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Total Wine & More Software Engineer Interview Guide

Total Wine & More Software Engineer interview guide: reported rounds, questions and how candidates describe the process.

The 60-second brief

A Software Engineer at Total Wine & More plays a pivotal role in developing and maintaining the technology solutions that support the company’s operations and enhance customer experiences. As the largest independent retailer of fine wine in the U.S., the impact of this position extends to various facets of the business, including e-commerce platforms, inventory management systems, and customer engagement tools. By leveraging innovative technologies, you will help optimize processes, improve user interfaces, and ensure that our software solutions align with business goals. In this dynamic position, you will collaborate with cross-functional teams to build scalable applications that serve millions of customers.

This guide is scoped to a Software Engineer candidate at Total Wine & More.

Focus areas

  • Database Fundamentals
  • Object-Oriented Programming (OOP)
  • Service-Oriented Architecture (SOA)

The Total Wine & More interview process

Total Wine & More candidates report 2 rounds over 2-4 weeks. The stages below are what candidates describe, not a published process.

Phone Screening

Initial phone screening to assess candidate's background and fit for the role.

What to demonstrate

  • Initial phone screening to assess candidate's background and fit for the role
  • Depth in Database Fundamentals

How to prepare

  • Be able to walk your CV end to end in two minutes, and say why this company specifically.
  • Have your salary expectations, notice period and location constraints ready, and ask for the rest of the loop in writing.

Technical Interviews

One or more technical interviews focusing on coding challenges, system design, and behavioral questions.

What to demonstrate

  • One or more technical interviews focusing on coding challenges, system design, and behavioral questions
  • Depth in Database Fundamentals

How to prepare

  • Answer aloud and timed: Describe a software project you worked on and the technologies used.
  • Answer aloud and timed: How do you approach debugging and troubleshooting code?

Where candidates lose points

Research the Company

Familiarize yourself with Total Wine & More's mission, values, and product offerings to demonstrate genuine interest during your interview.

Prepare for Technical Questions

Brush up on coding challenges and technical topics relevant to the role. Practice coding on platforms like LeetCode or HackerRank.

Showcase Your Projects

Be ready to discuss specific projects you've worked on. Highlight your contributions, challenges faced, and outcomes achieved.

Practice Behavioral Questions

Use the STAR (Situation, Task, Action, Result) method to structure your responses to behavioral questions, ensuring clarity and depth in your answers.

Questions & practice

Write a function to reverse a string.

Medium · Coding / Algorithms

Approach

  1. Restate the input: its shape, its size, and what is guaranteed about it.
  2. Name the brute-force solution and its complexity before improving on it.
  3. Choose the data structure from the access pattern, not from familiarity.
  4. State the target complexity and say which constraint rules the naive version out.

Follow-up

  • How does this change if the input no longer fits in memory?
  • What is the worst case, and how likely is it on real data?

How would you implement a search algorithm in a sorted array?

Medium · Coding / Algorithms

Approach

  1. Restate the input: its shape, its size, and what is guaranteed about it.
  2. Name the brute-force solution and its complexity before improving on it.
  3. Choose the data structure from the access pattern, not from familiarity.
  4. State the target complexity and say which constraint rules the naive version out.

Follow-up

  • How does this change if the input no longer fits in memory?
  • What is the worst case, and how likely is it on real data?

Explain the concept of recursion with an example.

Medium · Coding / Algorithms

Approach

  1. Restate the input: its shape, its size, and what is guaranteed about it.
  2. Name the brute-force solution and its complexity before improving on it.
  3. Choose the data structure from the access pattern, not from familiarity.
  4. State the target complexity and say which constraint rules the naive version out.

Follow-up

  • How does this change if the input no longer fits in memory?
  • What is the worst case, and how likely is it on real data?

What are the time complexities of common sorting algorithms?

Medium · Coding / Algorithms

Approach

  1. Restate the input: its shape, its size, and what is guaranteed about it.
  2. Name the brute-force solution and its complexity before improving on it.
  3. Choose the data structure from the access pattern, not from familiarity.
  4. State the target complexity and say which constraint rules the naive version out.

Follow-up

  • How does this change if the input no longer fits in memory?
  • What is the worst case, and how likely is it on real data?

Describe how you would solve a problem involving data structures like trees or graphs.

Medium · Coding / Algorithms

Approach

  1. Restate the input: its shape, its size, and what is guaranteed about it.
  2. Name the brute-force solution and its complexity before improving on it.
  3. Choose the data structure from the access pattern, not from familiarity.
  4. State the target complexity and say which constraint rules the naive version out.

Follow-up

  • How does this change if the input no longer fits in memory?
  • What is the worst case, and how likely is it on real data?

