that? No! Try this instead: 1. Admit when you mess up. Accountability builds trust faster than perfection ever could. 2. Share what you’re learning… not just what you’ve mastered. 3. Ask real questions like: “What am I missing?” or “How could I have handled that better?” 4. Normalize “smart mistakes.” Teams that can discuss failure without fear are the ones that grow. The best teams I’ve worked with weren’t led by perfect people… They were led by real ones… honest ones. Psychological safety isn’t soft. It’s how high-performing teams are built. What would shift if you led with that kind of strength today? ⸻ Follow me (Jon Macaskill) for leadership insights, wellness tools, and real stories about humans being good humans. And yeah… feel free to repost if someone in your life needs to hear this. 📩 Subscribe to my newsletter here → https://lnkd.in/g9ZFxDJG You’ll get FREE access to my 21-Day Mindfulness & Meditation Course—packed with actionable tools to lead with clarity and resilience.

As leaders, when you make a mistake, is it better to admit you are at fault or prioritize your reputation? The answer is actually both. By admitting fault, you build stronger trust and respect. A few years back, I was coaching a sales team through what I thought was a rock-solid strategy. But as the quarter unfolded, the results just weren’t there. The team put in the effort, but my approach didn’t hit the mark. I could feel my ego creeping in—should I double down and push harder, or admit that my plan wasn’t working? I chose the latter. I called a meeting and simply said, “I was wrong.” That moment changed everything. By admitting my mistake: 1. The team rallied because it showed them that leadership is about owning missteps and being flexible. 2. It strengthened trust because my example of open communication built a culture of honesty. 3. We found a better solution by gathering everyone’s input. We ended up pivoting and turning the quarter around. As leaders, the need to be “right” can be overwhelming. But the true value lies in acknowledging when you’re not. It sets an example, encourages growth, and builds a foundation of trust that can push your team to new heights. 💡 Takeaways: • Admitting mistakes isn’t weakness, it’s leadership. • Ego limits growth. Openness fuels it. • Teams thrive in cultures of trust. And that starts with YOU. Have you ever had a moment where admitting a mistake led to a stronger outcome? Share your story below.. Hit the 🔔—> @Alex Wisch for more insight on #leadership, #Teamwork, and #mindset.