At Three Hills Family Office, which serves nearly 30 relatives across two branches and four living generations, Chief Learning Officer Katherine Dean is building a learning engine. “It’s been a slow and steady build — it takes time,” she says, describing how the team first defined core competencies and then put a process in place for each person to set goals over a specific period, backed by fact sheets, visuals, videos, podcasts and other multimedia.
This year, the work expands again: Three Hills is cost-sharing a curriculum designer with two peer family offices to deepen materials and make them more accessible. The curriculum itself centers on 12 competencies, including a foundational pillar Dean calls “Who am I?” — self-awareness work that may include assessments to surface strengths, explore career paths and decode communication styles so family members can “flex” and connect better with others. “These are practical life skills that make a difference not just inside the family, but out in the wider world too,” Dean says.
The learning isn’t just technical; it’s personal. Conversations often move into wealth and identity, where Dean uses somatic coaching to help people understand how they actually feel about money — whether they’re operating from a standpoint of scarcity or abundance — and how that mindset shows up in daily choices. “We’re trying to reframe wealth as part of overall well-being,” she says. “Not just dollars and cents.”
Practical skills sit alongside the inner work. Negotiation and conflict resolution are a major competency, supported by external coursework (including a Harvard offering) and internal practices. Dean leans on a framework known as Crucial Conversations to help the family address hard topics directly rather than avoid them. Avoidance, she notes, tends to turn small tensions into future blowups.
Delivery is intentionally varied. Much of the growth happens one-on-one, matched to individual goals, while small group sessions create shared language and accelerate learning through discussion. Behind the scenes, Dean is building systems so colleagues across offices can run programs consistently, track engagement and keep quality high even as the effort scales.
Governance education follows the same practical arc. Three Hills began by mapping the roles that already exist across businesses — an easy place to start — and then widened the aperture to create new on-ramps for different talents, including roles focused on connection and culture, not just numbers. The aim, Dean explains, is a portfolio of “big roles, small roles and everything in between” so any family member, regardless of career track, can engage meaningfully. The next phase of that expansion is slated for later this year.
To make governance tangible, Dean first built a one-page visual of all roles, then partnered with operators to define time commitments, responsibilities and qualifications — work that will fold into the broader learning toolkit. Her signature visual, the “Stewardship Roadmap,” outlines four evolving lanes: operating (day-to-day roles plus governance), governing (governance without operating jobs), informed (staying current and showing up) and supporting (delegating decision-making while backing those who serve). The lanes aren’t rigid. “People move between them over time,” she says.
Last summer, Dean conducted an exercise in which members of the rising gen placed sticky notes on an oversized version of the roadmap, showing where they are now and where they want to be in five or 10 years. “It was the first time they’d seen, as a group, how others were thinking about their roles in the future — and it really sparked some powerful conversations,” she says.
Dean’s team is also reimagining how new spouses are welcomed. A warm orientation begins with a call or meeting and a high-level booklet: the family’s history, values, vision and mission; how the family thinks about wealth (with an emphasis on human capital); an overview of businesses and available services; even a favorite recipe and plenty of photos. New spouses are invited to share their own family stories so the relationship feels mutual from day one.
Because one touchpoint isn’t enough, she’s mapping follow-up sessions: what to expect in family meetings and when participation begins; how to contribute within the family-business ecosystem; and practical guardrails for complex structures like trusts with multiple discretionary beneficiaries. She wants clear pathways for married-in spouses to express interest, prepare for roles and step in with confidence.
Threaded through it all is a simple idea: build learning that’s personal, visual and actionable — then keep lowering the barriers to participation. As Dean puts it, the work is about turning stewardship into something you can see yourself doing, and giving every generation the tools to start.