Chicago Software Engineer Interview Guide

The 60-second brief

A Software Engineer at Chicago serves a critical function in maintaining the technical infrastructure that supports the city’s complex operations. You will be tasked with building, scaling, and optimizing systems that facilitate essential public services. This role is not merely about writing code; it is about solving high-stakes problems that impact the daily lives of millions, ranging from web-based service delivery to managing databases that track vital civic resources. The environment is unique, characterized by a mix of legacy system modernization and the urgent need for new, responsive digital solutions. You will work within teams that must balance rapid development cycles with the constraints of public sector requirements.

This guide is scoped to a Software Engineer candidate at Chicago.

Focus areas

• PHP
• Understanding of JOIN Operations
• Databases

Where to focus your preparation

No round sequence has been reported for Chicago. Confirm the format with your recruiter.

Preparation focus

No round sequence has been reported for this company, so confirm the format with your recruiter and work the reported questions below.

What to demonstrate

• Breadth across the topics this company reports testing
• Whether you confirm the format before preparing for it

How to prepare

• Ask the recruiter for the sequence, the duration of each stage and whether you will be writing code
• Work the reported questions below and time yourself

Where candidates lose points

Respect the formality

Arrive early, dress professionally, and treat every interaction with the same level of seriousness as the final interview.

Know your resume

Be prepared to dive deep into any project you list. If you mention it, you should be able to explain the "why" behind every technical decision.

Connect to the mission

Research the city's current technical challenges. Being able to discuss how your skills directly address these needs will set you apart.

Practice under observation

Since your answers will be recorded, practice speaking your thoughts aloud. This helps you avoid filler words and improves the clarity of your delivery.

Questions & practice

Merge partitioned event streams into one ordered feed with bounded lateness

Hard · k-way merge · watermarks · out-of-order streams

The read-model service consumes 64 log partitions carrying about 4,000 events per second in total. Each partition is ordered within itself, but partitions drift by up to 30 seconds, and the activity feed must present a tenant's events in occurred_at order. Produce the merge. State its complexity, the buffer it requires in events and in bytes, what happens when one partition is idle, and what you do with an event that arrives after you have already emitted its position. Payloads average 1 KB.

Approach

1. Merge with a min-heap over the 64 partition heads keyed on (occurred_at, event_id): O(log P) per event and O(n log P) overall. The tie-break on event_id is what makes the output deterministic when two partitions carry the same millisecond, which matters because the feed is paginated and a non-deterministic order reorders pages under the reader.
2. Emitting the heap head is only correct once every partition has produced everything up to that timestamp, so the emit condition is a watermark: the minimum across partitions of the highest occurred_at seen, less the allowed lateness. Events are held until the watermark passes them, which is what turns individually ordered streams into a jointly ordered one.
3. Size the buffer from the lateness rather than guessing: 4,000 events per second times 30 seconds is 120,000 buffered events, and at 1 KB each about 120 MB of heap. That number is the real price of the ordering guarantee and belongs in front of whoever asked for it.
4. Handle the idle partition explicitly, because it fails the feed rather than corrupting it: a partition with no traffic never advances its own maximum, so the watermark freezes and output stops entirely. Either every partition emits a periodic idle marker carrying the broker's current time, or the watermark falls back to wall clock for a partition silent beyond a threshold.

Follow-up

• The lateness budget is raised to five minutes. What is the new buffer, and what besides memory changes?
• The consumer restarts. Where does it resume from, and what does the feed look like for the first 30 seconds?

Track a rolling failure rate per destination for circuit decisions

Easy · sliding window · ring buffer · circuit breaker

The egress service delivers about 1,500 webhooks per second across roughly 40,000 destinations, each call bounded by a 10 second timeout. Maintain, per destination, the failure rate over the trailing 60 seconds so a caller can ask before dispatch whether the circuit should open. Attempts arrive as (destination_id, finished_at_ms, outcome). Requirement: amortised O(1) per attempt, with total memory bounded by the destination count rather than by traffic. Give the structure, its exact memory, and the rule that stops a destination with three attempts from opening a circuit.

