Real-Life Examples of Project Management Failures

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 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.

We lost millions on New Year’s Eve. Our ad servers crashed. Everything went down. No impressions. No revenue. On the single biggest ad day of the year. We were a mobile ad tech company moving hundreds of millions. But that night? • Our best engineers were partying • No one was on call • AWS alerts were misconfigured • PagerDuty didn’t go off • And no one noticed until I checked the dashboard the next morning: $0 revenue The team thought it was a frontend bug… Until angry customers started calling! That one outage triggered a domino effect: • We lost our biggest advertiser • Publishers jumped to Applovin • Our reputation cratered • The board demanded blood • We spent a fortune on consultants • We fired our CTO • Paused our roadmap for 6 months That night changed how I think about infrastructure forever. If you’re building anything that runs at scale, learn from our scars. 5 lessons I wish we knew earlier: 1. If you make money while you sleep, someone needs to be awake. Holidays don’t apply to production. Build a real on-call system with teeth. 2. If your customer notices the outage before you do, you’ve already failed. Monitoring is a product. Treat it like one. 3. Latency is a product issue. Uptime is a company issue. Founders should obsess over “5-9s” (99.999% uptime) the way they obsess over MRR. 4. Run game days. Simulate disasters. Practice escalation. Know what failure looks like. 5. DevOps isn’t a role. It’s a culture. If only one person knows how your system stays online, you’re already offline. You just don’t know it yet. We rebuilt from the ground up and also changed our culture: AWS with Azure failover. System status dashboard accessible to our BOD. Expectations clearly set that work/life balance doesn’t apply during an emergency. We never blinked during another holiday. If you’re building something important, DevOps is not optional. Don’t wait for a disaster to take it seriously. I did - and it cost me millions. Most expensive lesson ever learned!

I walked into a $20M disaster—and realized our real problem wasn’t the product. It was how we made decisions. Our flagship SaaS tool had a 92% user rejection rate. Why? Because it was built on the instincts of the highest-paid person in the room—not user insight. • PMs were just order-takers • Feedback loops were broken • Ego > Evidence We didn’t just need better features. We needed a better system for thinking. So we borrowed a page from Ray Dalio. At Bridgewater, Dalio didn’t just build a company—he built a decision-making machine. We applied his core principles to rebuild our product org: 1. Truth > Comfort We made radical transparency our default: • Public mistake logs • Multi-directional feedback • Customers critiquing roadmaps live One feature pivot saved us 3 months of wasted dev time. 2. Merit > Hierarchy We used “believability-weighted decision-making”: • Domain experts (not titles) held more voting power • A junior PM’s dashboard idea beat the exec favorite • It boosted adoption by 89% in 90 days 3. Systems > Stars We built playbooks and decision journals to scale wisdom: • Pre-mortems to test assumptions • Post-mortems weighted by expertise • A living product ops manual in Notion The result? • 3–5x faster innovation velocity • 88% feature adoption (up from 29%) • Cross-sell rate grew from 12% → 53% • Exec override rate dropped from 67% → 9% Lesson: The smartest teams don’t rely on brilliant individuals. They build systems that surface the best ideas—consistently. If you want a product org that thinks better, not just works harder, start by fixing how you decide. Because as I tell my team: “Truth flows > Title wins.” Want to learn how we did it? Read the article linked below:

You did everything right, you had an amazing team, and you had the resources... but you still failed. I learned this lesson the hard way in 2018 when I was leading an effort to reduce child hunger via free clinics during my masters program at Stanford Med. The Problem: Children in poverty rely heavily on free school lunches for their only meals, but don't have access to this resource when schools are on break. The Solution: Deliver school lunches to free clinics to give to pediatric patients and their families, as free clinics often served as main resource points in low-income communities. The resources already existed in silos, and we just needed to coordinate efforts. Our Resources: 1. A free clinic to run the pilot program out of. 2. A school district nutrition director who already had established programs and grant funding to feed children during breaks. 3. A leader at a regional food bank to provide additional food and a industrial refrigerator to store food at the clinic. 4. A set of interns to operate the program and provide food during clinical workflows. 5. Stanford Med researchers to evaluate the program, establish the experimental design, and with IRB approval. We had everything... but it was shut down a week before the program was to start. Out of nowhere, the CEO of the free clinic asked to meet with me and in short, the meeting can be summarized as "Why is there a industrial refrigerator in my clinic? Who are you? This is going to have to stop." This was heart crushing, but over time I've come to understand that the CEO made the right decision. The Issue: There was miscommunication on the clinic side, where we were told everything was okay but it was never brought up to clinic leadership as it was assumed it was too small scope to include them. I quickly learned that assumption was false in my meeting with their CEO. The CEO was new, and was brought in to refocus the clinic on a clear initiative (i.e. turnaround)-- and this food program was a distraction from that important goal. A huge lesson from this project was that you need to further support your key stakeholders. Even if you get "it's okay to do it," you need to probe and ask if there "are any considerations that could prevent this project's success, and if so how can we support you in either preventing or overcoming that challenge?" In addition, a reminder that you can do everything (that you control) right, but still end up failing. This is all part of the process of solving complex problems. You do everything in your power to help, and hope that luck and timing are on your side.

