The benefits of “failing fast” have been well documented and embraced in startup circles. Yet in IT, project cancellations are rare. Organizations exert tremendous energy on making the best of IT initiatives that are bound to fail. When failure is not an option, failing fast is a foreign concept.

There are many factors contributing to the fear of failure in IT: culture, governance, strategic alignment, budgeting practices, contract structures, and more. That said, IT leaders need to learn from others.

Freshman Year

In my first semester of college, on my first English course assignment, I got an F.

In high school, though my spelling was atrocious and my grammar just slightly better, my ideas and logic were somehow good enough to pull in As in English. What got me into college wasn’t going to work at college.

What I experienced then, but couldn’t yet put in words, was literally failing fast. I went to see my English professor in tears. He constructively pointed out what I needed to change to pass. Little did I know then, this was the best thing that could have happened. I realized the bar had been raised and I needed to do things radically different.

What would have happened if I hadn’t gotten an F on this paper early in the semester? I would have failed English, but also other courses. I ended up with an A- in that English course and what I learned through this experience carried me throughout my undergraduate and graduate education.

I propose we examine other examples of failing fast and how it helps organizations and individuals. I am choosing examples outside of traditional business and IT for a reason: we often learn more from examples far removed from our own experiences. We can be more open to a new idea when we aren’t nitpicking on details in the narrative and can’t hide behind the adage “my business is different or unique.”


Let’s look at how successful football teams fail fast. Though disliked by most fans outside of New England (I am a fan), no one can deny the Patriots have been the most consistently successful NFL team in this century. There are many reasons for this, but one key is their ability to make adjustments during halftime—or to fail fast.

“The Patriots are playing a dominant brand of football, but they are also coaching at a level that is giving them the ability to put opponents away with their halftime adjustments…. Basically, anything the Patriots were doing wrong in the first half was suddenly wiped away in the second half, and everything they did right in the first half continued in the final 30 minutes of play.” – Eric Frenz Bleacher Report

But the Patriots are not alone. We researched the point differentials for all 32 teams over the 2013-2015 seasons. The teams with the greatest 2nd half spread (i.e. the difference between the points scored by each team in the 2nd half) are Seattle, New England, and Denver, in that order. It just so happens they also have the best regular season records, and each won a Super Bowl during those three years.

Failing fast and adjusting in the second half is certainly a competitive advantage for these winning teams.


In Art & Fear, authors Ted Orland and David Waylon share a story about a ceramics teacher who tried an experiment with his class.

The teacher divided students into two groups. Those sitting on the one side of the studio were to be graded solely on the quantity of their work, while those on the other side, solely on the quality. The teacher informed the students in the quantity group that a simple rule would be applied to evaluate their grades: those who produced fifty pounds of pots would get an A; those who produced forty pounds, a B; etc. To the quality group, the teacher said they would be given a course grade based on the single best piece produced over the duration of the semester. If a student created a first-rate piece on day one of the course and did nothing else for the term, he or she would still get an A.

At the end of the quarter, the teacher made an interesting finding: the students who created the best work, as judged by technical and artistic sophistication, were the quantity group. While the quantity group was busy producing pot after pot, they were experimenting, becoming more skilled at working with the clay, and learning from the mistakes on each progressive piece. The students in the quality group cautiously planned each pot and tried to produce superior, flawless work, and so they only produce on a few pieces over the length of the course. Because of their limited practice, they showed little improvement.


The most significant accomplishments arise out of hundreds of mistakes and failures. What about seasoned standup comics, such as Jerry Seinfeld or Chris Rock?

They and many other comedians try thousands of jokes, most of which flop (fail). They do this in small clubs and venues. Only a few of their ideas, after many modifications and enhancements, are used on national audiences.


I like these stories because they illustrate an important principle: successful people and organizations act and learn as quickly as possible, even though the immediate outcome may not be what they’d hoped.

Instead of trying to avoid failing, they actively seek opportunities where they can face the limits of their skills, knowledge, products or services, and quickly adjust. This strategy improves the overall performance and outcomes of the endeavor.

We in IT can and should apply these lessons to our organizations. Who is going to lead the way?