A Better Financial Planning Process Starts With Simpler Questions

I recently worked with an advisor on a client in their 40s with what looked like an incredibly sophisticated financial situation.

Millions coming in through RSU vesting. A high six-figure salary. Multiple properties. Three kids heading toward college. And a real estate tax strategy designed to aggressively offset income taxes.

I reviewed hours of planning meeting transcripts while building the financial plan. Taxes were clearly the priority.

But before handing the plan back to the advisor, I flagged one question:

Does this client’s wife even want to do what this strategy requires?

The strategy depended on his stay-at-home wife materially participating in real estate activities for roughly 750 hours a year.

There was just one problem. She hadn’t attended a single planning meeting.

The advisor asked the client if his wife actually wanted to spend that much time managing properties. His response was basically, “I’m not sure.” So he asked her directly.

Her answer:

“If I’m being honest, no.”

I don’t blame her.

This family was already earning a multi-seven-figure income, funding college for their kids, and realistically could become work-optional whenever they wanted. The strategy worked mathematically, but it didn’t align with the life they actually wanted to live.

So we rebuilt the plan and removed the strategy entirely.

That moment reinforced something I see constantly in financial planning. Many advisors find a prospect, convert them into a client, and immediately start solving for taxes, insurance, retirement projections, estate structures, and optimization strategies before fully establishing the destination.

But the reason people hire an advisor in the first place is because they feel overwhelmed. Most clients have spent years collecting financial advice from podcasts, internet forums, social media, and conversations around the office. By the time they sit down with an advisor, they’re carrying a pile of disconnected strategies they barely understand.

Every client thinks they have the most complicated financial situation you’ve ever seen. Usually, they’ve just accumulated noise. This is where great advisors create the most value. Not by stacking more complexity onto the pile, but by simplifying it.

Ask the obvious questions. Kill the noise. Help clients make decisions that actually align with the life they want, not just the strategy that looks smartest on paper.