Senior Systems Engineer - Microsoft
Posted Sep 22, 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
The team believes in relentless automation of repetitive tasks. Tell me about something manual you automated with PowerShell and what it saved.
What they are checking: Whether automation is a habit they act on, measured by real time or errors saved, not a buzzword.
Tell me about the hardest Exchange, Microsoft 365 or Intune problem you have solved. How did you work it out?
What they are checking: Whether they dig to the real cause with logs and tools instead of reinstalling until it goes away.
The philosophy says the right thing matters more than rigid job boundaries. Describe a time you fixed something that was not technically your job.
What they are checking: Whether they take ownership across team lines while still keeping the owning team in the loop.
What would you do
A trader cannot log in ten minutes before the market opens, and it looks like a Group Policy or authentication problem. What do you do?
What they are checking: Whether they can restore the person to work fast under pressure first, then chase the root cause afterward.
How would you treat trading desks as customers when you have to deliver bad news, like a request you cannot safely support?
What they are checking: Their ability to give excellent service while still saying no clearly and offering a workable alternative.
You inherit a Microsoft environment with years of undocumented changes. How do you get it under control without breaking things?
What they are checking: Whether they inventory and stabilize carefully before making big changes to a system they do not fully understand.
About the work
Walk me through how you have run Active Directory at scale. What does a healthy domain look like to you, and what do you check first when it is not?
What they are checking: Depth with replication, DNS, sites and FSMO roles, which every other Microsoft service at the firm depends on.
How would you manage identity and devices across on-premises Active Directory and Entra ID in a hybrid setup?
What they are checking: Understanding of sync, conditional access and where hybrid identity tends to break in practice.
How do you roll out Windows patches to a trading floor where an unexpected reboot or broken app during market hours is not acceptable?
What they are checking: Their use of rings, maintenance windows and rollback plans to balance security against trading uptime.
How do you approach securing privileged access in a Microsoft environment?
What they are checking: Knowledge of tiered admin, least privilege and protecting domain admin credentials, since a firm trading its own capital is a target.
How do you decide between configuration as code and making a change by hand in the console?
What they are checking: Whether they value repeatable, reviewable changes and know when a one-off manual fix is acceptable.
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As published by DRW.