How to use Ask Writer

Who can use this feature

  • Supported on Team and Enterprise plans
  • Also available in Mac.
This article walks you through our new and improved Ask Writer chatbot experience, introduced in Autumn 2023. Our original Ask Writer experience is still available as Legacy Ask Writer, which you can learn about in this Help Center article.

If you can’t find an out-of-the-box app for exactly what you’re writing or you’re finding yourself staring at a blank page, try using Ask Writer. It’s completely open-ended, so it can be a nifty writing companion or research assistant. This guide will give you some ideas for how you could use Ask Writer, and tips for how to use it most effectively.

What's in this article:

What is Ask Writer?

Ask Writer is our chatbot which can answer questions and generate outputs based on Writer-built LLMs and your files and data.

Here's what makes Ask Writer our most popular generative AI feature:

  • Flexible: You can make just about any open-ended request to Ask Writer. Use Ask Writer to brainstorm, generate, transform, summarize, rewrite, or analyze written content.
  • Easy to use: Since it remembers conversational history, you can refine your queries and ask followup questions. No need to create the perfect prompt; you can chat back and forth with Ask Writer, giving feedback until you generate the output you want.
  • Accurate: LLMs have a limited understanding of your business data. With Ask Writer, you can upload your most important files, or reference trusted URLs, to get answers and outputs based on data you trust.

How to use Ask Writer

From the dashboard, select the Ask Writer shortcut.

Do you need Ask Writer to reference any files or websites? In the chat box, select Add source to upload files, paste text, or add URLs. Writer will consider these sources when generating output or answering a question. See more about uploading files below.

Tell Ask Writer what you'd like it to do! Write out your query and type enter. Ask Writer helps you create great content, whether you're brainstorming possible topics for a blog post, coming up with error messages for a website, or transforming technical documentation into a support article. Ask Writer also helps you analyze written content, whether you're searching for an answer within a document or trying to identify trends, themes, and takeaways within key documents. See more about submitting queries here.

Ask Writer is a conversational chatbot, meaning it retains your history and lets you ask follow-up questions or provide feedback on output. For example, if you use Ask Writer to summarize a PDF into a list and it provides 8 bullet points, you could reply with, "Please narrow this list down to five bullet points" and Ask Writer will understand what you're referring to.

Once you're satisfied with Ask Writer's output, hover over the output until the copy icon appears. Select Copy text to save the output to your clipboard.

Click the arrow in the top left corner to navigate back to the Dashboard. In the top right corner, select the pencil and paper icon to create a new document. Paste your output into a new document, then check it against Writer suggestions to ensure the output follows your company's brand and style guidelines. Learn more about Writer suggestions here.

What kinds of things can I do with Ask Writer?

Writer can address a wide variety of requests, whether you're trying to get over writer's block or extract a few insights out of a spreadsheet. The best way to learn about different types of requests, discover new use cases, or format your queries efficiently is to explore our Prompt Library. From within Ask Writer, select the Writer Prompt Library button. Then, when you find a prompt you want to work with, select Use to insert it into Ask Writer. Replace anything within [[brackets]] with your own information, then submit.

Here are a few examples of the types of output Ask Writer can provide:


  • What are some common engineering questions that I should ask candidates interviewing for a [[Senior Engineer]] position at [[Brickly, a real estate listing search engine]], and how can I tailor them to the [[real estate startup market]]? Optional: Reference the skills and qualifications listed in this job description: [[add URL of job description or upload file]]
  • My team at [[Brickly]] is launching an online community for [[retail store owners]] to share knowledge, ask for advice, and talk about the latest digital trends. Generate 5 catchy names that will attract users to our new community.
  • I work at a [[real estate listing search engine]] and I'm writing the newest edition of our customer newsletter. What are 5 potential topics I could discuss?


