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Using Projects with Sidekick

How to set up reusable project foundations—so your team can build consistent deliverables without starting from scratch every time

 

Projects Overview

Projects are reusable workspaces that hold your goals, audience, documents, and preferences in one place. Instead of re-explaining your context every time you start a conversation, you set it once in a project and every conversation inside it — whether you're asking a quick question or building a full deliverable — starts with that foundation.

What Goes Into a Project?

  • Description — what the project is about

  • Goal — what you're trying to accomplish

  • Audience — who the work is for

  • Files — PDFs, assessments, style guides, strategic plans, or datasets that Sidekick should reference

This context shapes every conversation in the project. The more specific you are, the more relevant Sidekick's responses will be.

How to Create a Project

  1. From the navigation or Projects page, select Create New > Project

  2. Fill in the basics: project name, description, goal, and audience

  3. Upload any documents you want Sidekick to reference

You can update any of these details later as your project evolves.

Working Inside a Project

Once a project exists, you can start conversations directly from it or select it from the project dropdown when starting a new conversation from the main Sidekick screen. Both Ask and Build conversations can live inside the same project.

When to Use a Project vs. a Standalone Conversation

Use a project when you'll return to the same topic more than once, when multiple conversations should share the same context, or when a team needs consistency across related work.

Use a standalone conversation for quick, one-off questions where you don't need persistent context — like checking a single data point or exploring an unfamiliar topic.

Team Benefits

Everyone on your team has access to the same projects. That means the same goals, audience definitions, tone preferences, and knowledge documents inform every conversation — no matter who's doing the work. Less time setting up, more consistency across outputs.

Using Projects in Sidekick Ask Mode

Projects aren't just for building deliverables. When you ask questions or work through analysis inside a project, Sidekick draws on your project context — goals, audience, uploaded documents — to give you more relevant, grounded responses.

Why Use Projects for Sidekick Ask Mode

Without a project, every Ask conversation starts from zero. You need to explain who you are, what you're working on, and what matters to your organization. Inside a project, that context is already there.

This matters most when:

  • You ask recurring questions. If you regularly check on the same indicators, trends, or geographies for a program or initiative, a project keeps that context ready.

  • Your questions depend on organizational context. "How does this trend affect our strategic plan?" only works if Sidekick knows what your strategic plan says. Upload it as a knowledge document and it becomes part of every conversation.

  • Multiple team members are exploring the same topic. A project ensures everyone gets responses grounded in the same goals and documents, even if they ask different questions.

How Project Context Shapes Responses

When you ask a question inside a project, Sidekick considers:

  • Your stated goal and audience — responses are framed for relevance, not just accuracy

  • Uploaded knowledge documents — Sidekick can reference your policies, plans, and data alongside mySidewalk's curated indicators

For example, asking "What are the biggest housing challenges in our region?" in a standalone conversation returns broad data. Asking the same question inside a project that includes your housing strategic plan and targets low-income families as the audience produces a more focused, actionable answer.

Tips

  • Start with Ask, graduate to Build. Use Ask and Think conversations inside a project to explore and refine your understanding. When you're ready to create a deliverable, start a Build conversation in the same project — all your context carries over.

  • Keep project context current. If your goals or priorities shift, update the project details. Outdated context leads to outdated responses.

  • Use descriptive project names. When your project list grows, clear names make it easy to find the right workspace fast.

Using Projects in Build Mode

Projects give your Build conversations a reusable foundation. Instead of re-explaining your goals, audience, and source documents every time you create a deliverable, you set that context once and Sidekick applies it across every Build conversation in the project.

How Projects Improve Deliverables

When you build inside a project, Sidekick uses your project context to shape every deliverable:

  • Goals and audience guide the narrative angle and framing

  • Tone preferences keep the voice consistent across outputs

  • Knowledge documents — strategic plans, style guides, past reports — become source material Sidekick references directly

The result: first drafts that are closer to final, with less back-and-forth to get the framing right.

Three Project Types That Work Well

1. Initiative-Specific Projects

For big, ongoing efforts

Examples:

  • 2026 Comprehensive Plan
  • Downtown Mobility Initiative
  • Community Health Improvement Process

All the context for that initiative lives in one place. When you need to build something related—a section of the plan, a stakeholder presentation, a progress report—Sidekick already knows the background. Upload your strategic documents, stakeholder input, and previous reports. Every deliverable draws from the same source of truth.

2. Recurring Work

For regular deliverables on a cycle

Examples:

  • Quarterly grant applications
  • Monthly economic reports
  • Annual housing assessments

Each time, you follow the same structure, but you don't have to re-upload or re-explain your core documents. Your organizational profile, standard language, and style preferences are already there. Just tell Sidekick what's new this cycle, and it builds from the foundation you've already laid.

3. Multi-Jurisdictional Projects

For the same deliverable across multiple geographies

Examples:

  • Housing assessments for 5 council districts
  • Needs analyses for 3 neighborhoods
  • Economic reports for multiple counties

Create the framework once—the structure, data approach, narrative style, and context. Sidekick adapts it for each geography. Consistent quality across all your reports, in a fraction of the time.

Tips

  • Be specific in your project goal. "Create a needs assessment" is fine. "Create a needs assessment for HUD CoC funding that emphasizes chronic homelessness trends" gives Sidekick a much stronger starting point.

  • Upload voice documents. Past annual reports or stakeholder communications help Sidekick match your organization's distinct tone — not generic report language.

  • Tell Sidekick how to use your documents. Rather than uploading passively, include instructions like "Reference the tone of this annual report when writing the executive summary" or "Use attached survey data to support impact narratives."