Answer Open Questions on Application Forms with AI

Oct 24, 2026·7 min read

Most of an application form takes a minute: name, email, phone, a link to a profile. The time goes into the boxes underneath. "Why do you want to join us?" "Tell us about a project you are proud of." "Describe your experience with X in 100 words." Each one wants a few sentences, and the next form asks the same thing in slightly different words.

This guide shows how to fill those boxes with FillWise, a Chrome extension we build, from text you already have: your CV, a short bio, notes about the company. It also covers what the AI is told not to do, because the risk with written answers is not a typo. It is a confident sentence about something you never did.

Why the long questions eat the time

• They repeat with small changes. "Why this role", "why our company" and "what are you looking for" are three versions of one answer, and each form has its own character limit.
• The limits are strict. A box that takes 300 characters cuts the end of a pasted paragraph, often mid-sentence, and the form does not always warn you.
• Generic AI makes things up. Paste a CV into a chatbot and ask for "why I want this job", and the answer tends to grow: a team you did not lead, a number you never measured, "5+ years" when you wrote three.
• Copying back and forth breaks the flow. Write in one tab, trim, paste, check the count, go back. Ten questions is ten round trips.

Two modes for open questions

FillWise treats a field as an open question when it is a multi-line text box or its label reads like one ("Describe...", "Why...", "Tell us about..."). What it writes there depends on one switch in the side panel.

By default (switch off), an open question gets facts from your text only, short and neutral. If your text says "Python and SQL, 3 years, data pipelines", the box for "Describe your technical skills" gets that. If your text has nothing on the question, the box stays empty. Nothing is invented to fill the space.

With "Write answers to questions" on, FillWise writes a real answer in sentences. The rules stay strict:

• It writes in a neutral tone, and in the first person only where the question is about you: motivation and background, such as "Why do you want to work here?"
• It adds no new facts. In particular, nothing about how a piece of work went unless you wrote it, no numbers or ratings you did not give, no bigger role than the one in your text, no conclusions or feelings on your behalf, nothing about the market or competitors.
• General questions about you, like "Why do you want to work here?" or a short cover letter box, are answered from what your text says about who you are and what you are looking for. A question about something specific that your text does not cover, such as "Describe your experience with Kubernetes" when Kubernetes is not in it, stays empty.
• Before the answers come back, the AI checks each one against your text and drops what it cannot back up.

The workflow

1. Open the form in Chrome: an application on a careers page, a grant or program application, a contact form with a "Tell us about your project" box.
2. Open the FillWise side panel and paste your text into the input field. Plain notes work: a CV, a LinkedIn "About", a few lines on why this company. You can also attach a PDF of your CV or a screenshot.
3. Turn on "Write answers to questions" under Advanced settings. Its hint says what it does: answers questions like "Tell us about your project" from your text.
4. Press Fill form. The short fields get your details as usual, and the open questions get written answers.
5. Read every answer before you submit. Edit it in the form like any text you typed.

The page itself helps the answer

With the switch on, FillWise also reads the text of the page when the form has a long-answer box: the job description, the program rules, up to 4,000 characters. That helps it understand what "this role" or "the program" refers to. It does not borrow from the page when it writes about you: the tasks and team from a job ad never turn into experience you claim.

Character limits

When a field has a limit, either set on the box or written in its label ("50 characters or less"), a longer answer is cut at the last whole word that fits. Single-word values are left alone. If the cut answer reads short, ask for less in your text or trim it in the form.

Random data for the rest

The "Fill empty fields with random data" switch still works next to this one, for test runs of your own forms: your data goes in first, then the written answers, then random values for whatever is still empty. See test data for forms.

What to check by hand

• Every written answer. It is your application. The rules cut out made-up facts, but only you know whether a sentence sounds like you and says what you mean.
• Questions that ask for a story. "Tell us about a time you resolved a conflict" needs a story you wrote. If your text has none, the box stays empty: write it yourself or add the story to your notes and fill again.
• Numbers and dates. They come from your text as written. If your CV says "since 2021", the answer says the same.
• Cut answers. If a limit cut the answer, read the last sentence.
• Checkboxes with legal weight. Consent, "I confirm the information is true", work authorization: tick them yourself after reading.

Where it works and where it does not

It works on web forms in Chrome, including multi-step application flows: fill each page as you reach it. PDF forms do not use this switch yet: on a PDF the long boxes get facts from your text, as in the default mode. For filling PDFs, see the PDF form filling guide.

For recruiting teams that fill forms for many candidates, the guide for recruiters covers the rest of the flow.

Privacy

On web forms, the field list and your text go to our server so the AI can match values to fields; with this switch on, the page text goes with them. They are processed and not stored. What is kept and what is not is on privacy and security.

Pricing

A form with written answers costs the same as any other fill: one fill per web form. The Free plan starts with 20 fills, then tops up to 5 every week, no card needed. Paid plans and their limits are on the pricing section.

FAQ

Will it write a full cover letter? It fills a cover letter box on a form with a short letter built from your text. It is not a cover letter generator and will not write a page of claims it cannot back up from your notes.

Can it invent achievements to make me look better? No. It is told not to add facts that are not in your text: no new numbers, no bigger role, no outcomes you did not mention. If a question has no answer in your text, the box stays empty.

Does it copy phrases from the job description? It reads the page to understand the question, but answers about your experience use only your text.

Does it work on PDF applications? Not this mode yet. On PDFs, long boxes get facts from your text, without written answers.

Do I need to turn it on every time? It is a switch in the side panel's Advanced settings. Turn it on for applications and leave it off for forms where you only want your details.

Add FillWise to Chrome and try it on the next application you open.