4 Must-Dos for Leading a Safe and Successful DevOps Transformation

Sep 23, 2020

When a company invests in DevOps, it’s investing in speed: speed to market, speed to new ideas, speed to respond, and speed to recover. DevOps is a lot like roller coasters, sports cars, or anything else that goes zoom — if you don’t first build in safety, nobody will be comfortable going fast. The consequences of disregarding this could be disastrous, and it is up to leadership to provide that support and vision to ensure a successful transformation.

This safety concept will apply throughout the transformation, but it has to begin with giving the team the psychological safety to experiment. DevOps can be phenomenally scary for all sorts of people. Some of the most common, fear-based questions I’ve answered when coaching DevOps include:

  • Will I automate myself out of a job?
  • What if my automation fails and causes an incident?
  • What if I fall behind in my other work while I’m experimenting with this difficult new thing?
  • How can I implement DevOps when I need so many other people to help?
  • How will these measurements be interpreted?
  • Will there be an impact to our performance review?

If leadership doesn’t ruthlessly eliminate the underlying fears, then the DevOps transformation is doomed to tepid success at best, but more likely it will fizzle out like wet campfire wood—a few pops and some smoke, but nothing worth being excited about.

The best thing a leader can do is to give the team their full-throated support for investing time and energy into the DevOps Transformation. What does this look like? It means:

  • Dedicating sprint capacity for your development teams to get educated and focus on opportunities to improve their daily work.
  • Drawing attention to the initiative vocally, via public town halls or other large scale events,
  • Collaborating with peers to engage their support (as we’ll see below, a DevOps initiative can only go so far before it touches multiple departments).
  • Clearly and unambiguously stating and showing that the only result of any failed experiment will be learning, and that success will be rewarded with new opportunities and not job elimination.

Once a leader has created psychological safety for the team, it comes time for the hard part. A great DevOps transformation LOOKS like an automation effort, but it’s really a cultural transformation around what the technology organization prioritizes and values. Automation is the symptom, but the root cause is a culture of safety, measurement, continuous improvement, and intellectual curiosity. As leaders, it’s our job to let the team focus on the automation while we establish and nurture the culture.

I can hear you now asking, what, specifically, is a leader responsible for when leading such a transformation? Like any other Agile product creation, we should start by providing the team with a clear, manageable objective that they can independently complete and demonstrate. In many organizations, this is the creation of a small-scale automated test suite. In others, it’s a metrics dashboard that can guide future sprints’ work by giving insight into what’s working good enough and what needs to be fixed right away. The state of the organization, where the burning platform is, and what resources are immediately at your disposal will guide where you start, but I suggest the following based on my experiences:

Leading a transformation
  1. Let the team pick what to build (automation-wise) first. They will frequently already know, as a result of their daily frustrations, which is the most important first target. If they don’t know or are unsure, suggest building the metrics platform first to gather measurements. This will encourage intellectual curiosity in the culture, too. Measure, then make a change based on the observed data, and then measure the results again to plan the next change.
  2. Emphasize that learning is more important than success. If the team learns something from every action, then success will follow. This can be done with things like failure parties, where the team comes together to share what they learned and celebrate their failed experiments.
  3. Incrementally invest in the right training, infrastructure, and tools for success. Remember, the most successful teams have the safety to experiment. Such safety includes test laboratories and robust live systems that are failure tolerant. If the organization doesn’t already have these, ask the team how building them can be achieved, so that the remaining efforts can be done with a higher degree of freedom (and, therefore speed).
  4. Monitor the team roadmap for when the time is right to expand the effort. Market the learning and successes widely so that when the time comes to involve other departments (such as IT Operations, Service Delivery, Info Sec, or Development groups). They are excited, willing participants to support the continued efforts.

There you have it, the four key items to consider when leading a safe and successful DevOps transformation.  This article is just a starting point; a place from which to inspire and begin the DevOps transformation journey.

In summary, start by creating psychological safety for the team, expand into self-directed improvement of daily work supported by canny investments, and continue into a broader organizational movement, inflamed by localized wins. The ultimate goal of a DevOps transformation is to implement the fast, consistent flow of value to our customers. It starts by creating a safe, learning-oriented environment within our own organization, long before the customers ever see a change. Building such an environment is a technology leader’s most challenging modern task, but the market has proven that such a journey is not optional, and, thankfully, bears rewards equal to the difficulty.

This post is slightly altered from it’s orginal version with permission from Goldmind Consulting

Want to speed things up when bringing a culture of safety and experimentation to your organization? Not only are our coaches DevOps experts, but they also know how to coach culture change.

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