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Why You Have to Let People Fail Now So They Can Succeed Later Letting people fail helps them think critically and make their own decisions.

By Darian Shimy Edited by Micah Zimmerman

Key Takeaways

  • As a leader, your job isn't to do everything yourself.
  • It's about balancing the risks of a given situation with the opportunities it presents and then providing an appropriate level of guidance.

Opinions expressed by Entrepreneur contributors are their own.

My daughter once asked me if she could drive her friend home from school. The catch? She was a brand new driver, and we lived in California — where this wasn't allowed.

I quickly realized how fraught the situation was. If I had given her permission, I would have taken responsibility for any problems that occurred as a result of her actions. But if I had simply laid down the law and told her no, she wouldn't have learned to think critically about her own actions.

Instead of giving my daughter a direct answer, I told her she needed to consider the potential consequences and make the decision herself. I also explained that this would make her entirely responsible for the outcome, and whatever she decided, I would support her decision.

Although I'll never share the decision she made on that day, she walked away with higher self-awareness and a better ability to assess risks. The key lesson here applies in business as well: people become more successful when you encourage them to own the outcome of their decisions.

Related: 6 Ways to Encourage Autonomy With Your Employees

Why you should remove the safety net of approval

As a leader, it can feel safer for everyone when you make the big decisions yourself. But when you give easy answers to employee questions like "Is this okay?" you also take something away from them: their agency.

Imagine that you have an employee working on a press release. Once it goes out, there's no way to get it back. They might ask you whether you want to review it beforehand. But if you answer either way, the decision isn't theirs anymore — you'll bear some responsibility for any delays caused by the review process or any issues that don't get flagged.

Absolving someone of responsibility for their actions isn't doing them a favor. At best, it teaches them that failure has no consequences — and at worst, it can teach them that nothing they do has any significance at all.

Employees also tend to seek this kind of approval as a kind of safety net, even if they don't realize they're doing it. But your business will grow far faster and with far more stability if you trust them to own the results of their choices instead.

Related: The Biggest Obstacle Facing Leaders Is Distrust. Here's How to Build Confidence in Your Team.

The costs of failure versus the costs of enfeeblement

Of course, letting your employees make their own decisions and own the outcome means that failure becomes a real risk. But in many cases, the costs that come from depriving your team of agency are much greater.

The truth of this was made evident to me years ago when I was scheduled to take a vacation from my job. We had a decision to make about one of our products while I was away, so my boss suggested I give instructions to my engineering manager on what to do. I declined and opted to let them make the decision themselves.

I explained to my boss the logic was simple: if they did it the right way, we would learn that they were more capable than we previously thought and could make better use of their talents. If they made the wrong decision, I would have a coaching opportunity when I got back to help them understand what they should have done and how.

But if I simply told them what to do, the person in question would only learn to come to me whenever decisions needed to be made. This would slow down our decision-making, stagnate our growth, and likely eat into future revenue.

Related: Be a Coach, Not a Referee — How to be a Good Mentor and Manager from a Coaching Perspective

Balancing risk with responsibility as a leader

Critically, this was a project that would only cost us a few days of lost work if the wrong decision was made and we had to undo it. If it was a larger undertaking with more at stake, leading from the top might have been more appropriate.

But as a leader, your job isn't to do everything yourself. It's to balance the risks of a given situation with the opportunities it presents and then provide an appropriate level of guidance.

In most cases, the rule of thumb is simple: the more you have to lose in a situation, the more hands-on you should probably be. By saving learning opportunities for situations that likely won't cause catastrophic damage even if they do happen to go off the rails, you provide your team with a way to grow that doesn't require you to take existential risks with the business.

Still, letting people fail is a necessary part of helping them flourish. It helps them build confidence, make better decisions, and increase the scope of their responsibilities over time. Eventually, it also prepares them to take on leadership roles in the future. Whether you're a parent or a mentor in a professional setting, that's the kind of role modeling that prepares people for success.

Darian Shimy

Entrepreneur Leadership Network® Contributor

Founder and CEO of FutureFund

Darian Shimy is the founder and CEO of FutureFund Technology, a fundraising and selling platform for K-12 school groups. He has 25+ years in web-based technologies and managing engineering teams.

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