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Customer deployments

A forward deployed engineer interview on finding the real problem, shipping inside a customer's systems and rules, and being honest about limits.

These prompts are original practice. They are not questions from a named employer or a live hiring loop.

  1. 1.A regional grain co-op asks for a dashboard of every silo sensor. In the first call you learn managers mostly worry about spoiled grain they find too late. What is the best next step?

  2. 2.What is the main risk of treating a customer's feature request as the requirement itself?

  3. 3.A county library director wants AI search for the catalog. Staff say patrons mostly fail to find items because branch holdings are listed under inconsistent names. What does this suggest?

  4. 4.At a clinic, the manager says no-shows are the top scheduling problem. Front-desk staff say double-booked rooms lose more appointments. What do you do first?

  5. 5.In discovery, why ask a user to walk through a task live on their own screen instead of describing it?

  6. 6.A freight broker asks you to speed up the quoting API. Tracing one quote, you find the API answers in 300 ms but reps wait two hours for a manager to approve rates. What do you tell the sponsor?

  7. 7.Which discovery question best shows whether a problem is worth solving for a customer?

  8. 8.A school district asks for an integration that syncs all student data to your platform. The pilot only needs attendance to flag chronic absence. What is the best response?

  9. 9.The operations lead at a shipping yard keeps saying the system is slow. What is the most useful follow-up?

  10. 10.A water utility wants a 90-day pilot for leak alerts. Which success criterion is the strongest?

  11. 11.Why agree on pilot success criteria in writing before the pilot starts?

  12. 12.Midway through a hotel group's pilot for room-turnover forecasts, the sponsor asks to add staffing forecasts too. What do you do?

  13. 13.A dental chain's pilot ends. Two of three success criteria were met. The third could not be tested because the chain never provided billing data. How do you report it?

  14. 14.Which is the best scope for a first pilot at a mid-size insurer?

  15. 15.A customer wants a pilot just to see if it works. What is missing that you should help define?

  16. 16.You are scoping a six-week pilot at a hospital lab. The lab's IT team needs eight weeks to approve any new data connection. What is the best move?

  17. 17.What do exit criteria mean for a pilot?

  18. 18.A logistics customer's pilot goal is to reduce manual work. What is the strongest way to make that measurable?

  19. 19.A farm-supply store lists one item as Fertilizer 10-10-10, FERT 10/10/10, and 10-10-10 fert. What is the best first approach?

  20. 20.A property manager's CSV export has dates written as 03/04/2025 and as 2025-04-03 in the same column. What should you do before loading it?

  21. 21.A wholesale bakery's order export has a customer_id column. You find the IDs were reset after a system migration in 2022. What is the main risk?

  22. 22.Why profile a customer's data, such as null rates, distinct values, and ranges, before building on it?

  23. 23.A transit agency sends GPS pings for its buses. About 5 percent place buses in the ocean. What is the best way to handle them?

  24. 24.An HR customer's employee feed has blank departments for contractors. Your org chart feature needs a department. What is the best choice?

  25. 25.A customer says their data is clean. Your first sample load fails on 12 percent of rows. How do you raise it?

  26. 26.Two systems at a hardware retailer report different weekly sales for the same store. What should you check first?

  27. 27.You join addresses from a power utility's billing system to its outage system, and only 40 percent match. What is the best next step?

  28. 28.A credit union's core banking system only exports nightly fixed-width files over SSH File Transfer Protocol (SFTP). The customer wants near real-time alerts. What should you tell them?

  29. 29.A manufacturer's legacy enterprise resource planning (ERP) system has a SOAP API that times out on requests over 500 records. What is the most practical approach?

  30. 30.Why is writing directly into a legacy application's database tables usually a bad idea?

  31. 31.A county court runs a mainframe that its IT team will not change. Clerks re-key case data into a newer system by hand. What is a reasonable first integration?

