Stop Training Prompts. Start Training Judgment. - Episode #130
Everyone's learning prompt engineering. Almost nobody's learning the skill that actually matters: judgment.
In this episode, I break down why prompt skills have a short shelf life, why the best prompt won't save you if you don't know what good looks like, and how to develop the thinking that AI can't replace.
I cover:
- Why prompt engineering is a skill with an expiration date
- The difference between asking AI a question and knowing whether to ask at all
- How confident-sounding outputs fool people who haven't trained their judgment
- Why AI doesn't know what matters to your business, your customer, or your team
- How speed without judgment creates faster mistakes at a bigger scale
- What the leaders who win will actually be good at
If you've been focused on getting better at prompts, this might change your priority.
19 Feb 2026
Building Trust Through Skip Levels (Not Just Gathering Intel) - Episode #129
Skip levels aren't about gathering intel. They're about building trust two levels down - and that trust compounds over time.
If your only goal is information extraction, people will figure it out fast. In this episode, I break down how to run skip levels that build relationships instead of eroding them, the questions that actually unlock honesty, and why the trust you build now pays off in moments you can't predict.
I cover:
- Why interrogation-style skip levels backfire
- The real purpose of skip levels (hint: it's not going around your managers)
- Why skip levels that only happen during problems create panic
- How to make people feel safe enough to share the unfiltered version
- The one question that opens doors others keep closed
- What it means to leave someone feeling heard, not used
If your skip levels feel awkward or surface-level, this one will help you reset.
17 Feb 2026
Hard Isn't Inherently Bad - Episode #128
Hard isn't the problem. Avoiding it is. Here's how leaders get this wrong - in both directions.
Somewhere along the way, we started treating discomfort like a warning sign instead of evidence that we're doing something that matters. In this episode, I break down why hard is part of the job, how to calibrate the push for your team, and what to do when someone's struggling not because they're weak - but because they're in the wrong seat.
I cover:
- Why we've been sold a lie about discomfort at work
- The reality that business pressure isn't going away
- How to know when to push and when to let the team breathe
- The difference between stretching someone and breaking them
- Why moving someone out of a role isn't failure - avoiding the conversation is
- How to lead hard conversations without leading with judgment
If you've been wondering whether you're pushing too hard or not hard enough, this one's for you.
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