How to use Ask Writer

Who can use this feature

Ask Writer is an open-ended generative AI tool which allows you to tell Writer what you need, then chat back and forth with Writer until you get the results just right. It’s by far our most popular generative AI tool, because it’s easy to use, it’s powerful, and it’s flexible. You can use Ask Writer to do anything from drafting emails, analyzing spreadsheets, summarizing PDFs into neat paragraphs, and more. This guide will help you understand how Ask Writer works, when to use each “mode” of Ask Writer, and offer advice about how to use it most effectively.

Ask Writer is also available in our extensions for Chrome and Mac.

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, reference URLs, or search through your company’s internal data to get answers and outputs based on data you trust.

How to use Ask Writer

From the dashboard, select the Ask Writer shortcut.

Select the Ask Writer mode which best supports the work you’re trying to accomplish:

  • General: ideate, generate text, or ask questions of our Writer-built LLMs
  • Document: ask questions and generate content based on a few specific documents
  • Knowledge Graph: ask questions and generate content based on your company data and files

Once you've selected the appropriate mode, simply enter your question or command and submit it. You can type in your input, or use voice dictation to say it out loud. You can chat back and forth with Ask Writer, asking followup questions until you're satisfied with the results.

Ask Writer turns each conversation into a session. You can access previous sessions and switch between them using the Sessions menu in the bottom left corner. You can select New session to create a blank chat session. We recommend creating a new session whenever you start working on a new query – there’s no limit to the number of sessions you can create!

Under Settings in the bottom left corner, you can add instructions. You can describe how you’d like Writer to behave when generating responses, such as specific formatting, style, voice, do’s and don’ts, and more.

You can set different instructions for each session. This means you could have a Document mode session with certain instructions, another Document mode session with different instructions, and a Knowledge Graph session with completely different instructions.

Select the purple tab or the chat bubble icon in the input field to open the Prompt Library.

Team prompts are created by your team admins to create and share frequently-used prompts with your colleagues. Learn more about team prompts here.

For many new users, the hardest part is knowing where to start. We can help!

Selecting Writer prompts will open the Writer Prompt Library, with tons of pre-written prompt templates you can try out. The Writer Prompt Library is a great way to learn how other teams like yours are using Writer: you can search for ideas by team type, task type, content type, and more.

Select the copy icon to copy a prompt to your clipboard, or select the Use button to insert the prompt directly into your Ask Writer input field.

Once you’ve inserted a prompt into the input field, you can select any variables to customize them with your own context.

When you’re satisfied with the output, select the Copy icon at the bottom of the output to copy it to your clipboard, or select Send to doc to create a new doc in Writer with your output.

Send to doc is a great option if you want to use Writer suggestions to check your output against your company’s style guide. Learn more about using suggestions here.

In a doc, you can also use the rewrite functionality to rewrite your Ask Writer output using a brand voice. Learn more about rewriting in a voice here.

Working in General mode

You don’t have to overthink it when you use Ask Writer - just ask a question the same way you’d ask a coworker for help. If you have feedback on the output you received, chat back and forth with Ask Writer, refining the output until it’s exactly right.


Using General mode is as simple as giving Ask Writer a request:

What are 10 eye-catching subject lines I could use for an email about a 40% off sale on selected winter outerwear that ends on February 28th?

Want more? Want to give it more specific instructions?

Rewrite these with emojis.

Now you’ve got a bunch of examples to workshop!

Working in Document mode

Ask Writer is especially popular because it can work with source files. Simply drag and drop your file or select Add source in the top right corner to include a URL, copy-pasted text, and more.

Writer will take a moment to crawl the PDF. When it’s done, you’ll see the Files Added #/10 count in the bottom right corner get updated, and you’ll be able to view your source.

You can add up to 10 files to each session, and each session can analyze up to 10 million words (approximately 25-50MB).

Ask Writer will show its thought process by breaking your question down into subquestions and providing answers – and sources – for each subquestion.

When Ask Writer cites a source from your source files or URLs, you can select the source to see the specific excerpt within the source which supports our answer.


Need to show your boss that you’re on top of industry news? One company just published its quarterly earnings report, but you don’t have time to read through the lengthy document? Download the report as a PDF. In the input field, select Add source and Upload from computer.

Summarize this PDF into a bulleted list using language you'd use to explain something to a friend. Identify good indicators and concerning indicators for investors.

Working in Knowledge Graph mode

For more information about working with Knowledge Graph, see our article How to use Knowledge Graph. Knowledge Graph is available to certain Enterprise plans.

Sometimes, Ask Writer’s Document mode isn’t sufficient enough to answer your questions:

  • You need to access internal company data which isn’t easily exportable and might be spread across different sources
  • You aren’t sure which documents have the answer – it could be in any of thousands of files!

Knowledge Graph allows you to search across multiple sources of internal data, structured and unstructured, then analyzes all of the most relevant results, and finally composes a reasonable answer for you – in moments, not hours.

Select the most relevant Knowledge graph from the dropdown menu in the input field, and ask a question.

Ask Writer will show its thought process by breaking your question down into subquestions and providing answers – and sources – for each subquestion. You can access the thought process, subquestions, and sources for subquestions by selecting Thought process below the output.

When Ask Writer cites a source from your Knowledge graph, you can select the source to see the specific excerpt within the file which supports our answer.


This customer has a budget of $120,000. They need multiple help centers and localization support. Which plan makes the most sense for her and why?

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 View prompts button in the input field. Then, when you find a prompt you want to work with, select Use to insert it into Ask Writer. Replace any variables with your own information, then submit.

Here are a few examples of the types of output Ask Writer can provide – replace text in [[brackets]] with your own context:


  • General mode:
    • 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: Switch to Document mode. Upload the URL of a relevant job description as a source.
    • 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?
  • Knowledge Graph mode:
    • What’s a great customer quote about using [[Brickly]] to work more efficiently?


