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Hudson River Trading·Software Engineer·Technical Phone Screen·Senior

Senior
Jun 2026

Summary

Interviewed at Hudson River Trading for a software engineering role and got hit with a full Wordle solver implementation question. It was a deep coding and design exercise that covered everything from constraint tracking to information-gain strategy to complexity analysis and unit tests. More involved than I expected for a single session.

Questions Asked (6)

Q1

Implement a Wordle-style word guessing game solver. The solver should maintain constraints from per-character feedback (correct position, wrong position, or absent), handle repeated letters correctly, and keep guessing until it finds the word or hits a maximum attempt limit.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

The repeated-letter handling is where I stumbled.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and edge cases, then outline a constraint-based filtering approach using a candidate word list. Discuss how to handle repeated letters correctly by tracking minimum and maximum counts per letter, and describe the guessing loop with a max attempt limit. Finally, analyze time/space complexity and potential optimizations.

Pro tip: Demonstrate awareness of repeated-letter pitfalls by explicitly walking through an example like guessing 'e' when the answer has two 'e's but feedback shows one correct and one absent. This shows attention to detail and robustness.

1. Clarify requirements and assumptions

Ask about word list size, allowed guesses, feedback format, and whether the solver must be optimal or just functional. Confirm if the word list is fixed or dynamic.

2. Design constraint representation

Define data structures to track exact positions, present letters with min/max counts, and absent letters. Explain how to update these from each guess's feedback.

3. Implement filtering logic

For each candidate word, check if it satisfies all constraints: exact matches, letter presence with correct counts, and absence of forbidden letters. Handle repeated letters by counting occurrences.

4. Build guessing loop

Iterate: pick a guess (e.g., first candidate or heuristic), get feedback, update constraints, filter candidates. Stop when word found or max attempts reached.

5. Analyze and optimize

Discuss time complexity (O(N * L) per guess) and possible optimizations like pre-indexing or entropy-based guess selection. Mention trade-offs between simplicity and optimality.

Key Points to Mention

  • Handling repeated letters: track minimum and maximum counts per letter, not just presence/absence.
  • Constraint propagation: update constraints incrementally after each guess to narrow candidates.
  • Edge cases: words with duplicate letters, feedback indicating multiple same letters, and empty candidate set.
  • Max attempt limit: define behavior when limit reached (e.g., return best guess or error).
  • Time/space complexity: filtering is O(N*L) per guess; space O(N*L) for word list.
  • Optimization trade-offs: simple filtering vs. entropy-based guess selection for fewer attempts.

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

Q2

Design the data structures used to represent and update constraints after each round of feedback, and explain how you prune the candidate word list efficiently.

Algorithms & Data StructuresSystem Design
Author's notes

Went with a set of remaining candidates plus a constraint object tracking known positions, excluded positions per letter, and minimum/maximum counts per letter.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the game rules and feedback format (e.g., Wordle-style with exact/partial matches). Then propose a data structure that tracks per-position constraints and global letter counts, and explain how to prune the candidate list using these constraints, emphasizing efficiency with bitsets or precomputed indices.

Pro tip: Mention that you can precompute a mapping from letters to words containing them at specific positions to enable O(1) lookups during pruning, and discuss trade-offs between memory and speed.

1. Clarify requirements and feedback model

Ask about the exact feedback mechanism (e.g., green/yellow/gray) and whether constraints are per-position or global. Confirm the goal: maintain a set of possible words and update it after each guess.

2. Design constraint representation

Propose a structure with: (a) an array of sets for allowed letters per position, (b) a set of required letters with minimum counts, and (c) a set of forbidden letters. Optionally, track exact positions for green letters.

3. Update constraints after feedback

For each letter in the guess, update the constraints: green fixes a position, yellow adds to required letters and excludes from that position, gray excludes from all positions unless already required.

4. Prune candidate list efficiently

Use the constraints to filter the candidate list. For speed, represent each constraint as a bitset over the dictionary and intersect bitsets. Alternatively, use precomputed indices (e.g., letter-position to word list) to quickly narrow down.

5. Discuss optimizations and trade-offs

Mention incremental pruning (only re-filter the current candidate list) and data structures like tries or inverted indices. Discuss time/space trade-offs and potential for parallelization.