  32. 32.A legacy inventory system returns HTTP 200 with an error message in the body when a request fails. What must your integration do?

  33. 33.A trucking firm's legacy system stores local timestamps with no time zone offset. What is the main risk when you load them?

  34. 34.You must integrate with a legacy app whose only documentation is a 2011 PDF, and its behavior differs from the PDF. What do you trust?

  35. 35.A distributor's order system can only be reached through a Windows desktop client with no API. Which assessment is most honest?

  36. 36.A defense supplier runs your product on an air-gapped network. How do you deliver an update?

  37. 37.What does single sign-on (SSO) through Security Assertion Markup Language (SAML) or OpenID Connect give a customer's IT team?

  38. 38.A hospital lets you in only through a virtual private network (VPN) that drops every 8 hours. Your data sync job takes 10 hours. What do you do?

  39. 39.A bank's security team rejects your plan to run a support agent with outbound internet access on their servers. What is the best response?

  40. 40.An on-prem customer uses a corporate proxy that intercepts TLS. Your app fails with certificate errors on outbound API calls. What is the right fix?

  41. 41.A city government requires that no customer data leave its cloud account. Your product sends logs to your hosted monitoring by default. What should you do?

  42. 42.What does the principle of least privilege mean when you request access to a customer system?

  43. 43.You want to use Secure Shell (SSH) to debug a customer's on-prem server. Their policy allows only screen-sharing sessions where their admin types. What do you do?

  44. 44.A customer's identity provider sends group names in SAML assertions. After a reorganization, some users lose access to your app. What is the most likely cause?

  45. 45.A pharmacy chain wants your product on servers with no internet access. Your installer pulls containers from a public registry. What must you prepare?

  46. 46.To debug a matching bug at a health insurer, a colleague asks you to copy a sample of member records to your laptop. What do you do?

  47. 47.A school district gives you read access to a database. You find a table of student disability records unrelated to your work. What should you do?

  48. 48.A retailer wants your product to use purchase history to personalize offers. Its privacy notice says data is used to fulfill orders. What do you raise?

  49. 49.Which is the best practice for credentials a customer gives you for an integration?

  50. 50.A customer asks you to delete all their data at the end of a pilot. Besides the main database, what must you check?

  51. 51.In a data processing agreement, what does the processor role usually mean for your company?

  52. 52.A clinic wants you to train a model on visit notes. What should you agree on first?

  53. 53.In two days you built a prototype that pulls a bakery chain's orders with a script on your laptop. The sponsor loves it and wants it live Monday. What do you say?

  54. 54.When is a quick prototype the right choice over a durable integration?

  55. 55.A prototype for a ferry operator works on 100 sample bookings. The real feed has 2 million a day. What should you test before calling it ready?

  56. 56.Which sign best shows that a temporary script at a customer has become production?

  57. 57.A nonprofit needs a report integration fast for next week's board meeting. How do you keep it from becoming permanent debt?

  58. 58.A prototype hard-codes a customer's warehouse codes. Which change most moves it toward a durable integration?

  59. 59.What does making an integration job idempotent buy you in a customer deployment?

  60. 60.A customer wants a one-time migration of 10 years of records from an old customer relationship management (CRM) system. How durable should the code be?

  61. 61.Three customers in one quarter ask you to build the same export to a common accounting format. What should you do?

  62. 62.A large customer asks for a change to the core data model that only they need. What is the main risk of merging it into the product?

  63. 63.Why do products offer extension points such as webhooks or plugin hooks?

  64. 64.You built a custom connector for a regional library network. Product says it is useful but not a priority. What should you do with it?

  65. 65.Which signal is the strongest reason to move custom work into the core product?

  66. 66.A product manager asks why your customer forks keep drifting from the main branch. What practice would most reduce that?

  67. 67.A customer wants a feature the product team plans for next quarter. Building it custom now takes two weeks. What is the best approach?

  68. 68.Which field report is most useful to a product team?

