In this episode, I talk with Kate Pond, a software engineer and former park ranger who turned self-documentation into a career superpower. We discuss her practical system of using Google Forms to track daily work and accomplishments, how this helps with performance reviews and job interviews, and why documenting your own work is essential for professional growth.

Kate Pond and I discuss her unique path from park ranger to software engineer and how documentation played a crucial role throughout her career transitions. She shares how creating personal runbooks as a college RA taught her that writing things down once saves countless hours of reinventing the wheel later. We explore how this philosophy extended into her transition to software engineering, where she documented everything she learned at technical meetups.

The heart of our conversation centers on Kate's Google Forms system for self-documentation, which she created to track her daily work, accomplishments, and professional development. She explains how the system uses a mix of checkbox ratings (like "how do you feel right now?" on a 1-10 scale) and free-form text fields to capture what she worked on, who she collaborated with, what she learned, and what she's proud of. We discuss how this creates both quantitative data you can graph over time and qualitative records you can mine for performance reviews, peer feedback, and interview preparation.

We also explore the broader philosophy behind self-documentation, including how it helps combat the reality that we simply can't remember everything we do, the value of having "retro docs" when taking breaks from projects, and how documentation for yourself follows the same principles as documentation for users. Near the end of our conversation, Kate shares practical advice from her career coach about doing "scary hour" sessions with a friend to tackle procrastinated tasks.

About Kate Pond:

Kate Pond is a Seattle-based software engineer, technical storyteller, and former park ranger. With a background in both environmental education and backend engineering, she brings a systems-thinking approach to everything from documentation to distributed systems.

Through her studio, The Pond’s Edge, Kate is building climate-tech and AI-powered tools that support sustainability and reduce waste—most recently focusing on circular economy solutions rooted in local community needs.

Kate is passionate about making complex ideas accessible and mentoring others to grow as thoughtful technologists. She’s spoken at GopherCon, REdeploy, and SeaGL, and actively contributes to the PNW tech and climate communities through events like CascadiaJS and PNW Climate Week.

Recommendation from Kate Pond:

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If you’re based in or near one of those cities and looking for a supportive, mission-driven space to work or connect, definitely check them out.

✨ Referral perk: If you sign up for a membership and mention my name (“Kate Pond”) as your referrer, we both get a free month (or up to $150 off). Win-win!

Learn more at 9zero.com

Resources discussed in this episode:

• Kate Pond - DEV Community
• Kate Pond – Medium
• Google Forms for Self-Evaluation
• Talks from Write the Docs Portland 2025

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In this solo episode, Kate talks about her latest content update progress. She also reflects on Dennis Dawson’s interview (S3:E22), the ways she’s already using Dennis's tips, and the power of doing small things or repairs to affect larger change.

I’ve continued my work to update the KnowledgeOwl Support Knowledge Base to align with major navigation and UI changes we rolled out in December 2024. My previous punchdown list of fewer than 50 articles was wrong, but I do think I’m below 100 now, after I found a chunk of content I’d completely missed.

I reflect a bit on some of the detailed, specific next steps Dennis Dawson offered. Thanks to some of his points, I won’t be including a floating copy of my head in upcoming videos. I’m also starting to think of visual ways I can help give my readers a pause during conceptually-heavy content, to let them shift from focused mind to diffuse mind.

I also reflect on the piece of advice that most stuck out to me from Dennis’s interview: “Get over yourself. Get over your reticence”, and a new practice I have of picking up trash along the main road near my house. Along the way, I tie in quotes from Abby Covert, Ari Weinzweig, and Harrison Gardner.

So much of tech writing boils down to what we might classify as “small things” (Weinzweig) or “repairs” (Gardner). In both cases, these small actions can add up to big change and momentum over time. They’re also one of the ways we can most express care and commitment to a project. This month, I’m doubling down on these small things and repairs, and I invite you to join me in finding small ways to care for your documentation.

