20 Tech Leaders Share Lessons Learned From Failed Initiatives

Forbes

5 hours ago

Every technology leader has a project (or three) that didn't go exactly as planned. But wise leaders don't treat these moments as wholly wasted efforts, since they often teach more than the wins by exposing blind spots, shaky assumptions and opportunities to improve.
The way a tech leader responds to a failed initiative often reveals their and their team's strengths more than the original plan ever could. Below, members of Forbes Technology Council discuss takeaways from their own project missteps that can help their fellow leaders navigate setbacks with greater clarity and confidence.
1. Maintain A Startup Mindset
Setting up a team and structure too rigidly at the start can become a burden, not a foundation of success. We assumed early alignment would carry us forward, but it turned into an obligation, which was slowing decisions and working against change. Adopting a startup mindset—asset-light, adaptable and day-by-day focused—taught me that success comes from clarity, not fixed roles or plans. - Yogesh Malik, Way2Direct
2. Prioritize User Workflows Over Cool Tools
A failed tech project showed me to focus on how users work, not just build cool tools. We made a great system, but users didn't use it because it didn't fit their needs. Now, I always ask users early to get it right. That means a user-centric and prioritized backlog for implementation. This has made me a better leader by keeping me practical and focused on what really helps people. - Rishi Kumar, MatchingFit
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3. Don't Rely On Benchmarks Achieved In Isolation
I shipped an early NLP voice agent before wiring in real-time, context-based hand-off to human CSRs. Accuracy benchmarks looked perfect in isolation, but customers got stuck and churned. That failure taught me to pair every model metric with a 'Can users finish the task?' metric. Now, new launches mandate shadow-mode pilots, field-tech feedback loops, and an instant human escape hatch. - Somil Gupta, Broccoli AI
4. Validate Assumptions
Early in my career, I learned a key lesson: 'Don't assume; ask questions.' We launched a feature-rich solution that missed the mark because we didn't validate user needs. It led to poor adoption and wasted effort. Since then, I have focused on early stakeholder inputs, user impact and clear outcomes, shaping a more empathetic, communicative and outcome-driven leadership style. - Uttam Kumar, American Eagle Outfitters
5. Look Beyond Technology
Technology alone isn't the answer. You need the business strategy, processes, data and skills to have a successful tech initiative. In fact, I would say that the tech is often the least important factor of that set of requirements. - Jason Kurtz, Basware
6. Anchor Decisions To Clear, Near-Term Priorities
One key lesson I took from a failed initiative was to anchor every decision to the single highest-value problem I'm committed to solving within a one-year horizon. Since the world beyond 12 months is inherently unpredictable, I now use a simple rubric: Will this choice move us closer to that goal, or will it pull us off course? If it's the latter, I say 'no,' unless exceptions demand it. - Bharath Balasubramanian, Salesforce
7. Treat Interoperability As Nonnegotiable
Early in my career, I saw clients invest millions in advanced enterprise systems only to abandon them because poor interoperability made real-world use impossible. It taught me early on that interoperability isn't optional. It is foundational to usability, adoption, long-term product success and future growth. - Ashish Singh, SeemaS, Inc.
8. Protect Your Integrity—Even If It Means Walking Away
I learned that alignment matters more than revenue. In a co-managed IT setup, our security recommendations were ignored, putting both the client and us at risk. Walking away wasn't easy, but it reinforced the principle that protecting our integrity and setting clear boundaries is essential to long-term success and leadership growth. Parting ways professionally was a far better decision than trying to 'fix' it. - Ann Westerheim, Ekaru
9. Respect Cultural Context
The definitions of right and wrong can vary dramatically from one country to another. This ends up being painfully evident on global projects that lack highly qualified PM oversight. Even the best software solution, if arrogantly configured from a myopic point of view (perhaps one that is right only in one location), can be viewed as a failure of the entire department, impacting IT's reputation. - Ken Feyder, Hermès of Paris
10. Find The Right Audience And Adapt To Their Needs
I scaled a startup devoted to developing OCR technology to transcribe doctors' handwriting, but the market wasn't ready for it. So we pivoted to education: Teachers needed our solution to interpret messy student handwriting. The lesson I learned is that success is in finding the right audience and adapting to their needs. It shaped my leadership approach toward solving real problems for the right people. - Craig Crisler, SupportNinja
11. Set Clear Expectations With Customers Early On
From a professional services perspective, every red account started its decline in the sales cycle. Mismanagement of customer capabilities and expectations is a key factor in failed initiatives. Change management and transformation are complex endeavors that require total alignment from leadership down to the line of business worker to ensure adoption and maximum ROI attainment. - David Pauli, Newton3
12. Do Your Homework Carefully
It's important to get detailed information before beginning. There are always hidden stakeholders that we forget to account for in large tech initiatives. Solutions are often over-engineered and take more time to implement, only to fail due to misaligned expectations. Finally, it's essential to detect risks and manage them wisely. - Devendra Goyal, Think AI
13. Proceed With Curiosity, Not Just Conviction
I learned not to fall in love with my own ideas. I built a product I loved, assuming others would, too, without validation. When no one used it, I realized the importance of customer feedback. It taught me to lead with curiosity, not just conviction. - Jason Penkethman, Simpro Group
14. Lead With Empathy
A failed IAM rollout taught me the cost of skipping user engagement. We focused on technology, not user experience, leading to poor adoption. Since then, I have led with empathy, ensuring alignment between security goals and real-world user behavior. - Premsai Ranga, T.Rowe Price
15. Align Teams Around Purpose, Not Platforms
One lesson I learned is that technology alone is not transformation. Early on, I focused too much on the technology as the solution and not enough on people and processes. That misstep taught me to lead with empathy and clarity, aligning teams around purpose, not just platforms. That shift made all the difference in driving real, lasting change with technology as the connector. - Lee Cage Jr., BDO
16. Recognize That Innovation Can't Be Outsourced
I once led an initiative using a white-labeled product that wasn't designed for our specific needs—it was like forcing a square peg into a round hole. The experience taught me that innovation can't be outsourced and that clear, proactive communication is essential when managing client expectations during setbacks. - Chandler Barron, Barron Advisory™
17. Establish A Realistic Strategy Early On To Guide Investments And Decisions
I am passionate about developing sensitive biomarker detection technologies that will eventually be used for patient selection. These assays are often expensive and complex, making their implementation in prospective trials challenging. They must navigate regulatory processes. I've learned the importance of establishing a realistic strategy early on to make smart investments and decisions. - Rachel Tam, Bristol Myers Squibb
18. Fight Against Complacency
Nothing will kill innovation faster than complacency. As a leader in the tech world, if you are more afraid of a deadline than you are of releasing a mediocre improvement, your company will fail. Somewhere out there is a company that is being forced to innovate in order to close the gap with you, and with every incremental improvement, you lose ground to their innovation. - Matthew Areno, Rickert-Areno Engineering, LLC
19. Value Early User Input And Iterative Improvement
A failed tech initiative taught me that isolated development without early end-user involvement poses high risks. Our product launch failed to achieve its goals due to unvalidated assumptions. The experience taught me the importance of leading through curiosity while valuing user input and committing to iterative improvement. This experience taught me humility while helping me evolve into a collaborative and grounded leader. - Amit Ojha
20. Never Build In A Vacuum
A failed tech launch taught me the hard way: Never build in a vacuum. We had a solid plan but skipped early user feedback—and it showed. The product missed the mark. That experience made me a stronger leader by showing the power of listening early and often. Now, I focus less on having the perfect answer and more on staying curious and connected to real user needs. - Bhupendra Singh, Marriott International