Automation & DevOps

Stop Testing CLI Trivia in DevOps Interviews: A 2026 Manifesto

Emma Wilson

Emma Wilson

February 26, 2026

8 min read 2 views

Walking out of an interview over obscure tar flags? You're not alone. This deep dive explores why CLI trivia questions fail to identify real DevOps talent and what interviewers should focus on instead.

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Introduction: The Interview That Broke the Engineer

You know the feeling. You've architected systems that handle millions of requests, debugged production issues at 3 AM, and automated entire deployment pipelines—but in the interview, they're asking about the exact flag combination for tar to preserve symlinks while excluding .git directories. The original Reddit post that sparked this discussion resonated with hundreds of engineers because it hit a nerve. We're testing memory, not engineering. We're evaluating who can be the best dictionary rather than who can solve the hardest problems. And in 2026, with AI assistants and documentation just a keystroke away, this approach isn't just outdated—it's actively harmful to building effective engineering teams.

The Anatomy of a Bad Question: What Makes CLI Trivia So Useless?

Let's break down exactly why these questions fail. A good interview question should predict on-the-job performance. CLI trivia does the opposite. Think about it: when was the last time you needed to recall an obscure kubectl flag from memory? Probably never. You'd type kubectl --help, check the docs, or search your command history. The real skill isn't memorization—it's knowing what to look for and how to find it quickly.

I've interviewed dozens of candidates over the years, and the ones who ace trivia questions often struggle with actual system design. Meanwhile, the engineer who needs a moment to recall whether it's -xvzf or -xzvf might be the same person who can diagram a fault-tolerant multi-region architecture on a whiteboard. We're selecting for the wrong traits. The tools change constantly—what mattered in 2024 might be deprecated by 2026—but problem-solving ability remains constant.

What We're Actually Testing (And Why It Matters)

When interviewers ask about specific tar flags or obscure awk syntax, what are they really trying to assess? Usually, they're looking for "experience" or "depth of knowledge." But here's the thing: experience shows up in how you approach problems, not in your ability to recite man pages. Depth of knowledge reveals itself in understanding why you'd use a tool, not just the syntax.

Consider this alternative. Instead of "What flag compresses with bzip2?" try "We need to archive and compress 50GB of log files for long-term storage. Walk me through how you'd approach this, including tool selection and trade-offs." See the difference? The second question reveals so much more: understanding of compression algorithms, storage considerations, automation potential, and practical constraints. It's not about memorization—it's about reasoning.

The Documentation Paradox: Why Knowing How to Find Beats Knowing

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Here's a controversial take: in 2026, knowing how to efficiently use documentation is a more valuable skill than having commands memorized. The original poster mentioned checking the man page in five seconds—that's the real competency. Can you navigate complex documentation? Do you know where to find authoritative sources? Can you distinguish between Stack Overflow answers that work and those that create security vulnerabilities?

I once worked with an engineer who had incredible recall for command syntax. Impressive, right? Except they'd implement solutions without checking if there were better approaches or security updates. Meanwhile, another team member who constantly referenced documentation implemented more robust, maintainable solutions because they were always working with current best practices. The first engineer was a walking reference manual; the second was an actual engineer.

Real-World Skills vs. Interview Theater

Let's contrast interview trivia with what actually matters in production environments. That kubectl syntax question? In reality, you'd probably have it in a script or use a tool like Helm or Kustomize. The tar flags? They'd be in a Dockerfile or build script. The real skills are different entirely:

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  • Understanding when to automate something versus doing it manually
  • Knowing how to debug a failing pipeline when the error message is cryptic
  • Designing systems that fail gracefully rather than catastrophically
  • Communicating technical constraints to non-technical stakeholders
  • Prioritizing which fires to put out first when everything's burning

None of these appear in trivia questions. All of them matter every single day.

