Top 15 Awkward Questions You Were Afraid to Ask Your Accountant

Ever found yourself dying to ask your accountant, “Can I deduct my cat as an emotional support animal?” or “Why does looking at a spreadsheet make me dizzy?” These are the questions you probably secretly want to ask but don’t because, well… shouldn’t you already know?

Today we set aside the usual curiosities and embark on even more reflective questions you probably never considered. In this Synder webinar, we asked the uncomfortable but insightful questions most people would rather not. With candid explanations, we navigated through a range of topics, from why your profit margin may be quietly disappearing to what “nexus” really is (and no, it’s not a term taken from science fiction).

So, grab a cup of coffee and get comfortable in the land of the uncomfortable! Here are the top 15 questions—along with real answers—to give you the clarity you’ve been looking for in your financial life. 

Meet the guest speakers

Together, Michelle and Ellen bring a wealth of expertise to the webinar, ready to answer those tricky financial questions and share insights you can use.

Let’s see those questions! And some Synder tips as well!

Question 1. My books are a mess! Can I just start from here?

Have you ever tried to build a house on an unstable foundation? It’s only a matter of time before the whole thing comes crashing down. Running a business without cleaning up the books is like that. The balance sheet is the whole history of your business, not just a snapshot of your finances. If it’s cluttered with errors or missing information, you’re setting yourself up for failure, especially when you need accurate records to secure financing or make informed decisions.

That’s not just a little problem—that’s a big one. With 82% of businesses failing because of cash flow issues and only 52% of invoices being paid on time, messy books can turn into a financial disaster. Without clean records, you’re just guessing your next move, not making solid, data-driven decisions.

Ellen puts it best: “Think of it as a rescue project. A good accountant can help you get your books in shape so you can move forward confidently.”

Synder’s tip

First, tackle those critical problem areas: reconcile the old transactions, correct classification errors, and address duplicate entries. Now that you have a clear financial picture, you’ll not only avoid future headaches but lay a base for sustainable growth.

Question 2. Why do I need a W-9 from vendors?

Think of the W-9 form as your financial safety net, wrapping up essential tax information from contractors and vendors, such as their Tax Identification Number (TIN) and legal business name, so that you can be ready when it’s time to hand out a 1099. If you don’t have it, tax season might just become a real pain.

So, let’s say you hired a freelance designer in February but forgot to get their W-9. Then, come January, when you’re trying to prepare 1099s, you’re running around trying to find them for information you could have snagged ages ago. Just one easy step at the beginning can totally save you from a headache later on.

Michelle sums it up perfectly: “It’s a best practice to request a W-9 as soon as you start working with a new vendor. This way, you have all their information ready for tax season, and you’re not scrambling in January.”

Ellen adds, “If you’re wondering whether a vendor needs a 1099, the W-9 can clarify. For example, if they’re incorporated, you’re not required to issue a 1099 for them—but it’s often difficult to know unless you have that W-9 on file.”

Synder’s tip

A W-9 is like a guest list for your tax season party—you need to know who’s on it and what they bring to the table. Collecting W-9s upfront ensures you stay in compliance, keeps you organized, and saves you last-minute headaches when you need to file your 1099s.

Question 3. Why does it feel like I’m paying double tax?

Double taxation may sneak up on you as a result of disorganization in processes or misposting of transactions. For example, you may manually make an entry for a deposit against a payment, whereas your accounting software already has that sale recorded and posted as duplicate income. All of a sudden, your revenues look overstated, and your tax liability shoots unnecessarily high.

Michelle explains, “The key is to follow your software’s workflow. If you’re using an automated tool like Synder, let it handle transaction recording to avoid double entries.”

Many people make the mistake of not keeping business and personal spending separate. It becomes really confusing if you don’t categorize transactions correctly, and sometimes, it can even lead to double taxation. Ellen points out, “It’s all about process. Don’t post deposits and sales manually if your system is already automated. Trust the automation to prevent double-taxation headaches.”

Synder’s tip

Double taxation is like buying the same coffee twice—totally avoidable if you know what you’re doing. So, let your software take over and stick with its workflow to keep your tax records tidy and on point every time.

Question 4. Should I always keep my financial info updated?

Keeping your financial records updated is non-negotiable if you want to make smart business decisions. It’s like trying to estimate quarterly taxes or plan for growth without knowing what your cash flow, income, or expenses currently are—driving blindfolded, so to speak.

