Trust Associate I
Posted Aug 28, 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
Trust work involves families in difficult moments — a death, a dispute. How would you handle a call from a grieving beneficiary?
What they are checking: Whether they can handle grieving or distressed family members with patience and care, since trust work often happens during very difficult moments.
How do you work with a trust officer who is on the road seeing clients?
What they are checking: Whether they can support a busy trust officer who is often away, keeping work moving and communication clear without constant direction.
What would you do
How would you handle a beneficiary asking for a distribution the trust terms do not clearly allow?
What they are checking: Whether they read trust terms carefully and know when to escalate rather than decide, because acting beyond the document can create real liability.
Two family members give you conflicting instructions. What do you do?
What they are checking: Whether they handle conflicting family instructions by following the trust terms and escalating, rather than picking a side between beneficiaries.
What would you not discuss, and with whom, in a family trust?
What they are checking: Whether they understand confidentiality inside a family, since beneficiaries are often related but not entitled to the same information about the trust.
This is a first-level associate role in Lake Forest. What do you want this to lead to, and what would you want to know about the team before you took it?
What they are checking: Whether they have a real sense of where they want to grow and ask thoughtful questions about the team before committing to this role.
About the work
This is an entry trust role supporting a wealth management business serving high net worth clients and institutions, based in Lake Forest. What do you understand a trust to be and why someone sets one up?
What they are checking: Whether they understand what a trust is and why people create one, which is the basic knowledge this wealth management role builds on.
What is the difference between a trustee's duty to a beneficiary and a bank's duty to a customer?
What they are checking: Whether they understand fiduciary duty and how it differs from ordinary customer service, since that distinction shapes every decision in trust work.
You'd support administration across accounts. How do you keep records accurate on something that runs for decades?
What they are checking: Whether they keep careful records that will hold up over decades, because trusts can run for generations and errors compound over time.
Trust accounts carry tax and reporting deadlines. How would you make sure none of them slips?
What they are checking: Whether they have a reliable system for tracking tax and reporting deadlines, because a missed trust deadline can cause real financial consequences.
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As published by Wintrust.