Katherine Dean is chief learning officer of Three Hills Family Office, which serves almost 30 members of a family with two branches and four living generations (G3 through G6). She discusses her responsibilities as CLO:
What does the role of chief learning officer encompass?
I have three primary responsibilities: family culture, learning and development and governance.
How do you help with family culture?
I help families be really intentional about the culture they’re creating. I think of culture as the vibe — like, when you walk into a room, what do you feel? Where do you feel it in your body? Does it lift you up? Make you want to show up, contribute and be part of something meaningful? Culture isn’t something you just declare — you have to live it. My job is to help families figure out what that vibe is and then actually bring it to life.
I do this through a mix of one-on-one coaching and systems work, pulling from my background in executive and relationship systems coaching. Sometimes that means checking in with someone before a meeting, asking something like, ‘How do you want to show up today? What kind of energy are you bringing into the room?’ Other times, I’ll follow up afterward with, ‘How do you think that comment landed? Would you have done anything differently?’
And during meetings, I’ll sometimes name what I’m seeing in real-time so the whole group can reflect and respond together. Like saying, ‘Hey, I noticed some tension just now — what do you think the system needs in this moment?’
Some family members joke that I’m part sheriff, part priest — holding people accountable, but always showing up with empathy and care. At the end of the day, I’m there to hold up a mirror, gently but honestly, and walk with them as they grow into the culture they want to build.
What does the learning and development part of your role look like?
We often frame learning and development as something for the rising gen — but honestly, everyone in the family is learning. It’s not just the young folks. We cover everything from the basics of financial literacy to more complex stuff, like how different governance structures might work for the family. It’s a pretty wide range.
I’ve built a curriculum framework with 12 core learning competencies that anyone in the family can tap into. Right now, for example, I’m working with a 60-year-old family member who’s diving into macroeconomics and financial literacy — not because they have to, but because they want to feel more confident in meetings, ask sharper questions and actually understand the documents in front of them.
What I’ve found is, the more I can get the older generations to lean into their own learning, the better it is for the whole family. It sets the tone that learning isn’t just for kids — it’s a lifelong thing. And it sends a powerful message: It’s OK not to know everything. It’s OK to ask, to be curious, to grow.
How do you help with governance?
Here’s a recent example we’re still in the middle of working through. Our G5s — folks in their 20s, give or take — are starting to be invited into governance roles. Naturally, the big question they kept asking was, ‘What are the roles, exactly?’
So, the first step I took was creating a simple, visual one-pager that laid out the different roles across various parts of the family enterprise. Once they had that clear snapshot, we could have more meaningful conversations about what each role actually involves — the responsibilities, what kind of experience or background is helpful and how much time it realistically takes.
We’re also putting all this into a format that’s easy to reference and understand, so it’s not overwhelming. The whole point is to bring clarity to governance — when everyone knows what’s expected, it levels the playing field and helps avoid misunderstandings down the line.
How else do you help family members learn?
One cool thing we’ve rolled out recently is a learning fund for the family — it’s actually built into my budget. Family members can apply for it once a year, and it can go toward anything from a course or credential to a conference they’re excited about.
It’s another way we’re sending a clear message: we’re investing in our human capital, not just the financial stuff. That’s really the heart of why I’m here as chief learning officer — to champion the idea that people are the most valuable asset in the system. When we support individual growth, we’re also building the collective capacity of the whole family.
The hope is that when someone uses the fund to learn something new, they bring it back and share their insights at our quarterly family assembly meetings — so the learning keeps spreading.
You mentioned, when discussing culture, creating a culture where family members want to be part of something meaningful. What does that mean for this family?
With this family, there’s always been a strong sense that they’re better together. You can see it in so many aspects of how they operate — whether it’s giving back through their time, talents and resources, investing together or tapping into their shared wisdom to make decisions.
One of the core values that drives them is the idea of “replanting the forest” for future generations. It’s a belief that’s been passed down and continues to ground them. They have a deep respect for what earlier generations sacrificed to get them here, and they don’t take that lightly. When they plan and dream, they’re thinking in terms of seven generations out — not just what’s right in front of them.
But what’s most striking is how deeply they care about one another. That kind of genuine connection — the kind where people show up for each other with love and intention — isn’t something you can just find out in the world on your own. It’s been cultivated over time, and it’s part of what makes this family so special.