Creating a culture of Initiative — the importance of failure

How you treat failure will determine how much initiative your team will demonstrate.

Joseph Gefroh
4 min readFeb 22, 2020



It’s a bias for action. It’s a mindset that always boils down to a “just do the thing” moment. It cuts through analysis paralysis, and ensures forward movement on ideas.

It’s so important that it is one of the Marine Corps key leadership traits. It’s Amazon’s 8th principle. It’s what many leaders want, but few get.

How do you create a culture of initiative on a team? In this post I’ll talk about the importance of accepting failure in creating a culture of Initiative.

Encourage failure.

Most leaders unintentionally nip initiative right in the bud, killing it before it even has a chance to exist. In their quest to create excellent teams, they cause teams to have less initiative through a very common behavior: punishing failures.

It’s counter-intuitive, but how a leader reacts to failure is a large determinant in whether their culture they create is one of initiative or not.

Reactions to failure that crush initiative may take on many forms.

  • A snide remark made in jest.
  • A public spotlighting of the person and the failure.
  • A pursuit of a scapegoat or culprit.
  • A black mark kept in a ledger of failures.

In any of these cases, the issue is simple: the behavior isn’t about fixing the problem or preventing it in the future — it’s about punishment.

What’s wrong with punishing failure?

For one, it focuses exclusively on whether a positive outcome was achieved or not. Counter-intuitively, that’s not the most important determinant in deciding what behaviors to punish or not.

Suppose I withdraw all of the money from the company’s corporate bank account and take it to Vegas. I drop the entire amount on a single turn of roulette, betting it all on red, and I win, instantly doubling my company’s cash. This is a fantastic outcome — should I rewarded?

No. Absolutely not! Any sane leader would not reward this behavior, despite the dramatically positive outcome. Why? Simple — it is because outcome is not the only thing that matters.

Likewise, if I have a product idea in a market the business wants to enter, take the initiative to do the research on a product idea, validate the concept in test markets, analyze competitors, and then execute on various minimum viable products, all achieving solid successes, and then finally build a full-scale offering that falls flat on its’ face due to an unexpected oversight or issue, should I be punished for the failure?

The sane leader’s answer is no — I did my due diligence, and executed with the resources and information I had available at the time in accordance with decision-making values aligned with the organization. Counter-intuitively, the organization should reward the depth of effort I went through and the initiative I took.

Initiative comes with Risk

Here’s the hard fact about initiative — it requires risk-taking. It requires the ability to identify an opportunity, marshal effort and divert resources away from a pre-determined path, and take on a chance of failure to achieve a payoff.

Some of these efforts are probably going to fail. You can’t have initiative without risk, and you can’t have risk without the chance of failure.

If you punish the failures, you create a culture where people would rather play it safe. They’ll only take action when information is fully known and a bet is a sure thing, waiting and delaying forever to make a “perfect” decision.

Once the decision is made, people will always choose to follow the plan, no matter whether the plan is effective or not. The plan could be doomed from the start, but as long as they follow it and it was approved, they’re not at risk of being punished. They’ll put on blinders to potentially significantly better opportunities, letting them pass by.

The result? Decreased speed, efficiency, and effectiveness. Your organization will miss out on opportunity after opportunity and rot from within.

You can’t have initiative without risk, and you can’t have risk without the chance of failure.

What should you do instead?

Turn failure into a productive moment by emphasizing it as a learning opportunity. Look into why the failure occurred, and what lessons can be learned from it to help everyone improve.

Don’t look for scapegoats or people to blame or point fingers. It only leads to defensiveness, and defensive people rarely learn the lessons you want them to learn.

An interesting thing we did at our organization to help promote a culture that was open about failure was to host a contest: “Share a Fail”. The contest was simple — share a failure and what you learned from it, read it to the rest of the team, and potentially win a $100 gift card.

Multiple people submitted their failures and the learning opportunities, and they shared it with the rest of the team. This provoked follow-on discussions amongst the team members on what practices they could adopt to either take advantage of the lesson learned, or avoid the situation in the future.

It lead to a lot of constructive conversation and provided the entire team a new tool to handle that situation, and reduced the stigma of failing.

Ultimately, if a failure occurs, it is the leader’s responsibility for having creating an environment that allowed it to occur. If a leader attempts to prevent failure through forceful compliance, it doesn’t prevent failures. Rather, it hides them and makes them harder to detect.

Instead, they are better off focusing on ensuring better judgement in the future by aligning people towards tradeoffs and factors the organization values and empowering people with the knowledge and resources they need to succeed.

This post is a part of a series of blog posts I’m writing on how to create and cultivate effective team cultures. Stay tuned for more!



Joseph Gefroh

VP of Product and Engineering @ HealthSherpa. Opinions my own. Moved to Substack.