The team had an interview process when I arrived. Meetings were scheduled, a design challenge existed, and there was a general sense of what we were looking for. What was missing was precision — clear success criteria for the challenge, a consistent question structure across roles, and a way to bring co-interviewers into alignment before the process began.

The design challenge in particular was more complex than it needed to be. Complex challenges take longer to run, are harder to evaluate consistently, and can disadvantage strong candidates who get tripped up by the complexity rather than the thinking it was meant to test.

My goal wasn't to replace what existed — it was to tighten it. Make it repeatable. Make the signals legible to anyone participating, not just the hiring manager who knew what to listen for.

• Fully remote. All interviews and design challenges were conducted remotely. This meant the challenge needed to work over a digital whiteboard, and how candidates used remote tools was itself a signal — Copperleaf's design team worked in a distributed environment and remote collaboration fluency was a real job requirement.
• Role range. Co-ops and senior designers have very different baselines. A single evaluation framework wouldn't serve both. The process needed to flex across role levels without becoming inconsistent.
• Co-interviewer variability. Design challenges work best when multiple people observe. But co-interviewers — often product managers or developers — don't always know what to look for in a design session. Templates had to make the signals self-evident.
• Keeping it fair. A good process creates equal conditions. The challenge brief had to be genuinely open-ended — not hinting toward a correct answer — so that every candidate had the same starting point.

Interview series template

A structured guide defining the number of interviews, their duration, who should be present at each stage, and the purpose of each conversation. This eliminated repeated coordination and ensured every candidate experienced a consistent process regardless of which team members were available.

Role-specific question banks

Questions tailored to the role being hired. A co-op conversation looks different from a senior designer conversation, which looks different from a design manager conversation. Conflating these leads to unfair evaluation — asking a co-op about systems leadership, or a manager only about craft. Each role had its own bank of questions mapped to what mattered at that level.

Co-ops did not complete a design challenge. The challenge was reserved for intermediate and above, where it was the most informative signal available.

Candidate comparison matrix

A scoring spreadsheet with a dedicated tab for each role — co-op through director — populated with real questions from actual hiring rounds, organized by interview stage. Each interviewer scores responses on a 1–7 scale, and all candidates sit side by side in the same view. The matrix replaced post-interview gut-feel with a structured debrief: scores first, discussion second, which meaningfully reduced anchoring on the first strong opinion in the room.

Design challenge template with evaluation rubric

A brief, a facilitation guide, and a clear set of signals for what strong and weak responses looked like. The rubric was written so that a product manager or developer co-interviewing could follow along and mark observations in real time — not just watch and share vague impressions afterward.

The structure below reflects how the process was run at Copperleaf. It's a reference point — in practice, it's often adjusted based on team size, hiring velocity, and how many cross-functional interviewers are available. A smaller team might collapse stages; a larger one might add a dedicated portfolio review. The purpose of each stage matters more than the exact sequence.

The challenge runs live over a video call with a shared digital whiteboard. The candidate is given a brief and works through the problem in real time with the panel observing. We're not evaluating polish — we're evaluating how they think.

The brief is deliberately simple: "We'd like you to design a parking lot for us."

That's it. No additional context is offered upfront. What the candidate does next is the entire signal.

Two distinct scenarios are available — a highway rest stop and a carnival grounds — so the brief stays fresh across multiple hiring rounds. Both use the same evaluation rubric and produce equivalent signals.

What we're watching for

Both briefs map to real, constrained scenarios — one a rest stop off a highway serving everything from motorcycles to semi trucks, the other a converted farmer's field during a carnival. Both have safety considerations, wayfinding needs, surface requirements, and spatial constraints that only emerge through questions.

Strong candidates don't start drawing. They start asking. Who is this for? What's the context — is this a commercial lot, a rest stop, something else? What are the constraints? What does success look like? Are there accessibility requirements? Safety concerns?

These questions reveal a candidate who understands that design decisions downstream are only as good as the context established upstream. In enterprise product design, starting from the wrong assumptions — regardless of execution quality — produces the wrong solution.

What failure looks like

Candidates who assume without asking will default to the most familiar mental model — usually a shopping mall parking lot. They'll start laying out rows of spaces, thinking about traffic flow for passenger cars, maybe sketching a central entrance. This has happened. They've designed the wrong thing with complete confidence, and no amount of craft or fluency with tools will rescue it.

The challenge also gives us a window into how candidates use remote tools in real time — another practical signal for a fully distributed team.

There's a direct connection between what makes a strong design challenge response and what makes a strong design requirements process. The questions a good designer asks before starting work — about personas, benefits, assumptions, limitations, and use cases — are exactly the questions that reveal the right solution in the challenge.

A candidate who asks "who will be using this space?" is thinking about persona. One who asks "what are the constraints on the site?" is thinking about limitations. One who asks "what does a successful outcome look like?" is thinking about benefits. These aren't abstract design principles — they're practical thinking skills that determine whether a designer spends three weeks building the right thing or the wrong one.

The challenge isn't a trick. It's a compressed version of the first conversation that should happen on every real project. Candidates who know how to start a project well will naturally pass it. Those who have developed a habit of assuming — of jumping to solutions before establishing context — will struggle regardless of their portfolio.

The templates and tools from this process are available as a public resource. Whether you're running the process or going through it, there's something here for you.

For hiring managers

For applicants

A good design challenge is precisely constrained, not complex. Complexity doesn't reveal thinking — it creates noise. The parking lot prompt is disarmingly simple. That simplicity is the point. It gives candidates room to demonstrate depth if they have it, without penalizing them for navigating unnecessary difficulty.

Alignment before the interview is as important as the interview itself. When co-interviewers don't know what they're looking for, post-interview calibration becomes a conversation about competing impressions rather than observed behaviors. The templates ensure everyone arrives knowing what a strong response looks like — which makes the debrief faster and the decision more defensible.

Role-appropriate evaluation matters more than role-consistent evaluation. A co-op and a senior designer should not be evaluated against the same criteria. Being fair doesn't mean asking everyone the same questions — it means asking questions that are appropriate to where someone is in their career and what the role actually requires.