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Grammarly·Software Engineer·Onsite - System Design / Architecture·Senior

Senior
Jul 2026

Summary

System design round at Grammarly for a software engineer role. The whole thing was a single deep problem: build an AI chat layer on top of a spreadsheet product. Lots of ground to cover and the discussion kept branching into areas I hadn't fully thought through.

Questions Asked (5)

Q1

Design an AI chat interface for a spreadsheet product that translates natural-language commands into structured spreadsheet operations via a tool-calling layer.

System DesignAPI & IntegrationsTechnical Trade-offs
Author's notes

This is a big one.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the product context and user needs, then propose a high-level architecture that separates natural language understanding, tool-calling orchestration, and spreadsheet operation execution. Focus on how you would design the tool-calling layer to be robust, extensible, and safe, and discuss trade-offs around latency, accuracy, and user control.

Pro tip: Emphasize the importance of a confirmation step for destructive operations and the need for a fallback to manual editing, showing you prioritize user trust and safety. Also, mention how you would handle ambiguous commands by asking clarifying questions rather than guessing.

1. Clarify Requirements and Scope

Ask questions to understand the target users, supported spreadsheet operations, and constraints like latency, accuracy, and privacy. Define what 'natural-language commands' means (e.g., simple edits vs. complex transformations).

2. Design the High-Level Architecture

Outline components: a chat interface, an NLU module (possibly LLM-based), a tool-calling layer that maps intents to structured operations, and a spreadsheet engine that executes them. Explain how data flows between them.

3. Define the Tool-Calling Layer

Specify the schema for tools (e.g., functions like 'insertRow', 'applyFormula', 'sortRange') and how the LLM selects and parameterizes them. Discuss validation, error handling, and how to handle multi-step operations.

4. Address Key Trade-offs and Challenges

Discuss trade-offs: accuracy vs. flexibility, latency vs. complexity, and how to handle ambiguous or unsupported commands. Cover safety (e.g., confirmation for destructive actions) and extensibility (adding new tools).

5. Summarize and Iterate

Recap the design, highlight how it meets requirements, and suggest potential improvements or future work (e.g., learning from user corrections, supporting macros).

Key Points to Mention

  • Use of LLM with function calling (e.g., OpenAI function calling) to translate natural language to structured tool invocations.
  • Tool schema design: clear, typed parameters, and idempotent operations where possible.
  • Handling ambiguity: asking clarifying questions or providing suggestions.
  • Safety and confirmation: requiring user confirmation for destructive or large-scale changes.
  • Error handling and fallback: graceful degradation to manual editing, logging for improvement.
  • Performance considerations: caching, batching, and asynchronous processing for long operations.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

How would you handle ambiguous user commands and design a confirmation flow before applying changes to the spreadsheet?

Adaptability & AmbiguityProduct Sense & IdeationSystem Design
Author's notes

I leaned into a clarification-before-execution model and described surfacing a plain-language summary of the interpreted operation for the user to confirm.

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AI HintsAI Generated

Suggested Approach

Start by acknowledging that ambiguity is inherent in natural language commands and that the goal is to balance user efficiency with safety. Then outline a systematic approach: detect ambiguity, resolve it through clarification or confidence thresholds, and design a confirmation flow that is informative and non-intrusive. Emphasize user control and transparency throughout.

Pro tip: Tie your answer to Grammarly's product philosophy: suggestions should be helpful but never overbearing, and users should always feel in control. Mention that confirmation flows should be adaptive—more intrusive for high-impact changes and seamless for low-risk ones.

1. Detect and Classify Ambiguity

Identify sources of ambiguity (e.g., vague references, multiple valid interpretations, missing parameters) and classify the command's intent and potential impact. Use confidence scores from NLP models to flag uncertain commands.

2. Resolve Ambiguity Proactively

When confidence is low, ask targeted clarifying questions or present likely interpretations as options. For high-confidence commands, proceed but still consider impact.

