by Joseph Flahiff

Why you should teach your IT team to fail

Jun 11, 2015
CIOIT LeadershipMentoring

Failure has a stigma in business, we avoid it at all costs. Yet if you are not failing you are not learning. Failure IS an option. Here's how to balance these two seemingly opposing ideas.

My clients all want their teams to succeed, but what they really need is for their teams to fail. There is so much stigma built up around the word that you probably had a negative reaction to even reading that sentence. According to, “Fail” is defined as:



  1. be unsuccessful in achieving one’s goal.
  2. neglect to do something.

synonyms:       let down, disappoint;

  1. break down; cease to work well.


  1. noun: fail; plural noun: fails

Wow, who wants to do that? Let’s take a closer look though. Can you think of any times when failing is good? 

If you ski or snowboard, you have experience with a time when failure was a good thing.  Really, to learn any skill you need to fail, and fail a lot. Imagine if you wanted to learn to ski, but you didn’t want to experience failure of any kind. How long would it take you to learn to ski? Would you ever learn? Nope. It even seems absurd to suggest. Yet every day, people approach projects this way, and they evaluate their employees this way. They believe that if people would just plan enough, think long enough, and drive hard enough, they would be able to do something that they have never done before without error or failure.


Well, part of the problem is the consequence of failure. When you fall while learning to ski, you poof down in the cold soft snow. You might bruise your bum and your pride, but you won’t die. If the result of falling in skiing was death, it would warrant a lot more planning. When the risk is high, one way to compensate for that risk by planning more. But it isn’t the only way.

snowboarding Ripley119

In truth, the risk of death can be very real in skiing.  If you decided to try ski jumping the first day you went skiing, there is a very real risk of death.  But no one does that. They start out by skiing the bunny slope. Not a lot of risk on the bunny slope. The most dangerous thing there are the other skiers. They fall a lot, and they learn a lot. Once they learn to ski on the bunny slopes, they move up to the green circle slopes, then the blue squares and finally the black diamonds and double black diamonds. We mitigate the risk of death in skiing by making small investments in learning. We try something, and we learn. We try something else, and we learn. We fall, and we learn.

You can do the same thing in your IT efforts. Make small investments in learning.

Historically in IT efforts, we have tried to do large, single release projects which take 6 months, 12 months, or even 2 or 3 years to implement. The longer the project, the more risk you pile up. It is like driving a snowplow, the pile of risk you are pushing just keeps growing and growing. The alternative is to break the work up into smaller efforts ̶ as small as you can get them. 

If a project is a year-long, try breaking it into two independent pieces. Each piece should deliver value to your customer(s). If you have a multiphase project, try to split your phases into pieces. If you have 2 phases, make it 4. If you have 4 phases, make it 8. By doing this, you will deliver value to your customers faster, while you also reduce the overall risk of the project. Once something is in place and customers are using it, the risk for all of that effort is reduced to nearly zero. If one of those phases does happen to fail, you have contained the failure to only that part of the work. Learn from the failure and it will turn that failure into a success! 


What is the prevalent attitude toward failure in your organization? How much risk are you bottling up in your projects? Are you snowplowing risk? What work are you doing right now that could be broken up into more releases to reduce the risk? 


Actively monitor your attitude toward risk. Keep track of the risk  in your organization. Can you mitigate that risk by breaking it up into smaller pieces? Double your number of releases of value to your customers. 

bigstock motivational background 55704071


Start talking in your organization about failure. What is the prevalent attitude toward failure? Do people understand that it can be good? Share this article with them and share your experiences below in the comments.