And What the Answers Actually Mean

These questions will get you professional, balanced answers. But they rarely reveal the complete picture:

• “Is our company’s 401(k) fund lineup competitive?”
• “What’s a typical employer match?”
• “What happens if our plan fails nondiscrimination testing?”
• “Who actually administers our plan—and are they qualified?”
• “Should I work with a financial advisor or just use our payroll company?”

AI will give you a thoughtful, nuanced breakdown. It’ll explain how “every situation is unique” and provide general guidance.

But here’s what most people miss: In the retirement plan industry, problematic plans don’t look broken—they just silently underperform while excessive fees compound in the background.  They don’t always break down on the highway.  They leak oil.

If AI tells you your plan is “average,” that’s not necessarily reassuring. In this industry, average often means unnecessarily expensive and inefficiently designed.

Using AI to Look Beyond the Surface

Think of AI as your impartial investigator:

• It has no financial stake in your plan
• It won’t soften uncomfortable truths to maintain relationships
• It can analyze complex documents in seconds
• It can compare your plan against true best practices, not just industry norms

The real value comes from looking where others don’t.

More Revealing Questions to Ask AI About Your 401(k)

Try asking these questions that dig deeper:

About Fee Structures:

• “Are there any indirect compensation arrangements in our 408(b)(2) disclosure that could create conflicts of interest?”
• “How do our all-in plan costs compare to plans of similar size according to the most recent NEPC or 401k Averages Book benchmarks?”
• “Are there any revenue-sharing arrangements embedded in our fund lineup that might not be immediately apparent?”

About Plan Design:

• “Is our current auto-enrollment percentage and auto-escalation design aligned with research on retirement readiness?”
• “What plan design features are we missing that could improve outcomes while remaining cost-efficient?”
• “Would our employees be better served by a different qualified default investment alternative (QDIA) structure?”

About Investment Selection:

• “Why might our provider recommend their own proprietary funds over alternatives?”
• “What criteria were used to select our target date fund series, and were alternatives meaningfully considered?”
• “Are managed account services truly beneficial for our employee demographic, or primarily a revenue source for the record keeper?”

About Governance:

• “What potential conflicts of interest should we be monitoring with our current provider arrangement?”
• “Is our plan governance structure robust enough to demonstrate procedural prudence?”
• “What documentation should we maintain to demonstrate we’re fulfilling our fiduciary responsibilities?”

How to Get More Insightful Answers

Most people don’t realize AI will provide more direct assessments if you push for clarity.

Try these follow-up prompts:

• “What are the potential disadvantages of this approach?”
• “What would an independent fiduciary consultant identify as areas for improvement?”
• “What important considerations might be overlooked in standard provider presentations?”

Pro Tip: Upload your actual plan documents and ask for analysis:

• “Please review our 408(b)(2) disclosure and identify any areas of concern.”
• “Analyze this investment lineup for potential redundancies, gaps, or fee inefficiencies.”
• “Review these plan documents and suggest improvements that would enhance retirement outcomes.”

For best results, provide multiple documents for context—fee disclosures, investment lineups, plan documents—so AI can give a more comprehensive assessment.

Interpreting AI’s Measured Responses

AI is designed to be balanced. Here’s how to read between the lines:

When AI says: “Your plan uses a standard fee arrangement.”
Consider asking: “How does this compare to the lowest-cost arrangements available in today’s market?”

When AI says: “Your target date funds are from a reputable provider.”
Consider asking: “What potential benefits would a different approach like collective investment trusts or an open-architecture target date solution provide?”

When AI says: “Your plan meets regulatory requirements.”
Consider asking: “What design improvements could significantly enhance outcomes while maintaining compliance?”

What To Do With What You Learn

Here’s the reality: AI can identify potential issues, but it can’t implement solutions.

It’s like getting a thorough diagnostic on your car—incredibly valuable, but you still need a qualified mechanic to make the repairs.

If you discover opportunities to improve your plan, you’ll still need someone who can:

• Translate AI insights into actionable improvements
• Navigate the complex retirement plan ecosystem
• Coordinate with recordkeepers and other service providers
• Implement changes while maintaining compliance
• Monitor ongoing performance and make adjustments

That’s where I come in.

I specialize in helping companies transform their 401(k) plans from checkbox obligations into strategic benefits that work harder for both the business and its employees.

For Employees:

If you are a plan participant curious about the inner workings of your 401(k), share these insights with your HR team or benefits committee. Let them know there are tools and resources available to evaluate your plan objectively.  Or if you are feeling motivated take your latest fee disclosure and do exactly what I just said.  It’s that thing you get every year and probably never bother opening.

For HR Leaders and Business Owners:

Let’s talk. I can help you make sense of what AI reveals and develop a clear roadmap for improvement.

The Next Step Is Simple

You can absolutely use AI to gain insights into your 401(k). It’s smart and cost-effective.

But when it identifies opportunities for improvement, you’ll want a partner who can help you execute changes effectively.

AI can diagnose. I help you implement.

Give me a call 1-619-942-4510

Or email me directly: jason@missionretirementplans.com

P.S. Yes, I actually use AI regularly to help clients analyze plan documents and identify opportunities. It’s not just a marketing angle—it’s a powerful tool for cutting through complexity and delivering better outcomes.

Recommended AI Tools for 401(k) Analysis:

Want to evaluate your plan using AI? Here are solid options to start with:

• ChatGPT (OpenAI) — Excellent for interpreting documents and comparing investment options
• Claude (Anthropic) — Particularly effective at summarizing complex disclosures and regulatory documents
• Perplexity.ai — Strong at researching plan-related regulations and industry benchmarks
• Copilot (Microsoft) — Good integration with Office documents if you’re working with Excel-based reports
• Other tools worth exploring: Grok (quirky but improving) and DeepSeek (early-stage, open-source option)

Upload your plan disclosure documents and ask: “What aspects of this plan could be improved to benefit participants while maintaining cost-efficiency?”

Then bring those findings to me—we’ll separate the significant opportunities from the minor details and develop a practical improvement strategy.