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Retool·Software Engineer·Technical Phone Screen·Intermediate

Intermediate
Jun 2026

Summary

Retool had me build a mini SQL engine in Python during a technical screen, which sounds manageable until they start layering on GROUP BY and HAVING and asking you to justify your operator ordering out loud.

Questions Asked (3)

Q1

Implement a SQL execution engine over an in-memory table in Python. The table is a list of dicts. Support SELECT with column projection, WHERE with comparison operators, and LIMIT.

Algorithms & Data StructuresSystem DesignTechnical Trade-offs
Author's notes

I started with WHERE filtering since that felt most natural, then bolted on SELECT projection and LIMIT after.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and defining a clear interface for the query engine, then design a modular pipeline that parses the query, applies WHERE filtering, performs column projection, and enforces LIMIT. Implement each stage as a separate function to keep the code testable and extensible, and discuss trade-offs like performance and error handling.

Pro tip: Mention that you would push down predicates and projections to minimize intermediate data, and use lazy evaluation or generators to handle large tables efficiently—this shows you think about scalability beyond the basic implementation.

1. Clarify requirements and interface

Ask about the expected query format (e.g., SQL string or structured object), supported operators, and whether the table schema is fixed. Define the function signature and return type.

2. Design the query pipeline

Break the query into stages: parsing, filtering (WHERE), projection (SELECT), and limiting (LIMIT). Decide on the order of operations for efficiency, such as filtering before projecting.

3. Implement core operations

Write helper functions for each stage: a parser to extract clauses, a filter function that evaluates conditions, a projector that selects columns, and a limiter that truncates results.

4. Handle edge cases and errors

Consider missing columns, invalid operators, empty tables, and type mismatches. Decide whether to raise exceptions or return empty results, and document the behavior.

5. Optimize and discuss trade-offs

Talk about performance improvements like indexing, lazy evaluation, and predicate pushdown. Discuss trade-offs between simplicity and extensibility, and how you would add features like ORDER BY or JOINs.

Key Points to Mention

  • Modular design with separate functions for parsing, filtering, projection, and limiting
  • Efficient order of operations: filter before projecting to reduce data movement
  • Use of generators or lazy evaluation to handle large datasets without loading everything into memory
  • Error handling for invalid queries, missing columns, and type mismatches
  • Extensibility: how to add new operators or clauses (e.g., ORDER BY, GROUP BY) with minimal changes
  • Testing strategy: unit tests for each component and integration tests for end-to-end queries

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

Q2

Extend the engine to support GROUP BY with aggregate functions (COUNT, SUM, AVG, MIN, MAX), then add HAVING to filter on aggregated results.

Algorithms & Data StructuresTechnical Trade-offsSystem Design
Author's notes

This is where I fumbled a bit.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the engine's current architecture and data model, then propose a pipeline: parse GROUP BY and HAVING clauses, build groups using a hash map, compute aggregates per group, and finally filter groups with HAVING. Discuss trade-offs between hash-based and sort-based grouping, and how to handle NULLs and memory constraints.

Pro tip: Mention that HAVING filters after aggregation, unlike WHERE which filters before, and that you can optimize by pushing down predicates where possible. Also, consider using a two-phase aggregation for distributed scenarios.

1. Clarify requirements and constraints

Ask about the engine's current capabilities, data volume, memory limits, and whether distributed processing is needed. Confirm the expected SQL semantics for NULLs and data types.

2. Design the grouping mechanism

Choose between hash-based grouping (for unsorted data, O(n) time) and sort-based grouping (for sorted data, O(n log n) time). Explain how to handle memory by spilling to disk if needed.

3. Implement aggregate functions

Define an interface for aggregates with methods like init, accumulate, and finalize. Implement COUNT, SUM, AVG, MIN, MAX, handling NULLs and data types appropriately.

4. Add HAVING clause support

Parse HAVING as a post-aggregation filter. Evaluate the condition on each group's aggregated values, and only output groups that satisfy it.

5. Optimize and test

Discuss optimizations like predicate pushdown, parallel aggregation, and using hash tables efficiently. Outline test cases for correctness and performance.

Key Points to Mention

  • Difference between WHERE (pre-aggregation) and HAVING (post-aggregation) filtering
  • Hash-based vs. sort-based grouping and their trade-offs in time/space complexity
  • Handling NULL values in aggregates (e.g., COUNT(*) vs. COUNT(column), SUM ignoring NULLs)
  • Memory management strategies: spilling to disk, streaming aggregation, or using external sort
  • Parallel or distributed aggregation using map-reduce style partial aggregation
  • SQL semantics: GROUP BY with multiple columns, aggregate functions on expressions, and HAVING with complex conditions

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

Q3

How would you design the API so these operators compose cleanly, for example using an iterator or operator-tree style? What are the time and space complexity tradeoffs?

System DesignTechnical Trade-offsAlgorithms & Data Structures
Author's notes

Probably the part I was least prepared for.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and constraints of the operators, then propose an API design that supports composition, such as an iterator-based pipeline or an operator tree. Compare the time and space complexity of each approach, and discuss trade-offs in terms of performance, memory, and extensibility.

Pro tip: Emphasize that the best design depends on the specific use case—for example, iterator-based composition is often more memory-efficient for streaming data, while operator trees enable better optimization opportunities. Showing awareness of these trade-offs demonstrates senior-level thinking.

1. Clarify requirements and constraints

Ask about the types of operators, expected data volume, latency requirements, and whether the API needs to support lazy evaluation or parallel execution.

2. Propose iterator-based composition

Describe how operators can be implemented as iterators that pull data from upstream, allowing chaining (e.g., map, filter). Discuss time complexity (O(n) per operator, so O(k*n) for k operators) and space complexity (O(1) extra per operator, excluding buffering).

3. Propose operator-tree composition

Explain how operators can form a tree where each node represents an operation and children are inputs. Discuss how this enables optimizations like predicate pushdown or fusion, and analyze time/space complexity (e.g., tree traversal overhead, memory for intermediate results).

4. Compare trade-offs

Contrast the two approaches: iterators are simple, memory-efficient, and good for streaming, but may lack optimization opportunities; operator trees allow global optimization and parallelization but have higher memory overhead and complexity.

5. Recommend a design and justify

Based on the context (e.g., Retool's need for flexible data transformations), recommend a hybrid or one approach, explaining how it balances performance, memory, and developer experience.

Key Points to Mention

  • Lazy evaluation vs eager evaluation and its impact on performance and memory.
  • Time complexity: O(n) per operator for iterators; tree traversal may add overhead but enables optimizations.
  • Space complexity: iterators use O(1) extra space per operator; operator trees may store intermediate results or metadata.
  • Composability: iterators chain naturally; operator trees allow more complex compositions and optimizations.
  • Extensibility: adding new operators should be easy without modifying existing code (open-closed principle).
  • Real-world examples: Java Streams, Apache Spark RDDs, or LINQ as references.

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