So, I work for a bookkeeping company, and recently I was in an onboarding meeting with a new client. We were talking through project tracking etc and they asked how to track personal spends through the business.
Obviously not allowed of course, but how do I go about even bringing this up to anyone? Do I just go straight to my boss? It was so awkward in the meeting as we all knew it was dodgy but I didn’t want to ruin the relationship with the client and tell them they are wrong.

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To the client I would explain the IRS rules on that particular subject.

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Thing is, I don’t run the company and if the client got annoyed that I’ve said that it would look bad on me. I feel like going to my boss and explaining would be the better idea? I’m not sure, it’s a difficult one

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Have to set expectations early. Educational moment for the client, for sure. I would probably run it by my boss, just to let them know what we are getting into.

Right. The boss could potentially shed some light on how best to handle it as well. Some people, even when you try very hard to stay neutral, will take anything they’ve done wrong very personally.

The trick is to explain in a “I’m on your side” way rather than accusatory. See if you can bring it up gently maybe framed as you not wanting them to get in trouble w the government for it down the line?

At the end if the day, make sure you document your efforts so that they can’t turn around and sue you if they choose not to listen to you.

100% agree. I have no experience in this though and don't want to potentially ruin a great relationship with a client. As they are projected to bring in a lot of money for us! Hence the speaking to the boss scenario instead maybe?

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