Hold a per-tenant active cap against concurrent creates

Hard · write skew · isolation levels · constraints

A tenant on the standard plan may hold at most 50 resources with status='active'. The create handler runs SELECT count(*) FROM resource WHERE tenant_id = $1 AND status = 'active', compares to 50, then inserts. Two creates arrive 3 ms apart on different instances and the tenant lands at 51. Name the anomaly, say whether PostgreSQL 16 READ COMMITTED or REPEATABLE READ prevents it and why, then give an implementation that holds the cap at READ COMMITTED with the exact statements. Finally, say what changes when the cap is 'at most one running export per tenant' on job_run.

Approach

  1. Name it: write skew. The two transactions read an overlapping set and write disjoint rows, so there is no row-level conflict for the engine to detect and each commit is individually legal.
  2. Rule out the levels precisely. READ COMMITTED takes a fresh snapshot per statement and takes no lock on the counted rows, so both see 49. PostgreSQL's REPEATABLE READ is snapshot isolation: it removes non-repeatable reads and phantoms within the snapshot but still admits write skew, because the anomaly is not a re-read of a changed row, it is a read of a set that a concurrent transaction invalidates. Only SERIALIZABLE closes it, by tracking the read dependency and aborting one transaction with SQLSTATE 40001 — a guarantee that exists only if the application re-runs the whole transaction from the read.
  3. Convert the set predicate into a single-row conflict: keep tenant.active_resource_count and run UPDATE tenant SET active_resource_count = active_resource_count + 1 WHERE tenant_id = $1 AND active_resource_count < 50 in the same transaction as the INSERT. Zero affected rows is the cap, returned as 409. The row lock serialises the decision at any isolation level, and contention is bounded to one tenant's row — which is also the fair-scheduling unit, unlike a global counter that would convoy every tenant behind one row.
  4. State the cost you just took on: a counter is a second source of truth that can drift, so every path that changes status must adjust it inside the same transaction, and a periodic reconciliation has to exist, with resource_revision as the authority for what the count should have been.

Follow-up

  • A resource moves from archived back to active. Which statements change, and what breaks if the counter update and the status change land in different transactions?
  • The cap becomes plan-dependent and a plan can change mid-month. Where does the number 50 live, and who reads it?

Denormalise tenant onto revisions and backfill it live

Hard · denormalisation · online migration · backfill

resource_revision (revision_id, resource_id, version, actor_user_id, change_kind, patch, request_id, created_at) has 400M rows and no tenant column; tenant_id lives only on resource. Two reads need it: a tenant-scoped audit feed ordered by created_at DESC, and an offboarding purge. Both join back to resource today. Justify adding tenant_id to resource_revision against those two reads, name the anomaly the copy introduces and the constraint that prevents it, then give the ordered migration for a live table taking 1.2k writes/second — the lock each step takes, how the backfill is batched, and where each step stops being reversible. PostgreSQL 16.

Approach

  1. Justify from the access path rather than from taste. Without the column, the audit feed either scans resource_revision by created_at and discards other tenants' rows, or resolves the tenant's resource_ids first and probes with them — both proportional to the tenant's whole history rather than to one page. With (tenant_id, created_at DESC, revision_id DESC) it is a seek that stops at 50 rows, and the purge becomes a ranged delete instead of a join.
  2. Name the cost exactly: a second copy of a fact can disagree with the first. Make the disagreement unwritable rather than documented — add UNIQUE (resource_id, tenant_id) on resource so it can serve as a foreign-key target, then FOREIGN KEY (resource_id, tenant_id) REFERENCES resource (resource_id, tenant_id) on the revision table. A revision can then only ever carry its parent's tenant.
  3. Step one, expand: ALTER TABLE resource_revision ADD COLUMN tenant_id BIGINT NULL, with no default, so it is a catalogue change and no rewrite. It still needs ACCESS EXCLUSIVE for an instant, and that instant queues behind the longest open transaction on the table while every later query queues behind it — set lock_timeout to 2s and retry rather than wait.
  4. Step two, dual-write: deploy the writer that populates tenant_id on every new revision while reads still use the join. Reversible by redeploying the previous build, because nothing reads the column yet.

Follow-up

  • The backfill is half finished and a rollback is required. What state is the table in, and what does the previous build do with a half-populated column?
  • How do you verify the backfill actually finished, given rows are still being inserted while it runs?

What programming languages are you proficient in, and how have you used them in past projects?

Medium · Technical / Domain Questions

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?

Can you explain the difference between object-oriented programming and functional programming?

Medium · Technical / Domain Questions

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 a software project you worked on and the technologies used.

Medium · Technical / Domain Questions

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?

What experience do you have with cloud services, such as AWS or Azure?

Medium · Technical / Domain Questions

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 would you approach optimizing a slow-performing application?

Medium · Problem-Solving / Case Studies

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?

Given a set of requirements, how would you design a simple software solution?

Medium · Problem-Solving / Case Studies

Approach

  1. Fix the scope first: who calls this, how often, and what they do when it fails.
  2. Name the read and write paths separately; they rarely have the same bottleneck.
  3. Choose a partition key and say what query it makes expensive.
  4. State the consistency you need, and where you are willing to be stale.