  • General mode:
    • 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.
      • Optional: Switch to Document mode. Upload the conference URL as a source. Include the following sentence: Reference the URL for information on the conference.
    • 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]]
  • Document mode:
    • Generate five takeaways from this ebook. [[upload ebook file as a source]] >> Now, draft a marketing email promoting this ebook using those five takeaways.
  • Knowledge Graph mode:
    • How can I explain how to use [[Knowledge Graph]] to a new user with very little technical knowledge?
    • What’s an approved statistic about how [[Brickly]] has helped a customer cut costs?
    • Write an LinkedIn post featuring 3 quotes from retail customers.


  • Document mode
    • 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.
      • Upload the article as a source (URL, paste as text, or file upload).
    • Summarize this white paper in 10 bullets. [[upload file as a source]]
      • Upload the article as a source (URL, paste as text, or file upload).
    • Give me five takeaways from these meeting notes. [[upload file or add URL]]
      • Upload the article as a source (paste as text).


  • Document mode
    • 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)]].
      • Upload the email as a source (paste as text).
    • Rewrite this paper in a professional, academic tone.
      • Upload the paper as a source (URL, paste as text, or file upload).
    • Analyze this content and explain the tone in which it is written. Then, write an [[email]] using the same tone.
      • Upload the content as a source (URL, paste as text, or file upload).


  • Document mode
    • 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 the instruction manual as a source (URL, paste as text, or file upload).

        Turn the following thought leadership blog post into a LinkedIn post.

        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.

      • Upload the blog post as a source (URL, paste as text, or file upload).


General mode:

  • How does [[SSO]] work?

Document mode:

  • Was the overall sentiment from these 10 user interviews positive or negative?
    • Upload the spreadsheet as a source (file upload).
  • What were the common themes across this spreadsheet of support tickets?
    • Upload the spreadsheet as a source (file upload).

Knowledge Graph mode:

  • Which customers have asked for a [[dislike button]] feature?
  • What stats do we have on [[the cost of cloud computing this year]]?
  • What kinds of pricing plans include access to [[Ultra+ Support]]?
  • What’s an approved statistic about how [[Brickly]] has helped a customer cut costs?

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.

When should I use Document mode vs. Knowledge Graph mode?

The user’s account does not have Knowledge Graph enabled. Ask Writer
The user already knows which file the answer is located in. Ask Writer
The answer can be generated using 1-10 source files, of less than ten million total words. The source files are immediately available. Ask Writer
The user does not know which file the answer is located in. Knowledge Graph
The type of question requires accessing lots of varied source data, maybe even a mixture of structured and unstructed data Knowledge Graph
The answer requires using sources longer than 10 million total words or using more than 10 source files. Knowledge Graph
The answer doesn't have one straightforward answer, but requires reading multiple sources to decide which one best helps answer the question. Knowledge Graph

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, the Writer for Chrome extension 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 us know.

Is there a limit to how long my input can be?

Yes, your input (the request or message you're submitting to Ask Writer) can be no longer than 500 words. This limit does not include the words within your source files.

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.”

Do voice commands work in all modes?


Which browsers support voice commands?

Chrome and Safari. The microphone option won't appear in Edge or Firefox.

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.

Are custom instructions only available at the user level?


How many sets of custom instructions can you set?

You can set different instructions for each session. This means you could have a Document mode session with certain instructions, another Document mode session with different instructions, and a Knowledge Graph session with completely different instructions.

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 10,000,000 words. You can upload up to 10 sources to a single Document mode session, as long as their total number of words does not exceed 10,000,000 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. We recommend our image analyzer app for this.
  • 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. Our image analyzer app will parse images.

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 (ten).

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.

Citing sources

Will subquestions always show a highlighted excerpt?

Yes. Sources are always in subquestions.

What should I do if the subquestion doesn’t match the question I was intending to ask?

Rephrase your question to better express what you’re trying to ask.

Ask Writer modes

Does this upgrade mean that Writer has extended the context window length of its LLMs?

No, we haven't changed the context window of the underlying LLM. Instead, we’ve integrated the same graph-based RAG technology that powers Knowledge Graph to Ask Writer to complete the knowledge retrieval step of the process. Once it retrieves the relevant pieces of data, it still relies on the LLM to generate a response.

Why'd you integrate your graph-based RAG technology into Ask Writer?

Since we launched file uploads in Ask Writer last year, one of the top requests we’ve received from customers is to support files with higher word counts.

In the current version of Ask Writer, when answering a question about an uploaded file, we'd send the entirety of the source file along with the question to our LLM. LLMs have context windows, or a limit in the number of tokens it can take in as an input when generating a response. This means file length was capped by the size of the context window of our LLM.

At first, we considered increasing the context window. But both third-party research and our own technical experimentation has shown that increasing the context window often resulted in a decrease in the accuracy of outputs. So instead of relying on the LLM to process your files, the new version of Ask Writer will use our graph-based RAG technology to retrieve the relevant pieces of data to answer your question and sends them to the LLM to reason and generate a response.

By applying the same technology that powers Knowledge Graph to Ask Writer, you will soon be able to summarize and analyze files with up to 10 million words. At this time, we are not increasing the output limit (how many words you can generate). That will remain at 1,000 words.

Why did we create modes?

Ask Writer supports a wide range of requests, but to date, it’s relied on a simple, open-ended chat interface. From working with customers, we’ve learned that giving users the same interface to complete all tasks, without any guidance or restrictions, doesn’t yield the best answers or outputs. With modes, the user can let Ask Writer know how they'd like to work and get a tailored user experience that optimizes for that workflow.

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