Lisa Doverspike has spent her career leading a multigenerational family enterprise that has evolved into a dynamic organization spanning technology, real estate, healthcare, and philanthropy.
Lisa Doverspike’s background is a mix of structure and people — She hold master’s degrees in both Organizational Psychology and Business Taxation — and that combination really shapes how she leads. Numbers matter, but people make the numbers work.
Our growth over the past decade has been remarkable, but what she is most proud of is that they’ve managed to expand while keeping our values intact. Lisa has learned that success means very little unless it’s shared — with your team, your community, and the next generation coming up behind you.
What is your typical day, and how do you make it productive?
Most mornings start early and quietly. I’ll work out, take a few minutes to center myself, and look over the day. Years ago, I used to dive right into email and wonder why I felt behind by 9 a.m. Now, I spend the first part of the day on the most strategic work — the kind that requires clear thinking.
I also make a point of touching base with at least one team member I don’t normally see. A quick conversation — even five minutes — keeps me grounded in what’s happening across the organization and reminds me why we do what we do.
How do you bring ideas to life?
Ideas usually start as questions. I’ll ask, “What would happen if we tried it this way?” or “What’s missing here?” Once an idea takes shape, I gather a small cross-section of the team — finance, operations, creative — to stress-test it.
One of my favorite memories was a brainstorming session for a philanthropic project that ended with sticky notes all over the walls. What started as a simple community grant evolved into a lasting partnership because everyone had a hand in shaping it. Collaboration is where vision becomes reality.
What’s one trend that excites you?
I’m encouraged by how leadership is becoming more human. We’re finally talking openly about emotional intelligence and psychological safety. Twenty years ago, those topics were considered “soft.” Now, they’re seen as essential to performance — and it’s changing how organizations grow and how people show up at work.
What is one habit that helps you be productive?
At the end of each day, I ask myself two questions: “What mattered most today?” and “What can I do better tomorrow?” It’s a simple check-in that keeps me honest. Sometimes I’ll jot a note about a conversation I want to revisit or a decision I want to rethink. Reflection has become my reset button.
What advice would you give your younger self?
I’d tell my younger self not to wait until everything feels certain before moving forward. Early in my career, I wanted to have all the answers before taking the next step. I’ve since learned that real growth happens when you’re willing to step out into the unknown — to make thoughtful moves even when the path isn’t fully clear. That’s where confidence and resilience are built.
Tell us something you believe that almost nobody agrees with you on?
That fast growth can strengthen culture instead of eroding it. I’ve seen it happen — when trust and communication are strong, expansion actually gives people more reason to rally around shared purpose. It’s not the pace of growth that breaks culture; it’s neglecting the relationships that hold it together.
What is the one thing you repeatedly do and recommend everyone else do?
Mentorship — both ways. I still have mentors I call for perspective, and I try to make time for those coming up behind me. One of my former analysts now runs an entire division, and we still meet once a quarter to talk through her leadership challenges. Those conversations remind me how important it is to pass along what you’ve learned — and to keep learning yourself.
When you feel overwhelmed or unfocused, what do you do?
When things feel especially complex, I step back and reconnect with the “why.” Clarity comes from remembering the larger purpose behind the work — why it matters, who it serves, and what success will enable next. That perspective helps me refocus quickly and move forward with intention.
What is one strategy that has helped you grow your business or advance in your career?
Hiring for values alignment. Years ago, we made a hiring decision based purely on technical skill — and it didn’t work. Since then, I’ve learned that capability matters, but chemistry matters more. When people share the same principles, they solve problems faster and treat each other better. It’s what keeps teams strong when things get tough.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early in my career, I led a project that didn’t meet expectations as quickly as it could have if the team had been communicating more openly. We had to rebuild trust, which took time and honesty. That experience reinforced my belief that having all the answers isn’t what matters most — it’s about creating an environment where people feel safe enough to raise questions before small issues become big ones.
What is one business idea you’re willing to give away to our readers?
I’d love to see a platform that helps families document not just their history but their values — something that captures stories, decisions, and lessons across generations. It could bridge the gap between financial planning and family storytelling, helping the next generation understand not only what they inherit, but why.
What is one piece of software that helps you be productive? How do you use it?
Asana keeps our projects on track, but I pair it with something low-tech — a handwritten list at the start of the week. I’ve learned that technology works best when it complements human habits, not replaces them.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
The Culture Code by Daniel Coyle is a favorite — it captures how trust and vulnerability build great teams. And I’m a regular listener of Adam Grant’s WorkLife podcast. His mix of humor and evidence-based insight is refreshing; it reminds me that leadership is both art and experiment.
What’s a movie or series you recently enjoyed and why?
The Crown. I’m fascinated by how it portrays duty, identity, and the weight of decision-making. It’s a good reminder that leadership always involves trade-offs — and that grace under pressure is a skill worth cultivating.
Key learnings
- Psychological safety is the foundation of lasting growth.
- Hire for shared values, not just skills.
- Reflection and perspective build resilience.
- Mentorship sustains both leaders and teams.
- Growth and culture can strengthen one another when grounded in trust.