Chicagotrading Software Engineer
Interview Guide

• Take a slow piece of your own code, write down in advance where you believe the time goes, then profile it and record how wrong the guess was. The cost is usually an allocation you did not notice or an accidental quadratic membership test.
• Replace one list membership test inside a loop with a set and measure at a thousand, ten thousand and a hundred thousand elements, confirming the shape of the curve rather than only that it got faster.
• Write down the three quantities you can now measure instead of assert: wall time, peak memory, and call count for the function you suspected.

Deliverable: A before-and-after profile of real code plus a written note on the size of the gap between the guess and the measurement.

• Write the function with a mutable default argument, call it three times, and explain the accumulating result: the default is evaluated once when the function is defined, so every call shares one object.
• Build a nested structure, take a shallow copy, mutate an inner element, and show that both views changed, because a shallow copy duplicates the container and not the elements. Then fix it with a deep copy and state the cost you just accepted.
• Write two functions, one mutating its argument in place and one rebinding the local name, and predict the caller's view of each before running it. That single distinction produces most of the bugs that pass their tests.

Deliverable: Three small programs whose output you predicted correctly before running, each with a one-line statement of the rule underneath.

• Port one module you have already written, roughly a hundred lines, into a statically typed language, and record every place the compiler demanded an answer your original had left implicit: a value that can be absent, a numeric width, a case never handled.
• Write the same signature in both languages and state what the static one guarantees before the program runs and what it does not, since it will not save you from a wrong algorithm or an index out of range.
• Write the difference between an interface satisfied by declaration and one satisfied structurally, with one case each where the other approach would miss the mistake.

Deliverable: One module in two languages plus a list of the questions the type checker forced you to answer.

• Run the same CPU-bound function across four threads and four processes and measure both. Under the default CPython build the threaded version will not speed up, because only one thread executes bytecode at a time; the process version will. Check which build you are on first, since free-threaded builds remove that lock and change the result.
• Then run a blocking I/O workload across four threads and measure it speeding up, because the interpreter releases that lock around blocking calls, which is why treating threads as useless is wrong as a general claim.
• Build the lost update: two threads each incrementing a shared counter a hundred thousand times, and show a final value below the expected sum, because an increment is a load, an add and a store and the thread can be suspended between them. Fix it with a lock and then measure what the lock costs.

Deliverable: Three measurements, threads against processes on CPU work, threads on I/O work, and a demonstrated lost update, each with the mechanism written underneath.

• Work one real failure as a bisection: find a revision or an input size where it is good and one where it is bad, halve repeatedly, and state the two assumptions bisection needs, that the property changes exactly once across the range and that the test is reliable.
• Minimise one failing input to the smallest version that still fails, and record how many rounds it took.
• Keep a hypothesis log for one bug in three columns, what I believe, what would disprove it, what I observed, and stop yourself the first time you are about to change two things at once.

Deliverable: One bug worked to root cause with a written hypothesis log and a minimised reproducing input.

• Implement an LRU cache with a capacity bound, then write the three test cases that would catch an off-by-one in eviction: insert exactly capacity items and assert nothing was evicted, insert one more and assert the least recently used key is the one gone, and read an old key just before that insert so the eviction victim changes.
• Add a property test comparing your implementation against a deliberately slow reference, an ordered list scanned linearly, over a few thousand random operation sequences, because a slow reference finds the cases you would not have thought to write.
• Write one numeric test that fails under exact equality and passes with a tolerance, and state why the tolerance has to be relative rather than absolute once the magnitudes grow.

Deliverable: An LRU implementation with three boundary tests, one property test against a slow reference, and one tolerance-based numeric test.

• Have someone plant three defects in a two-hundred-line program, an off-by-one, a shared mutable state bug, and a wrong error-handling path, then find them while narrating, under a fixed rule: state the hypothesis before touching anything.
• Time each one and record which tool found it, reading, a printed value, a debugger, or a test, because the question asked in interviews is how you would find it rather than what it was.
• Write the sentence you will use when you do not yet know the cause, one that names the next measurement instead of offering a guess.

Deliverable: A recorded debugging session with time-to-find per defect and the method that found each.