Resources discussed in this episode:

• KnowledgeOwl Support Knowledge Base
• Abby Covert’s How To Make Sense of Any Mess, excerpted from chapter 7: Be the filter, not the grounds
• Ari Weinzweig’s Small Actions Matter in Much Bigger Ways Than We Might Imagine: Pint-sized ideas, the struggle of self-doubt, and learning to take action anyway
• Harrison Gardner:
  • Subscribe to his newsletter on his website
  • Build Your Own: Use what you have to create what you need
  • Common Knowledge

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In this episode, I talk with Dennis Dawson, a technical writer with 40 years of experience who creates the sketchnotes for Write the Docs talks. We talk about how humor and visual elements can make documentation more engaging and memorable, the science behind why graphics help information stick in long-term memory, practical tools and techniques for adding visual content to your docs, and why you don't need to consider yourself an artist to create effective illustrations that enhance your documentation.

Dennis and I discuss his unconventional path into technical writing, starting with an English degree and progressing through roles as an editor, typist, secretary, and eventually desktop support in the early days of personal computing. His technical writing career began at startups in the 1980s, where he combined training and documentation work. Throughout his 40-year career, Dennis has consistently advocated for using humor and visual elements in documentation.

Our conversation centers on the science behind why visual content and humor make documentation more effective. Dennis shares how reading Richard Mayer's Multimedia Learning and Barbara Oakley's books on learning validated many of his instinctive approaches. We explore concepts like how visual information sticks in long-term memory more easily than text, the importance of reducing cognitive load through strategic use of graphics, and how breaking up text with visuals gives readers' brains time to process information by switching between focused and diffuse modes of thinking. Dennis also discusses when to use graphics and shares examples like using whimsical robot characters to represent different software components.

We dive into the practical side of creating visual content, including Dennis's collaborative approach of sketching ideas and working with design teams to polish them into professional graphics, and tools like Gimp, Inkscape, Keynote, and Google Slides that make visual creation accessible. Dennis emphasizes that you don't need to consider yourself an artist to create effective illustrations—the key is getting over your reticence and recognizing that drawing is a skill developed through practice, not innate talent. We also discuss his approach to creating educational videos, including using Doc Detective to automate video updates when UIs change. Throughout our conversation, Dennis stresses the importance of using visual humor and plain language to help make documentation digestible and accessible.

About Dennis Dawson:

Like many baby-boomers, Dennis still hasn't decided what he wants to be when he grows up. He's a technical writer with 40 years' experience in technical communications providing documentation, training, and user support; a sketchnotes artist for Write the Docs; a 3-time Distinguished Toastmaster and Past District 57 Governor who's won District Champion titles in Humorous, Tall Tales, and Evaluation contests; a volunteer Santa Claus at San Jose Christmas in the Park; and a volunteer drawing teacher at local elementary schools.

Resources discussed in this episode:

• Free tools:
  • Doc Detective: Manny Silva’s open source tool for testing and validating documentation
    • Doc Detective tutorials that Dennis created
    • As a reminder, we also did an episode with Manny Silva on Doc Detective S3:E14
  • GIMP: free alternative to Adobe Photoshop
  • Inkscape: free alternative to Adobe Illustrator
• Books:
  • Multimedia Learning by Richard E. Mayer
  • Learning How to Learn by Barbara Oakley, Terrence Sejnowski, Alistair McConville
  • A Mind for Numbers by Barbara Oakley
  • Uncommon Sense Teaching by Barbara Oakley, Beth Rogowsky, Terrence J. Sejnowski
• Dennis Dawson’s sketchnotes:
  • Write the Docs Portland, May 2025
  • Write the Docs Atlantic, September 2024
  • Write the Docs Portland, April 2024
  • Write the Docs Atlantic, September 2023
• Write the Docs Portland 2023 talks:
  • Lightning Talk: Dennis Dawson - Sketchnoting: Engaging both brains
  • Caitlin Davey - The visuals your users never saw…wait that’s most of them
  • Ryan Young - Is it (layer) cake: Thinking in content levels

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In this solo episode, Kate shares an update on her content update progress. She also reflects on Fabrizio Ferri-Benedetti’s interview (S3:E20) and the ways exploring models like his Seven-Action Documentation model have helped her interrogate her own beliefs about tech writing, the benefits of self-knowledge in becoming a better writer, and the ways that maintenance docs work helps her recharge.