Better Questions: What to Ask Instead of CLI Trivia

So if we shouldn't ask about tar flags, what should we ask? Here are concrete alternatives that actually assess engineering ability:

Scenario-based questions: "Our application is experiencing intermittent timeouts. Describe how you'd investigate, starting with what you'd check first and why." This reveals troubleshooting methodology, prioritization, and systems knowledge.

Tool selection rationale: "When would you choose Ansible over Terraform, or vice versa? What factors influence that decision?" This tests understanding of tools' purposes and trade-offs rather than syntax.

Debugging exercises: Provide actual (sanitized) error output or configuration and ask how they'd approach fixing it. This mirrors real work far better than syntax recall.

Architecture discussions: "How would you design a CI/CD pipeline for an application that needs to deploy to three different cloud providers?" This assesses system thinking and practical experience.

The pattern here is assessing judgment and reasoning, not recall. These questions don't have single right answers—they have better and worse approaches, which is exactly what engineering is about.

The Interviewer's Dilemma: Breaking the Cycle

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Many interviewers use trivia questions because that's what they were asked. It's a self-perpetuating cycle. But breaking it requires conscious effort. Start by asking yourself: "What does success look like in this role?" Then design questions that map to those success criteria. If the role involves writing lots of shell scripts, maybe ask candidates to review a script with intentional bugs rather than recite syntax. If it involves Kubernetes, present a problematic YAML file and ask what's wrong.

Here's a pro tip: include a "documentation allowed" portion in your technical assessment. Give candidates access to the internet or man pages during a practical exercise. You'll be amazed at what you learn. Some will flounder even with documentation—that's telling. Others will efficiently find what they need and implement elegant solutions—that's what you want. This approach mirrors real work where nobody expects you to code without references.

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FAQs: Addressing Common Concerns and Pushback

"But don't we need basic CLI proficiency?" Absolutely. But there's a difference between proficiency and trivia. Proficiency means understanding what commands do and when to use them. Trivia means memorizing obscure flags. Test the former, not the latter.

"Won't candidates just Google everything?" Yes—and they should! The goal isn't to prevent resource use; it's to ensure they can use resources effectively. Knowing what to search for is a skill. Evaluating whether search results are appropriate is a skill. Implementing the solution well is a skill. Memorization isn't.

"How do we filter candidates quickly then?" This is the lazy interviewer's excuse. Good filtering takes work. Consider take-home assignments (paid, and reasonable), portfolio reviews of GitHub contributions, or focused technical discussions about past projects. These take more effort but yield better hires.

"What about junior vs. senior roles?" The difference should be depth of understanding, not breadth of memorization. A senior engineer should understand why certain tools work certain ways, not just how to use them. A junior might need more guidance on tool selection but should show good learning methodology.

The Future: AI Assistants and the Memory Obsolescence

Here's where it gets interesting. By 2026, AI coding assistants are ubiquitous. They'll suggest correct command syntax, flag combinations, and even entire scripts. What value does memorization have then? The engineers who thrive will be those who can evaluate AI suggestions, understand trade-offs, and apply judgment—not those who can out-memorize the machine.

We're already seeing this shift. Tools that auto-suggest commands based on natural language descriptions exist today. In this environment, interviewing for memorization is like testing carriage drivers on whip-cracking technique after automobiles have been invented. It's not just irrelevant—it signals that your organization is stuck in the past.

Conclusion: Be the Change in Your Next Interview

The original Reddit poster walked out of an interview. Maybe you've wanted to. The good news? You can be the change. Whether you're interviewing or being interviewed, shift the conversation. Ask why instead of what. Discuss trade-offs instead of syntax. Focus on problem-solving rather than recall.

In 2026, the best DevOps engineers aren't walking man pages. They're system thinkers, troubleshooters, and architects. They know how to find information efficiently and apply it judiciously. Let's interview for that. Let's hire for that. And let's finally stop with the CLI trivia that tells us nothing about who can actually do the job.

Next time you're in an interview—on either side of the table—remember: we're building systems, not memorizing dictionaries. Act accordingly.

Emma Wilson

Emma Wilson

Digital privacy advocate and reviewer of security tools.