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Beyond Productivity: Ask AI Smarter Questions

Liza Adams · September 24, 2025 ·

Many teams use AI like a Magic 8-Ball. They ask a question, get an answer, and move on to the next task.

The teams making real impact go beyond using it to do a task quickly. They’re using AI to make better decisions and find approaches they’d never think of alone. As they say…

we can’t reimagine the future by simply automating the past.

While everyone else stops at productivity gains, some leaders are going further, using AI to pinpoint blind spots and challenge their assumptions. Most just haven’t seen how.

This week, I saw this change happen IRL with 60+ marketers at Cox Automotive Inc., the company behind Kelley Blue Book and Autotrader that helps dealers and partners buy and sell millions of vehicles each year.

When teams stopped asking AI to do tasks and started asking it to poke holes in their plans, the team dynamics changed. Conversations went deeper and were more insightful. People started spotting problems they’d missed.

Here are some key learnings:

  • ➡︎ Teams using AI just for speed miss the real opportunity to make better decisions and come up with fresh ideas

  • ➡︎ The probing questions that make your AI conversations better show up in every meeting and planning session

  • ➡︎ This approach works on everything from email subject lines to campaign plans and expansion strategies

Because we’ve long been rewarded for good answers, many may not be as adept at asking thoughtful questions. Every AI conversation becomes critical thinking practice. Pushing AI then becomes automatic and a habit.

I break down the complete three-level critical thinking framework with sample questions and a starter kit to help you apply this to your specific projects. Full details in the newsletter below.

Prefer audio? There’s a 13-minute AI podcast version in the comments, perfect for your commute or while multitasking.

Huge thanks to Mandy Dhaliwal (CMO of Nutanix), Ramon L. Cortes (AVP of Cox Automotive), and Sydney Sloan (CMO of G2) for sharing insights on how they use AI as a thought partner for both tactical and strategic work.

How much do you use AI to speed up work? Make better decisions? Find new ways?

AI cover image

Here’s the 13-min AI podcast version of this newsletter to support different learning styles. Listen while driving, walking the dog, or having lunch 😉

https://drive.google.com/file/d/1KZzMxGeR-dSiTgugukPVqxJigyRKaaDv/view?usp=share_link

Give it a few seconds to load after you hit play.

Note: AI-generated using Google’s NotebookLM and reviewed by me for accuracy and responsible AI use. See original post here

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