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Understanding how Tooli’s AI agents handle conversation history is essential for getting consistent, relevant responses throughout your construction projects. This guide explains context windows and strategies for managing conversations effectively.
Tooli’s agents don’t have memory across separate conversations - they only remember what’s in the current conversation’s context window.

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What is a Context Window?

Think of the context window as the AI agent’s “working memory” - it’s how much of your conversation the agent can “see” and remember at any given moment during your project discussion. Construction Analogy: Imagine reviewing project drawings through a small window that only shows you a few sheets at a time. As you slide to see new drawings, the earlier ones slide out of view. That’s how a context window works with your conversation history.

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Why It Matters for Construction Work

Project Continuity

The agent can only reference project details within its current context window.

Technical Consistency

Complex project specifications from early in long conversations may be “forgotten.”

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What Happens When Context Fills Up?

When a project conversation exceeds the context window, the agent “forgets” the earliest parts of your discussion. This can lead to:
  • Loss of original project specifications or client requirements
  • Inconsistency with earlier design decisions or material choices
  • Confused responses when you reference earlier project phases
If you reference project details from much earlier in a long conversation and get a confused response, the context window may be full. Start a new conversation and summarize the relevant project context.

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When to Start vs. Continue Conversations

Knowing when to continue a project conversation versus starting a new one is crucial for maintaining quality construction advice. When to Start a New Conversation Start a new conversation when:

New Project Phase

Moving from planning to execution, or starting a different trade’s work.

Different Project Entirely

Switching from residential to commercial work, or different clients.

Agent Getting Confused

The agent references incorrect project details or gives inconsistent advice.

Long Technical Discussions

Extended conversations about complex structural or systems issues.
If responses about your project decline in quality, starting fresh with a good project summary is more efficient than trying to course-correct.
When to Continue a Conversation Continue the current conversation when:

Same Project Phase

Each response directly relates to the current work scope.

Iterative Design

You’re refining quotes, plans, or specifications discussed earlier.

Related Project Elements

Exploring different aspects of the same renovation or construction project.

Sequential Work Planning

The agent needs to remember earlier decisions about materials, timeline, or methods.
Ask yourself: “Does the agent need to remember our previous project discussion to give good construction advice?” If yes, continue. If no, start fresh.

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Building on Previous Responses

Effective project conversations build naturally on construction work already discussed. Example progression: You: “What are the key considerations for a kitchen renovation in a 1960s home?” Agent: [Provides explanation including plumbing updates, electrical compliance, and structural considerations] You: “You mentioned electrical compliance as important. What specific upgrades are required to meet current Belgian electrical codes for kitchen appliances?” You: “Given those electrical requirements, how should we sequence the work to minimize disruption to the family living there?” In longer project conversations, periodically summarize key decisions to reinforce important context: So far for this bathroom renovation we’ve established:
  1. Budget is €15,000 maximum
  2. Client wants walk-in shower instead of bathtub
  3. Plumbing needs updating to current Belgian standards
  4. Work must complete in 3 weeks before family holiday
Given these constraints, what’s the critical path for scheduling trades?

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Project-Specific Conversation Strategies

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Managing Multi-Trade Projects

For complex renovations involving multiple trades, organize conversations by work package: Conversation 1: “Kitchen Renovation - Structural & Plumbing” Conversation 2: “Kitchen Renovation - Electrical & Lighting”
Conversation 3: “Kitchen Renovation - Finishes & Timeline” This keeps technical discussions focused and prevents mixing incompatible advice.

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Client Communication vs. Technical Planning

Use separate conversations for different purposes: Technical Conversation: “Structural analysis for load-bearing wall removal” Client Conversation: “How to explain structural work to homeowner in simple terms”

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Rehydrating Project Context

When starting a fresh conversation about an ongoing project, provide a concise summary: “Project context: We’re doing a complete bathroom renovation in a 1980s townhouse in Ghent. Client budget is €18,000, timeline is 4 weeks, and we’ve already confirmed the structural floor can support a new tile installation. The plumbing rough-in is complete and inspected. New question: What’s the optimal sequence for tiling, fixture installation, and final plumbing connections to minimize rework?”

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Agent-Specific Conversation Management

Different Tooli agents work best with different conversation approaches:
Best for: Extended project discussions and guidance to other agents Strategy: Continue conversations when exploring related aspects of the same project When to restart: When switching to completely different project types
Best for: Focused quote development sessions Strategy: One conversation per quote or major scope revision When to restart: For each new client project or major scope change
Best for: Iterative quote improvement Strategy: Continue while refining the same quote When to restart: When reviewing completely different quotes or project types
Best for: Single document analysis sessions Strategy: Usually one conversation per document review When to restart: For each new bill of quantities or project phase
Best for: Individual change request development Strategy: One conversation per change order or variation When to restart: For each distinct project change or different contract
Best for: Single meeting or documentation session Strategy: One conversation per report or meeting summary When to restart: For each new meeting or different project milestone

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Common Construction Conversation Pitfalls

Problem: Discussing multiple client projects in one conversation, leading to mixed specifications and recommendations.Solution: Use separate conversations for each client project, even if they’re similar work types.
Problem: Long technical discussions where original client requirements get forgotten in the context window.Solution: Periodically restate key project parameters (budget, timeline, client preferences) in long conversations.
Problem: Starting a new conversation with “As we discussed about the Smith kitchen project…” without re-establishing context.Solution: Always provide relevant project context when starting fresh conversations.
Problem: Using one conversation for planning, quoting, execution, and client communication, leading to confused responses.Solution: Separate conversations by purpose and project phase.

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Best Practices for Construction Conversations

One Project Per Conversation

Keep client projects separate to avoid mixing specifications and requirements.

Summarize Key Decisions

Periodically restate important project parameters in long technical discussions.

Fresh Start for Major Changes

New conversation when project scope significantly changes or new phase begins.

Context Reset When Confused

If responses decline in quality, restart with clear project summary.
Think of each conversation as a focused work session. Just like you wouldn’t mix electrical planning with finish selection in a real meeting, keep your AI conversations focused on related topics.

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Next Steps

Asking Great Questions

Learn how to structure effective construction prompts for better results.