Approach

1. Name the exact-deque version and then reject it as the default. Holding timestamps and advancing a tail pointer past anything older than now minus 60 seconds is a correct two-pointer window at amortised O(1) per attempt, but its memory tracks in-window traffic, so one destination in a retry storm holds hundreds of thousands of entries while thousands of quiet destinations hold none.
2. Use a ring of 60 one-second buckets per destination, each bucket a pair of counters for attempts and failures. On an attempt, advance the ring by the elapsed whole seconds, zeroing at most min(elapsed, 60) buckets, then increment the head. That is amortised O(1) with a fixed footprint per destination.
3. State the footprint: 60 buckets times two 4-byte counters is 480 bytes of payload per destination, so 40,000 destinations is roughly 20 to 25 MB with per-entry overhead, bounded by the catalogue rather than by the rate. The cost is granularity, since the oldest bucket ages out in whole seconds, which is far tighter than the decision needs.
4. Require a minimum sample before the circuit may open. A destination with three attempts and three failures reads as 100 percent and is not evidence; a floor of roughly 20 attempts in the window makes the ratio meaningful, and below that floor use a run of consecutive failures as the trigger instead.

Follow-up

• The fleet is 30 instances and each sees roughly a thirtieth of a destination's traffic. Where does the rate actually live, and what does a per-instance answer get wrong?
• A destination answers in 9.5 seconds and succeeds. It is not failing but it is consuming your per-destination concurrency. What signal should open the circuit here?

Diff a projection against the primary without per-row point reads

Hard · reconciliation · range hashing · throttling

The listing projection has drifted and some rows show a stale version. The primary holds 40,000,000 resource rows across 12,000 tenants while serving 1,200 writes and 14,000 reads per second. The obvious repair, reading each resource row and comparing its version against the projection, is correct and would eventually finish. Explain precisely why it is unacceptable here, then give a diff that finds the differing rows, state its complexity, and make it safe to run against a live primary. Replication lag is usually under 100 ms and is not bounded.

Approach

1. Quantify the naive cost rather than calling it slow: 40,000,000 point reads at even 0.5 ms each is over five hours serialised, and the only lever is concurrency, which is exactly what you cannot spend. The primary's pool is sized for the write path, and 40,000,000 random reads evict the buffer cache that sustains the 85 percent cache hit rate, so the audit degrades the system it is auditing.
2. Replace random access with one ordered pass per side. Both sides can be read in (tenant_id, resource_id) order, which is a sequential scan on each and a merge join in O(n) time and O(1) memory. For a dense diff that is the whole answer, and it reads the primary once instead of 40,000,000 times.
3. For the expected sparse case, compare range hashes instead of rows: partition the key space, compute per range an order-independent aggregate over hash(resource_id, version), compare aggregates, and descend only into ranges that differ. With d differing rows and branching factor B, at most d ranges mismatch per level, so the drill-down examines O(d log_B(n/d)) ranges and reads full rows only in mismatching leaves.
4. Aggregate with a sum modulo 2^64 or a multiset hash, never XOR. XOR is order-independent but self-cancelling, so two rows wrong in the same way, or a row duplicated on one side, leave the range aggregate matching and the range is declared clean.

Follow-up

• The diff reports 900 stale rows. How do you decide between patching those rows and rebuilding the projection from resource_revision?
• Same job, but the projection lives in a search index that cannot be scanned in key order. What changes?

How do you optimize a database query for better performance?

Medium · Technical Foundations and Web Developmen

Approach

1. Name the grain you start from and join outward from it.
2. Check whether any join is one-to-many before aggregating, or the sums inflate.
3. Say which index the query would use, and what makes it unusable.
4. Handle the rows that do not match: that is usually the actual question.

Follow-up

• How does the query change if that join becomes one-to-many?
• What happens to this when the table is ten times larger?

Can you explain the difference between various types of SQL joins and when to use them?

