I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
I Have Some Questions...
176: "Is Talking to Your Boss the Same as Talking to a Brick Wall?" ft. Alli Murphy
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Alli and Erik work through a familiar leadership bottleneck: a team is burning out, a senior leader brings data and requests support, and the boss keeps asking for more data or dismisses what’s already been presented. Erik frames the real problem as a reality and agency issue, then lays out several ways to break the stalemate without losing credibility or steam.
🧭 Conversation Highlights
- Erik reframes the situation: if you keep hitting the same wall, it’s time to do something different, starting with acknowledging whether change is possible above you.
- He offers three response paths: adapt because you won’t get support, confront your boss more directly so the responsibility shifts, or seek support by going around them when appropriate.
- Alli shares a practical tactic that reduced friction with her CEO: weekly “above the line / below the line” clarity, showing prioritization and what’s feasible when additional resources are not coming
- They discuss negotiation and communication upgrades: agreeing on what data actually matters, using your boss’s narrative space (including having leadership’s words on slides) so the message lands even
💡 Key Takeaways
- Clarity beats persistence: repeatedly re-presenting the same evidence to an unreceptive system will erode the leader and teach the wrong lesson to the team.
- You can negotiate the data request itself by aligning on what the decision-maker needs to see, rather than accepting “show me the data” as a blank check for endless reporting.
- If skip-level escalation is risky, you can still get the impact by positioning your case so the skip level and your CEO hear the substance without you necessarily being in the room.
- When support is unavailable, the work becomes: reshape the work deck, reduce pressure, and build a credible plan forward that respects the team’s reality while you keep moving.
❓ Questions That Mattered
- What changes in your strategy when you accept “nothing is going to change above me”?
- If you bring your boss the information they asked for and nothing shifts, how would you like them to retain talent, retain customers, and deliver results given that reality?
- If “show me the data” is the instruction, what specific data set would actually change their mind, and what pieces are unnecessary?
- If the company or your boss truly can’t say yes, how do you deliver “bad news” to your team while still creating dignity, respect, and a forward plan?
🗣️ Notable Quotes
- “I’d rather square with reality.”
- “If you keep slamming your forehead against the brick wall, it’s obviously time to do something different than you were doing before.”
- “How would you like me to dot dot dot.”
- “If I ever split the difference, I came home with half a human being. There was no such thing.”
🔗 Links & Resources