🎙️ Executive Series — Managing Up with AI Episode 9: From Two Pages to 100 Words (and Why Timing Beats Brevity)

In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, dig into one of the most overlooked leadership skills: managing up.

Act I: We put a two-page update on the chopping block—distilling it into a high-impact, 100-word brief for a senior leader. You’ll hear why “shorter” isn’t the goal—decision-ready is—and how to use meta-prompts and guardrails (“with high accuracy”) to get AI-generated summaries that hit 97% of the mark in seconds.

Act II: We zoom out to the strategy: managing up as timing, not just content. From building a “priority heat map” to experimenting with digital twins of senior leaders, Alex and PS explore how to align updates with what’s actually on the radar. We close with three AI-powered tactics you can use today to make your boss’s decisions easier, faster, and safer—plus a challenge to rethink objection handling as a daily habit.

Whether you’re reporting to a VP or briefing the C-suite, this episode will help you shift from proving your team’s worth to steering leadership’s focus—at the right moment, with the right message.

🎯 Your Challenge: Email alex@lololai.com or tag Alex on LinkedIn with the next executive pain point you want decoded.

Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.

Connect: alex@lololai.com