I’ve continued my work to update the KnowledgeOwl Support Knowledge Base to align with major navigation and UI changes that we rolled out in December, and I’m finally nearing the light at the end of the tunnel: my initial punchdown list has less than 50 articles remaining! Along the way, I’ve also had to re-update docs I already updated as we rolled out more changes to existing features–ahhh, the life of a tech writer.

In his interview, Fabri mentioned that part of his motivation for creating the Seven-Action Documentation model was a frustration that people were taking frameworks like Diátaxis and just rote-applying them to their documentation. We discovered some very deep common ground: that models and frameworks are useful because they help you, as a writer, surface and interrogate the deeply-held beliefs you have about technical writing. They’re tools for exploration rather than step-by-step guides on what to do. In my case, engaging with the Seven-Action Documentation model helped me realize how strongly I felt about appraisal and troubleshooting as user needs. While I’m not necessarily crafting new content templates to handle this, my site structure has naturally incorporated them, and I’m now exploring the idea of review checklists or user journeys that might help me assure that I’m handling all the user needs in some way.

I’ve also been sick with Covid, which slowed down my velocity for more strategic, creative work and prompted me to return to a lot of maintenance work. Fabri mentioned that maintenance work helps him recharge, and I found the same thing. I often call maintenance work “productive procrastination”, since it’s not usually the single most important thing, but it is something I can do when my energy or focus are low so that I’m still improving my docs every day. Consider this your invitation to spend the next month paying attention to which writing tasks fill or drain your cup, what kinds of energy those tasks demand, and how you can better manage that moving forward.

Resources discussed in this episode:

• KnowledgeOwl Support Knowledge Base

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In this episode, I talk with Fabrizio Ferri-Benedetti about moving beyond strictly following documentation frameworks to embrace strategic thinking, his Seven-Action Documentation model that prioritizes user needs over content types, and how technical writers can grow and adapt in the AI era while positioning themselves as essential strategic partners.

Fabri and I discuss his background as a cognitive psychology student who transitioned into technical writing through his love of computers and writing. He shares his journey from academia to becoming an editor at Softonic, and eventually to his current role as a principal technical writer at Elastic working on OpenTelemetry documentation. We explore his concept of technical writers as shapeshifters who adapt to different roles and contexts.

The conversation centers around Fabri's Seven-Action Documentation model, which he developed as a more descriptive and user-focused alternative to prescriptive documentation frameworks. Unlike content-type-focused approaches, his model identifies seven key user actions that address real user needs that are often overlooked by traditional frameworks. We discuss how this model encourages writers to think strategically about user needs rather than simply following rigid content templates, and why starting with user needs rather than content types leads to more effective documentation.

We also explore professional growth for technical writers, particularly in the AI era. Fabri emphasizes the importance of meaningful skill growth, advocating for work that demonstrates strategic thinking rather than just high-volume output. He shares his philosophy of embracing AI as a tool while maintaining critical evaluation of its limitations, arguing that technical writers must understand emerging technologies to maintain credibility and influence in organizational decisions about documentation and AI implementation.

About Fabrizio Ferri-Benedetti:

Fabrizio Ferri-Benedetti is a technical writer and documentation engineer with over 15 years of experience. Through his blog Passo.uno, he shares insights on documentation strategy, API design, and the evolving role of writers in the tech industry. When not championing better documentation practices or contributing to open source projects like OpenTelemetry, he explores ways to make technology more accessible.

Resources discussed in this episode:

• passo.uno
  • The Seven-Action Documentation model
  • How to grow as a technical writer
  • Beyond Content Types: A Human-first Model for Technical Documentation
• The Diátaxis framework
• The Write the Docs Slack
• The Magical Number Seven, Plus or Minus Two: Some Limits on our Capacity for Processing Information

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• passo.uno
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In this solo episode, Kate shares an update on her content update progress. She also reflects on Sarah Walker’s interview (S3:E18) and the concepts of Asteya, giving great service, and going the extra mile.

