The Smart Way to Answer Hard Questions

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Hey Reader,

Picture this: You're in a meeting and someone asks about your team's biggest failure. Your project that went over budget. The client you lost. The strategy that backfired.

What do you do?

Most professionals panic. They deflect ("That wasn't really my fault..."), make excuses ("We didn't have enough resources..."), or worse—they ramble for five minutes, hoping to confuse everyone into forgetting the original question.

The CEO Test

I recently studied Sam Altman's speaking style, and while he has plenty of flaws, there's one situation where he absolutely nails it: answering the questions that make CEOs squirm.

When tech journalist Cleo Abram asked him about OpenAI's biggest mistake, Sam could have easily deflected. Most executives would. Instead, he did something that turned a potential PR disaster into a masterclass in leadership communication.

The PET Framework in Action

Here's exactly what Sam said when asked about their biggest screw-up:

"I think the worst thing we've done in ChatGPT so far is we had this issue with sycophancy where the model was kind of being too flattering to users, and for some users—most users it was just annoying—but for some users that had fragile mental states, it was encouraging delusions..."

He then explained the context and ended with: "We now have a service that is so broadly used, society is co-evolving with it. We have to operate in a different way and have a wider aperture to what we think about as our top risks."

Notice the structure? He used what I call the PET Framework:

• Point: Owns the mistake completely ("the worst thing we've done...")
• Explanation: Provides specific context and details (sycophancy issue, impact on vulnerable users)
• Takeaway: Ends with a forward-looking perspective (broader worldview for future development)

Why This Works

This isn't just damage control—it's strategic leadership communication. By owning the mistake upfront, providing authentic details, and pivoting to lessons learned, Sam maintains credibility instead of losing it.

The alternative? Watch any politician dodge a tough question and see how that lands with audiences. Deflection destroys trust. Authenticity builds it.

Your Turn

Next time someone asks about your failure, mistake, or what went wrong, try PET:

1. Own it immediately - No deflection, no blame-shifting
2. Explain with specifics - Show you understand what actually happened
3. End forward-looking - What you learned, what you're doing differently

🎥 Want to see more examples of Sam's speaking techniques? I analyzed his entire hour-long interview and broke down exactly what works, what doesn't, and how you can communicate better than a tech billionaire.

By the way, since you're in The ISA, you can join me in The ISA Accelerator for 3 months of live coaching calls with mend practice sessions with fellow students. There's an exclusive discount for ISA students like you, and the program begins on September 4. Hope to see you there.

Don't let difficult questions derail your success. Learn to handle them like a leader.

Best,

Preston

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