Key Points to Mention

  • Use of bitsets for fast set intersection when filtering candidates.
  • Precomputed inverted indices: mapping from (letter, position) to list of words.
  • Handling of duplicate letters in guesses (e.g., multiple yellows require careful counting).
  • Incremental pruning: only filter the current candidate set, not the entire dictionary.
  • Trade-offs between memory usage and query speed (e.g., bitsets vs. hash sets).
  • Potential for using a trie to prune based on prefixes, though less efficient for arbitrary constraints.

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

Q3

Propose and justify a strategy for choosing the next guess. For example, a letter-frequency heuristic or an information-gain approximation.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

I talked through two options: picking the word that maximizes expected information gain (basically minimax entropy over the remaining candidates) versus a simpler frequency heuristic that scores words by how common their letters are in the remaining pool.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the problem constraints (e.g., word length, dictionary size, allowed guesses) and then propose a hybrid strategy that balances letter-frequency heuristics with information-gain (entropy) to maximize expected reduction of the candidate set. Justify the trade-offs between computational cost and guess quality, and suggest a practical implementation that can adapt based on remaining possibilities.

Pro tip: Mention that in early guesses, maximizing information gain (e.g., using entropy over possible feedback patterns) is often more valuable than trying to guess the actual word, but as the candidate set shrinks, switching to a frequency-based heuristic can be more efficient. This shows you understand the exploration-exploitation trade-off.

1. Clarify constraints and assumptions

Ask about the dictionary size, word length, allowed guesses, and whether feedback is exact (e.g., Wordle-style). This sets the scope and informs the choice of heuristic.

2. Define the objective

State that the goal is to minimize the expected number of guesses, which can be framed as maximizing information gain per guess or minimizing the expected size of the remaining candidate set.

3. Propose a hybrid strategy

Suggest using an information-gain (entropy) approach for early guesses to quickly narrow down possibilities, then switch to a letter-frequency or positional-frequency heuristic when the candidate set is small to pick the most likely word.

4. Justify trade-offs

Discuss computational complexity: entropy calculation can be expensive (O(N^2) over candidates), but can be optimized with precomputation or sampling. Frequency heuristics are faster but less optimal. Choose based on time/memory constraints.

5. Outline implementation and evaluation

Describe how to implement: maintain a candidate list, compute feedback patterns for each possible guess, and select the guess that maximizes expected information gain or minimizes expected remaining candidates. Evaluate by simulating on a word list to compare average guesses.

Key Points to Mention

  • Information gain (entropy) as a measure of how much a guess reduces uncertainty about the target word.
  • Letter-frequency and positional-frequency heuristics as simpler, faster alternatives.
  • The exploration-exploitation trade-off: early guesses should explore (maximize information), later guesses should exploit (guess likely words).
  • Computational complexity: entropy-based methods can be O(N^2) per guess, but can be optimized with precomputation or sampling.
  • Adaptive strategies: switching heuristics based on the size of the remaining candidate set.
  • Evaluation metrics: average number of guesses, worst-case guesses, and computational cost.

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

Q4

Implement the solve(dictionary, feedback_api, max_attempts) interface that returns the final guess and number of attempts used.

API & IntegrationsAlgorithms & Data Structures
Author's notes

Pretty clean once the rest was in place.

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AI HintsAI Generated

Suggested Approach

Clarify the problem constraints and the feedback API's behavior, then design an algorithm that efficiently narrows down the dictionary using feedback. Implement the solve function with a loop that makes guesses, processes feedback, and tracks attempts, ensuring it handles edge cases like max_attempts exhaustion.

Pro tip: Discuss the trade-offs between different strategies (e.g., information gain vs. simplicity) and mention how you would test the solution with unit tests and mock feedback APIs. This shows you think about correctness and maintainability, not just getting a working answer.

1. Understand the problem and constraints

Ask clarifying questions about the dictionary size, feedback format, and whether the feedback API is deterministic. Confirm the goal: return the final guess and number of attempts used, or indicate failure if max_attempts is exceeded.

2. Choose a strategy

Decide on an algorithm to select guesses, such as filtering the dictionary based on feedback (like in Wordle) or using a minimax approach to maximize information gain. Consider time and space complexity given potential large dictionaries.

3. Implement the solve function

Write code that initializes the candidate set, loops up to max_attempts, calls feedback_api with a guess, updates the candidate set based on feedback, and returns the final guess and attempt count. Handle cases where no candidates remain or attempts run out.