Follow-up

  • What breaks first when traffic grows ten times?
  • How does this behave when that dependency is down for an hour?

What steps would you take to identify and mitigate risks in a software project?

Medium · Problem-Solving / Case Studies

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 how you would implement a new feature based on customer feedback.

Medium · Problem-Solving / Case Studies

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 stay updated with the latest industry trends and technologies?

Medium · Problem-Solving / Case Studies

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 approach debugging and troubleshooting code?

Medium · Technical / Domain Questions

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 rounds and topics Total Wine & More candidates report.

Day 1 — Map the Total Wine & More loop

  • Write out the reported sequence: Phone Screening, Technical Interviews.
  • For each round, write one sentence on what it is judging, from the description above, and mark the one you are least ready for.

Deliverable: A one-page map of the 2 reported rounds, with the weakest marked.

Day 2 — Work Database Fundamentals

  • Spend the session on Database Fundamentals, which Total Wine & More candidates report being tested on.
  • Write one worked example in Database Fundamentals and time yourself on it.

Deliverable: One timed worked example in Database Fundamentals.

Day 3 — Work Object-Oriented Programming (OOP)

  • Spend the session on Object-Oriented Programming (OOP), which Total Wine & More candidates report being tested on.
  • Write one worked example in Object-Oriented Programming (OOP) and time yourself on it.

Deliverable: One timed worked example in Object-Oriented Programming (OOP).

Day 4 — Work Service-Oriented Architecture (SOA)

  • Spend the session on Service-Oriented Architecture (SOA), which Total Wine & More candidates report being tested on.
  • Write one worked example in Service-Oriented Architecture (SOA) and time yourself on it.

Deliverable: One timed worked example in Service-Oriented Architecture (SOA).

Day 5 — Answer out loud: Technical / Domain Questions

  • Answer aloud, timed: What programming languages are you proficient in, and how have you used them in past projects?
  • Answer aloud, timed: Can you explain the difference between object-oriented programming and functional programming?

Deliverable: Spoken answers to 2 reported Technical / Domain Questions question(s), under time.

Day 6 — Answer out loud: Behavioral / Leadership

  • Answer aloud, timed: Tell me about a time you faced a significant challenge in a project. How did you handle it?
  • Answer aloud, timed: How do you prioritize tasks when working on multiple projects simultaneously?

Deliverable: Spoken answers to 2 reported Behavioral / Leadership question(s), under time.

Day 7 — Answer out loud: Problem-Solving / Case Studies

  • Answer aloud, timed: How would you approach optimizing a slow-performing application?
  • Answer aloud, timed: Given a set of requirements, how would you design a simple software solution?

Deliverable: Spoken answers to 2 reported Problem-Solving / Case Studies question(s), under time.

Behavioural preparation

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

Tell me about a time you faced a significant challenge in a project. How did you handle it?

Medium · Behavioral / Leadership

Approach

  1. Pick a story where you made the decision, not one where you watched it.
  2. State the situation in two sentences and spend the rest on the reasoning.
  3. Give the blast radius: what could have broken, and what you measured.
  4. Name the disagreement and how you resolved it with evidence.

Follow-up

  • What would you do differently if you ran that again?
  • How did you know your change caused the improvement?

How do you prioritize tasks when working on multiple projects simultaneously?

Medium · Behavioral / Leadership

Approach

  1. Pick a story where you made the decision, not one where you watched it.
  2. State the situation in two sentences and spend the rest on the reasoning.
  3. Give the blast radius: what could have broken, and what you measured.
  4. Name the disagreement and how you resolved it with evidence.

Follow-up

  • What would you do differently if you ran that again?
  • How did you know your change caused the improvement?

Describe a situation where you had to collaborate with a difficult team member.

Medium · Behavioral / Leadership

Approach

  1. Pick a story where you made the decision, not one where you watched it.
  2. State the situation in two sentences and spend the rest on the reasoning.
  3. Give the blast radius: what could have broken, and what you measured.
  4. Name the disagreement and how you resolved it with evidence.

Follow-up

  • What would you do differently if you ran that again?
  • How did you know your change caused the improvement?

What motivates you to work in a team environment?

Medium · Behavioral / Leadership

Approach

  1. Pick a story where you made the decision, not one where you watched it.
  2. State the situation in two sentences and spend the rest on the reasoning.
  3. Give the blast radius: what could have broken, and what you measured.
  4. Name the disagreement and how you resolved it with evidence.

Follow-up

  • What would you do differently if you ran that again?
  • How did you know your change caused the improvement?

How do you handle constructive criticism?

Medium · Behavioral / Leadership

Approach

  1. Pick a story where you made the decision, not one where you watched it.
  2. State the situation in two sentences and spend the rest on the reasoning.
  3. Give the blast radius: what could have broken, and what you measured.
  4. Name the disagreement and how you resolved it with evidence.

Follow-up

  • What would you do differently if you ran that again?
  • How did you know your change caused the improvement?