Hiring a technical writer isn’t just about finding someone who can write well. You need someone who can navigate technical complexity, collaborate with engineers, and bring clarity to the chaos of development processes. It’s about finding a curious, resourceful problem-solver who thrives in ambiguity.
Over my career, I’ve conducted more than 70 interviews for technical writing roles. My very first interview? It happened during my second week as a tech writer. I barely knew what I was doing, let alone how to evaluate someone else. But stepping in as a last-minute replacement turned into an invaluable learning experience that shaped how I approach interviews today.
What makes a great tech writer?
When interviewing a technical writer, focus on four key areas:
- Tech savviness: Can they learn and explain technical concepts effectively?
- Collaboration and empathy: Do they communicate well with engineers and adapt to different personalities? Do they recognize their audience and understand their needs?
- Research skills: Can they gather information and create structure from ambiguity?
- Self-direction: Are they proactive and able to prioritize tasks without constant guidance?
The following questions are tailored to uncover these traits across various levels of experience.
/Of course, these questions should be done after going over introductions and some questions to help build rapport.
Tech savviness: Do they embrace complexity?
A good tech writer doesn’t need to write code, but they should feel comfortable diving into technical topics and asking the right questions to learn.
Junior-level questions
- “What’s a technical concept you’ve learned recently? How did you approach learning it?”
- Reasoning: This reveals their curiosity, resourcefulness, and how they break down unfamiliar topics.
- “If I showed you a Python function, how would you figure out what it does?”
- Reasoning: This tests their ability to approach code with curiosity and identify questions to fill knowledge gaps.
Mid-level questions
- “Tell me about a complex system you documented. How did you get up to speed?”
- Reasoning: This helps assess their ability to handle large, technical subjects and their process for learning.
- “How would you explain a basic API to a non-technical audience?”
- Reasoning: This evaluates their ability to simplify complex information for different audiences.
Senior-level questions
- “How do you approach documenting a system with incomplete or outdated documentation?”
- Reasoning: This shows their problem-solving skills and ability to navigate messy or ambiguous situations.
- “What’s your process for keeping up with fast-evolving technologies in your documentation?”
- Reasoning: This reveals their adaptability and ability to future-proof their work.
Collaboration and empathy: Can they work with engineers? Do they understand and take their audience in consideration?
Tech writers often depend on busy engineers for information. Strong collaboration skills are essential for extracting knowledge without wasting anyone’s time.
Junior-level questions
- “How would you ask an engineer to explain something you don’t understand?”
- Reasoning: This evaluates their ability to communicate clearly and respectfully with technical experts.
- “What would you do if two engineers gave you conflicting information about the same feature?”
- Reasoning: This explores how they handle conflicting inputs and resolve ambiguity.
Mid-level questions
- “What’s your strategy for working with an engineer who’s too busy to help?”
- Reasoning: This uncovers their resourcefulness and ability to find alternative ways to gather information.
- “Tell me about a time you built trust with a skeptical engineer. How did you do it?”
- Reasoning: This tests their interpersonal skills and ability to overcome resistance to documentation.
Senior-level questions
- “How do you handle team dynamics when documentation isn’t prioritized?”
- Reasoning: This evaluates their ability to advocate for documentation in a challenging environment.
- “Have you led cross-functional collaboration for a large documentation project? How did you manage it?”
- Reasoning: This assesses leadership skills and their ability to coordinate across multiple teams.
Research skills: Can they ask the right questions?
Tech writers must extract useful information from subject matter experts (SMEs) and synthesize it into cohesive documentation. I’ve written a bit about interviewing SMEs.
Junior-level questions
- “Imagine I’m describing an internal tool. What questions would you ask to create a user guide?”
- Reasoning: This tests their ability to structure their questions and identify relevant details.
- “How do you research a topic you know nothing about?”
- Reasoning: This shows how they approach uncertainty and gather information independently.
Mid-level questions
- “Tell me about a time you pieced together documentation with little guidance. How did you do it?”
- Reasoning: This evaluates their initiative and ability to make sense of incomplete information.
- “What’s your approach to prioritizing details when writing under tight deadlines?”
- Reasoning: This reveals how they manage time and focus on what matters most.
Senior-level questions
- “How do you approach documenting a highly complex system that spans multiple teams?”
- Reasoning: This tests their ability to manage large-scale projects and synthesize cross-team inputs.
- “Have you ever conducted usability testing on documentation? How did the results influence your work?”
- Reasoning: This shows their commitment to creating effective, user-centered content.
Self-direction: Can they handle ambiguity?
In many teams, tech writers must prioritize tasks and drive projects without explicit instructions.
Junior-level questions
- “What would you do if no one assigned you tasks, but there were many potential documentation needs?”
- Reasoning: This evaluates their ability to identify and prioritize work independently.
- “How do you stay productive when you’re unsure about the next steps?”
- Reasoning: This explores their problem-solving skills in ambiguous situations.
Mid-level questions
- “How do you balance multiple documentation requests from different stakeholders?”
- Reasoning: This tests their ability to prioritize and manage competing demands.
- “What’s an example of a gap you identified in documentation? How did you address it?”
- Reasoning: This shows their initiative and focus on adding value.
Senior-level questions
- “When managing a large documentation project, how do you decide what to tackle first?”
- Reasoning: This evaluates their strategic thinking and ability to manage complexity.
- “Have you ever created a documentation strategy from scratch? What steps did you take?”
- Reasoning: This reveals their leadership and ability to build frameworks for long-term success.
Other questions
Depending on your organization, the experience of the writer, or your current teams, there are other questions that may be interesting to ask and that have given me great results:
- “How would you explain the internet underlying tech/REST APIs/databases to a 7 year old?”
- Reasoning: This evaluates their ability to communicate complex topics effectively by tailoring their explanations to a specific audience.
- “What tools or platforms have you used for documentation, and how do you approach learning a new tool?”
- Reasoning: This evaluates their familiarity with industry-standard tools (e.g., Confluence, Markdown, Git) and their ability to adapt quickly to new systems, which is often required in fast-paced environments.
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“What’s the most common mistake you see in technical documentation, and how do you avoid it?”
- Reasoning: This highlights their awareness of best practices and their focus on creating clear, effective content.
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“What do you think makes technical documentation stand out and truly impactful?”
- Reasoning: This explores their personal philosophy on technical writing and their vision for high-quality documentation.
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“Do you use AI tools for your technical writing tasks? If so, what is your workflow?”
- Reasoning: This explores their ability to adapt to the latest trends, but also understanding their advantages and limitations. (See this excellent post by Fabrizio Ferri Benedetti discussing how he uses AI in tech writing if you are interested in the topic.)
Wrapping it up
When I look back on that first interview during my second week as a tech writer, I realize how much I’ve learned since then. Despite my nerves, I didn’t do as badly as I thought—so much so that I was later invited to join a hiring committee.
Interviews are more than an evaluation. They’re an opportunity to learn, refine your approach, and connect with talented professionals. Focus on uncovering curiosity, collaboration, research skills, and self-direction, and you’ll find a writer who doesn’t just document your systems but enhances your team. And remember that interviews are about helping candidates showcase their best abilities and experience. And they are great learning opportunities for both parties.
Got your own favorite interview questions? Share them in the comments—I’d love to hear what works for you!
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