  69. 69.Field teams keep building the same retry wrapper around one core API. What should you report?

  70. 70.Why should field feedback separate the customer's problem from the customer's proposed solution?

  71. 71.A product team has not acted on your feedback for months. What is the most effective next step?

  72. 72.A fuel distributor asks for a feature you suspect is niche. How should you log it?

  73. 73.Customers keep misunderstanding one product setting. What is the most useful feedback to send product?

  74. 74.A customer executive emails angrily that your integration lost a week of orders. What do you do first?

  75. 75.During an incident at a grocery chain, the sponsor asks when it will be fixed. You do not know yet. What do you say?

  76. 76.A customer's account team promised a feature by March that your product does not have. You learn about it in February. What should you do?

  77. 77.Why set a regular check-in cadence with a customer during a deployment?

  78. 78.An escalation at a warehouse turns out to be caused by the customer's own firewall change. How do you communicate it?

  79. 79.A customer expects your forecasting product to be 99 percent accurate. Your tests show about 85 percent on their data. When should you tell them?

  80. 80.A frustrated user at a transit agency calls you directly, going around their own IT team. What is the best response?

  81. 81.What is the purpose of a blameless postmortem after a customer-facing incident?

  82. 82.A customer asks whether your product can process live video from 500 cameras. It handles about 20 today. What is the best answer?

  83. 83.A sponsor asks you to write that the pilot met all goals in a board memo. It met two of three. What do you do?

  84. 84.Why is saying not yet, and here is what would need to be true, often better than a flat no?

  85. 85.A lender wants your product to make final loan approvals automatically. The product is built to support human review. What do you say?

  86. 86.A customer asks for a delivery date for a feature engineering has not committed to. What do you say?

  87. 87.A veterinary practice asks you to add a feature in one week. You estimate four. What is the most useful answer?

  88. 88.When a customer pushes back on your no, what keeps it credible?

  89. 89.You are handing off an integration to a regional airline's IT team. Which document helps them most?

  90. 90.What is the best test that a handoff is complete?

  91. 91.Before leaving a pharmacy deployment, you find the sync job runs under your personal service account. What should you do?

  92. 92.Which handoff item do teams most often forget, and later pay for?

  93. 93.A customer's team is new to your product. What is the best handoff approach?

  94. 94.A customer asks you to stay on call for their integration indefinitely after handoff. What is the best response?

  95. 95.You leave a monitoring dashboard as part of a handoff. What makes it useful to the customer?

  96. 96.Why write down the reason behind an unusual configuration choice in a deployment?

  97. 97.After go-live at a property management firm, logins are high but key workflows are rarely completed. What does this suggest?

  98. 98.What is a good leading indicator of adoption in the first weeks after go-live?

  99. 99.Adoption at one branch of a credit union is far lower than at the others. What do you do first?

  100. 100.A customer's users have gone back to a spreadsheet for one step of the workflow. What is the best reading of this?

  101. 101.Three months after go-live at a fleet maintenance shop, usage is steady but the promised cost savings are not visible. What should you check?

  102. 102.Some staff at a museum stopped using your scheduling tool. What is the best way to learn why?

  103. 103.Your integration works in your test setup but fails at a customer site with connection reset errors. What should you check first?

  104. 104.You cannot get shell access to a customer's server. How do you gather useful debug data?

  105. 105.An on-prem install fails only on Tuesdays around 2 a.m. What is the most likely cause to check?

  106. 106.Why should your product's logs include the version, a config hash, and timestamps with a time zone?

  107. 107.A fix works on your staging copy but not at the customer site. What is the best next step?

  108. 108.A customer reports wrong totals in your report, but you cannot see their data. How do you start?

  109. 109.Your app runs in a customer's Kubernetes cluster and restarts every few hours. Logs show nothing before each restart. What should you check first?

  110. 110.A customer site runs the same version as your test setup, but some numbers parse differently. What is often overlooked?