AI in Family Offices: A Trustee's Governance-First Approach
Charlie Douglas is an attorney, certified financial planner, and trustee in a single family office. In this conversation, he discusses how the trustee role actually functions across three distinct obligations — investment oversight, trust administration, and distribution — and how artificial intelligence has changed the way he works across all three.
Key Takeaways:
The trustee role holds three functions. Investment oversight, trust administration, and distribution each carry different fiduciary exposure. A trustee may work with a CIO, but the trustee makes the final call on investment decisions. Douglas names distribution as the most important function, an exercise of the duty of care aimed at helping beneficiaries realize their potential.
Inside trusteeship trades objectivity for relational capital. Knowing the family builds trust and reduces friction. It also makes the trustee's no harder to deliver. An outside trustee brings that distance by design.
Trusts carry competing interests by design. Current beneficiaries seek income and remainder beneficiaries seek growth. Douglas manages the trade-off through a total-return approach and by explaining to every beneficiary how the trust works, including the difference between grantor and non-grantor trusts.
AI cuts working time by at least half, inside clear limits. Douglas uses it for analysis, drafting, and negotiation preparation. He redacts identifying information, cross-checks outputs across platforms, and leaves legal and tax advice to counsel and accountants.
The second half-hour carries the value. When a one-hour task takes thirty minutes, Douglas spends the recovered time going deeper on the same problem. That depth depends on knowing which question to ask next.
Informed adoption sets the standard. Raw AI output is easy to recognize. Douglas argues that advisors in every discipline need to learn to work with AI, and that judgment built over years is what makes the output useful.