3. Design a Tiered Confirmation Flow

Implement a confirmation mechanism that scales with the risk of the change: for low-risk edits, show a non-blocking preview or undo option; for high-risk changes, require explicit confirmation with a clear summary of what will change.

4. Provide Clear Feedback and Reversibility

After applying changes, show a concise summary of what was done and offer an easy way to undo or modify. This builds trust and allows users to correct mistakes quickly.

5. Iterate Based on User Behavior

Instrument the system to track how often users accept, modify, or reject suggestions, and use that data to refine ambiguity detection and confirmation thresholds over time.

Key Points to Mention

  • Use of confidence thresholds to decide when to ask for clarification vs. act automatically
  • Importance of context (e.g., selected range, recent actions) in resolving ambiguity
  • Designing confirmation dialogs that are informative but not annoying (e.g., inline previews, undo toasts)
  • Considering different user personas (novice vs. power user) and allowing customization of confirmation strictness
  • Ensuring accessibility and clarity in confirmation messages
  • Leveraging Grammarly's existing suggestion UI patterns for consistency

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

What are the main prompt injection and safety risks in this system, and how would you mitigate them?

System DesignTechnical Trade-offsAPI & Integrations
Author's notes

Knew this was coming but still felt underprepared.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the system context—likely an LLM-powered writing assistant with user inputs and external API calls—then systematically categorize risks into direct prompt injection, indirect injection via retrieved content, and safety/abuse risks. For each category, propose layered mitigations spanning input sanitization, output filtering, architectural isolation, and monitoring, emphasizing defense-in-depth and trade-offs.

Pro tip: Show maturity by acknowledging that no single mitigation is foolproof; instead, advocate for a layered defense and continuous red-teaming, and mention that you'd measure residual risk and iterate based on real-world attack data.

1. Clarify the system and threat model

Briefly restate the system architecture (e.g., user prompts, LLM, external APIs, data sources) and identify the trust boundaries and potential attackers. This grounds your answer in the specific context.

2. Enumerate risk categories

List the main risks: direct prompt injection (user manipulates model), indirect prompt injection (malicious content in retrieved documents or third-party APIs), data exfiltration, unsafe outputs (e.g., harmful advice), and abuse of integrated tools.

3. Propose layered mitigations

For each risk, suggest concrete mitigations: input validation and sanitization, prompt hardening (e.g., delimiters, role separation), output filtering and moderation, sandboxing of tool calls, and least-privilege API access.

4. Address trade-offs and limitations

Discuss how mitigations impact latency, cost, and user experience, and acknowledge that some risks (like novel injections) cannot be fully eliminated. Emphasize monitoring, logging, and rapid incident response.

5. Summarize with a defense-in-depth strategy

Conclude by advocating for a multi-layered approach that combines prevention, detection, and response, and mention the importance of continuous evaluation and red-teaming.

Key Points to Mention

  • Direct vs. indirect prompt injection and their different attack vectors
  • Input sanitization and prompt engineering techniques (e.g., delimiters, instruction hierarchy)
  • Output validation and content moderation to prevent harmful or biased responses
  • Sandboxing and least-privilege access for external API/tool integrations
  • Monitoring, logging, and anomaly detection for prompt injection attempts
  • Trade-offs between security, latency, and user experience, and the need for continuous red-teaming

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q4

How would you approach authorization and permission validation before executing spreadsheet operations triggered by the AI?

System DesignAPI & Integrations
Author's notes

Felt more comfortable here.

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AI HintsAI Generated

Suggested Approach

Start by framing authorization as a critical security layer in the AI-triggered spreadsheet operation pipeline, emphasizing least privilege and defense in depth. Then walk through a concrete design that validates user permissions, scopes, and resource ownership before any operation executes, and discuss how to handle edge cases like token expiration or permission changes.

Pro tip: Mention that you would treat the AI's requested operation as untrusted input and re-validate permissions at execution time, not just at request time, to prevent TOCTOU (time-of-check to time-of-use) vulnerabilities. Also, highlight the importance of logging authorization decisions for audit and debugging without exposing sensitive data.

