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...
038: The Leadership Hack That Eliminates 80% of Check-Ins
Check-ins are killing your calendar. In this episode, Erik breaks down why endless reminders are actually a symptom of low confidence and poor expectation-setting—and he teaches a simple leadership “play” that flips the script. Instead of you chasing progress updates, your team will push you the information you need—freeing up your time, building accountability, and strengthening trust.
❓ The Big Question
What if you could eliminate 80% of your check-ins and still have full confidence that the work is getting done?
💡 Key Takeaways
- Most check-ins are rooted in lack of confidence—either yours or theirs.
- Telling someone what to do creates dependence; having them tell you creates accountability.
- Check-ins aren’t about progress—they’re about reassurance.
- The right system flips responsibility back onto the person doing the work.
- When leaders stop chasing updates, they reclaim time and build trust.
🧠 Concepts, Curves, and Frameworks
- Confidence vs. Check-Ins → Your need to check in is usually a sign of shaky confidence.
- Expectation-Setting Game → Don’t tell; ask them to articulate their plan and timeline.
- Push vs. Pull Communication → Move from chasing updates (pull) to receiving them automatically (push).
- Calendar Hack → Put the expectation in their calendar—and yours—as a self-triggered accountability system.
🔁 Real-Life Reflections
- The “reminder monster” in your calendar probably has a name—what if you flipped that relationship?
- This approach has been tested with thousands of leaders and eliminates ~80% of check-ins.
- When people state their own commitments and log them, they are psychologically more likely to follow through.
🧰 Put This Into Practice
- Identify one person who dominates your check-in calendar.
- Next time, don’t set a check-in—have them set the reminder in both of your calendars.
- Ask: What progress should you expect to have made by then?
- Have them block time in their calendar with the title: “[Name] to update [Leader] on [specific milestone].”
- Watch as updates come to you—without you ever having to chase.
🗣️ Favorite Quotes
“Confidence and the check-in are two sides of the same coin.”
“The game isn’t telling them what to do—it’s getting them to tell you.”
“Stop pulling for updates. Build a system where they push you the information.”
“This one hack eliminates about 80% of reminders and check-ins.”
“Everybody wins when you run this play: you gain time, they gain trust, and the work gets done.”