by Rich Hein

IT Leadership Lessons You Can Learn From Failure

Jan 06, 20148 mins
CareersCIOIT Leadership

Although you work tirelessly to prevent them, failures happen in IT. It's important that you discover the secret for turning mistakes into lessons you can use to become a more effective leader.

In the world of IT, things can and will go wrong. Failure can come from a number of things such as rushing to get too much done in a single project instead of breaking it down into smaller, more manageable projects. It can come from not allowing enough lead time for developers to do their part on the back-end or even from a consultant or vendor that led you down the wrong path.

Data security issues in the workplace

Whatever the case, failure does happen; it’s to be expected and as the saying goes life is “10 percent what happens to you 90 percent how you react to it.” Failure doesn’t have to be a negative. With the right attitudes and processes in place it can be educational, informative and sometimes transformative.

You know from a logical perspective that you should learn from your mistakes. That is drilled into many of us beginning in childhood. The problem, according to experts, is that in the corporate world, a lot of companies don’t handle failure well. They don’t have adequate processes in place to examine why something failed, but that is a huge necessary part of the learning process.

“Looking back over the past 15 years of our [IT & Tech] industry I didn’t see enough thorough, objective reporting on these kinds of failures to help people like myself in the trenches. I thought it was so important to learn these lessons that I spent two years researching and writing the case studies in my book. I selfishly wanted practical guidelines based on actual industry failures that I could use in my own work,” says Victor Lombardi, Rosenfeld Media consultant and author of Why We Fail.

In this world if you can’t learn from your mistakes you are doomed to repeat them. In the business world, if you make the same mistakes a few times you could be looking for another career. Steve Jobs had failures in his career before he changed the game as did Elon Musk, founder of SpaceX, Tesla Motors and PayPal.

What separates bad leaders from good leaders and possibly good leaders from visionary leaders is their ability to gain insight from those failures that will help them succeed the next time around. These tips from experts to help you make the most of bad situation and possibly avoid future IT project failures.

Create a Safe-to-Fail Environment

For large complex companies, learning and evolving can be a slow road. Behavior has to change at a myriad of levels. In order for IT to keep pace and deliver what the business needs to succeed you’ve got to empower your team to try new things.

The problem arises when new things don’t work out and you or your organization are more focused on placing blame then solving the problems at hand. How willing and enthusiastic will workers be to step out of the normal routine? The answer is, not very, so the question becomes, do you as an IT leader create an environment where people on your team feel comfortable to speak up and voice objections large or small?

“A safe-to-fail environment by design encourages creativity, risk-taking ability and innovation. It allows employees to experiment with new ideas and provides an environment where failure is an acceptable outcome. At NutriSavings and Edenred, we actively promote innovation and help our colleagues take calculated risks to ensure on-going learning,” says Niraj Jetly, senior vice president-COO & CIO of NutriSavings LLC.

IT leaders, understandably, don’t want to create an environment where there is no accountability for failure. They can be concerned that if they appear too accepting of failure, workers won’t necessarily be motivated to perform at their highest standards but rather what they feel they can get away with.

According to Amy C. Edmondson, Harvard Business School Professor and author of the 2011 HBR article, Strategies for Learning from Failure, that isn’t the case. According to her research, there are in actuality very few blameworthy acts that are what she calls, “deliberate deviance.” The rest fall into more of a grey area where placing blame isn’t very easy or useful.

Don’t Shoot the Messenger

“Failures are an inevitable part of business and technology. Empathy is the best way to respond to a failure. Empathy communicates trust and people perform best when they feel trusted. If a person is already low on confidence due to guilt of failure, our focus should be to help the person to come out of that guilt and later on help them reflect back on what could have been done differently,” says Jetly.

Avoid the Blame Game

“The blame game is still such a challenge because it is so deeply ingrained in our psychology and as small children we learn pretty early on if we do something wrong we get blamed. It’s an emotionally unpleasant feeling. We don’t want to experience it we try to push it away. That childhood feeling follows us through our developing and adult years. We bring it into the workplace and again for reasons that are both emotional and quite logical; connected with promotions and other activities. We don’t want to be blamed for things going wrong, according to Edmondson.

Own Your Mistakes

If it was your fault, don’t try to shift blame own up and move forward. “Everyone makes their fair share of mistakes. One of the lessons that I have learnt through experience, is that rather than defending yourself, accept the mistake as soon as it is realized. Early acceptance helps significantly in aligning efforts to quickly take corrective action. In addition this provides much needed peace of mind,” says Jetly.

Set Up Processes Where Failures Are Examined and Learned From

Finding out why things went wrong is important and, of course, if there were blameworthy mistakes they should be handled, but the real purpose is not to find out who is at fault but instead to get to the heart of the problem, to find a solution, a workaround or a new direction.

“What you learn from [mistakes] is not to make that same mistake again. That is the net sum. This is the most difficult concept to let go of, especially if you are the one with the clipboard and or the one with the hammer,” says Roy J West, founder and CEO of The Roy West Companies, an organization that focuses on talent management and employee/customer engagement.

Jetly likes to perform what is referred to a “sunset review” or “post mortem” report and offers the outline below on how this type of evolution typically goes. The designated meeting chair outlines the objective of the meeting and encourages everyone to share ideas without judging anyone else. Every team member is allocated pre-defined time to answer the following three questions:

  1. What went well on the project?
  2. What did not go well?
  3. What could have been done differently?

Designated scribe takes notes and after everyone has shared their opinion, the meeting is open for discussions and analysis.

“Though this may seem like a stretch at times, these meetings provide valuable insight into how things really went during the course of project and hold a store of valuable lessons for the future,” says Jetly.

Lombardi, on the other hand, offers this advice: “There’s been a lot of progress in the past few years to combine iterative, testing-oriented methodologies like agile with the metrics-based approaches of online marketing. Formal methods such as lean startup and customer development are essentially a way to reinstate the scientific method back into our work, almost like we’re reinstituting the practice of having R&D departments but in a more practical, customer-oriented way that’s integrated with our normal project work. Using these methods, my recommendations center around distinguishing hypotheses from facts and knowing how to prioritize, test, and learn from your hypotheses.”

Be an Effective Communicator and Know Your Workers

Communication skills are one of the most important skills an IT leader can have. Not communicating effectively has been the downfall of many an IT project. “Don Clifton, former chairman of The Gallup Organization and the father of strengths-based thinking, believed that fastest way to destroy someone was to demand or expect something of someone they are not capable of. Failure is predictive when the person(s) being charged with a task/mission does not have the talent to perform to success. It is also predictive when the Coach/Manager/Leader has not provided the desired outcome with great clarity and is not focusing on what the employee does best,” says West.

To be an effective leader, you many times have to communicate to people the reasons things are being done to help them understand what’s important.

Learn From the Competition

Successful leaders help their organizations by looking at the mistakes and failures (as well as successes) of others in their industry. Being able to identify possible issues this way could help your organization side step a problem that caused other companies to miss the mark.

Incentivize Workers

Create a program where IT pros are encouraged to report unforeseen problems and have those who stave off failure are rewarded.

“Don’t fall in love with ideas, or personalities or progress for the sake of progress,” says Lombardi “When we remember that new, untested ideas are really hypotheses and run experiments to find out if they work or not we’re on the path to avoiding failure.”

Rich Hein is Managing Editor for He covers IT careers. You can follow Rich on Twitter, Google+ or connect on LinkedIn. Follow everything from on Twitter @CIOonline, Facebook, Google + and LinkedIn.