Vulnerability and Trust in Product Development

This is the paradox of founder authenticity: You must be 100% confident in your direction, yet 100% vulnerable about your weaknesses. It's a tightrope walk that defines great leaders. Most founders get this wrong. They project unwavering certainty, hiding doubts. Or they overshare insecurities, eroding trust. Neither works — you need both confidence and vulnerability. Confidence isn't just saying "we'll succeed." It's showing how you'll navigate specific market challenges. It's having a clear plan for your next funding round. It's knowing your key metrics in real-time, anytime. Vulnerability isn't admitting defeat, but acknowledging that your product has flaws, but you're actively fixing them. It's sharing that you struggled with a recent hire, but here's how you're improving your process. In board meetings, confidently present your growth strategy, then openly discuss the execution challenges you're facing. During team all-hands, passionately share your vision, then admit where you need the team's help to fill your knowledge gaps. In customer calls, proudly showcase your product roadmap, then honestly address the features you're still developing. This balance transforms how you lead: → Turn "I don't know" into "I don't know yet, here's how we'll find out." → Replace "We can't fail" with "If we fail, here's how we'll learn and pivot." → Shift from "I have all the answers" to "I value your input." Remember: People don't follow perfect leaders. They follow authentic ones who balance unwavering vision with genuine humility.

Ask any founder about their biggest failure, and they’ll point to the obvious one. Big failures get headlines. But the real collapse rarely gets noticed. Products rarely die from a single mistake. They bleed out in silence every time trust is traded for a shortcut. Betray your best users, lose your edge. Your earliest adopters do more than provide feedback or cheer from the sidelines. They troubleshoot, stretch your product, and set new expectations. When their needs go unmet, or when you break their workflows, you are losing the resilience that keeps your product alive in tough moments. Most teams only notice the damage after the fact, when those users are already gone. How you end matters as much as how you launch. Product migrations and sunsets are never just technical. Every missed detail, whether it’s a broken export, a lost file, or a confusing transition, creates another fracture in user trust. The companies that get this right pay attention to the small stuff and respect what users built with them. The ones that treat it as a checklist always leave a mess behind. A clean, clear ending tells your customers that their time and work mattered. Chasing breadth, losing depth. Expanding into new markets or adding features can look like progress. What usually happens is you lose the discipline and detail that made people care in the first place. Winning new jobs means putting in more effort, not less. Most teams spread themselves thin and become forgettable. The teams that win stay focused long enough to build depth users can’t find anywhere else. Friction is a slow exit. Forced signups and hidden paywalls push users to start searching for alternatives, even if they don’t leave right away. The short-term gains from adding friction almost always come at the cost of long-term loyalty. In the end, trust is what keeps people around. Lose it, and all you’ve done is start a countdown for your competitors. The pattern repeats: The slow decline of a product begins each time trust is traded for a shortcut or a quick win. Protect user trust as fiercely as you fight for every launch or metric. The best teams never make their top users regret the energy or belief they put into the product.

Show vulnerability. Build trust. Navigating the fear of mistakes is tough. 1. Sharing own mistakes openly ↳ Shows errors are opportunities for growth ↳ Creates an authentic space for others 2. Shifting focus from blaming to understanding ↳ Learns from what went wrong ↳ Builds a culture of continuous improvement 3. Normalizing continuous learning ↳ Promotes resilience ↳ Encourages a growth mindset When the CEO I worked with embraced these actions, her leadership style transformed. Her team became more resilient and open to learning. Why? Because showing vulnerability is powerful. It creates a safe space for everyone to express their challenges. And in a high-pressure environment, that’s invaluable. Remember: Mistakes aren't failures. They’re steps to success. It’s about learning, growing, and moving forward. --- Considering working with a coach? https://lnkd.in/dC4tYDSS

Leaders: create an environment where your team doesn't second guess themselves. Failure is okay. Difficult conversations need to happen. Worthwhile work is hard. But here's the thing: your team will fail to execute according to your standards when you've built a system around fear (whether intentional or not). And even worse, the standards they can achieve. Here's how I try (and fail at times) to build a culture of trust on the marketing team: Encourage Transparency: Make it safe for your team to share challenges, ask for help, and voice concerns. Have monthly or quarterly meetings with every team member, make it a safe space to share their concerns. Show Your Vulnerability: Lead by example, show your own vulnerability. Admit your mistakes, and model how to learn and move forward. Get Agreements: Fear often arises from uncertainty. Be clear about goals, priorities, and what success looks like. Share Before Ready: Encourage your team (and yourself) to share work-in-progress ideas, drafts, and projects. Waiting for "perfect" never works. Give Feedback With Empathy: Feedback should be constructive, not destructive. Focus on the behavior, not the person. Fear can stifle even the most hardworking and intelligent. It also blunts creativity, slows your team, and severely limits trust. It's your job to remove the barrier.

Trust isn’t built through perfection. It’s built through authenticity, vulnerability, and humility. In the best teams, people don’t need to have all the answers. They need to show up honestly, ask good questions, and stay open to learning. That kind of culture only works when leaders model it from the top. When they don’t, it creates distance. People start managing impressions instead of solving problems. Energy gets spent on appearances instead of outcomes. I once worked for a boss who really wanted to be a great leader, but never quite showed up fully. He said all the right things about collaboration, strategy, and innovation, but there was always a filter. Something about him felt slick. I remember inviting him to an offsite about our product roadmap. It was an early-stage, messy kind of conversation: technical debates, half-formed ideas, back-and-forth about what might work. Inviting him was a bit of a risk, given what I’d observed. He sat in, but you could tell he was uncomfortable. He wasn’t used to that level of transparency. He was used to polished slides and confident answers, not the raw process of figuring things out together or dealing with uncertainty. That moment stuck with me. I realized he maintained trust by appearing right and in control. He saw our openness to uncertainty as a weakness, when in reality, it was how we built great products and strong teams. That’s when it clicked: I couldn’t work for someone who equated vulnerability with incompetence. Real trust requires showing up as a human. And if you can’t do that, no amount of talk will prove you are qualified.