I’ve continued my work to update the KnowledgeOwl Support Knowledge Base to align with major navigation and UI changes that we rolled out in December. I also created about 30 articles for the launch of KnowledgeOwl’s new Owl Analytics feature, taking my total to 618. 🎉

Sarah’s interview gave me a lot to think about, and I spent the bulk of this episode reflecting on some key points from that conversation. First, I focus on the concept of Asteya she shared, in the context of not stealing time and energy from other people. This concept is so central to well-written documentation and is a compelling argument in favor of clear, consistently applied style guidelines. I coined the phrase “Style guide adherence is an anti-theft device” to summarize this idea. Our conversation reminded me so much that creating great documentation is an act of giving great service. I outline the three-step guide to giving great service that KnowledgeOwl uses, which is based on Zingerman’s Guide to Giving Great Service: 1) Find out what your customer wants; 2) Get it for them accurately, politely, and enthusiastically; 3) Go above and beyond, or go the extra mile.

Step one is often the hardest piece of giving great service since people often don’t know how to articulate what they actually want. At KnowledgeOwl, we use Disney’s “What time is the 3 o’clock parade?” example to show our new support and success owls how what someone asks for isn’t necessarily the question they want answered.

Great documentation helps deliver step two by creating the accurate answers your readers need.

Step three ties very nicely back to statements Sarah and I both made—about the idea of crafting a solid experience for others in our documentation, of distilling what they need and making it as streamlined as possible. This discussion builds on the ideas of craft we’ve previously discussed, the idea of care I discussed in Episode 17, and Sarah’s comments about crafting something FOR others. Sharing knowledge is an inherent piece of our humanity and of building human communities. Documentation isn’t merely transactional—it’s also an act of care, a gift of time and knowledge, and a gift of saved time so people can pursue other interests.

Resources discussed in this episode:

• KnowledgeOwl Support Knowledge Base, especially the Owl Analytics documentation
• Zingerman’s Guide to Giving Great Service
• ZingTrain’s The Art of Giving Great Customer Service
• Disney Institute Blog’s How Would You Respond If Asked: ‘What Time Is The 3 O’clock Parade?’
• The Disney 3 o’clock parade question: Insights from KnowledgeOwl support team

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In this episode, I talk with Sarah Walker, a technical writer and yoga instructor, about how yoga principles like establishing foundations, respecting people’s time, and embracing practice over perfection can transform your approach to technical writing and help you create more mindful, user-centered documentation.

Sarah and I discuss her path into technical writing, which began with yoga instructor training where she discovered how much she enjoyed breaking down complex processes into foundational steps. This experience taught her that effective instruction—whether for yoga poses or technical procedures—requires understanding your audience's needs and building from core principles. We explore how yoga's emphasis on establishing solid foundations directly translates to documentation, where starting with fundamental concepts helps both beginners learn and experienced users refresh their understanding.

We explore the yoga principle of Asteya (non-stealing), particularly how it applies to respecting readers' time and attention. Sarah explains how this philosophy shapes her approach to writing clear, concise documentation that helps users efficiently get to their goals. We discuss practical applications like using consistent style guidelines to reduce cognitive load and being mindful of which content is essential to include in your docs.

Our conversation also covers how yoga's concept of practice over perfection applies to technical writing careers. Sarah shares how documentation evolves alongside products and why embracing this constant change rather than striving for perfect static content leads to better outcomes. We explore the parallels between sequencing yoga poses and sequencing information in documentation, the importance of observing your audience's needs, and how both practices require patience, self-compassion, and continuous learning.