“Having real-time data is crucial, especially when estimating quarterly taxes,” Ellen explains. “It’s hard to make good business decisions if you don’t know your current financial standing.”

Although some business owners may believe an end-of-year cleaning is enough, Michelle disagrees. “An end-of-year cleanup is fine, but staying on top of your records monthly will save you so much stress. Build the habit of reviewing your accounts every month to catch any discrepancies early.”

Synder’s tip

Keeping your books current is like checking the fridge before cooking dinner. With up-to-date records, you’ll avoid nasty surprises and be prepared for whatever comes your way.

Question 5. Why is my profit margin lower than expected?

Profit-margin problems usually occur due to timing, seasonal expenses, or inventory costs not being correctly accounted for. For instance, buying inventory long before the revenue is generated from those sales can make your profit margin seem smaller than it is.

 “Expenses like inventory purchases may hit before the revenue from those sales does. This can temporarily lower your profit margin, but it’s just part of managing your cash flow.”

Seasonality can also play tricks on your monthly numbers. Ellen suggests, “Seasonality can skew monthly results. Try looking at your profit margin on a quarterly basis to get a clearer view of your business performance.”

Synder’s tip

Profit margins can be slippery, like that friend who says they’ll “pay you back next week.” You really have to keep a close eye on your expenses, timing, and seasonality to get a clear view of your financial health and set some realistic expectations.

Question 6. What if I’m based in one state but hire or sell in other states?

When your business brings on new employees or sells products in different states, it can create a tax “тexus”—basically meaning you have to collect sales tax or pay income tax there. Say your company is based in Florida but you have remote workers in New York and California, then you might have to sign up for payroll taxes in those states. Or you may have to collect and remit sales tax in Texas if you sell anything to customers who live in this state.

“Every state has different Nexus requirements,” Ellen points out. “It’s your responsibility to know them. Tools can help, but staying on top of your obligations is essential.”

Michelle adds, “When you have employees in other states, payroll tax registration is mandatory. Ignoring тexus obligations could result in penalties, so it’s best to be proactive.”

Synder’s tip:

Think of тexus as that distant relative who shows up for dinner—uninvited but inevitable. Keeping track of your tax filing requirements ensures there are no surprise “guests” at your tax table.

Question 7. Why are my accounts receivable so high?

High accounts receivable usually means that customers are taking their time to pay up, and that can really put strain on your cash flow. For instance, if you’re giving them 60 days to pay and they’re sending paper checks, you might be waiting ages to get your cash.  “Are you making it easy for customers to pay?” Michelle asks. “If they’re waiting to find a checkbook, that’s slowing you down. Offer digital payments and set shorter payment terms to keep your cash flow healthy.”

Your billing process could be causing some issues too. If you send invoices late, it creates a ripple effect—if the client doesn’t get the bill when they’re supposed to, their payment will be late too. Ellen points out how crucial timing is: “If you’re sending invoices late, clients will pay late. Consistency in billing is key to keeping receivables under control.”

Synder’s tip:

High accounts receivable is just like letting your friends “Venmo you later” for dinner: it adds up fast, and then you’re short. Try streamlining your process by setting shorter payment terms, sending out invoices right away, and offering digital payment options. That way, cash flow is always healthy, and your business will run smoothly.

Question 8. Why don’t I have any money?

It’s pretty common to feel strapped for cash even if sales are doing great. Usually, the problem comes from not managing expenses well or having a messy accounts receivable system. For example, if you’re paying your vendors right away but then waiting 60 days to get money from your clients, that’s going to affect your cash flow. “Check your payables,” Michelle suggests. “Are you paying bills too soon or not taking advantage of payment terms? Every day counts when it comes to managing cash flow.”

Ellen emphasizes that balancing payables and receivables is critical: “A well-organized accounts receivable process helps, but managing payables effectively is just as important. Ensure your cash is going toward growth, not unnecessary expenses.”

Synder’s tip:

No cash with good sales is a clear signal something just doesn’t add up. Balance your financial ingredients: optimize expense management and accounts receivable, and keep your cash flow steady to keep your business thriving.

Question 9. How can I shorten the time it takes for clients to pay?

Faster client payment can be the lifesaver of cash flow. The secret? Make paying as easy as possible. For instance, if your system is based on paper invoices and checks, you’re asking for delays. A business can cut its average payment time by 15 days simply by adding digital payment links to invoices so that clients could instantly pay online. Michelle says, “Make it as easy as possible for your clients to pay. People want to pay, but if you make them hunt for a checkbook, you’re creating delays.”

