Learning how to apply ‘fail fast’ thinking to your business

by | Oct 12, 2017

“Fail fast, fail often and learn from your mistakes.” This mantra has long been touted by entrepreneurs and leaders of start-ups. But while many executives agree in principle with this philosophy, they struggle to incorporate the concept into their everyday business practices.

An early and apt metaphor

Throughout college I volunteered for an ambulance service that provided emergency care in Burlington, Vermont. With the goal of providing the best medical care under unpredictable and often chaotic circumstances, the new members of this organization had a tremendous amount to learn in a short period of time. Aside from required classes and state certifications, there was constant training with our team.

This training prepared us to respond to the mix of casual or life-threatening scenarios we faced daily. With lives on the line, we needed to quickly learn from our successes and mistakes. How could we iteratively improve both as individuals and as a team?

After each emergency call, the team promptly debriefed on what had just transpired while it was still fresh in our minds. This was a required, nearly sacred discussion and it allowed us to consider the numerous aspects of the call, all of which provided opportunities to learn.

The ongoing process of debriefing after calls resulted in regular procedural changes, new training scenarios, improved teamwork and refined individual skills. It continually made us better EMTs.

Sprint Retrospective

While typical business projects don’t involve actual crisis management, there are similarities to the emergency services model. The Agile software development process includes a comparable, but often-undervalued step: the Sprint Retrospective.

The retrospective is facilitated by a ScrumMaster and allows the project team members to express their opinions and concerns in constructive ways. This formal process occurs at the end of each sprint cycle and includes three main discussion points:

  • What went well?
  • What went wrong?
  • What can we do differently to improve?

Like the ambulance crew debriefing, this objective and non-judgmental review formalizes the opportunity for both the team and the individuals to learn from their successes and failures, and to incorporate these learnings onto future sprint cycles. With Agile, both the product and team develop iteratively.

Apply Everyday

Executives can embrace the fail-fast and fail-often philosophy in an even more practical way than through the Sprint Retrospective process.

Consider these two scenarios:

First: A customer support department could incorporate a debriefing into their routine by reviewing the onboarding process for each new client.

Facilitated by an account manager, the department could review the post-sale experience for the customer from contract signing through product delivery. Were deadlines or SLAs achieved? Were expectations met? How well did the organization coordinate across the business units? Were people, processes or systems available as needed? What could the company—both the individuals and teams involved—do differently for the next new client?

Second: The head of an events company could hold a debrief session after the close of each event.

Facilitated by a business lead, the management team could review the event from inception through completion. How well was the event planned? Were sales and attendance goals achieved? Was the event content well produced and well received? Were people, process or systems available as needed? What could the event team members do differently for the next event on the schedule, or for the same event next year?

Without a ScrumMaster or detailed methodology, an executive can institute a practice of required debriefing with their staff after every milestone. Be it the end of a quarter, the monthly close, or a weekly review of sales figures, opportunities abound for a leadership team to pause, review and learn. What matters is that you embrace the culture of learning from your mistakes and systematically apply it every day in order to become a better organization.

What would a retrospective look like in your organization? How can you fail fast, fail often and truly learn from your mistakes?

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David Saabye


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