Cultural Transformation: Fail Fast, Learn, and Move On

Oct 17, 2018 7:10:32 AM By Sylvia Fronczak

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We’re several hours into 2018’s All Day DevOps, and things are moving right along. Next, we’ll cover Glynn Wilson’s discussion of cultural transformation and how the “fail fast, learn, and move on” mantra applies.

First, Wilson wants to pause to consider what “fast fail” means. It’s a concept that doesn’t come naturally. Failure is a mistake. And we’ve all worked in command-and-control organizations where we’re punished for those mistakes.

All this turns us into risk-averse people that avoid failure. And outcomes include denial and blame.

So how do we counter that behavior? Well, we should take a reflective stance, pause, and isolate what went wrong. From this, we cultivate the self-awareness to move forward. And another question: what are good outcomes? The important thing is a desire to learn. We want to be retrospective-minded and keep what works well. This will encourage us and keep us going forward.

Speaking of keeping going, Wilson mentions that failure rarely requires a complete restart. Like other processes, it’s iterative.

More important than failing fast, we want to foster a culture of innovation and experimentation.

We want to create that fearless culture. Ultimately, the people on the ground need to be on board. Teams need a sense of purpose and a goal. Without a purpose, teams fail.

Wilson reflects on some real-life examples from his experience. First, he remembers when an agile adoption missed the mark and created an “us and them” culture. He also remembered a DevOps adoption in which he got a key thing right; he created product teams driving towards the right outcome. Unfortunately, this resulted in a large silo. Because of that, his second initiative also failed.

In a final example—another DevOps adoption—the process was more fun. He brought the board along for a ride through agile learnings like the Phoenix Project book and transformational exercises. Through that, the board was introduced to the concept that DevOps wasn’t an IT problem but an organizational problem. He broke down silos across the business to get IT teams working together.

This last adoption has been going for about a year. The transformation is making positive change. And other teams not going through the transformation are taking notice.

Wilson emphasizes that it's more than just “fast fail” or “fail well” or “fail safe” and other sayings. It’s really about innovation and experimentation. And, it’s about empowering your people with the learning mindset.


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Missed Glynn Wilson’s session, or want to see some other great presentations from October 17? Head over to https://www.alldaydevops.com/live and make sure you’re registered. Then, catch up on what you missed (or re-watch your favorites)!

About the author, Sylvia Fronczak

Sylvia Fronczak is a software developer that has worked in various industries with various software methodologies. She’s currently focused on design practices that the whole team can own, understand, and evolve over time. You can find her at sylviafronczak.com.