Town of Bluff workshop participants raised operational concerns about contractor classification, payroll timeliness and insurance coverage, and discussed steps to reduce legal and administrative risk.

A participant summarized the issue as confusion over when a worker should be considered an independent contractor (1099) versus an employee (W‑2). The discussion cited three practical tests used in previous work: who provides tools and equipment, whether the worker sets their own hours, and whether the town or the worker controls the work schedule. Participants pointed to IRS guidance and workforce services materials as primary external references for classification decisions.

Staff described an existing procurement packet that includes a W‑9 and proof of insurance and said it can be formalized and required for new vendors. One staff member said, “We can make it more formal, but we've got that packet,” and suggested a decision tree to standardize determinations rather than handling them on a case‑by‑case basis.

Attendees also discussed payroll and timekeeping. Staff reported recurring delays in employees turning in hours and the administrative burden of chasing late timesheets; the group discussed setting a clear payroll cutoff (for example, no payment for time sheets submitted after a fixed deadline) and putting that requirement in writing and in orientation materials.

Liability and insurance were highlighted: staff noted the town’s insurance generally covers injuries on town work but that elected officials are not covered by the town’s errors‑and‑omissions insurance until they take office (one participant said coverage attaches on Jan. 6). Participants urged consistent verification of contractor insurance and clearer guidance on the town’s exposure when contractors or temporary workers are injured.

Recommended follow‑ups included: formalizing the procurement packet and contractor checklist; drafting a clear decision tree or one‑page guide (IRS/workforce services sources referenced) for classifying contractors vs. employees; setting and distributing a payroll cutoff and timecard policy in orientation materials; and verifying proof of insurance before work begins. The facilitator marked the item for follow‑up and recommended adding a “star” item for resources that the town needs but does not yet have.

No formal policy changes or votes were taken during the workshop. Participants agreed to document the procurement packet and create clearer onboarding language so staff and contractors face consistent expectations.