Trade Support Specialist - Middle Office
Posted Aug 19, 2026 · We last checked this listing on Oct 6, 2026
Likely interview questions for this role
Written from this job description, not a generic list. Each one notes what the interviewer is really checking.
About your past
Tell me about a time you improved a workflow using a tool, script or better process.
What they are checking: Whether they look for better ways to work, which the role explicitly asks for.
Tell me about a mistake you made at work. How did you handle it?
What they are checking: Honesty and speed in raising errors, which matters more than never making one.
Why middle office at a proprietary trading firm?
What they are checking: Real interest in markets and operations rather than seeing the role as a stopgap.
What would you do
Our P&L and the clearing firm's statement are off by a meaningful amount. How do you find out why?
What they are checking: A structured approach to breaks across trades, prices, fees and corporate actions.
A trader disputes a fill and says it was booked wrong. How do you handle it?
What they are checking: Calm investigation using records and fair communication, even when a trader is frustrated.
Several desks need things from you at once near the close. How do you decide what comes first?
What they are checking: Whether they rank tasks by risk and deadline, not by who is loudest.
About the work
You will support equity options trading desks. Walk me through the middle office checks you would run at the end of each trading day.
What they are checking: Knowledge of trade, position and P&L reconciliation that keeps the books right.
How does a corporate action like a stock split affect an options position?
What they are checking: Understanding of contract adjustments, which commonly cause errors in options books.
What happens to equity options on expiration Friday, and what can go wrong operationally?
What they are checking: Awareness of exercise and assignment, pin risk and the deadlines that make expiry demanding.
How would you use SQL or Python to spot trades that look unusual or misbooked?
What they are checking: Practical data skills that let them check large volumes instead of eyeballing.
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Practice this out loudThe full job description
As published by DRW.