Table Of Contents
- How Proactive are You Throughout The Year?
- Do You Understand My Industry?
- What’s Your Approach to Helping Clients Grow?
- How do You Handle Unexpected Issues?
- Who Will I Actually be Dealing With?
- Can You Explain Things Without Using Jargon?
- Do You Offer Strategic Tax Planning or Just File Returns?
- What’s Your Communication Style?
- What’s Included in Your fee?
- Hiring a CPA: Don’t Just Hire for Today
Hiring a CPA? Here’s What Most Business Owners Forget to Ask
What if the person you’re trusting with your finances is missing something important, and you don’t even know to ask about it?
Hiring a CPA might feel like a straightforward task. You find someone qualified, experienced, maybe even recommended. But here’s the problem: most business owners only scratch the surface. They ask about tax filing, bookkeeping, and hourly rates. And sure, that’s all important. But there are other questions, deeper ones, that often get overlooked.
These are the questions that can help you figure out if this person is just going to keep your numbers straight or if they’ll actually support your business growth.
How Proactive are You Throughout The Year?
Most business owners talk to their CPA once or twice a year. Usually during tax season, and maybe briefly at year-end. The rest of the time? Silence.
But here’s the thing: Reactive accountants just process paperwork. Proactive CPAs help you make better decisions before things happen. Ask them how often they check in. Do they offer quarterly reviews? Will they flag issues as they come up or just deal with them later?
If they wait until tax season to look at your numbers, you’ve already missed opportunities. You want someone who’s keeping an eye on things all year long, not just cleaning up after the fact.
Do You Understand My Industry?
Not all businesses are the same, and not all CPAs understand the nuances of different industries. Construction, retail, creative agencies, and medical practices… they each have their own quirks when it comes to revenue, expenses, tax rules, and growth strategies.
If a CPA doesn’t know how your industry works, they’re more likely to miss deductions or give advice that doesn’t really fit.
Ask if they’ve worked with other businesses like yours. Don’t assume they’ll figure it out as they go. That learning curve can cost you.
What’s Your Approach to Helping Clients Grow?
This is a big one. Too many business owners think of their CPA as just a tax person. However, the right CPA NYC can be a strategic partner.
Someone who spots opportunities, helps plan for future cash flow, and offers insight on how to scale without unnecessary risk.
Some CPAs are more compliance-focused. They’ll file the right forms, keep you legal, and that’s it. Others lean toward advisory services, helping you understand your numbers and make smarter choices.
Ask how they work with clients who are scaling. What kind of conversations do they have? Are they comfortable talking about margins, pricing strategy, or expansion plans? You’ll get a feel pretty quickly for whether they think like a business partner or just a number cruncher.
How do You Handle Unexpected Issues?
No one likes surprises, especially when it comes to taxes or compliance. But they happen. An audit letter. A payroll mistake. A cash flow dip that turns into a crisis.
When hiring a CPA, ask about their ways to handle those curveballs. Do they have a system for responding quickly? Will they represent you in front of the IRS? Do they charge extra for urgent support?
You need to know how they react under pressure, not just how they operate when everything’s going smoothly. That’s what really shows you their value.
Who Will I Actually be Dealing With?
You might meet with the CPA during the sales process, but once you’re a client, that could change. Some firms hand you off to junior staff or delegate everything to bookkeepers. It’s not necessarily a problem, but you want clarity.
Find out who your main point of contact will be. Will you have direct access to the CPA if you need it? Or will you be filtered through multiple layers before you get answers?
Consistency matters. If you constantly talk to someone new or wait days for a reply, it slows everything down and creates gaps in communication.
Can You Explain Things Without Using Jargon?
Finance can get technical. But your CPA should be able to break things down in plain language. You need someone who doesn’t make you feel like you’re in a lecture whenever you ask a question.
Test this out during your meeting. Ask them to explain a financial concept you’ve always found confusing. If they can’t do it clearly or they talk in circles, that’s a red flag.
You don’t need a walking dictionary; you need a translator who helps you make sense of your numbers.
Do You Offer Strategic Tax Planning or Just File Returns?
There’s a big difference between preparing a return and planning your taxes ahead of time. Tax filing is reactive. Tax planning is proactive.
The right CPA will look ahead, not just back. They’ll help you make decisions in real time to reduce your liability, legally and strategically. That could mean adjusting how you take income, changing how your business is structured, or shifting the timing of purchases and investments.
Ask how they help clients plan before the year ends. Do they run projections? Do they suggest tax-saving strategies before it’s too late to use them? If the answer’s no, you might want to keep looking.
What’s Your Communication Style?
It sounds simple, but communication can make or break a relationship. Some CPAs prefer emails, while others prefer phone calls or in-person meetings. Some will answer a text, while others will not touch their phones outside business hours.
None of this is right or wrong. But you want to be on the same page. Make sure their approach fits how you work. If you hate waiting days for a response and they’re more “slow and steady,” that mismatch will get old fast.
Set expectations early. Ask how quickly they respond. What’s the best way to reach them? Do they send regular updates, or must you chase them down?
What’s Included in Your fee?
It’s easy to assume that once you’re paying a monthly retainer or annual fee, everything’s covered. But that’s not always the case. Some CPAs charge extra for tax planning, IRS responses, or advisory calls. Others include it all in one package.
You need to be clear on what’s part of the deal and what’s considered an add-on. Otherwise, you’ll either avoid asking questions to “save money” or be shocked by surprise invoices.
Break down the pricing. Ask what’s covered, what’s optional, and what might come up that isn’t included. That transparency can save a lot of frustration later.
Hiring a CPA: Don’t Just Hire for Today
It’s tempting to choose a CPA based on what you need right now. Maybe you’re behind on taxes. Maybe you just want the books cleaned up. But take a longer view.
When hiring a CPA, ask yourself whether this person can support the business you’re building, not just the one you have today. Are they aligned with your goals? Can they grow with you? Do they challenge your thinking in a good way?
When you ask the right questions upfront, you’re more likely to find someone who brings more to the table than just math skills. You get a partner who actually helps move your business forward. And that’s what really counts.
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