How to fight your team's fear of failure

IT people were taught to avoid failure at all costs – until they were encouraged to fail fast and iterate. Here's how to help people make the mental leap
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Ask any job hunter to describe a time they took a risk or persevered through adversity to achieve great results, and they’re likely to have an example (or two) at the ready. Ask them to share a time they failed, and chances are they will clam up or change the subject. That’s because failure still carries a negative stigma along with it, says Sanjay Malhotra, CTO of Clearbridge Mobile.

“There is a stigma that surrounds failure that drives professionals to disassociate themselves from thinking outside of the box, instead playing it safe, not allowing for new and truly innovative ideas to be heard,” says Malhotra. 

That's a problem at a time when agile and DevOps ways of working encourage teams to iterate their way to success. Some failures will come with the iterating. 

There's also a reason many innovative companies – whether they're following agile methodologies or not – have a “fail fast” mantra baked into their culture. Failure is often a necessary step on the path to greatness. And if leaders want their people to embrace this mantra, they have to do more than talk the talk, says Colin D. Ellis, author of “The Conscious Project Leader.”

“The workplace has to 'feel' safe in order for failure to be acceptable,” says Ellis. “If a person feels that they will be admonished or blamed when something goes wrong, then failing fast will simply be something that senior managers talk about but never achieve.”

[ How strong are your soft skills? Read also: Emotional intelligence test: 5 self-evaluation tools for leaders. ]

We asked leaders to share their tips for making failure OK for everyone on their team. Read on for eight practical tips: 

1. Be the example, leaders

Robert Reeves, CTO, Datical: “Walk the walk, IT leader. You need to highlight your own failures, discuss with your team why you made the wrong call, what you learned from it, and how you are going to improve in the future. Until you create a safe place for failure, you will continue to see risk- averse behavior. Failure is embarrassing. But leaders need to model behavior for the team. When leaders make mistakes, they need to own up to them, share lessons learned, and ways to guarantee it doesn’t happen again. That’s what healthy, responsible adults do.”

2. Try failing small

"Define the success criteria for the next few months as opposed to years ahead."

Daniel Viveiros, CTO, CI&T: "First and foremost, failing fast must also be failing small. There’s much to be learned from failures, but in this case, big failures can have severe consequences, so failing small is important when failing fast. That's why this mantra is often seen in the context of a lean mindset. Prioritize small chunks of work and short cycles over moonshot projects and a big bang approach. Define the success criteria for the next few months as opposed to years ahead.  As scarcity is the most powerful mechanism for prioritization and focus, use metered funding instead of the traditional yearly budget. With this mindset, failure will be inexpensive and become more of an opportunity to learn."

3. Kill off your own pet projects

Colin D. Ellis, author, “The Conscious Project Leader: “Senior managers have to set the tone for failure by killing pet projects that produce little or no value. There is still a myth that surrounds sunk costs in projects, but a bad investment won't suddenly become a good one just by spending more money and time on it. Being clear on priorities and sticking to them is critical if failure is to become OK as it allows staff to be able to reject lower priority or lower value work. The 'who shouts loudest' approach is then redundant and the process for accepting new work becomes more disciplined.”

4. Consider a failure award

"Leaving opportunities unexplored is just as high risk as trying something bold."

Murli Thirumale, CEO, Portworx: “I see ‘nothing tried, nothing gained’ as a failure. Leaving opportunities unexplored is just as high risk as trying something bold. This encourages my teams to try risky or unusual items and worry less about failure. Something else we’ve done in the past that worked quite well to encourage and build this culture initially is to give a quarterly ‘Out of the Box’ award. We awarded this for a high-risk, creative effort, regardless of success in the traditional sense or not. It helped people see the value of failure.”

5. Look in the rearview mirror

Gonçalo Gaiolas, vice president of digital, OutSystems: “Every failure can be viewed as an opportunity. We often forget that failure can lead to even better outcomes. Look back on a failed initiative, find small things that worked, and identify options that would have been much better. After connecting the dots backward, you will likely be celebrating more successes. This approach has led our digital team at OutSystems to do ‘pre-mortems’. Before we start a big project, we create a newspaper cover that outlines how we will fail. This allows us to understand failure as a possible outcome and to explore it ahead of time.”

6. Focus on iteration more than "failing fast"

Sanjay Jupudi, CEO, Qentelli: “The fail-fast, fail-often credo has been around for decades. It is not something that started with IT pros, however, we have come to adopt and integrate it into our core methodology. The real aim is not to fail, but to successfully iterate. Continuous iteration should be rewarded more than just failure – the more we fail, the more we are able to learn, pivot, tweak, restart, and redo. The true success of an IT pro lies in how we learn from and use it to better then next iteration. We reward employees when they learn from mistakes and have the next iteration ready quickly, with lessons from the first iteration. This is a successful way to support a true fail-fast culture.”

7. Normalize failure

Ajeet Singh, co-founder and executive chairman, ThoughtSpot: “My goal is to normalize failure to get employees to see past the negativity and focus on the opportunity. At ThoughtSpot, we measure both successes and failures. The data on what doesn’t work is oftentimes more valuable than the data on what does, especially when it comes to growing and scaling a startup. Through this process, our employees have become desensitized to the stigma of failure and instead now see it as an opportunity for growth.”

8. Encourage people to leave the failure behind

Sanjay Malhotra, CTO, Clearbridge Mobile: “In my view, failure should not be categorized as something bad or something to shy away from. Failure shows determination and a willingness to take risks. By failing we are not only receiving feedback on our ideas and assumptions, we are also learning how to improve and grow."

"One strategy that I’ve picked up throughout my career that I use to help employees deal with failure is to simply think forward. The failure is in the past, nothing can be done to change the outcome. However, something can be done to achieve more favorable outcomes in the future. I challenge employees to leave the failure behind, and move forward by focusing their energy on identifying what learnings from this failure can help their next challenge achieve success.”

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Carla Rudder is a community manager and program manager for The Enterprisers Project. She enjoys bringing new authors into the community and helping them craft articles that showcase their voice and deliver novel, actionable insights for readers.