Tax Season Tips From A Pro

The What, When and How of Working with your Tax Pro


preparing taxes

Once January gets rolling, whether you are an on-time tax filer or not, a vague sense of burden begins to grow on us. Yes, my friends, it is Tax Time again!  If you use some form of electronic transaction tracking throughout the year, the burden may not be too heavy.  If your records are scattered, or not complete, procrastination sets in, and the burden gets heavy.


So, I am here to help you get organized!  Here is the pro-scoop on what you need, when it is needed, and how to get it there.  Your tax preparer will appreciate your efforts!


We started creating an annual checklist of what to save.  We put all documents in one (digital) folder throughout the year and as tax documents arrive.  (We scan everything and no longer keep paper but use whatever system works for you.) 


Brokerages provide terrific reporting on investments bought & sold so keep those 1099s! If you buy or sell investments or have holdings outside of a brokerage, you may have to keep more detailed records for capital gains purposes.  Otherwise, most people just need to track their charitable contributions and medical expenses.  End of year consolidated statements are the ones to keep.  You do not need to save trade notices or even monthly statements once the year is complete.  They have all been posted to your annual statement.

1099s come in many flavors.  All are used to report income and your CPA will need copies. 

1098s report expenses that can reduce your tax bill.

W2s report earned income from employment.

Any other income records.


Credit card statements are not tax records.  They do not provide enough information. They do provide clues as to what you might need a receipt for, as do bank statements.

Medical expenses are subject to a 7.5% AGI limit.  So unless .075 * (your “total” income) is less than your total unreimbursed medical costs…don’t worry about them.  Medicare and your pharmacy are good sources of receipts for paid expenses.

You can deduct up to 50% of your AGI for legitimate charitable donations.  Receipts should include the organization, date, amount, or market value, and what was donated (if not cash) and a statement of whether any goods or services were exchanged.

Include records of tax payments you have made.

Business expenses are outside the scope of this article, but many are deductible.

Here is a list from TurboTax: Documents for my tax preparer


Here is the rough schedule we use and maybe it will work for you.

  • Prior Year:  save tax related receipts and documents in one place.
  • January
    • Review medical expenses in my tracking software and make sure you have receipts.
    • Review donations & verify that you have receipts.
    • Download Medicare & pharmacy reports.
    • Gather records of any asset sales or major purchases (home, stocks, energy credit qualified items, etc.)
    • There may be other things specific to you.
    • Jan. 29th, 2024 is the earliest you can file.
    • Jan. 31st is the deadline for employers to mail W-2’s and some 1099s are sent.
  • February
    • Complete/review the accountant’s checklist based on last year
    • If you do your own return(s), get started!
    • Tax forms are rolling in.  Keep them in one place.
      • As they come in, check them off on your annual checklist.
      • Upload them to your accountant if you can
    • Feb. 15th is the deadline for consolidated broker reports
    • By late February, you should have most everything and can send information to your preparer.  We try to have it done by Feb. 28th.  Try!    (Note: We do this for quite a few people!)
  • March
    • Your accountant probably has an early March deadline for getting tax documents to them for timely filing as they are in serious crunch mode by now.
    • K-1s are due out by March 15th, if you own part of an S-corporation or Partnership.  We send these when we get them.
  • April
    • Once your return is available, pick it up or download it promptly and review it carefully for errors or omissions.
    • Return signed eSignature forms so your accountant can file your returns electronically (faster and safer).
    • April 15th is the payment deadline and the filing deadline.  Even extension filers must file for an extension and pay an estimated amount.  Your first quarter estimated payment, if any, will also be due.

What NOT to Send

Do not send last year’s return if you are using the same provider.

Do not send a box of receipts and expect the preparer to figure out what they are for (unless you like big bills)!

Do not upload or send monthly statements if an annual summary is available.

Paper should be grouped by type of income or expense, preferably not stapled, or taped (that takes more time).


Do not send anything via email attachment!  The hackers are just waiting for you!

  1. Use your accountant’s online portal.
    •   Easiest for them (less costly?)
    •   Upload documents when they arrive (faster processing?)
    •   Safer than mail (and especially safer than email)
    •   Requires no driving, no meeting, and no return trips for things that you forget or that arrive later.
    •   Hint, hint: We do this for our clients.
  2. Drop off
    •   This is more secure than mailing but requires driving and sometimes several trips.
    •   Your accountant now has all of your records, unless you make temporary copies, which is a waste of time and paper.
  3. Mail
    •   The least preferred method, due to the risk of tampering and identity theft.  Sidebar:  The hackers have ruined life for honest people. 
    •   Can be costly if there is a lot to send and you use certified mail.
  4. Carrier Pigeon.
    •   Probably not.

Just for the record, we are not CPAs, so if you have tax questions, contact a tax professional.  We just help you interface with your CPA, so they get what they need and you satisfy Uncle Sam with the least stress possible.  And, we can make referrals.

Happy Taxing!