𝐓𝐡𝐞 $𝟗𝟎 𝐌𝐢𝐥𝐥𝐢𝐨𝐧 𝐋𝐞𝐬𝐬𝐨𝐧: 𝐖𝐡𝐲 𝐒𝐭𝐚𝐧𝐥𝐞𝐲 𝐁𝐥𝐚𝐜𝐤 & 𝐃𝐞𝐜𝐤𝐞𝐫’𝐬 𝐀𝐮𝐭𝐨𝐦𝐚𝐭𝐢𝐨𝐧 𝐃𝐢𝐝𝐧'𝐭 𝐖𝐨𝐫𝐤 𝐐𝐮𝐢𝐜𝐤 𝐒𝐮𝐦𝐦𝐚𝐫𝐲 𝐨𝐟 𝐭𝐡𝐞 𝐅𝐚𝐢𝐥𝐮𝐫𝐞: Stanley Black & Decker, Inc.'s ambitious $90 million automation project in Fort Worth, Texas, aimed to revive the Craftsman brand by producing tools domestically with unprecedented efficiency. However, equipment issues, slow production, and the impact of COVID-19 led to the closure of the factory 3½ years after its inception. 𝐋𝐞𝐬𝐬𝐨𝐧𝐬 𝐋𝐞𝐚𝐫𝐧𝐞𝐝: 1. 𝐒𝐞𝐥𝐞𝐜𝐭 𝐄𝐱𝐩𝐞𝐫𝐢𝐞𝐧𝐜𝐞𝐝, 𝐋𝐨𝐜𝐚𝐥𝐥𝐲 𝐒𝐮𝐩𝐩𝐨𝐫𝐭𝐞𝐝 𝐌𝐚𝐜𝐡𝐢𝐧𝐞 𝐁𝐮𝐢𝐥𝐝𝐞𝐫𝐬: • SBD selected a machine builder from Belarus. Although the company demonstrated its machines could forge with minimal waste, the machines didn’t work properly when installed and were difficult to fix. • SBD had to wait weeks for overseas parts and tooling to arrive for repairs. 2. 𝐓𝐡𝐨𝐫𝐨𝐮𝐠𝐡 𝐓𝐞𝐬𝐭𝐢𝐧𝐠 𝐚𝐧𝐝 𝐕𝐚𝐥𝐢𝐝𝐚𝐭𝐢𝐨𝐧: • The automation technology wasn't fully tested before scaling up, leading to persistent production issues. This was likely due to pressure to finish quickly to support the increased demand during COVID. 3. 𝐇𝐮𝐦𝐚𝐧 𝐄𝐱𝐩𝐞𝐫𝐭𝐢𝐬𝐞 𝐯𝐬. 𝐀𝐮𝐭𝐨𝐦𝐚𝐭𝐢𝐨𝐧: • The loss of senior experienced workers, mostly due to retirements during COVID, and over-reliance on untested automation systems underscored the value of human expertise. 4. 𝐔𝐧𝐬𝐭𝐞𝐚𝐝𝐲 𝐋𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩: • SBD had two CEOs and five Presidents of the Global Tools Group during this period. • Leadership focus is critical for complex projects. 5. 𝐑𝐞𝐚𝐥𝐢𝐬𝐭𝐢𝐜 𝐓𝐢𝐦𝐞𝐥𝐢𝐧𝐞𝐬 𝐚𝐧𝐝 𝐄𝐱𝐩𝐞𝐜𝐭𝐚𝐭𝐢𝐨𝐧𝐬: • Overly aggressive timelines, disrupted by the pandemic, compromised the project's success. • Setting realistic goals and being adaptable to unforeseen challenges are essential for complex projects. Leadership was critical here. 𝐅𝐮𝐭𝐮𝐫𝐞 𝐃𝐢𝐫𝐞𝐜𝐭𝐢𝐨𝐧𝐬 𝐚𝐧𝐝 𝐏𝐨𝐭𝐞𝐧𝐭𝐢𝐚𝐥 𝐌𝐢𝐬𝐬𝐭𝐞𝐩𝐬: Stanley Black & Decker may have learned the wrong lessons from this experience. The company's recent consideration towards manufacturing parts in Mexico, rather than further investing in automation within the USA, suggests a retreat from the challenges faced rather than a strategic approach to overcoming them. 𝐏𝐨𝐬𝐢𝐭𝐢𝐯𝐞 𝐄𝐱𝐚𝐦𝐩𝐥𝐞: Snap-on gradually integrated automation into its U.S. factories, evolving from a 100-to-1 ratio of workers to robots in 2010 to an 8-to-1 ratio over twelve years. This phased approach allowed Snap-on to identify optimal roles for both humans and machines. Snap-on's CEO, Nick Pinchuk, emphasized the importance of understanding the intricacies of the product and the manufacturing process. ATI Industrial Automation supports reshoring #manufacturing with the help of #robotics and #automation.  #robotrevolution https://lnkd.in/eaGwt2V5