Ellen highlights the importance of follow-ups: “Sending reminders at regular intervals helps keep payments on track. And if clients have options to pay instantly, they’re more likely to do so.” Tools like automated reminders and recurring payment options can go a long way in helping that. 

Synder’s tip:

Convenience is everything! When you offer quick and easy payment methods, like online payment links or automated options, it’s like adding a drive-thru to your business—clients pay faster and it’s less of a hassle, plus your cash flow stays smooth.

Question 10. Why is my business always running out of cash, even with strong sales?

It’s really frustrating when sales are booming, yet cash is constantly tight. This generally comes from either mismatched timing between what you make and what you spend, not keeping up with accounts receivable, or not prepping for seasonal ups and downs. As Ellen puts it,  “Cash flow projections are your best friend. They help you see when cash will come in and go out so you can plan ahead.”

Let’s consider a catering business. They do most of their business in summer weddings, but might have real problems every spring paying for ingredients and staff. Such a catering company can use cash flow projections to obtain a short-term line of credit to cover those expenses, smoothing out their finances until revenue starts rolling in.

Michelle points out another problem area: “The accounts receivable process is a big part of cash flow management. If clients are slow to pay, you’ll always feel short on cash.”A construction company, for example, can handle this by tightening up their payment terms: 50% upfront and the rest due within 15 days after completion. Such a change can keep cash coming in smoothly and ease the stress during slower months.

Synder’s tip:

Cash flow sometimes feels like juggling—you want to keep all the balls in the air. Use projections to look ahead and identify where there could be timing issues. Have the ground rules for clear payment terms, and match expenses with income. Whether it’s adjusting vendor payments, securing credit for peak seasons, or tightening receivables, these steps will help you stay on top of your cash game.

Question 11. Why do they keep asking me about the balance sheet?

The balance sheet serves as your business’s report card—it shows what you’ve got, what you owe, and what’s been put in. It’s the document lenders, investors, and accountants always check out, since it gives a view into your company’s financial health. As Ellen explains, “Accountants love the balance sheet because it shows the big picture. If you know what’s in each category, you’ll have a clearer understanding of your business.”

Take a small retail store that started having problems with cash flow. A quick glance at their balance sheet might reveal they have too much inventory, for instance, which is tying up their cash. Knowing that, they can cut back on orders and put more energy into sales, freeing up the cash they need to keep things running smoothly.

Michelle emphasizes the importance of digging into the details: “Print out your balance sheet and look at every number. Does it make sense? If you don’t understand something, ask.” Reach out to your accountant or financial advisor for clarification, and use their guidance to make necessary adjustments. 

Synder’s tip:

Think of your balance sheet as your money map. Use it to guide your business the right way—whether it’s tackling a cash flow issue, cutting down on debt, or finding those underused assets. Get into the habit of checking it regularly, and you’ll always be in the loop about where you’re at.

Question 12. Why do I have to pay sales tax?

Sales tax can feel like a headache, but it’s a legal obligation for certain transactions, like selling electronics or clothing. That’s what really makes it complicated: the rules differ in each state, and if you fail to follow them, you could face some serious fines. Michelle puts it plainly: “Sales tax isn’t your money—it belongs to the state. Collect it correctly to avoid unexpected tax bills later.”

As Ellen points out, automation is your ally: “Consider using software to automate sales tax tracking. It’s better to collect it right the first time than to owe it later.” Dealing with sales tax calculations manually can cost your business hours and cause compliance issues across multiple states.

Synder’s tip:

Think of sales tax as a relay baton: it’s not yours to keep. You have to pass it to the right state at the right time. Automating that whole thing can save you time, stress and those annoying penalties.

Question 13. Why is my inventory not turning over quickly?

Inventory that sits around too long is similar to cash locked in a drawer—it’s not possible to use this to pay your bills, invest in growing your business, or handle unexpected expenses. Slow-moving stock ties up your cash flow, making it tougher to tackle urgent business needs. 

Michelle advises: “Look at your inventory in detail. Are certain items moving slowly? Consider promotions or discounts to clear out stock.” This way your company will know what isn’t selling as projected, clear out the inventory and reinvest your money into faster-moving products by running a flash sale with a steep discount, for instance.

Ellen adds: “Knowing your inventory helps you make better purchasing decisions. Don’t be afraid to mark down items that aren’t moving to free up cash.” 

