Insights Gained From a Failed Project Kickoff

I once oversaw a 3-month implementation that our team executed exactly to plan. When the CXO finally reviewed it, he said bluntly: "This isn't what we need at all." I thought everything went exactly according to plan. The project was scoped, approved, and executed perfectly. Our team followed the direction the customer gave us. We hit every internal milestone. But in that moment, I realized how dangerous it is to assume that perfect execution equals success. The mistake we made was that we built out exactly what the POC had asked for, but never aligned with leadership on outcomes after the kick-off. This is one of the biggest traps in project delivery:  Teams often gather goals and direction from POCs without consulting executives and then realize late that leadership has entirely different success metrics.   That gap (between what the user wanted and what executives expected) costs us ~300 billable hours and a complete project reset. Now, we do things differently. We align with the right stakeholders early. We ask the leadership what reports and dashboards they want to see. Getting inputs on what KPIs they want to monitor is a big clue into what to prioritize and how to drive decisions through the rest of the implementation. We also ask questions like: “Six months from now, what needs to be true for this project to be considered a success?” And so, we resolve conflicting priorities before we touch the configuration. Because the only thing worse than a failed implementation… is a perfectly executed one that still misses the mark.

My Failure - #1: Slow down so you don’t F up. When we kicked off our website refresh, my goal was clear: move fast and free up my CEO’s time so she could stay focused on the bigger picture. As VP of Marketing, I felt confident our team could handle the execution - easy right. Ha. Here’s the reality- no one at a company has a stronger pulse on evolving priorities than the CEO. By the time I looped her in, the work no longer aligned with her evolving vision. Deadlines were missed. Back to the drawing board. It wasn’t that the work was wrong—it’s that I skipped a crucial step. I thought I was saving time, but I was creating friction. What I learned: 1. Leadership isn’t just about driving strategy; it’s about aligning with key stakeholders. The CEO doesn’t need to be in every detail, but they do need to feel connected to the process. 2. A CEO’s input is less about tactics and more about ensuring the work aligns with the broader vision. Ignoring that early leads to rework later. 3. Moving fast without alignment isn’t speed—it’s inefficiency disguised as progress. Looking forward: • Stakeholder alignment is step one for every major project. Especially when it involves the CEO • Build processes that enable quick, meaningful check-ins at key points—this keeps momentum without losing alignment • Prioritize clarity over speed. A little extra time upfront saves a lot of time downstream. 👇🏻 This was a humbling lesson/reminder in leadership. I didn’t just learn how to avoid this mistake—I learned how to create better processes that continue to support the big picture. - - - - - - Hoping to be more vulnerable in 2025 and share mistakes publicly to force growth but also help show it’s sometimes the little mistakes that fuel growth. No judgement please as you start to see more of these from me :)

Embracing Failure: Lessons Learned from a Recent Experience LinkedIn is often a platform where we highlight our successes, but I believe it's equally important to share our failures and learning experiences. Allow me to take you through a recent setback and the valuable lessons it offered. Last November, our team received an invitation to respond to an RFI alongside 10 other global negotiation training companies. This opportunity came from one of the largest corporations in their industry headquartered in Europe. They sought a comprehensive global training program for 400 procurement professionals, a task well within our expertise. The RFI was extensive, leading us to submit a detailed 38-page proposal. We learned that we were shortlisted as one of the three potential suppliers. The client proposed an innovative agile procurement process, including a live workshop at their HQ. However, challenges arose from the outset. Negotiating cost compensation for our team's travel proved difficult, and scheduling the event became nearly impossible. Ultimately, the workshop shifted to a virtual format on an unfamiliar platform. Despite meticulous preparation, the workshop itself felt more like an interrogation than a collaborative session. Feedback was unexpected and critical, leaving us feeling disheartened and perplexed. During the workshop, frustration mounted within our team as we grappled with unexpected challenges and criticism. At one point, a colleague couldn't contain their exasperation and exclaimed, "If only you had spent all this time and preparation running a pilot workshop with each supplier, all of us would have saved so much time." This outburst encapsulated the frustration we felt at that moment. It underscored the hindsight realization that investing time in pilot workshops could have provided invaluable insights early on, potentially streamlining the process and avoiding the pitfalls we encountered. Following the workshop, we were informed that the client had decided to proceed without us. Their reasons? They perceived our approach as overly academic and doubted our ability to scale the workshop effectively. While disappointing, this experience provided some valuable insights: 1. Value Your Time: Don't invest significant hours in RFIs and engagements without ensuring appropriate compensation. 2. Know Your Medium: Creative workshops may not translate effectively to online formats; consider the limitations of virtual environments. 3. Clarify Expectations: Ensure clients have a clear understanding of their objectives and are prepared for the engagement. 4. As an advisor i often sit on the other side of the table and always recommend the buyer offer the supplier compensation for more time consuming proposals. Sharing this experience isn't merely about airing frustration; it's about embracing the opportunity to learn and grow. By reflecting on setbacks, we can refine our approach and ultimately achieve greater success.