1. Identify the actors and resources

Clarify who is initiating the operation (user, service account, AI agent) and what resources are involved (spreadsheet, specific sheets, cells, external data). This determines the permission model.

2. Define the authorization model

Choose an appropriate model such as RBAC, ABAC, or OAuth scopes. For Grammarly, consider integrating with existing identity providers and using scopes like 'spreadsheets.readonly' or 'spreadsheets' to limit access.

3. Implement pre-execution validation

Before executing any operation, validate the user's permissions against the required scopes and resource ownership. Use a centralized authorization service or middleware to avoid duplication.

4. Handle dynamic permission changes and failures

Account for cases where permissions are revoked mid-session or tokens expire. Re-validate at execution time and fail securely with clear error messages, without leaking sensitive information.

5. Audit and monitor

Log all authorization decisions (granted/denied) with sufficient context for auditing and anomaly detection, ensuring compliance and enabling debugging.

Key Points to Mention

  • Principle of least privilege: grant only the minimum permissions needed for the AI to perform its task.
  • OAuth 2.0 scopes and token validation for third-party integrations like Google Sheets.
  • Defense in depth: combine network, application, and data-level checks.
  • Time-of-check to time-of-use (TOCTOU) issues and re-validation at execution time.
  • Centralized authorization service to enforce consistent policies across services.
  • Audit logging and monitoring for security and compliance.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q5

How would you think about latency, cost, and scaling for this AI-powered spreadsheet assistant?

System DesignTechnical Trade-offsProduct Analytics & Metrics
Author's notes

Went through the usual levers: caching common command patterns, choosing smaller models for simple operations and routing complex ones to a more capable model, async execution for long-running multi-step commands.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the product requirements and user expectations for the AI-powered spreadsheet assistant, then systematically analyze each dimension—latency, cost, and scaling—highlighting trade-offs and proposing metrics to balance them. Emphasize a user-centric approach where latency is prioritized for interactive features, cost is optimized for background tasks, and scaling is designed for varying loads.

Pro tip: Demonstrate awareness that these dimensions are interdependent: for example, reducing latency often increases cost, and scaling may introduce latency. Propose a tiered architecture (e.g., fast/cheap models for simple tasks, powerful/expensive models for complex ones) and discuss how you'd measure and monitor each dimension with concrete metrics like p95 latency, cost per query, and throughput.

1. Clarify Requirements and User Expectations

Ask questions to understand the expected usage patterns, user tolerance for latency, budget constraints, and scale (e.g., number of users, queries per second). This ensures your analysis is grounded in real needs.

2. Analyze Latency

Break down latency into components (network, model inference, data retrieval) and propose strategies to minimize it, such as caching, model quantization, or edge deployment. Discuss acceptable latency thresholds for different interactions (e.g., real-time suggestions vs. batch processing).

3. Analyze Cost

Estimate costs associated with model inference, data storage, and infrastructure. Suggest cost-saving measures like using smaller models for simple tasks, batching requests, or leveraging spot instances, while monitoring cost per user or per query.

4. Analyze Scaling

Consider how the system scales with increasing users and data. Discuss horizontal scaling, load balancing, and auto-scaling groups. Address potential bottlenecks like model serving capacity and propose solutions like model sharding or serverless architectures.

5. Balance Trade-offs and Propose Metrics

Summarize the trade-offs between latency, cost, and scaling, and propose a balanced approach with clear metrics (e.g., p95 latency, cost per active user, throughput) to monitor and iterate on.

Key Points to Mention

  • Latency budgets and user experience: differentiate between interactive and background tasks.
  • Cost optimization techniques: model selection, caching, batching, and infrastructure choices.
  • Scaling strategies: horizontal scaling, load balancing, and handling peak loads.
  • Trade-offs: how improving one dimension affects the others (e.g., caching reduces latency but increases cost).
  • Metrics and monitoring: define SLAs/SLOs for latency, cost per query, and scalability targets.
  • Real-world examples: reference how similar AI assistants (e.g., GitHub Copilot) handle these challenges.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.