You ran a basic AI audit it raised some questions, didn’t it? That’s normal. Many plan sponsors discover concerning patterns when they dig deeper.

ChatGPT’s first answers are usually general and diplomatic. Want more specific insights? You need strategic follow-up questions that reveal industry patterns your provider might not voluntarily discuss.

Here’s how to get AI to provide more detailed analysis of how the 401k industry operates.

Tip #1: Initial responses are often surface-level. Follow-up questions yield more detailed analysis.

Tip #2: Ask for specific comparisons—that’s where patterns emerge.

Tip #3: Request data-driven analysis rather than general descriptions.

Tip #4: Tell your AI to give you real talk and take the gloves off…it usually will.

Tip #5: Don’t be afraid to load a pdf of your plan document, contract or fee disclosures.  It can dissect and summarize them in seconds.

401(k) AI Prompts That Actually Work

Ask Smarter Questions. Spot Hidden Problems. Push for Real Answers.

Your 401(k) probably looks fine on paper. That’s the problem.

Most plans don’t break. They just quietly underperform—loaded with unnecessary fees, outdated design, and advisor incentives nobody talks about.

AI can help uncover this, but here’s the catch:
It gives polite, politically correct answers by default.
You have to know how to push for the truth.

This guide shows you exactly how to do that.

🔍 Start Here: A Quick Diagnostic

Paste this into ChatGPT:

“I help manage a 401(k) plan, but I’m not sure if it’s well-designed or cost-effective. Ask me questions to help uncover possible compliance risks, hidden fees, or conflicts of interest.”

You’ll get a decent overview. But if the answers feel too neutral or vague—keep going. AI will usually go further if you tell it to.

🧠 Level Up with These Deeper Prompts

These are the questions most advisors don’t want you asking.

💰 Fee Structure

• “Does our 408(b)(2) disclosure include indirect comp, revenue sharing, or proprietary fund usage?”

• “How do our total plan costs compare to NEPC or 401k Averages Book benchmarks?”

• “Are we paying more than we should for recordkeeping, and who negotiated those fees?”

🏗️ Plan Design

• “Is our auto-enrollment and escalation setup strong enough to help employees retire?”

• “Are there design choices here that benefit the brokerage firm or recordkeeper more than participants—or vice versa?”

• “What’s missing that top plans usually include?”

📊 Investment Lineup

• “Are we using funds that generate extra compensation for the provider?”

• “What alternatives to our current TDF series should be meaningfully considered?”

• “Would an open-architecture lineup or collective trusts lower fees without hurting performance?”

📋 Fiduciary Duties & Oversight

• “What should we be doing annually to document procedural prudence?”

• “How often should we benchmark service providers, and what happens if we don’t?”

• “Could our current setup raise red flags in an audit or participant lawsuit?”

🥊 Tell AI to Take the Gloves Off

AI often pulls punches to sound balanced. You don’t have to let it.

Try these follow-ups to push past the PR-safe answers:

• “What would an independent fiduciary consultant likely criticize here?”

• “What’s the worst-case interpretation of this structure?”

• “If this plan were underperforming, how would it look on paper?”

• “What would a more cynical take on this advisor’s fund recommendations look like?”

And yes—it will answer those. Usually in more detail than you expect.

🤝 Found Something Sketchy? Here’s What’s Next.

I work with small businesses and HR teams who want to turn AI insights into real improvements. That means:

• Cutting wasteful fees

• Fixing broken design elements

• Replacing providers if needed

• Getting the plan running like it should’ve been from day one

Schedule an Educational Consultation

Let’s discuss what your research revealed and explore your options.

Initial consultation provided at no cost. Ongoing services competitively priced.

P.S. Try this analysis: “What would indicate that a financial services firm prioritizes long-term client outcomes over short-term revenue generation? Does my brokerage firm (insert name here) have more focus on recruiting new advisors or generating good client outcomes?  If yes, what industry does that mimic?”

The patterns you discover might be enlightening.

We work with employers across California—including San Diego, Los Angeles, Orange County, Sacramento, and the Bay Area.