Synder’s tip:

Inventory resembles fresh produce in a way—it needs to move quickly, or it spoils. Rotate your stock regularly and use strategic promotions in order to turn over slow-moving items before they cost you more than they’re worth.

Question 14. How do I know if my QuickBooks setup is correct?

Setting up QuickBooks properly is like building a house; everything else depends on it. When it’s set up right, you’ll get accurate reports, catch any financial issues early, and have the information you need to make smart business decisions.

Ellen shares, “A negative accounts receivable means something is off. Review your setup, and don’t hesitate to ask an accountant for help.” 

Michelle adds, “Run a profit and loss report by month and look for inconsistencies. A correct setup helps you make better business decisions.” 

Synder’s tip:

If your QuickBooks setup isn’t right, you’re most likely heading in the wrong direction. For instance, if your chart of accounts is set up incorrectly, you may misclassify income from different sales channels, which will lead to inaccurate profit margins. Regularly review reports, catch discrepancies early, and make adjustments to ensure your financial records guide your business in the right direction.

Question 15. I use automation in my books. How can I make sure I didn’t miss any data?

Accounting automation can feel like a dream for bookkeeping, right? But then a glitch or missed connection can come along and ruin your day. Sure, it makes your life easier, but you can’t just set it and forget it. You have to do regular checks, like bank reconciliations, to make sure nothing gets missed.

Ellen says, “Stay on top of bank feeds and software updates. Sometimes connections break, and you won’t notice until you reconcile.” It’s like when a company finds that their payment processor’s connection has been inactive for weeks. Reconciliation will not only flag the issue but prevent months of missing data from piling up.

Synder’s Tip:

Think of automation as having autopilot on a plane—it’s handy, but you still get to keep an eye on things. Doing regular reconciliations helps make sure your financial records are spot-on and in check, which gives you peace of mind about your business.

Bonus question: Why is Synder your new best friend (who also happens to automate your sales data)?

Picture this: you have a friend who truly understands your accounting struggles and takes care of them while you run your business. That’s Synder: the tool is designed to make your financial processes smoother and life much simpler.

Synder is the absolute game-changer for your business. Here’s why:

Automate transaction recording across multiple platforms

Imagine you’re juggling transactions from Shopify, Amazon, Etsy, PayPal, and Stripe,or other popular platforms, all while trying to keep your books straight. Synder is here to be that assistant that automatically logs virtually every single transaction as it happens right into your accounting software. Say goodbye to manual data entry and forget about human mistakes. It’s all smooth sailing with spot-on records.

Ensure accuracy with real-time reconciliation

Reconciliation used to be a nightmare. Synder changes that. Automating reconciliation processes across all bank accounts and platforms, Synder ensures that your records are always correct and up-to-date. No more late nights chasing mismatched transactions.

Simplify categorization with Smart Rules

Every business is unique, just like your categorization needs. Synder allows you to create customizable Smart Rules to classify your transactions automatically in the best way possible for your particular needs. Be it income, expenses, or taxes—Synder flawlessly organizes your data to fit your accounting structure.

Prevent duplicates and roll back changes with ease

Ever worried that duplicate entries might mess up your books? Synder’s got your back. The duplicate detection system will make sure your records stay clean, and with one-click rollback, you can undo mistakes without breaking a sweat.

Gain insights with real-time reporting

Good decisions require good data. Synder provides detailed, real-time financial reports that show you exactly how your sales, expenses, and cash flow are doing. Want to know how your business is really doing? The reports from Synder give you the answers.

Takeaway

Tax season? Financing prep? No problem. Synder isn’t just a tool, it’s your new accounting partner. It makes your workflows easier, keeps your data spot on, and gives you the insights to grow your business with confidence. Think of it as hitting a home run in your financial management—effortless, efficient, and tailored just for you. But you’re still the star player who’s running the show.

Why settle for stress when Synder can do the heavy lifting for you? Sign up for a 15-day free trial or join our Weekly Public Demo for a walkthrough around Synder’s capabilities by our specialists. 

Conclusion

Managing business finances can feel overwhelming, but don’t worry—we’ve got you covered. In this Synder webinar, we dug into some tricky accounting questions and sorted out everything from tax forms to cash flow issues.

But Synder goes the extra mile by making your accounting easy—keeping an eye on every transaction, bringing all your sales channels together, and giving you updates in real-time. With its clever categorization and simple reconciliation, Synder helps you keep your books spot-on while giving you more time to focus on scaling. Let Synder transform your finances from a total pain into a foundation that sets you up for growth!