I recently interviewed Stefan Klocek, an eight-year Google veteran who now leads design for HubSpot’s AI platform. I expected a conversation about pixel-perfect portfolios, but Stefan took it deeper—into the story a portfolio should tell. He emphasized why constraints matter as much as visuals, clarity beats cluttered slides, and embracing imperfection can set you apart.
In this article, you’ll learn how to shape case studies around real problems, constraints, and human-centered outcomes. By the end, you’ll know how to craft a portfolio that resonates with hiring managers and design leads—and how to position yourself for design’s next evolution.
Early Influences: A Nontraditional Path to Design
Stefan’s path into design wasn’t conventional. With a degree in communications and a curiosity for early web projects, he landed a role at a B2B speaker company—far from the sleek world of digital product design. But that experience became an unexpected advantage.
I learned how to solve real manufacturing problems. We weren’t just making pretty web page—we had constraints like production deadlines and budgets.
Working within those constraints forced him to think beyond aesthetics. He had to prioritize problem-solving, efficiency, and business realities—skills that later became invaluable at Google, where he spent eight years not only refining his craft but also shaping the company’s design job ladder.
By the time he moved on to lead design for HubSpot’s AI platform, he’d seen firsthand how the best portfolios weren’t just a collection of visuals. The most compelling ones told clear, constraint-driven stories—demonstrating how designers tackled real challenges, adapted to limitations, and created tangible impact.
Why Constraints and Clarity Beat Overstuffed Work
From agency projects to Google initiatives, Stefan has reviewed countless portfolios. Most designers try too hard to prove breadth, listing every wireframe or logo redesign, hoping to showcase versatility. But he warns:
“You have about 60 seconds to capture a hiring manager’s attention. If it’s just noise, I’m gone.”
He learned this lesson firsthand at Google when seeking a principal-level promotion. After two rejections, he trimmed his portfolio to three case studies that showcased his unique strengths—and was promoted immediately. It wasn’t the volume of work but the depth of narrative and constraints he overcame that made the difference.
Highlighting the Constraints
Portfolios that gloss over time pressure, stakeholder conflicts, or limited resources miss what Stefan calls the “real world of design.” He believes highlighting constraints demonstrates real skill:
“I’d rather see a design that isn’t perfect, with an honest explanation of why you shipped it that way, than a polished mock with no context.”
Actionable Insight: Turn Constraints into a Narrative Hook
If you had to complete user research in two weeks instead of a month, highlight that constraint. Show how you maximized resources or made tough trade-offs. This proves you can ship under pressure—precisely what recruiters and design leads want to see.
Constraint-based storytelling is one piece of the puzzle. Equally important is demonstrating judgment, especially in an era when AI handles more routine design work.
The Role of AI: Extending (but Not Replacing) Human Judgment
Stefan focuses on designing AI-driven tools for marketing and sales teams at HubSpot. He’s adamant that while AI will automate routine tasks—like generating layout variants or filling in brand guidelines—it won’t replace the need for critical thinking.
“AI can produce a screen or copy in seconds, but it won’t understand business constraints or user empathy the way you can.”
For Stefan, the best designers will:
Use AI to accelerate iterative tasks.
Show why they refined or rejected AI-generated elements.
Document trade-offs made along the way.
When telling the story of a product in your portfolio, a short section on how you used AI (or any tool) to handle repetitive tasks—then layering in your unique perspective—can highlight adaptability. That’s precisely the narrative hiring managers want.
Actionable Insight: Showcase Your AI-Enhanced Process
If you used ChatGPT or another tool to generate an initial copy, include the prompt and raw output in your case study. Then, please explain how you critiqued and improved it. This step-by-step approach showcases critical thinking and technical fluency.
AI tools may evolve, but Stefan insists that a portfolio’s real power is demonstrating sound design judgment. That’s what separates good designers from great ones.
Cultivating “Design Judgment” in Your Portfolio
“Design judgment is understanding which rules to follow, which to break, and why,” Stefan explains. It’s not about perfection—it’s about critical thinking. At Google, he co-authored the internal design job ladder to encourage designers to highlight the trade-offs they faced:
Did you have to cut research time?
Did a stakeholder insist on a specific feature?
Did engineers face database constraints?
By naming these factors, you show you can navigate real-world complexity rather than ignore it. That’s what hiring managers seek: someone who thrives under pressure and balances conflicting needs.
Pottery Lesson for Designers
Stefan likens design to a pottery class where students split into two groups—one focused on quality, the other on quantity. Surprisingly, the quantity group produces higher-quality work because they make more mistakes and learn faster. The same applies to designers: the more projects you tackle, the sharper your judgment.
Actionable Insight: Document Your Trade-Offs Clearly
In each portfolio case study, include a brief bullet list of 2–3 major decisions you made—plus the pros, cons, and outcomes. This shifts your case study from a passive ‘here’s what I made’ to an active ‘here’s how I decided what to make.’
With so many threads—constraints, AI, design judgment—how do you package your portfolio into a cohesive, compelling narrative?
Tying It All Together: Weaving a Consistent Narrative
Because designers juggle multiple roles or interests, portfolios often resemble scattered highlight reels. Stefan recommends a consistent narrative thread:
Open with Context: Define the project’s audience or problem space.
Frame the Constraints: Time, budget, technical limitations, or stakeholder demands.
Reveal Your Process: Show sketches, iterations, or AI-generated mockups—and how you refined them.
Explain Key Decisions: Why did you choose one user flow over another? How did constraints shape outcomes?
Show Impact: Metrics, user feedback, or next steps you’d take with more time.
This structure ensures each case study reads like a compelling story—engaging, logical, and relevant.
Wrap-Up
Stefan Klocek’s journey—from a B2B speaker manufacturer to shaping Google’s design standards and leading HubSpot’s AI initiatives—reinforces a key truth: A portfolio isn’t just a collection of pretty designs. It’s a narrative of navigating constraints, applying critical thinking, and delivering real user impact. Whether you integrate AI or rely on classic user research, your most significant differentiator is showing why you made specific decisions in messy, real-world contexts.
Questions for You:
What challenge or constraint in your recent project can you feature to showcase your design judgment?
How might you incorporate AI-assisted tasks to demonstrate adaptability?
Listen to the Full Interview
If Stefan’s insights resonated, check out our entire conversation on the podcast. You’ll gain deeper insights into developing a resilient mindset, balancing speed with quality, and positioning yourself for the future of UX—where clarity and constraint-driven thinking will always matter, no matter the tools.
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