I Have Some Questions…
I Have Some Questions...
Podcast Description
What if leadership wasn’t about having the answers—but about asking better questions?On "I Have Some Questions…", Erik Berglund – a founder, coach, and Speechcraft evangelist – dives into the conversations that high performers aren’t having enough. This isn’t your typical leadership podcast. It’s a tactical deep-dive into the soft skills that actually drive results: the hard-to-nail moments of accountability, the awkward feedback loops, and the language that turns good leaders into great ones.Each week, Erik explores a question that has shaped his own journey. Expect raw, unpolished curiosity. Expect conversations with bold thinkers, rising leaders, and practitioners who are tired of recycled advice and ready to talk about what really works. Expect episodes that get under the hood of how real change happens: through what we say, how we say it, and how often we practice it.This show is for driven managers, emerging execs, and anyone who knows that real growth comes from curiosity rather than charisma.Subscribe if you’re ready to stop winging it and start leading with intention.
Podcast Insights
Content Themes
The podcast focuses on critical leadership skills, self-awareness, and accountability, with episodes diving into topics like how to lead teams in an AI-enhanced environment and the significance of asking better questions for personal and organizational growth.

What if leadership wasn’t about having the answers—but about asking better questions?
On “I Have Some Questions…”, Erik Berglund – a founder, coach, and Speechcraft evangelist – dives into the conversations that high performers aren’t having enough. This isn’t your typical leadership podcast. It’s a tactical deep-dive into the soft skills that actually drive results: the hard-to-nail moments of accountability, the awkward feedback loops, and the language that turns good leaders into great ones.
Each week, Erik explores a question that has shaped his own journey. Expect raw, unpolished curiosity. Expect conversations with bold thinkers, rising leaders, and practitioners who are tired of recycled advice and ready to talk about what really works. Expect episodes that get under the hood of how real change happens: through what we say, how we say it, and how often we practice it.
This show is for driven managers, emerging execs, and anyone who knows that real growth comes from curiosity rather than charisma.
Subscribe if you’re ready to stop winging it and start leading with intention.
In this grounded, friendly and insightful conversation, Erik talks with Cassandra Asleson — a seasoned newborn care specialist and postpartum consultant who helps families move out of chaos and into confidence during one of life’s biggest transitions. They unpack how leadership shows up in home life and work, how guiding others in their most vulnerable moments mirrors leading teams, and why support systems matter just as much as systems. If you’re a leader, parent, or both — this episode gives you a fresh perspective on influence, care, and presence.
👤 About the Guest
Cassandra Asleson is the founder of Cassandra & Co., a firm focused on newborn consulting and postpartum support. Based in Tulsa but serving families regionally and beyond, she brings nearly two decades of experience as a certified newborn care specialist and professional nanny. Her mission: simplify and support the early parenthood journey so families can bond, sleep well, and avoid the overwhelm of decision‑fatigue, conflicting advice, and isolation.
🧭 Conversation Highlights
- Cassandra’s journey: from nanny to trusted advisor for families preparing for and recovering from birth.
- The connection between the “first 90 days” of a baby’s life and establishing strong foundations in any high‑stakes environment.
- How parenting systems (registries, nurseries, routines) parallel leadership systems in organizations.
- The value of support, delegation, and presence — whether for a baby or a team.
- What happens when you lead without the script: embracing uncertainty, creating calm from chaos.
- How the “helping role” in family life sharpens insights about culture, care, and influence in work life.
💡 Key Takeaways
- Support isn’t a luxury — it’s a strategic advantage. Whether in a household or a business.
- Clarity under pressure matters more than intensity. In those early parenting weeks and in leadership transitions.
- Delegation builds trust. The same way a parent relies on a skilled consultant, a leader relies on a capable team.
- Systems + heart = sustainable impact. You need both the structures and the care to thrive.
- The foundation phase is leadership practice. If you can lead through grief, change, and sleepless nights — you’ve built real capacity.
❓ Questions That Mattered
- “What did you learn about influence from your time as a nanny and newborn care specialist?”
- “How do you build systems that create calm — not just control?”
- “What’s the leadership parallel in helping a family prepare for a baby?”
- “How do you help people trust their own decisions when the options overwhelm them?”
- “What does ‘presence’ look like when everything else is spinning?”
🗣️ Notable Quotes
“I’m not just helping with gear — I’m helping families trust they’ll find themselves in the fog.”
“The choices you make in the first few weeks determine more than the sleep schedule — they shape presence.”
“Systems aren’t rigid — they’re the container that allows connection, care, and clarity.”
“You don’t wait until stabilize — you lead while it’s unstable.”
“When you support someone who’s terrified and exhausted — you learn more about leadership than any boardroom ever could.”
🔗 Links & Resources
- Connect with Cassandra & Co.: cassandraandcobaby.com

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