What can go wrong with DevOps? Plenty, but you can still learn from your mistakes and the mistakes of other people.

Guest Commentary, Guest Commentary

September 6, 2018

5 Min Read
Image: Pixabay

In the DevOps culture, failure isn’t exactly encouraged. Organizations want to succeed. They want every build, project and long-term initiative to achieve its individual goal. Still, DevOps failures are embraced as reality. If you’re going to fail, the thinking goes, make sure you fail fast, learn from it and leverage the newly gained insights in improving the process and product.

With this philosophy as a backdrop, we looked at a few common DevOps failures cited by CloudBees personnel and tried to draw some lessons from each one.

DevOoops #1: Unforeseen lock-outs

Name: Carlos Sanchez

Title: Principal Software Engineer
When you’re automating deployments using configuration as code, make sure you have the right protections in place (i.e., validation of configuration). Otherwise, it’s easy to lock yourself out, forcing yourself to manually log in to each machine to fix it when a bad change is pushed and deployed to all the machines.

Takeaway: As you bake quality into the processes and shift automation left, you need to make sure you validate all changes early and often.

This situation highlights how organizations need to implement proper processes, not only for application code changes but for infrastructure as code changes that manage environments. In automating in pursuit of DevOps it’s necessary to have a strategy for credentials and secrets management of permissions for your DevOps and production systems.

DevOoops #2: Deploying out-of-step

Name: Laura Frank Tacho
Title: Director of Engineering
Running in parallel during CI/CD can speed up your automated testing and shorten your feedback cycles. Just make sure deployment is not executing as a parallel step. That misconfiguration will cause your code to deploy at the same time the tests are running, regardless of their exit codes, pretty much defeating the purpose of automated testing before a deploy.

Takeaway: This story highlights how crucial it is to ensure that pass through certain gates and checks before being deployed out to the customer. You need to construct your CD pipelines so your parallel testing is managed as a gate to production, ensuring that properly tested and validated changes are not automatically deployed.

Another thing: While DevOps maintains that you should be able to comfortably deploy at any time, deployment needs to be treated as a managed and deliberate event. Deployment happens at the end of all the processes within a pipeline, and all required tests, validations, checks and approvals have been done before any change is deployed to the customer.

DevOoops #3: SCM conflicts

Name: Will Refvem
Title: Solution Architect
One of the biggest challenges in DevOps is SCM. Early in my career, being given access to Git repositories was a bit like handing a belt-fed machine gun to a drunken toddler. My biggest DevOops moment came when I was trying to master the basics of Git in a project that used Git submodules (don’t -- just don’t) and had a series of bash scripts that implemented a primitive CI/CD workflow by running in the environments we were deploying to (seriously). I can’t tell you how many merge conflicts and detached HEADs I encountered, or how I got out of them. Fortunately, we were using the fork-PR model, so I did no real damage.

Takeaway:  A proper branching and merging model is required to ensure that you are feeding the appropriate inputs into your DevOps pipeline to let you continuously integrate, test and ultimately deploy changes.

DevOoops #4: Poorly defined KPIs

Name: Juni Mukherjee
Title: Product Marketer
How we define KPIs can change the game. For example, one quality engineering team defined the number of tests executed per sprint as a success metric. Humans are driven by incentives and the natural tendency of the team was to add more and more tests, without even considering archival of outdated ones. Think of this; we could have a larger impact with fewer tests and, more importantly, fewer tests lower the test cycle time. So, instead of sheer quantity, we should focus on the coverage and effectiveness of tests.
 Similarly, a release engineering team defined the number of releases per sprint as a success metric. Number of releases reflect on velocity for sure, however, releases move bits from point A to point B without assessing the value added to business. So, it is critical to tie a business KPI (like, number of new customers acquired, percentage of revenue increase, etc.) to velocity, such that we know we are investing in valuable speed and not suicidal speed.

Take away: This is a critical, and often underemphasized, lesson in DevOps. You’re not implementing DevOps just to say you’re doing it. You need to develop goals and objectives for your initiative and align to them. Once we define these goals, we need to align KPIs and success metrics to those objectives. Properly defining these success metrics and KPIs will dictate what gets prioritized in when building pipelines

DevOoops #5: Failure to address organizational blockers

Name: Viktor Farcic
Title: Consultant
A real obstacle is cultural and caused by having siloed departments. When we start looking at a system as a whole, and detecting areas of improvements, the answer tends to be “this is not our department, we don’t know them, they won’t speak with us”. Those siloes are the main argument in favor of DevOps; it tries to remove them. But, in reality, most companies fake it by creating yet another silo that is, this time, called the DevOps department. DevOps in practice directly contradicts DevOps ideas.
Takeaways: Organize your teams around subjects like product and functionality and include all the stakeholders in the software development process in these product or feature teams. This better aligns stakeholders and prevents the “us vs. them” tribal mentality that often plagues traditional software development.

Culture in DevOps is just as important as process, practices, tools and technology, yet it’s one of the most difficult things to change.


Like any sophisticated process, DevOps is going to experience its share of failures. There will be missed hand-offs and miscommunications along the way. Organizations also will make mistakes in the way they implement their overall DevOps initiatives.

These “DevOoops” stories highlight how DevOps transformations are hard to pull off. There will be issues, but they’re solvable. You need to approach your transformation as an iterative process of learning and improvement. If you fail occasionally, keep going. You’ll succeed in the long run.

About the Author(s)

Guest Commentary

Guest Commentary

The InformationWeek community brings together IT practitioners and industry experts with IT advice, education, and opinions. We strive to highlight technology executives and subject matter experts and use their knowledge and experiences to help our audience of IT professionals in a meaningful way. We publish Guest Commentaries from IT practitioners, industry analysts, technology evangelists, and researchers in the field. We are focusing on four main topics: cloud computing; DevOps; data and analytics; and IT leadership and career development. We aim to offer objective, practical advice to our audience on those topics from people who have deep experience in these topics and know the ropes. Guest Commentaries must be vendor neutral. We don't publish articles that promote the writer's company or product.

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