15 Questions to Ask Before You Hire a Bookkeeper episode artwork

EPISODE · Aug 27, 2026 · 17 MIN

15 Questions to Ask Before You Hire a Bookkeeper

from Why Did We Start This?

On Tuesday we told the story of an owner who overpaid the IRS by about forty five thousand dollars because nobody was checking the work. Today is the follow up we promised: the questions to ask before you hand your books to anyone. Penny has roughly fifteen of them, and every one comes from something she has walked into. Will I get reports every single month, and by what date. Can I see the reconciliation reports themselves and not just a summary. Can you explain what these mean in plain English, and how does the profit and loss relate to the balance sheet. That last one matters more than it sounds, because if the person on the call cannot answer it, Penny says that is not a red flag, that is the end of the call. From there it gets into the parts most owners never think to ask about: exactly what access someone needs to your bank accounts and why read only is the only right answer, whether they carry errors and omissions and data breach insurance, whether they store your passwords and how, and whether anyone is talking to your tax preparer during the year instead of just in April. Along the way, the client whose bookkeeper emailed to say she was retiring and did not know how to fix what was wrong. Books where nothing had been done at all. And the owner who was with a CPA for twenty years and said Penny's team understood his business better in six months. If you want the whole list, they are giving it away, so DM Penny and she will send it.Book a Free Call with PennyConnect with us:FacebookInstagramLinkedIn1610 Financial SolutionsTakeaways:The bare minimum from anyone doing your books is a report every single month, with an agreed date. If you have never received one, that is your answer.Ask to see the reconciliation reports, not just a summary. You do not have to know how to read them. Asking says you intend to inspect the work, and that alone changes the relationship.Ask how the profit and loss relates to the balance sheet. Plenty of people doing this work only know how to clear a bank feed. If they cannot answer, end the call there.Read only access to your accounts is the right answer, and a good firm brings it up before you do. Too much access is how embezzlement happens, and some banks do not even offer the right permission level.Ask about the boring things nobody asks about: errors and omissions insurance, data breach cover, how your passwords are stored, and who is talking to your tax preparer between now and April.This show is for general information and encouragement. It is not tax, financial or legal advice. Please consult a professional about your particular situation before you make any decisions.

Episode metadata supplied by the publisher feed · Published Aug 27, 2026

Embed this episode

On Tuesday we told the story of an owner who overpaid the IRS by about forty five thousand dollars because nobody was checking the work. Today is the follow up we promised: the questions to ask before you hand your books to anyone. Penny has roughly fifteen of them, and every one comes from something she has walked into. Will I get reports every single month, and by what date. Can I see the reconciliation reports themselves and not just a summary. Can you explain what these mean in plain English, and how does the profit and loss relate to the balance sheet. That last one matters more than it sounds, because if the person on the call cannot answer it, Penny says that is not a red flag, that is the end of the call. From there it gets into the parts most owners never think to ask about: exactly what access someone needs to your bank accounts and why read only is the only right answer, whether they carry errors and omissions and data breach insurance, whether they store your passwords and how, and whether anyone is talking to your tax preparer during the year instead of just in April. Along the way, the client whose bookkeeper emailed to say she was retiring and did not know how to fix what was wrong. Books where nothing had been done at all. And the owner who was with a CPA for twenty years and said Penny's team understood his business better in six months. If you want the whole list, they are giving it away, so DM Penny and she will send it.

Distinct summary based on available episode metadata or transcript content.

Ready to play

15 Questions to Ask Before You Hire a Bookkeeper

0:00 17:48

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Why Did We Start This??

This episode is 17 minutes long.

When was this Why Did We Start This? episode published?

This episode was published on August 27, 2026.

Can I download this Why Did We Start This? episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!