Medium · Technical Foundations and Web Developmen

Approach

1. Name the grain you start from and join outward from it.
2. Check whether any join is one-to-many before aggregating, or the sums inflate.
3. Say which index the query would use, and what makes it unusable.
4. Handle the rows that do not match: that is usually the actual question.

Follow-up

• How does the query change if that join becomes one-to-many?
• What happens to this when the table is ten times larger?

What are the common security vulnerabilities in web applications and how do you mitigate them?

Medium · Technical Foundations and Web Developmen

Approach

1. Clarify what is being asked and what a complete answer contains.
2. State your assumptions explicitly before working the problem.
3. Say what you would check first and why it is the highest-information step.
4. Work from the requirement backwards to the design.

Follow-up

• What assumption would you test first?
• How would you know your answer was wrong?

How do you manage session state in a stateless web environment?

Medium · Technical Foundations and Web Developmen

Approach

1. Clarify what is being asked and what a complete answer contains.
2. State your assumptions explicitly before working the problem.
3. Say what you would check first and why it is the highest-information step.
4. Work from the requirement backwards to the design.

Follow-up

• What assumption would you test first?
• How would you know your answer was wrong?

Walk us through a significant technical project you led or contributed to.

Medium · Academic and Project Experience

Approach

1. Clarify what is being asked and what a complete answer contains.
2. State your assumptions explicitly before working the problem.
3. Say what you would check first and why it is the highest-information step.
4. Work from the requirement backwards to the design.

Follow-up

• What assumption would you test first?
• How would you know your answer was wrong?

Describe your process for debugging a complex issue in a production web environment.

Medium · Technical Foundations and Web Developmen

Approach

1. Establish what changed and when, before forming any theory.
2. Pick a bisection that eliminates candidates whichever way it turns out.
3. Check the instrumentation before believing the symptom.
4. Separate the trigger from the cause; the deploy is rarely the bug.

Follow-up

• What would you look at first, and what would it rule out?
• How would you tell a cause from a coincidence here?

Suggested practice checklist

Built from the topics and questions Chicago candidates report; no round sequence has been reported.

Day 1 — Establish the Chicago format

• No round sequence has been reported, so ask your recruiter for the sequence, the duration of each stage and whether you will write code.

Deliverable: A written reply from your recruiter confirming the format.

Day 2 — Work PHP

• Spend the session on PHP, which Chicago candidates report being tested on.
• Write one worked example in PHP and time yourself on it.

Deliverable: One timed worked example in PHP.

Day 3 — Work Understanding of JOIN Operations

• Spend the session on Understanding of JOIN Operations, which Chicago candidates report being tested on.
• Write one worked example in Understanding of JOIN Operations and time yourself on it.

Deliverable: One timed worked example in Understanding of JOIN Operations.

Day 4 — Work Databases

• Spend the session on Databases, which Chicago candidates report being tested on.
• Write one worked example in Databases and time yourself on it.

Deliverable: One timed worked example in Databases.

Day 5 — Answer out loud: Technical Foundations and Web Development

• Answer aloud, timed: How do you optimize a database query for better performance?
• Answer aloud, timed: Can you explain the difference between various types of SQL joins and when to use them?

Deliverable: Spoken answers to 2 reported Technical Foundations and Web Development question(s), under time.

Day 6 — Answer out loud: Academic and Project Experience

• Answer aloud, timed: Walk us through a significant technical project you led or contributed to.

Deliverable: Spoken answers to 1 reported Academic and Project Experience question(s), under time.

Day 7 — Dry run for Chicago

• Run one full mock under time, then write down the two questions you most want to ask your interviewers.

Deliverable: A completed timed mock and two questions to ask.

Behavioural preparation

Behavioural rounds judge the decision you made and what it cost.

