3 Ways to Make Your Accountant Happy This Tax Season


I hate tax return extensions. The only logical reason to file an extension – in my book – is to buy time to make contributions to a deferred compensation plan.  What? Not deferring comp this year – then why wait?  Savvy CEOs who manage by the numbers do not miss a beat when it comes to filing tax returns because the only extra “i” that needs to be dotted is the compilation of financial data for their CPA.

If you don’t have a solid bookkeeper and accountant, you may ask how this could possibly happen.  Ahem, allow me to pontificate.

You start with a solid financial plan, otherwise referred to as a budget. You then financially manage your company each month using the budget as a roadmap; digitally filing every receipt, bill and invoice each day so your bookkeeper can enter the information into your books essentially keeping record of all money coming in (revenue) and going out (expenses).

When done methodically as we number people do, you have accurate financial information that is not only ready to prepare annual tax returns with the push of a button, but more importantly, provides information to help you understand the number story and make strategic decisions to nimbly shift operations to meet goals.

Tips for a smooth tax season

Tax season is grueling. January through April many Chicago CPAs work more than 10 hours per day/7 days per week, sleeping at the office to meet incredible deadlines and keep clients happy. You already don’t relate to us folks who love numbers, so take one extra moment to empathize with the quarter of doom that your digit-loving experts dread yet work through each year. Pause to acknowledge that your CPA is responsible for filing tax returns for all of his/her clients within a 2-3 month period of time.  Although I am tempted, I won’t build a model to show you how difficult this job is, especially when companies enter into February with icky, sticky, hole-strewn data.

We love our Officeheads’ vetted CPA partners.  They hold small businesses in high regard and we don’t want to risk them pushing you into extension hell, so we follow these guidelines to keep our CPAs happy:

    1. Copy of Your Books
      Supply your CPA with a copy of your QuickBooks file that is complete, accurate and reconciled to date. If you don’t use QuickBooks or a comparable program, they will want:

      • P&L
      • Balance Sheet
      • General Ledger


    1. Complete Tax Documentation
      Supply your CPA with a copy of any document you received that is identified with “Important Tax Information Enclosed”. This includes 1099-MISC, 1099-INT, etc.


  1. Year-End Statements
    CPAs thrive on exact and complete information.  That means that quality checks and double checking are embedded in their DNA.  Supply your CPA with all year-end monthly statements from all financial institutions dated December 31 (or sometimes in January) so they can complete their due diligence to ensure your books are accurate enough to file a non-disputable tax return.

Three.  It’s a magic number.

Do you want to go the extra mile? “Get your information in early,” asks Kristi Glass of Smith Elliott Kearns & Company in Hagerstown, Maryland. Since you MISC forms, there is no reason why this information shouldn’t land on your CPA’s desk by mid-February. James Pepa of Porte Brown in Evanston, Illinois suggests, “If you have out-of-town travel scheduled between now and April 18, please let your CPA know in advance.” This helps them to schedule your tax return preparation around your travel plans. Bart Eilts of Eilts & Associates in Chicago recommends, “Send your information and questions in an email vs. calling so we can reply on our own timeline, and understand if it is not right away.” A unanimous plea from all three asks that you consolidate all of your information and submit it in one package. Information that arrives in dribs and drabs breeds inefficiencies.

If you rely on your financial reports to navigate your business, I expect your books to be spot on so your CPA should ask 5 questions or less. If your year-end last minute bookkeeping is creating the same amount of stress on your CPA, you will be granted an extension because of the time required to file an accurate return, or something worse, the realization that you are operating your business without financial intelligence.

Ouch. Please don’t be that CEO.

For more ways to run your business in a way that will keep your CPA smiling, be sure to check out our eBook, Financial Management for Small Businesses: An Owner’s Manual. If you’re interested in talking to Rebecca Berneck about tax and financial planning for your small business, you can get in touch here.