I was reading Mary Cianni, PhD’s excellent book on consulting, The Consultant’s Compass, and I was taken by her honesty about how she felt as she dived ‘into the pool’ of management consulting. Mary is candid about various situations that forced her to learn, and I think this is an excellent reflection on the necessary steps to grow as a consultant.
One of the ideas that stood out to me was the concept of a failure resume—an exercise in cataloguing the missteps, lessons, and growth moments that shape you professionally. In an industry like Tech Due Diligence, where precision, critical thinking, and adaptability are essential, embracing failure as part of the process is invaluable. As I often say it’s better to embrace imperfection.
Looking at my own experience, I recently reflected on my failure resume—not just in Tech DD but across my career. Inspired by this concept, I took a deep dive into my past missteps, including the ones that are now immortalised in my CV.
Lessons From My Own Failure Resume
1. Overworking and the Founder’s Trap
As the founder of Penman and Beyond, I turned a five-day workweek into a seven-day obsession. Instead of scaling effectively, I burned out. The lesson? Sustainable growth requires structure, delegation, and trust in others.
2. Sales and Prospecting Missteps
Early in my freelance career, I believed that knowing my subject well meant I could sell. I was wrong. I spoke too much and listened too little, failing to understand the nuances of prospecting and client needs. Now, I emphasise active listening and tailored solutions.
3. The Importance of the Customer
In building software platforms, I encountered repeated failures—one of the biggest being sales delays when I didn’t engage a CIO early enough. Tech Due Diligence has reinforced this lesson: businesses without enough customer input early in the process will struggle to execute effectively.
4. Underestimating the Human Element in Tech
During my time at Ford, I learned the hard way that technical competence alone doesn’t guarantee success. A misstep—like sending the wrong tape into courier services and costing the company thousands—highlighted how attention to process and communication is just as critical as raw capability.
5. Failure in Small but Costly Details
One of my most amusing yet educational failures was an email blunder—learning the nuances and sensitivities of particular market segments the hard way. In Tech DD, I apply the same principle: small details can make or break a deal, a product, or even a company’s valuation.
Why a Failure Resume Matters in Tech DD
In Tech Due Diligence, failure isn’t just about personal setbacks—it’s about uncovering hidden risks and blind spots before they become crises. A company’s ‘failure resume’ often tells us more than its success stories. We look at team resilience, lessons learned, and how past challenges shape their execution today.
So, what’s on your failure resume? If you’re in the world of tech, investment, or consulting, I’d love to hear the lessons that shaped you.
