7 key questions to ask your chosen trustee

Selecting a trustee is one of the most consequential decisions in wealth and estate planning. Your trustee will be the steward of your assets, the interpreter of your intent, and the one charged with balancing fiduciary responsibility, family dynamics, and legal compliance.

Whether you are considering a family member, a close confidant, or a corporate trustee, the right choice requires asking the right questions. These seven inquiries move beyond surface-level qualifications and help you understand how a trustee will act in practice.

1. How will you ensure my intentions are faithfully carried out?

A trustee’s role is more than following documents, it is honoring your intent. Ask how they reconcile the legal terms of a trust with the spirit of your goals and values, especially when the two may not perfectly align.

2. What depth of experience do you bring to trust administration?

Administering a trust requires knowledge of law, tax, accounting, investments, and family governance. Trustees should be prepared to share examples of situations they’ve successfully navigated, from complex tax filings to resolving disputes among beneficiaries.

3. How do you communicate with beneficiaries and advisors?

Trustees sit at the center of a web of relationships. Their ability to communicate consistently, document decisions, and coordinate with outside counsel, CPAs, and investment managers is essential. Ask about their cadence, methods, and commitment to transparency.

4. How do you balance impartiality with empathy?

Fiduciary duty requires impartiality, but beneficiaries are human. A skilled trustee must make objective decisions while managing relationships with diplomacy. Explore how they have resolved conflicts or navigated competing interests in the past.

5. What systems and infrastructure do you have in place?

Trusts involve more than investment oversight, they require bill payment, tax filings, insurance review, real estate management, and recordkeeping. Trustees need the operational capacity to manage these responsibilities reliably, year after year.

6. How do you approach investment oversight and risk management?

Trust assets often extend beyond traditional portfolios. A capable trustee knows how to oversee or coordinate management of concentrated stock positions, private business interests, or real estate holdings. Ask how they evaluate risk and monitor performance.

7. How do you prepare for the eventual settlement of the trust?

At termination, a trustee must gather assets, resolve liabilities, file tax returns, and make distributions. Their approach to this process will determine whether settlement is smooth or contentious. Inquire about their experience winding down trusts and protecting all parties during transition.

Moving Beyond Credentials

Credentials matter, but trusteeship is ultimately about stewardship and trust. The right trustee is one who can demonstrate not only technical competence, but also the discipline, impartiality, and foresight to carry out your vision over time.

At Enterprise Trust, we bring an integrated approach to trusteeship, combining fiduciary expertise, tax awareness, and investment oversight with a clear-eyed commitment to carrying out your intentions. Asking the right questions now ensures your legacy is administered with clarity and confidence.