Why do CPAs ask so many questions!?

Before co-founding Vivify, I was a wealth advisor for 175+ clients. I spent my days doing the hard work of planning - guiding clients through contributions, conversions, and complex financial decisions. And every tax season, without fail, I’d brace for questions from the CPA.

I’ll be honest: it often felt like nitpicking.

Why were they asking about the Roth conversion? Did they think that was the wrong call?

Why did they need to know which account the charitable donation came from?

Did they not trust that the planning had been done correctly?

Now that I’ve stepped across the aisle - reviewing hundreds of tax returns every season - I get it.

So I wanted to write this post for advisors who may, understandably, be wondering: Why do you keep asking us questions?

Here’s what I’ve learned on the other side:

Clients often mangle the message

Most clients don’t actually know what they did - or how to describe it in tax terms.

They might tell us, “I contributed $7,000 to my IRA,” when what actually happened was a Roth 401(k) deposit via payroll. Or a rollover. Or a backdoor Roth conversion. Each of those has completely different tax implications and the IRS cares a lot about which is which.

You, the advisor, likely know the correct version - because you helped facilitate it. But unless we double-check, we’re often working from partial, misremembered, or misunderstood client input.

So when we ask, it's not to challenge your advice. It's because we want to accurately reflect that advice on the return. And we would much rather confirm with you now than the client have a problem later (that we know you would inevitably have to help them unpack).

The tax forms can be incomplete or misleading

Even “official” forms leave gaps:

• QCDs (Qualified Charitable Distributions) historically haven’t been reported on 1099-Rs (this may be changing!!). We need to manually reduce the taxable amount of the IRA distribution. If we don’t know a QCD happened, or from what distribution, your client could get taxed on a charitable gift.

• IRA conversions are only half the story if there’s basis in play. If you’ve been guiding backdoor Roth strategies, we may need your help reconciling prior 8606 records or confirming intent.

• 529 contributions, HSA deposits, estimated payments - all things we might not see unless someone tells us. And unfortunately, even when we ask the clients for these things in our organizer, they might skip the question.

Here’s where we often need your help

These are the recurring blind spots where you often hold the key:

• QCDs - amount and account source

• IRA Contributions or Conversions

• Donor Advised Fund activity

• 529 plan contributions

• Estimated tax payments made outside of withholding

• Supplemental information regarding basis taxed as ordinary income for equity compensation (clients struggle to navigate to this!)
  

The holistiplan tax letters answer a lot of the above questions. We love them - especially when they’re shared in January (not March).

From suspicion to collaboration

I used to think questions from the CPA meant that my advice was being challenged. Now I know they’re often an effort to honor the planning that’s already been done by making sure it gets reported the right way.

So if a Vivify team member messages you mid-season, it’s not an indictment. It’s us saying: “help us protect your planning by reporting it accurately!” The goal is not more work for you - it’s less rework, fewer surprises, and a better client experience.

From one advisor to another: thanks for bearing with us.