Reverse your own decision and price the reversal

Medium · reversibility · measurement · migrations

Describe a technical decision you made and later reversed. Pick one that cost something: a service you split and merged back, a cache you added and removed, an index you created that pushed the planner onto a worse plan, a projection you rebuilt from scratch. State what you believed when you decided, the measurement that changed your mind, how long the wrong version ran in production, and what the reversal cost in migrations, dual writes, and a deprecation window for callers you did not own.

Approach

1. State the original rationale without irony, in the version you would still defend given what was known then. If it is not defensible, the story is about carelessness rather than judgement, and a different example serves you better.
2. Give the measurement that moved with a before and after: the p99 that did not improve, the cache hit rate that sat at 40%, the plan that flipped to a sequential scan once the table passed a size you can name.
3. Cost the reversal in steps, not adjectives: expand-and-contract deploys, the dual-write window, the callers who had to be notified, the rows already written in the wrong shape that had to be backfilled or abandoned.
4. Distinguish reversal from rewrite by naming what you kept. Most good reversals preserve the schema or the interface and undo one decision inside it, which is also why they were affordable.

Follow-up

• What in that decision was irreversible, and did you know it was irreversible when you made it?
• How did you tell the people who had already built on top of the original decision?

Ship under a deadline and bound the debt you chose

Medium · pagination · technical debt · tradeoffs

You have four days to ship a tenant-facing listing endpoint. The version you would defend uses keyset pagination over (tenant_id, status, updated_at DESC, resource_id DESC); the version you can finish uses LIMIT/OFFSET with no matching index. Describe a deadline call you actually made of this shape: what you shipped, what you knowingly deferred, how you bounded the damage with a mechanism rather than an intention, and the specific numeric condition that would force the follow-up. Name who you told and where you wrote it down.

Approach

1. Name the deferred failure precisely instead of calling it slow. OFFSET n makes the database produce and discard n rows, so cost grows with page depth; without an index matching the sort, every matching row is read and sorted before the limit applies; and rows inserted between two page fetches shift across the boundary so items are skipped or repeated with nothing in the response to signal it.
2. Bound the blast radius with something mechanical rather than a promise: cap maximum page depth, cap page size, restrict the endpoint to one internal caller, or keep it behind a flag. State which failure each cap removes and which it leaves standing.
3. Attach a number to the trigger and wire it to an alarm: the first tenant crossing N resources, or the endpoint's p99 crossing its share of the 400 ms budget, so the debt announces itself instead of waiting to be remembered.
4. Write it where the next engineer looks, which is the code and the ticket, not a chat message: what was deferred, why, the cap, and the trigger.

Follow-up

• At what page depth does the offset version breach your latency budget, given your page size and row counts?
• What breaks first when you switch to keyset pagination later, and what does a client holding an old page token see?

Tell callers you do not own that their integration breaks

Medium · deprecation · compatibility · stakeholders

A field in a write endpoint's response must change shape. You own the endpoint; you do not own the four internal callers or the outbound webhook consumers who read it. Describe a deprecation you were responsible for: what you shipped first, how you established who was actually reading the field, the window you gave and what set its length, what you did about the consumer who never moved, and how you decided removal was safe. Name the signal you used, not the announcement you sent.

Approach

1. Establish the reader set empirically rather than from a wiki of owners: per-field usage counters keyed by principal, or access logs attributed to a consumer. State the blind spot of whichever you pick, since a consumer that reads the field only on a monthly job will not appear in a week of logs.
2. Ship additive first. Populate the new field alongside the old one so no reader is forced to move, which is also what keeps a rolling deploy safe, because old and new instances answer the same requests at the same time and a rollback must still find the old shape present.
3. Set the window from the slowest legitimate consumer's release cadence, not from your calendar, and decide separately what to do for a consumer with no release process at all, such as an external webhook endpoint you can only email.
4. Convert silence into evidence before you rely on it: a short, low-traffic removal window that makes a still-dependent consumer fail visibly and loudly while you are watching, rather than at three in the morning after you have moved on.

Follow-up

• How would you detect a consumer that reads the field only during a monthly export?
• One caller refuses to move and has a commercial relationship behind it. What changes in your plan and what does not?