What You Don’t See Coming

“What can I do for you?” he asked.

A few weeks ago, I met this mentor‑type at the gym. A sharp guy. Older. Successful. One of those people you can tell just knows how power works in the world. 

For whatever reason, he seemed interested in helping me out. 

And I’m wise enough to accept an offer like that when given the opportunity. 

So back to his question: ““What can I do for you?”

This stumped me. 

I did NOT want to make a “level 1 request,” i.e. asking for a favor that I don’t need. 

Sure, he’s invested in dozens of companies that fit my ideal client avatar, but requesting an introduction feels only a few steps removed from saying “do my job for me” or “please give me money, Mr. Rich Man.”  

So I wanted to jump to a “level 2 question.” Let me explain:

Everything I can see coming, I can see coming. Everything I think I’m doing right, I think I’m doing right. So if I don’t fix those things, it’s not from ignorance, it’s from laziness, impatience, or lack of effort. The most helpful thing a mentor can do isn’t to reinforce what I already know or offer a handout. It’s to reveal what I don’t see coming.

“”

BLOCKQUOTE:

Level 1: “Please improve my situation” (Clients, Money, Connections)

Level 2: “Please help me improve” (Insight, Strategy)

“””

So I said, “Let me walk you through my situation, strategy, and goals. Tell me what I am missing. Tell me what I do not see coming.”

By telling him how I need his help, I’d be putting myself back in the driver’s seat as the wise one (silly given his success relative to mine). 

Instead, I wanted to shift that role back on him and put him back in the driver's seat as the wise one. 

So how can you apply this? (Even if you don’t stumble into a random mentor at the gym?) 

Play the same game, but with AI. 

If you ask a model to do your work for you, it will rarely challenge the premise and underlying strategic assumptions. It will comply. That’s great when you know you are working on the right thing, but very dangerous and chaotic if you are operating from a shaky foundation.

So until you’ve reached strategic maturity and can confidently transition from planning to executing, briefly invite AI to the driver’s seat. Ask it to interrogate your plan.

Use prompts like these:

• “Here is my current strategy, constraints, and targets: [paste]. Identify assumptions that are fragile. List second and third order effects that could derail this in the next 90 days.”
• “What are three plausible failure modes I am not considering? For each, give one leading indicator and one mitigation I can implement this week.”
• “Given these constraints [A, B, C], which priorities are likely non‑bottlenecks? What should I stop optimizing right now?”
• “Where does my plan likely break first: [a, b, or c]. Provide the simplest test to falsify my current belief.”

The obvious problems are obvious, but what you are missing can be just as powerful.

That is the advantage of a mentor or a capable model. Not to hand out answers, but to expose blind spots. To make sure you are working on the right thing instead of applying brute force to the wrong one.

If you’re able to, skip the requests for introductions, hacks, and lists of ideas.

Instead, ask for coaching that makes you better. Lay out your strategy. Ask what you don’t see coming. Let the wise one across the table pressure‑test your thinking, then get back to work.

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