4. Test and validate

Create unit tests with mock feedback APIs to verify correctness, including edge cases like empty dictionary, immediate success, and failure after max_attempts. Discuss how to measure performance and optimize if needed.

Key Points to Mention

  • Clarify the feedback API's contract: what does it return? Is it a string pattern, a score, or something else?
  • Discuss the trade-off between greedy filtering and more sophisticated strategies like minimax or entropy-based selection.
  • Consider the time complexity of filtering the dictionary on each iteration and potential optimizations (e.g., precomputation, indexing).
  • Handle edge cases: dictionary empty, no possible guesses, feedback inconsistent, max_attempts reached without solution.
  • Mention testing approach: unit tests with mocked feedback, property-based testing, and performance benchmarks.
  • Communicate assumptions and ask questions before coding to ensure alignment with interviewer's expectations.

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

Q5

Analyze the time and space complexity of your solution.

Algorithms & Data Structures
Author's notes

Each pruning pass is O(C * L) where C is the current candidate count and L is word length.

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AI HintsAI Generated

Suggested Approach

Start by clearly stating the time and space complexity of your solution using Big O notation, then walk through the reasoning by analyzing each part of your algorithm (e.g., loops, recursion, data structures). Finally, discuss any trade-offs and potential optimizations, especially in the context of large-scale systems like Pinterest.

Pro tip: Always relate the complexity to the problem constraints and Pinterest's scale—mention how your solution would perform with millions of users or petabytes of data, and if possible, suggest improvements for handling such scale.

1. State the complexities

Clearly and confidently state the time and space complexity of your solution in Big O notation, e.g., 'The time complexity is O(n log n) and space complexity is O(n).'

2. Explain the reasoning

Break down your algorithm and explain how you derived the complexities, referencing specific parts like loops, recursive calls, or data structure operations.

3. Discuss trade-offs

Mention any trade-offs between time and space, and why you chose this approach over alternatives, considering factors like readability, simplicity, and performance.

4. Consider optimizations

Propose potential optimizations or alternative approaches that could improve complexity, and discuss their feasibility and impact.

5. Relate to scale

Connect the complexity to Pinterest's scale, explaining how your solution would handle large inputs and whether further optimizations are needed for production.

Key Points to Mention

  • Big O notation for both time and space
  • Analysis of loops, recursion, and data structure operations
  • Trade-offs between time and space complexity
  • Potential optimizations and alternative algorithms
  • Impact of complexity on scalability and performance at Pinterest's scale
  • Amortized analysis if applicable (e.g., dynamic arrays, hash tables)

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

Q6

Write unit tests for your solution and walk through a sample run demonstrating it works.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

I wrote tests for the constraint update logic (especially the duplicate letter cases), the pruning function, and the full solve loop with a mocked feedback API.

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AI HintsAI Generated

Suggested Approach

First, briefly explain your testing strategy, covering edge cases and normal cases. Then, write clear unit tests for each component, and finally, walk through a sample run by tracing the execution with a specific input, showing how the tests pass and the solution works.

Pro tip: Use a table-driven test format to concisely cover multiple cases, and during the walkthrough, narrate your thought process to demonstrate systematic debugging and verification skills.

1. Outline Testing Strategy

Explain what aspects of the solution you will test, including normal cases, edge cases, and potential failure modes. Mention the testing framework you'll use.

2. Write Unit Tests

Write clear, isolated unit tests for each function or module, using descriptive names and assertions. Include tests for boundary conditions and invalid inputs.

3. Run Tests and Show Results

Execute the tests and show the output, confirming all tests pass. If any fail, explain how you would debug and fix them.

4. Walk Through a Sample Run

Choose a representative input and manually trace the execution step by step, showing intermediate states and final output. Relate this to the passing tests.

5. Summarize and Reflect

Summarize how the tests validate the solution and discuss any trade-offs or limitations of your testing approach.

Key Points to Mention

  • Edge cases such as empty input, single element, large input, and invalid types.
  • Test coverage metrics and how to ensure critical paths are covered.
  • Use of assertions and expected vs. actual output comparison.
  • Modularity and isolation of tests to avoid dependencies.
  • Performance considerations for large inputs and how tests might address them.
  • Readability and maintainability of test code.

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