I have never made any mistake in my PM career - Said no one ever — definitely not me. My biggest Product Management mistake? Building something I knew — deep down — wouldn’t work. We learned about a highly successful product concept in the industry. And we thought the obvious thing to do was to adapt it to our use case. We loved the idea and wanted to leverage it for a a high-stakes market moment. But I wasn’t too sure. As I went through Discovery with customers in the market, I kept learning the same thing - the customer context was different. There was no job that people were trying to progress in, no outcomes to achieve, the need wasn’t not there, no product that they were trying hire. The behavior just didn’t translate. Despite the consistent customer and market indications, we pushed forward. After months of building, we launched big time. While everybody was celebrating, I was dreading to look at the numbers. And the numbers validated my insights. We built a beautiful product but it wasn't the right one. It didn’t fail because of bad execution. It failed because we didn’t stop when we learned it wasn’t the right bet. 💡 Lessons learned: 🚩 Customer signals > internal momentum 📍 Success in one context doesn’t guarantee success in another. Do not copy a product that seems to be working for another company 🧭 Good product leadership isn’t just about building — it’s about having the courage to stop. And in my case it is about listening to your PMs and their insights. My insights weren't heard. Sometimes the boldest move isn’t launch. It’s saying: “This isn’t the right thing to build.” What’s a powerful lesson you’ve learned from a product mistake? 👇 I’d love to learn from yours.

Why 73% of Projects Fail and How I Stopped Losing Stakeholder Support Let me tell you a quick story. Years ago, I was leading an ops overhaul that was supposed to streamline internal reporting. Everything looked good on paper, timelines, budget, resource allocation. I checked every box… Except one: I didn’t fully engage the stakeholders who would actually use the system every day. 🚨Big mistake. Within 3 weeks of launch, adoption lagged, teams worked around it, and leadership questioned the ROI. That’s when it hit me—involvement doesn’t equal alignment. Just because stakeholders are informed doesn’t mean they’re invested. So I changed my approach. Here’s what I did: • Identified key influencers across departments, not just top execs, but daily users and frontline managers. • Used long-form discovery sessions to understand their actual pain points (not just the ones listed on a dashboard). • Built a feedback loop into every sprint cycle. Small changes. Real-time validation. • Created internal linkages between project goals and departmental KPIs (this one’s huge). The result? 🎯 41% faster implementation. ✅ 3X higher adoption in the first 30 days. 💬 Consistent stakeholder engagement from kickoff to post-launch. Why does this matter for you? If you’re a project manager, ops lead, or department head, especially in finance, tech, or healthcare, here’s your reality: 📌 You’re juggling timelines, compliance, and team bandwidth. 📌 You’re expected to “drive transformation” and still “not disrupt the day-to-day.” 📌 You’re measured by results but those results start with buy-in. So ask yourself: Are you just updating stakeholders or are you empowering them to shape outcomes? That’s the difference between a delivered project and a sustained solution. If you’re tired of rework, delays, or lukewarm adoption, start by rethinking how you engage your stakeholders. Involve early. Involve meaningfully. Involve often. ✅ Start with a 30-minute alignment session before you build your next project charter. ✅ Don’t just collect feedback—co-create the solution with the people who live it. You’ll thank yourself later. Let’s stop managing projects and start leading with people who matter. #ProjectManagement #StakeholderEngagement #LeadershipInAction