Why We Are Afraid of Failing in IT, and How to Get Over It

IT executives, IT managers and other techies: I am coming at you!

It’s time to embrace the concept of failing fast. (If you already have, how is it working for you? Please feel free to comment below and share your lessons learned.)

This doesn’t come naturally to a lot of people. We in the IT industry have baggage. So let’s process that baggage together.

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The IT Industry

Think of the industry as your extended family. No two IT organizations are exactly alike, but there are similarities. Like a family, we share a common history of dynamics which formed a general IT culture of certain norms, customs and models. One of the best bumper stickers I ever saw read: “90% of all families are dysfunctional, the other 10% are in denial.”

What in our IT family history drives us to fear failure? This neurosis began in the early days, with IT supporting Finance. Many IT organizations today still report to the CFO. Typically, CFOs are not so receptive to failing. In addition, the dawn of our industry centered around computational inputs and outputs and transaction processing—where perfection and keeping the lights on were paramount. Don’t let historical baggage hold you back!

Failing fast does not mean you put your business, and your job, at risk. It means trying to innovate quickly in areas that will provide new value to your organization, radically shortening the length of projects (smaller deliverables), getting continuous and immediate feedback from your customer, and—most importantly—learning.

Does this scare you? If so, let’s dig in a bit deeper.

“I have not failed. I’ve just found 10,000 ways that won’t work.”― Thomas Edison

Any advancement in technology, process, or other innovation produces expected and unexpected outcomes―not objective successes and failures. The only true failure is if you haven’t learned from a given outcome.

Your Organization

Maybe now you will consider that failure is OK in theory, but you’re thinking, “What about my organization, or my boss?” Are you part of an organization that when someone makes a mistake, it is held against him or her? I contend that there may be an equal number of people in your organization who are promoted for taking a risk for innovation’s sake, even though they failed.

Seek out these risk-takers and fast-failers. Start working with these people, because they have likely learned from their mistakes, and you can learn from them as well. What did they do differently from those whose mistakes were held against them?

“Failure is not the opposite of success, it’s part of success.” – Arianna Huffington

Your Boss

What if your boss is risk-averse? We know that bosses hate one thing more than anything else: Surprises! Communicate early and often with your boss about the opportunity, risks, likelihood of success, mitigations, and learnings to be gained. Make sure you are realistic and transparent with your boss.

tweet-graphic-transTweet: On how to #failfast: Be transparent with your boss about
opportunities, risks, mitigations, learnings http://ctt.ec/Wjeba+


We’ve discussed the IT industry’s ancient history, your organization’s hidden failure/success stories, and your boss’s aversion to surprises. What about you? It is easy to point fingers, but in the end, it is you who must step up and be ready to fail.

You might be thinking, “I am an introvert. Introverts are risk-averse.” This may be true, but habits are formed from repeated behaviors. Behaviors can be practiced and new skills can be learned. Don’t let your self-identity as an introvert hold you back.

Or you might be a pessimist. Perfect! You probably see lots of opportunities for innovation and improvements in your organization. You are also more likely see the obstacles. You are uniquely positioned to turn this pessimism into action and find real solutions. Turn what you see as problems into possibilities and then act.

Do you have a fixed mindset? This is one in which you think, “I am either good at something, or I’m not.” Look around at those who are most successful in your organization. They likely have a growth mindset. They believe they can learn almost anything. And, as you have experienced already (consciously or not), learning comes from failure.

“A person who never made a mistake never tried anything new” – Albert Einstein

Do you feel a spotlight on you as a team leader? When you’re in a leadership position, you have the opportunity to model the kind of behaviors which help others take risks and enable new innovation. You can help your team and others outside your team understand what failing fast means to them, their careers, and the organization. Be out front, helping move the culture forward one step at a time.

“I can accept failure; everyone fails at something. But I can’t accept not trying.” – Michael Jordan

Finally, you may feel exposed if you fail. So don’t do it alone. Find others to work with who will provide new insights and different solutions. In the end, you will have a greater chance of success, benefit from collective learning, and you’ll each be less exposed to direct criticism.

tweet-graphic-transTweet: To #FailFast does not mean to put your business & your
job at risk. It means to innovate quickly | http://ctt.ec/ZcVFp+

Feeling Some Discomfort? Good!

My intention with this blog was for you to be self-reflective, which can be uncomfortable. I hope through self-reflection you are able to take a small leap, and identify where and how you can create new value in your organization. Find others who see what you see, enlist your boss in this effort, and take small actions (risks). If you fail, do it quickly and learn from your experiences.

“Success is not final, failure is not fatal: it is the courage to continue that counts.” ― Winston S. Churchill

Categories: IT Management

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Andy Nemtzow

Andy is a Lean Six Sigma black belt with over 30 years of IT leadership, consulting, and project management experience, including oversight of ERP, Portfolio Management, Enterprise Architecture, Vendor Management, Business Planning, QA, and BI functions.


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