Lynda ArtesaniLegal Accountant and Data Migration Specialist at The Proper Trust

The Hidden Tradeoff of Milestone Billing

19 Jun 2026 · 1 min

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In this excerpt from Lynda Artesani’s YouTube video “The Hidden Tradeoff of Milestone Billing,” the speaker warns that milestone-type billing and evergreen retainers tend to generate more client communication than traditional end‑of‑project billing. By “opening the curtain” on work progress and moving portions of the client’s trust fund (e.g., a $2,500 payment) to the contractor as agreed, consultants often receive additional questions and scrutiny from clients that would not arise under a single, final invoice. The speaker cautions practitioners to anticipate and manage this increased dialogue when adopting milestone billing structures.

Chapters

And there's something I want to caution about that I've seen in the milestone-type billing and evergreen retainers is there's more communication going on with the client with these milestone billings where you're opening up the curtain and you're saying, okay, I've done this and I've done that. And I've taken that $2,500. I've moved that out of your trust and taken it as per our agreement. Quite often you'll get more questions from the clients as that goes along that don't occur in regular-style billing that happens at the end of everything. Yeah.