‘Pioneers Get Shot, Settlers Get Rich’: FOs Approach AI With Curiosity and Caution

As family offices look to harness technology for greater efficiency and impact in 2026, artificial intelligence looms large, across both operations and investing. With AI no longer just a theoretical discussion or future investment theme, family offices are (cautiously) asking not whether AI will affect them, but rather where it should — and should not — play a role.

As family offices look to harness technology for greater efficiency and impact in 2026, artificial intelligence looms large, across both operations and investing. With AI no longer just a theoretical discussion or future investment theme, family offices are asking not whether AI will affect them, but rather where it should — and should not — play a role.

“AI advancements and investments will be something to watch” for family offices in 2026, says Wendy Craft, chief executive officer of Elle Family Office.

AI presents both risks and opportunities for family offices’ portfolios and opportunities for operational efficiency.

“Everybody’s thinking and talking about AI,” says Stacy Dick, operating partner with Wingspan Legacy Partners. “What’s fascinating about AI in the family office context is it has implications for both sides of the business. In investing, you are worrying about parts of your portfolio that will be impacted negatively by AI, and opportunities that may arise for investing in and around AI. On the operations side, I think there’s tremendous opportunity for AI to streamline some of the processes that are necessary to run the administrative and legal end of a family office.”

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Hopes for streamlined processes may be balanced by realism about the difficulties of adopting new technology.

“Most of the family offices I’m seeing are cautiously optimistic about the potential use of AI,” says Christopher Dickson, national family office advisory leader for RSM US LLP.

Many family offices may prefer to wait for the tools to mature.

“You’ve probably heard this expression that pioneers get shot and settlers get rich,” Dick says. “Sometimes you don’t want to be the first one to adopt a technology, and I think the smartest family offices are proceeding very carefully not to be the first one in, not to spend hundreds of thousands or millions of dollars implementing a system which in a year will be off the shelf. You don’t want to be the guinea pig where, in effect, the software provider is using your money to develop their product.”

Image by Cassidy Reed

Family offices also have to contend with the heightened security risks that AI brings.

“With deepfake voices and deepfake images now, everybody’s scared to death that they’re going to wire $20 million to someone in, you know, Antarctica,” Dick says. “Family offices are seen as a soft target, because we have lots of assets, and our staff tends not to be at the cutting edge of technology, so we rely very heavily on our service providers and our counterparties.”

The cost of indecision 

The fear of being left behind is very real, though — and some family office leaders say they are forging ahead in 2026.

Thomas Ruggie, founder and CEO of Destiny Family Office, says one of his 2026 priorities is to evaluate the role AI will play to generate efficiencies.

“It is important to me to stay ahead of the curve, never be complacent,” he says.

Dickson says that in the near and mid-term, family offices that are moving slowly will likely be able to operate effectively without actively adopting AI tools, provided they have clear internal guidance so staff understand when and how AI should—and should not—be used. Over the longer term, however, family offices that do not engage with AI at all may face growing challenges — in both the technical arena and staffing.

“Family offices are not necessarily competing with one another on revenue or profit, but they are competing for talent,” Dickson says. Because many family offices recruit professionals from wealth management firms, multifamily offices, and public accounting firms, limited use of modern tools — including AI — could increasingly affect talent attraction and retention.

Image by Cassidy Reed

Building operational capacity with AI

When deployed in the right way, AI can help family offices create efficiencies, augment lean teams, and improve decision support.

And even family offices that have not made a conscious decision to adopt AI may find that they are using it. Most technology platforms used by family offices are beginning to incorporate AI capabilities, Dickson notes. As family offices modernize and upgrade their systems, they are likely to encounter AI as a built-in feature of their technology, even if they have not set out to adopt it directly.

“Family offices are already being exposed to AI. Most of the technology systems they are considering — or already using — have AI embedded in their functionality,” Dickson says.

This means family office leaders need to understand when AI features are optional and when they are a core part of the technology, as well as how those features interact with their broader technology ecosystem. For example, if the accounting book of record is not integrated with the investment book of record, an AI-driven analysis that looks only at one of them may not be reliable.

“AI analyses are only as good as the data available in the underlying reporting systems,” Dickson says. “If historical or portfolio-level data is missing, the system may generate incomplete — or potentially misleading — analysis or recommendations because it is not considering the full portfolio or asset allocation.”

AI is already shaping how family offices operate, compete for talent, and analyze information. As the technology becomes embedded across investment platforms and other tools family offices use, opting out entirely will become increasingly difficult. For many family offices, the work in 2026 will be to clarify where it adds real value, strengthen the data and systems it relies on, and design systems that include human oversight for AI-driven functions.

About the Author

Margaret Steen

Margaret Steen is the editor of FO Pro, The Family Office Professional. Based in Silicon Valley, she has written for Family Business Magazine for more than 15 years.


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