  • Please write me a B2B email cadence with 3 emails, targeting [[finance professionals]]. The CTA for the email is to [[get them to visit our booth at Money 20/20]]. Please use a [[professional and informative]] tone, and reference the following link for information on the conference: [[add URL]]
  • Generate 10 versions of 404 error messages for a [[real estate listing search engine]]. Use a fun, casual tone.
  • Generate 5 headlines about [[rising inflation rates]]
  • Generate five takeaways from this ebook. [[upload ebook file as a source]] >> Now, draft a marketing email promoting this ebook using those five takeaways.


  • I’m writing an article about [[layoffs in the tech industry]], and what impact that will have in the space going forward. Summarize the main points of this article: [[add URL]]
  • Summarize this white paper in 10 bullets. [[upload file as a source]]
  • Give me five takeaways from these meeting notes. [[upload file or add URL]]


  • Rewrite this email for each of the following audiences: [[college students in Seattle (reference student loans); retirees living in nursing homes (mention fixed incomes); tech employees who work from home (mention tax benefits)]].

    Subject Line: [[subject line]]

    [[ paste email ]]

  • Rewrite this paper in a professional, academic tone. [[add file as a source]]
  • Analyze this content and explain the tone in which it is written. >> Now, write [[an email]] using the same tone.


  • I'm a sales executive trying to market my new [[bluetooth-enabled mug]]. Turn this instruction manual into 4 exciting talking points that I can reference in emails and promotional materials. [[upload file or add URL as a source]]
  • Turn the following thought leadership blog post into a LinkedIn post: [[add URL]]

    The target audience is [[content marketers at technology companies]]. The blog post should be [[friendly and casual]] in tone. Highlight 3 takeaways from the blog post and include one key quote. Use no more than 200 words. Use short sentences. Use many, short, eye-catching paragraphs.


  • How does [[SSO]] work?
  • Which customers have asked for a [[dislike button]] feature? [[add file as a source]]
  • What stats do we have on [[the cost of cloud computing this year]]? [[add file(s) as a source]]
  • Was the overall sentiment from these 10 user interviews positive or negative? [[add file as a source]]
  • What were the common themes across this spreadsheet of support tickets? [[add file as a source]]

When should I use Ask Writer vs an out-of-the-box app?

Writer offers a wide variety of out-of-the-box apps. If you're just getting started with generative AI in Writer, these are a great place to get started, as they require no experience, and they're fine-tuned on similar content to product great outputs right away. However, these apps don't have flexibility, and you won't always be able to add specific criteria, or ask it to reference a specific source.

Prompts take any criteria into account: tone, audience, creator, word count, intent, and of course, source URLs and files. However, there's a bit more of a learning curve. When you first begin using Ask Writer, it's common to get results that aren't quite right - that's why our chatbot makes it easy for you to tweak your request and provide feedback on the output you've received.

How can I get better output out of Ask Writer?

So you've submitted a request to Ask Writer, but the output you've received isn't quite right. You know you can chat back and forth to refine your query - but how? What adjustments should you make?

A good rule of thumb is to consider the five most important questions:

  • Who - Who is the creator? Who is the audience?
  • What - What form should the output take? How long should it be? What tone should it use? Is there a specific call to action or bit of content which Writer should use?
  • Where - Where will your audience consume this content, i.e. TikTok, Facebook, a blog, etc?
  • Why - Why does the audience need this content? What are you aiming to achieve with it?
  • How - How should the output be structured? What should we reference to create the right content?

Of course, you don't have to answer all of these questions, but if you're stuck, unsure why your outputs aren't what you expected, consider telling Writer the answer to a few of the questions above.

Frequently asked questions


Where can I access Ask Writer? 

Ask Writer is available on the web app and our macOS app.

Is there a limit to how many words Ask Writer will generate?

The word limit is 1,000. This is based on the natural limitations of what LLMs can generate. It’s not on the short-term roadmap to increase this, but if you hear of use cases that require a higher word count, please let product know.

Can I still access the legacy version of Ask Writer? 

You can access the old version of Ask Writer by clicking on the button on the bottom left that says “Switch to legacy version of Ask Writer.”

Conversations and sessions

What is a session? 

