I Have Some Questions...
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.
I Have Some Questions...
081: "Support Isn't Weakness, Both for Leadership & Parenting" (lessons from Cassandra Asleson)
🧠Erik’s Take
In this reaction episode, Erik revisits his interview with parenting expert Cassandra Asleson, not just as a host but as a dad who's lived the transformation she helps create. With signature candor and strategic insight, Erik reflects on how Cassie’s approach reframes what’s “normal” in parenting—and how accepting support can radically shift the emotional and logistical weight of raising young children. This episode unpacks why working families feel crushed and what’s actually available on the other side of overwhelm.
🎯 Top Insights from the Interview
- It doesn’t have to be this hard — We accept too much pain in parenting as normal. Cassie’s work shows there’s another way.
- Regulation is everything — Emotional dysregulation isn’t just a kid thing. It’s a whole-family system challenge.
- Support isn't weakness — Asking for help isn’t failure. It’s how functional families get built.
- YouTube won’t solve this — In-the-trenches guidance beats fragmented, piecemeal internet advice every time.
- It’s okay to say it sucks — Naming the exhaustion and impossibility of modern parenting isn’t complaining. It’s liberating.
🧩 The Personal Layer
Erik brings raw honesty to the reality of parenting two young girls. He speaks openly about how his kids have thrown public tantrums, how exhausting the logistics can be, and how the myth of “figuring it out on your own” holds families back. From teaching his daughter to scream into a pillow at three years old to recognizing how much structure helps his family thrive, Erik shows what leadership looks like at home—not through control, but through emotional intelligence and humility.
🧰 From Insight to Action
- Normalize asking for help — Whether it’s a sleep consultant or a parent coach, bring in allies early.
- Create regulation rituals — Start small. A consistent bedtime, food schedule, or “calm-down” space makes a huge difference.
- Shift your mindset — Challenge the belief that hard equals noble. Instead, ask: What would make this easier for everyone involved?
- Invest where it matters — Don’t be afraid to spend on support that changes your family’s daily quality of life.
- Talk about it — Name the challenge in your circles. Make it okay for other parents to say, “This is brutal.”
🗣️ Notable Quotes
“It doesn’t have to be this hard to be a parent. We just don’t know what we don’t know.”
“The word regulation wasn’t even in my vocabulary until Cassie came into our lives.”
“You might find these resources on Reddit or YouTube, but let’s be honest—you won’t pull it together in the middle of sleep deprivation.”
“If you want your kid to be a functional member of their community, it starts with learning to regulate emotion at home.”
“It’s not complaining to say parenting is hard. It’s the first step toward doing something about it.”