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Uploading documents in Sidekick

How to teach Sidekick about your organization—so your deliverables sound like you, not a template.


Overview

Sidekick works best when it knows your organization — your priorities, your voice, your existing research. Uploading documents gives Sidekick that context, so responses and deliverables reflect your specific situation rather than generic defaults.
 

Supported Formats

  • PDF

  • Word documents (.docx)

  • Excel files (.xlsx)

  • CSV files

  • PowerPoint presentations (.pptx)

Three Types of Documents Worth Uploading

1. Direction Documents

What are we trying to achieve?

These tell Sidekick what you're trying to accomplish:

  • Strategic plans
  • Grant guidelines or RFPs
  • Program descriptions

When you upload a grant RFP, Sidekick can align your narrative to the funder's priorities. When you upload your strategic plan, it can connect data points to outcomes you've already committed to.

Example prompt addition:

Use the attached strategic plan to frame the community needs section around our three priority areas.

2. Voice Documents

How do we talk about our work?

These teach Sidekick how you sound:

  • Previous reports you're proud of
  • Annual reports
  • Stakeholder communications
  • Style guides (if you have them)

Sidekick generates smart, tailored writing even without voice documents. But when you upload your own materials, it can match your distinct tone, word choices, and personality.

Example prompt addition:

Use the attached annual report as a style reference. Match its tone and level of detail in the executive summary.

3. Data and Research

What do we already know?

These make your deliverable uniquely yours:

  • Community assessments you've conducted
  • Survey results
  • Internal research
  • Program data
  • Local reports not in public datasets

If you've already done the heavy lifting of gathering community input or analyzing local trends, don't make Sidekick start from scratch. Upload it.

Example prompt addition:

The attached survey results show what residents identified as top priorities. Incorporate those findings into the community needs section.

What to Avoid Uploading

  • Image-heavy or scanned documents. Sidekick processes text. Pages that are primarily images, charts without alt text, or scanned PDFs won't be usable.

  • Outdated materials. If a document contains information you don't want repeated or referenced, don't upload it.

  • Very long documents where only a small section is relevant. Consider extracting just the relevant pages or sections. Focused input produces more focused output.

Where Uploads Live

Documents can be uploaded in two places, depending on how broadly you want Sidekick to use them:

  • In a project — available to every conversation in that project (both Ask and Build). Best for foundational documents you'll reference repeatedly.

  • In a conversation — available only within that specific conversation. Best for one-off analysis or documents relevant to a single question.

Tell Sidekick How to Use Your Documents

Once you upload a document, Sidekick automatically looks for relevant information to incorporate. But you'll get better results when you tell Sidekick how to use what you've shared.

A couple more examples:

  • Reference the tone and structure of the attached annual report when writing the executive summary.
  • Use the data from the attached program report to support the impact narrative.

The more direction you give, the more intentional the output.

Quick Recap

  • Upload documents that show your direction, your voice, or your own data and research
  • Skip anything that's mostly images, outdated, or too long to be useful
  • Tell Sidekick exactly how to use what you've shared