About Sarah Walker:

Sarah's been writing and crafting stories since she was able to put pencil to a Peanuts 3x5 top-spiral memo pad and record her stories in her own scribbly alphabet. Since personal alphabets scribbled on tiny pieces of paper don't pay the rent, she embarked on her career as a professional writer and editor after graduating from St. Edward's University (Austin, TX) in 1998. As an industry editor with Hoover's for roughly seven years, she covered biotech, pharmaceuticals, health care systems, venture capital, investment firms, and other sectors as a member of the Finance and Health Care editorial team. She earned her Austinite bone fides by getting hired by and, 18 months later, laid off by Dell, where she served as a technical editor for the Global Technical Training and Curriculum Team for products and software for consumers as well as small and midsize businesses. Thanks to the Great Recession and other market forces and personal demands, she bounced around a bit from writing and editing features, self-help book summaries, U.S. Pharmacopeia monographs, and other technical-ish content.

She began her technical writing career in earnest at Libre Digital, where she spent much of the second decade of the 21st century documenting procedures for processing various magazine titles as well as a platform for book publishers to distribute their titles to digital marketplaces. After a two-year stint as the managing editor (and lone full-time, non-contract employee) of a local bimonthly magazine targeting affluent residents of "West Austin," at long last (in August 2020), Sarah landed a job that gave her the Technical Writer job title, and she's been writing about the Monetate platform ever since.

Sarah's second career as a yoga instructor (and briefly a Pilates mat instructor) began in 2005, after she completed her 250-hour instructor training with Yoga Yoga (now defunct, just like the college in Santa Fe, NM that she attended for the first two years of her undergrad studies). She taught part-time until 2012, when primary job demands and other responsibilities forced her to give it up.

Resources discussed in this episode:

• Garbl’s Writing Center
• On Writing: A Memoir of the Craft by Stephen King
• Sarah’s Elect a Raccoon Overlord article

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• Bluesky

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In this solo episode, Kate shares an update on her content update progress. She also reflects on Manny Silva’s interview (S3:E14), Ryan Macklin’s interview (S3:E16), and Liz Argall’s interview (S3:E13) and the importance of learning even when we don’t have explicit reasons to do so.

I’ve continued my work to update the KnowledgeOwl Support Knowledge Base to align with major navigation and UI changes that were rolled out in December. I updated an additional 15 articles since my last episode, taking my total to 565. 🎉This month’s velocity was a lot lower thanks to prepping for, teaching, and attending KnowledgeOwl’s July 2025 Summer Camp workshop series.

While teaching the classes was fun, it also triggered a lot of issues with my chronic illness, so I finished the month quite depleted on every level. This made me think a lot about the ambient and acute stress Ryan and I discussed in relation to empathy advocacy, and about how all documentation makes demands on readers’ cognitive capital. I share five documentation techniques that helped me get use from docs when I was struggling the most cognitively:

1. Provide a summary, synopsis, TL;DR, or 1-2 context-setting sentences at the start of a doc or each section.
2. Use strong page titles and headings, avoiding general catch-alls like “Frequently Asked Questions.”
3. Format your content consistently using semantic elements like sequential headings.
4. Use callouts, warnings, or admonitions sparingly but in consistent ways.
5. Practice screenshot restraint.

I also reflect on how tricky it is to actually accommodate learning as a tech writer if I don’t have a pressing need for it. We learn new tools or domains often since it’s required. We learn new tooling or scripting to make our lives easier or because it’s required. We attend classes, conferences, or certifications. But we often don’t take time on less formal, bigger picture learning. I share how doing research to teach a class on style guides led me to find all kinds of flaws and oversights in my existing style guide. I challenge all of us to carve out 2-4 hours in the next month to dig deep on a best practice or concept we want to learn more about. If you lack the time or discipline and have a professional development budget, you can also consider joining me for the Information Architecture Master Class I’m teaching in partnership with KnowledgeOwl in September and October. Use discount code NOTBORING.

Resources discussed in this episode:

• KnowledgeOwl Support Knowledge Base
• Our upcoming Information Architecture Master Class

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Learn how Ryan Macklin's "empathy advocacy" framework helps you design documentation that works for users in all emotional states (e.g. anxious, frustrated, exhausted, and curious/distractible) rather than assuming everyone comes to your docs in a perfect state of clarity.