A session is an instance of Ask Writer where the chat history and uploaded files will persist even if you leave the chat. If there is a set of files you’ll work with consistently, you can upload them into a session and return to it repeatedly.

Does Ask Writer consider the entire chat history when responding to a request? 

Ask Writer will consider the last three chat back-and-forths between you and Writer as context for what it generates next. If you do not want Ask Writer to consider previous chat history, you can clear the session.

Are sessions shareable with teammates? 

Not at this time.

How do you access previous sessions?

You can access previous sessions by going to the Sessions menu at the top right of the Ask Writer page. 

Can you delete previous sessions? 

Yes, you can delete previous sessions. 

What does it mean to clear a session? 

It'll erase the chat history but maintain the set of uploaded files in that session. 

Uploading files

Is there a limit to how long your source(s) can be? 

The number of words in all the files that you upload into a chat session can't exceed 5,000 words. If you try to upload a source which is too long, you'll see an error message: "wasn't added because it would exceed the max content limit of 5000 words." You can upload multiple sources to a single chat session, as long as their total number of words does not exceed 5,000 words; for example, you could upload one brochure with 600 words and one spreadsheet containing 3,890 words.

What types of files can Ask Writer handle?

  • Can parse text from these file types: xlsx/xls, csv, pptx/ppt, pdf, html, txt, srt, docx/doc, url, pasted text, past sources. 
  • Can parse text from tables but may not understand table formatting and layout. 
  • Cannot parse text from images or videos. 
  • Can parse PDFs but quality depends on how files were created. For example, if PDFs may have text that is an image, a file’s permission may not allow text to be copied, or the layout of a PDF’s layout may be hard for us to interpret (e.g., Writer may struggle to render that a newsletter with multiple columns). 

Can Ask Writer parse images? 

No, Ask Writer is limited to parsing text at this time. 

Can Ask Writer parse numerical data?

Ask Writer can fetch/receive numbers from uploaded sources, but it cannot perform operations at this time. For example, if you uploaded a document that said, "Brickly has 100 employees, 43 of whom are women" you'd be able to Ask Writer, "How many employees does Brickly have?" and "How many women are employed at Brickly?" but you couldn't ask "What percent of Brickly employees are women?" at this time.

Are the files you upload available to teammates?

No, they are private to just you.

Does Ask Writer store the files I upload? 

We store the files you upload to Ask Writer to our Google Cloud Platform (GCP).

Can Ask Writer analyze text across multiple files? 

Yes, Ask Writer will be looking across all source files you upload by default.

If you upload multiple files, how do you specify a specific file in your prompt?

If you need to refer to a specific file, it’s best practice to use /add to reference a specific file in your prompt. If you don’t specify, Writer will assume which files to use. 

Are there limits to the number of files you can upload?

No, there’s no limit to the number of files you can upload, but there's a limit to the number of words across all files you upload within the same session.

Can you upload multiple files at once? 

You can bulk upload 10 files at a time. 

Can you reference files you previously uploaded in a new session? 

You don't need to re-upload a file if you’ve previously uploaded it in another session. You can choose the option to Add from past source.

Can you delete files you’ve uploaded from Writer? 

Yes, you can delete a file by clicking on the folder icon. When you delete a file, it will be removed from all sessions that you’ve uploaded it to.

I've uploaded a PDF but I'm getting an error message after I submit my prompt, "I apologize, but as an AI text-based model, I am unable to directly access or analyze attached files."

Double-check whether your PDF is encrypted. For security reasons, we cannot override the settings of your files. To check whether your PDF is encrypted:

  • Adobe Acrobat:
    • Windows: Choose the hamburger menu > Document Properties > Security - Are there restrictions under Document Restrictions Summary, e.g. Page Extraction?
    • MacOS: File > Document Properties > Security - Are there restrictions under Document Restrictions Summary, e.g. Page Extraction?
  • MacOS Preview:
    • Open the file. Click the (i) Info button in the toolbar. Select the lock to view security settings.
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