Helping Millennials ‘Fail Forward’

They’re the self-esteem generation. The generation whose helicopter parents stood ready to swoop in to kiss every skinned knee and confront every perceived unfairness. So, is it any wonder that Millennials tend to not handle failure with aplomb?

Generationally speaking, Millennials engage in far less risky behavior—both good and bad risks—than previous generations. According to a Babson College survey, 41 percent of 25-34-year-olds cited “fear of failure” as their biggest obstacle to starting a business, up from 24 percent in 2001. How do you get your risk-averse team members to step out of their comfort zones?


First, understand that Millennials are keenly aware of risks and will generally try to mitigate risk by doing research. This isn’t always a bad thing.


Second, you can help your Millennial team members overcome their fear of failure by implementing the following practices recommended by Ryan Jenks in his book, The Millennial Manual: The Complete How-To Guide to Manage, Develop, and Engage Millennials at Work:


Display Empathy & Belief

Listen to what your team members say, express that you understand their disappointment, then let your Millennial employees know why you hired them, highlighting their strengths and skills.


Encourage Ownership & Emphasize the Journey

Don’t tolerate Millennials pointing fingers and taking a victim mentality. Help them understand learning and growth opportunities that exist in owning their failures. Help them to view failure as a tollbooth instead of a roadblock.


Facilitate and Contextualize Failure

Create environments where failing is easy and encouraged, without fear of consequence, by putting failure into perspective as a momentary event, not a symptom of a lifelong epidemic.


Challenge Them & Stress Their Strengths

When you challenge Millennials with tough assignments, you communicate that failure is all right, but you believe in their ability to rise to the challenge. Help Millennials avoid spending too much time overcompensating for their weaknesses, instead of working in areas where they’re strong.


Don’t Intervene. Coach.

Resist the urge to intervene to assist a struggling Millennial. Intervening robs the Millennial of opportunities to learn problem-solving, develop resilience, and cultivate confidence to take on new challenges. Then coach by affirming the effort made and unpacking the failure.


Help them understand that the past can’t be altered, but lessons can be learned to make the future better.


Failing forward is in invaluable skill for any individual in any industry, but it’s an underdeveloped skill in many younger workers. By engaging in some conscious behaviors, you can help your Millennial employees learn from their mistakes, instead of fearing them.

Please note: I reserve the right to delete comments that are offensive or off-topic.

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