Getting contractors through a 100-question assessment

Highwire clients ask contractors to fill out long safety and compliance assessments, and only about 70% of contractors got theirs to complete. The PM set which questions we needed, and I designed how contractors move through them: one topic per screen, a left nav and progress bar that show what's left, and updates that start from what changed. Completion went from 70% to 93%.

The problem: Contractors couldn't find what they'd missed

Highwire is a construction SaaS platform used by clients like Google, Intel, and Merck. One of its core services is vetting contractors through assessments. A client can invite hundreds of contractors at a time, and each one submits safety and compliance information through Highwire.

The old assessment used tabs. Depending on the assessment, contractors answered anywhere from 50 to around 100 questions, spread across tabs and subtabs of long scrolling forms.

• Completion sat at about 70%. Incomplete assessments meant clients weren't getting the data they needed.
• Contractors called support asking what they were missing. Required fields were easy to scroll past, and hard to find again.
• Internal teams spent time chasing contractors to finish.

The old assessment. Each tab was a long scrolling form, and nothing showed which questions were still missing.

Research was light and led by the PM, mostly working out which questions and pieces the assessment needed. We didn't run user testing. The signals we had were completion data and what support was hearing, and we used the same two to judge the result.

The bet: A guided, step-by-step flow

A guided flow wasn't a new idea. It had come up many times across the business, because we all wanted more contractors to get complete and needed a way to help them get there. TurboTax was a common reference: one thing at a time, with clear progress.

We tried splitting the tabs into sections first. With up to 100 questions, though, they didn't map cleanly onto tabs. The tabs also had no indicator for what was complete. We could have added one, but contractors would still have had to click between tabs to find what was missing. A guided flow gives them one focused area to work in.

The PM defined which questions were needed. Another designer did an early pass that structured those questions and explored a large modal over the screen. I took the design from there and worked through about three rounds in Figma, presenting each one to the PM and stakeholders and iterating on their feedback.

The cost of a guided flow is more clicking. Contractors move through more screens than they did with tabs, so the rest of the design was about keeping each screen small and showing progress along the way.

1. One topic per screen, on a full page

I dropped the modal for a full-page flow. A giant modal over the screen felt heavy, and a full page was cleaner and smoother to move through.

Each screen has one heading, so one topic. It can hold a few related fields, like the number of projects, contract value, and backlog schedule below. The alternative was what we had before: one screen with 30+ fields and a save button at the bottom.

Topics are grouped into sections, like company info, safety, and finance, the way e-learning platforms group lessons into modules.

One heading per screen, with a few related fields. Past answers sit next to the new ones, and the progress bar counts tasks in the update.

2. Check marks and progress show what's left

With tabs, we could point a contractor to the right tab, but a few missing radio buttons on a long page were still easy to scroll past. I designed a new left nav that lists the topics in the current assessment, with a check mark next to each one that's done.

A progress bar runs along the bottom of every screen, and each section ends on a completion screen that lists what's still to do. The check marks, the progress bar, and the completion screens all show contractors they're making progress, and help them stay focused on what's left.

Contractors start from the homepage, where assessments show up as a critical task.

On the contractor homepage, assessments show up in Critical Tasks with a due date.

The screen after the Company section is done, with a Start button for each assessment that's left.

Prompts to connect with clients only appear on these completion screens, after a section or update is finished. One suggests other clients to share assessments with. The other reminds contractors to finish connecting with a client, since the client can't see their data until they do.

I kept these prompts off the question screens so they don't interrupt anyone partway through. Connections are also how Highwire's network grows, since each one gives another client a contractor's data.

The last screen of an update suggests other clients to share assessments with.

When a connection to a client is still pending, the last screen asks the contractor to finish it. The client can't see their data until they do.

3. Updates start from what changed

Not all of this data is collected once. Some of it is evergreen and stays until the contractor changes it. Some is collected on a schedule, depending on the document: OSHA data yearly, and financial statements quarterly. The design had to keep those two apart, and the platform supports both.

Developers built a release system for the scheduled updates. An admin schedules a release and sets what's in it, and contractors see it as an update to complete.

On the contractor side, it's a small set of patterns:

• An update opens by asking what's changed.
• Past answers show next to each new input with an "As of" date, as in the screen in section 1.
• Each screen has a Skip button.
• Leaving partway through shows a warning that the update will be marked incomplete for connected clients.

Contractors coming back for an update can see what they entered last time and change only what's new.

The annual update opens by asking what changed in the past year.

Leaving partway through warns that the update will show as incomplete to connected clients.

4. Rules add or remove questions by industry

Assessments also change with the contractor. Account managers and PMs set rules for each client's assessments, so the questions a contractor sees depend on their answers.

A rule is either an addition or a deletion. An addition makes questions required for contractors who match a condition, like an industry code (NAICS). A deletion removes questions for contractors who match. When the two conflict, the deletion wins.

We first planned for more entry points and more configuration. We pulled back once it was clear that too many options would make the rules hard to maintain.

Adding a rule. Additions require questions for contractors in an industry code, and deletions override them.

During development I worked with the developers and did design QA, reviewing PRs and catching issues with padding, component usage, and whether the grouping and hierarchy matched the designs.

Results: Completion went from 70% to 93%

Completion here means the share of contractors whose assessments are marked complete, with everything filled out. It comes from in-app stats.

• Completion went from 70% to 93%.
• Support heard fewer questions about why an assessment wasn't complete.
• More complete assessments meant less time for internal teams chasing contractors.

We didn't test with users before launch, so these were the signals we used. For this project, I think they were enough: more contractors finished, and fewer had to ask what was missing.

Takeaways

• Show people what's left. The support calls were about missed questions. Check marks, a progress bar, and completion screens kept contractors focused on what was still missing.
• Plan for return visits. Contractors come back yearly or quarterly to update data they've already entered, so updates start from what changed and show past answers.
• Keep the configuration small. We planned more entry points and options at first. Pulling back kept the rules something the team could maintain.