Description

AI was supposed to make work easier. For many experienced business owners, it’s doing the opposite.

In this episode, Kim Lewis Howard and Hal Howard unpack a frustration they’re seeing everywhere—but almost no one isnaming clearly: why capable operators feel slower, less confident, and more mentally taxed when working with AI.

This isn’t a tools problem. And it’s not a competence gap. It’s a leadership shift no one trained you for.

What’s Actually Going On

Most AI tools are marketed like software upgrades—faster,cheaper, smarter. But AI doesn’t behave like software. It behaves more like delegated intelligence. And intelligence requires direction, standards, and judgment.

When those aren’t explicit, friction shows up fast.

In this conversation, Kim and Hal explain:

• Why “fine” AI output is more dangerous than bad output
• How AI exposes fuzzy goals, hidden assumptions,and unspoken standards
• Why prompting guides don’t solve the real problem
• The difference between asking AI for work and managing it
• Why frustration with AI is often a signal of leadership growth—not failure

They also ground the discussion in real operator experience, including a live event where “the tech worked”—but failed the business in real time.

This Episode Is for You If:

• You’ve tried AI and thought, “This took longer than doing it myself.”

• You know what “good” looks like—but AI keeps missing the mark
• You feel pressure to “keep up” with AI success stories that don’t match your reality
• You’re tired of being told to “just write better prompts”

This Episode Is Not About:

• AI hacks, shortcuts, or shiny tools
• Prompt formulas without context
• Hustle, hype, or performance theater

This is Part One of a three-part series, The Leadership Nobody Trained You For. In Part Two, Kim and Hal break down the specific leadership skill that turns AI from frustrating to genuinely useful—in real business conditions.

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• Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed for business owners → Email Howard & Howard Holdings, Inc.

• Have a question or an AI success story? DM us on LinkedIn or Facebook!

---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com

Sound Effects: https://pixabay.com/sound-effects/