In my experience working with accounting firms, sales tax rarely comes up proactively. It gets addressed when there's a problem: a notice, an audit, a client who just expanded into new states and is suddenly panicking. But by then the situation is already harder than it needed to be.
The good news is that the conversation doesn't have to be complicated to start. You don't need a full nexus study or a deep compliance review to open the door. You just need to ask the right questions.
These are five questions I'd put in front of every client, regardless of size or industry.
This is the foundational question, and the one that catches the most people off guard. After South Dakota v. Wayfair, physical presence is no longer the threshold for sales tax obligations. Economic nexus is. If a client is selling products or services across state lines, even entirely online, they may have obligations in states where they've never registered and never filed.
A lot of clients genuinely don't know this. They're not trying to avoid anything. They just haven't had anyone explain how the rules changed. Asking this question starts the conversation and signals that you're paying attention to something most advisors aren't.
Remote work created a wave of unintentional nexus that a lot of businesses still haven't fully accounted for. Hiring an employee in a new state can establish nexus there, even if the company has no other presence. The same goes for independent contractors in some jurisdictions.
This one is worth asking even if the client doesn't think of themselves as a multi-state business. A company headquartered in one state with three remote employees scattered across the country may have compliance obligations in four states without realizing it.
Taxability is one of the more underestimated pieces of sales tax complexity. It's not enough to know where you have nexus. You also need to know whether what you're selling is actually taxable in each of those places.
The rules vary significantly by state. Software is taxable in some states and exempt in others. Services follow completely different rules depending on the jurisdiction. Food, clothing, medical products, and digital goods all have their own patchwork of state-by-state treatment.
Clients who are collecting and remitting tax on everything, or nothing, without understanding taxability are almost certainly getting something wrong. This question opens a conversation that can uncover both over-collection and under-collection issues.
For clients who have been growing, expanding into new channels, or adding products and services, a nexus review from two years ago may not reflect where they stand today. Thresholds get crossed, new states get triggered, and the compliance picture changes.
Most clients have never done a formal nexus review at all. For those who have, asking when the last one happened is a useful way to surface whether it's time to revisit. This doesn't have to be a big project. Even a quick conversation about where the client is selling and where their employees are located can reveal gaps that need attention.
This is the question that gets at whether the client has any systematic approach to sales tax at all, or whether they're just hoping nothing changes and nobody notices.
The sales tax landscape moves fast. Rate changes, new nexus thresholds, updated taxability rules, marketplace facilitator laws. Keeping up with all of it manually isn't realistic for most businesses. Asking this question helps you understand where the client's process breaks down and where there's an opportunity to help them build something more reliable.
It also positions you as someone who thinks about compliance as an ongoing discipline rather than an annual checkbox. That framing matters for the relationship.
None of these questions require you to have all the answers before you ask them. They're conversation starters, not diagnostic tests. The value is in what they surface, and in the signal they send to clients that you're looking out for them in an area where most advisors aren't paying attention.
The firms that ask these questions consistently find something worth addressing almost every time. The ones that don't are leaving their clients exposed and leaving real advisory work on the table.
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