Ryan and I discuss his unique path into technical writing, starting from his early computer hacking days and role-playing game writing background. Ryan explains how writing and editing tabletop games taught him that documentation is harder than technical writing because it requires creating user interfaces for "disconnected, squishy brains" while making content engaging enough that users won't simply abandon it for alternatives. This experience, combined with his personal journey through therapy and understanding neurodiversity, eventually led him to develop the empathy advocacy framework.

Our conversation centers around Ryan's empathy advocacy concept, which focuses on writing for users who aren’t calm. These users might be in four key cognitive states: anxious, frustrated, exhausted, and curious/distractible. Rather than designing documentation for the "happy path" or optimal users, Ryan advocates for considering people who may be dealing with high ambient stress, acute stress from urgent problems, cognitive depletion, or distractibility. The "stupid users" developers complain about are often just busy, stressed people whose brains aren't optimally processing information.

We explore practical applications of empathy advocacy concepts, including strategic screenshot reduction to minimize cognitive load, restructuring and tightly scoping FAQs to avoid information architecture problems, and understanding that every element in documentation has a "tax" on your user’s mental energy.

The episode also includes practical advice on social capital management, documentation stewardship, and the importance of "failing forward" rather than getting stuck in perfectionism.

About Ryan Macklin:

Ryan splits his cerebral time between tech writing, UXing, coding, and game design. By day, Ryan writes and edits software and hardware requirements. Otherwise, he works on game or tooling projects, light woodworking, and land improvement projects on his homestead in southern Michigan. Warning: Ask him about UX in games, and he may talk your ear off.

Resources discussed in this episode:

• empathyadvocacy.org
• Ryan Macklin talk: WTD ECQ Nov '22: 7 doc techniques rooted in empathy advocacy
• Ryan Macklin talk: How to avoid "toxic tennis" — empathy in user communication
• Other technical communication talks by Ryan Macklin

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• Ryan's newsletter: buttondown.com/ryanmacklin
• macklin.cc
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In this solo episode, Kate shares an update on her content update progress. She also reflects on Nick Graziade’s interview (S3:E12) and Liz Argall’s interview (S3:E13) and the ways these interviews highlight some elements of “good” docs experiences.

I’ve continued my work to update the KnowledgeOwl Support Knowledge Base to align with major navigation and UI changes that were rolled out in December. I updated an additional 43 articles since my last episode, taking my total to 550. 🎉 I’m in the middle of updating our Contextual Help Widget documentation—one of the features I’ve been putting off updating—and I’ve been drafting content for our forthcoming AI Chatbot feature, too.

Nick and I share a tech writer villain origin story of absolutely adoring LEGO documentation, and it’s gotten me curious how many other tech writers also have this early exposure to documentation. And for some reason I’m seeing tech writing everywhere. I share a detailed story of Bont Cycling’s online shoe fit guidance, which I recently used and which has created a fairly positive product experience for me. Good documentation experiences can help create good product experiences.

I also reflect on Liz’s comment that “The best fertilizer is the gardener’s shadow.” She talked about this in the context of just showing up to work on docs, but I extend that metaphor to say showing up working with care. I gave two examples of this. I’ve been struggling with some personal losses, so a lot of my docs work lately has been a blitz of low-hanging docs fruit: a lot of small changes and improvements. None of these updates are substantive, but they’re good iterative improvements and they helped me get back into docs work. I also share a story of building a long-procrastinated-on bench for my entryway, which was more about accepting good rather than great just to get something built. Good docs are dynamic and iterative–they may not be perfect at first, but they’re constantly improving and always striving for a better reader experience.

Resources discussed in this episode:

• Our new merch store!
• KnowledgeOwl Support Knowledge Base, especially the Contextual Help Widget documentation
• Bont Cycling Shoe Size Finder (The docs I referenced in the episode are hyperlinked in the Print Sizing Page section.)

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