What Should a Small Business Do in a New Employee's First Week?

Run this checklist in order. Each item names the owner (Manager or New Hire), the federal document that requires it where one applies, and whether a Dave by voolama (hellodave.ai) workflow can draft or remind. Items marked [Workflow: draft] can be handled by an AI agent drafting content for a manager to approve. Items marked [Workflow: remind] can be handled by a Human Review task that prompts the manager to confirm the item is done. Items with no workflow tag require a person to act directly. Dave by voolama-specific items are sourced from the tasks and admin-users help documentation, DEV v0.11.0, confirmed 2026-08-30, and verified on the voolama production tenant on 2026-09-22. This is an operations checklist, not legal or employment advice.

Before day 1 (manager)

1. [Manager] Create the new hire's Dave by voolama user account. Navigate to Admin, then Settings, then Users and Roles, then Add User. Set role to Use (permissions: instances:*, tasks:*, artifacts:read). Only the Admin role can create users. Role changes take effect on next login. Verified 2026-09-22 on the voolama production tenant. Sourced from the admin-users help documentation, DEV v0.11.0, confirmed 2026-08-30. [Workflow: remind]
2. [Manager] Set up the new hire's email account and any business software accounts. Document which accounts were created and the date. Store in the personnel file. [Workflow: remind]
3. [Manager] Prepare the new hire's physical or remote workspace. Confirm equipment is ready, login credentials are set, and any physical keys or access cards are prepared. [Workflow: remind]
4. [Manager] Draft and approve the first-day schedule and welcome email. An AI agent in Dave by voolama can draft both from the manager's notes (new hire name, start date, role, first-day agenda). The manager reads the draft in the Human Review task Payload section and clicks Approve before sending. Dave by voolama does not send emails: the manager sends the approved draft through the business's normal email system. Verified 2026-09-22: Human Review task held the draft until Approve was clicked; decision recorded in audit log with manager's user ID and timestamp. Sourced from the tasks help documentation, DEV v0.11.0, confirmed 2026-08-30. [Workflow: draft]
5. [Manager] Prepare the new hire's paperwork packet. Include: blank Form I-9 (uscis.gov/i-9-central), blank Form W-4 (IRS Publication 15, irs.gov/pub/irs-pdf/p15.pdf), offer letter copy, any signed policies. [No workflow: legal documents requiring direct handling.]

Day 1 (Monday): paperwork and orientation

6. [New Hire] Complete Form I-9 Section 1. Required by 8 U.S.C. 1324a (uscis.gov/i-9-central) on or before the first day of work. The new hire must present original identity and work authorization documents. [No workflow: federal form requiring direct handling.]
7. [Manager] Complete Form I-9 Section 2. Required within three business days of the new hire's first day (8 U.S.C. 1324a, uscis.gov/i-9-central). For a Monday start, Section 2 is due by end of day Thursday. Examine original documents in person or via authorized remote verification. [No workflow: federal form requiring direct handling.]
8. [New Hire] Complete Form W-4. Required before the first paycheck. IRS Publication 15 (Circular E, irs.gov/pub/irs-pdf/p15.pdf) requires the employer to withhold federal income tax based on the W-4. If no W-4 is submitted, withhold at the default rate (single filer, no adjustments). [No workflow: IRS form requiring direct handling.]
9. [Manager] Walk the new hire through the first-day schedule. Confirm the new hire has the approved welcome email and first-week schedule. Confirm they know who to contact for IT issues, HR questions, and day-to-day questions. [Workflow: remind]
10. [Manager] Introduce the new hire to the team. In person or by video call. Name each team member and their role. [No workflow: relationship-building requiring direct handling.]

Day 2 (Tuesday): systems and first tasks

11. [Manager] Confirm the new hire can log in to all required systems. Check email, any project management tools, and Dave by voolama (if applicable). Confirm the new hire can see the Task Inbox (navigate to Tasks in the sidebar) and complete a test task. Sourced from the tasks help documentation, DEV v0.11.0, confirmed 2026-08-30. [Workflow: remind]
12. [New Hire] Complete any required policy acknowledgments. Sign and return any confidentiality, acceptable use, or other policy documents included in the paperwork packet. [No workflow: legal documents requiring direct handling.]
13. [Manager] Assign the new hire's first real task. Use a Dave by voolama workflow to create a User Interaction task assigned to the new hire. The task Payload should describe the assignment clearly. The new hire opens the task from the Task Inbox, reads the Payload, and clicks Approve to confirm they have received and understood the assignment. [Workflow: remind]

Day 3 (Wednesday): check-in and adjustment

14. [Manager] Confirm Form I-9 Section 2 is complete. If the new hire started Monday, Section 2 is due by end of day Thursday (8 U.S.C. 1324a, uscis.gov/i-9-central). Confirm the original documents were examined and the form is signed and dated. File the completed I-9 separately from the general personnel file, as required by USCIS. [No workflow: federal compliance requiring direct handling.]
15. [Manager] Hold a 15-minute check-in with the new hire. Ask: Do you have everything you need? Are there any systems you cannot access? Do you know who to ask for help? A Human Review task can prompt the manager to confirm this check-in happened. [Workflow: remind]
16. [New Hire] Complete any required online training. If the business requires compliance training (for example, workplace safety, data handling), confirm the new hire has access and has started. [Workflow: remind]

Day 4 (Thursday): first deliverable review

17. [Manager] Review the new hire's first task output. If the new hire submitted a deliverable, the manager opens the Human Review task in the Task Inbox, reads the Payload, and clicks Approve, Reject, or Request Changes. The decision is recorded in the audit log with the manager's user ID and a timestamp. Verified 2026-09-22 on the voolama production tenant. Sourced from the tasks help documentation, DEV v0.11.0, confirmed 2026-08-30. [Workflow: remind]
18. [Manager] Confirm all accounts are working correctly. Check that the new hire has access to every system they need for their role. If any account is missing, create it today. [Workflow: remind]

Day 5 (Friday): end-of-week wrap-up

19. [Manager] Hold a 30-minute end-of-week review with the new hire. Ask: What went well? What was confusing? What do you need for next week? A Human Review task can prompt the manager to confirm this review happened and add a Comment with the key points. [Workflow: remind]
20. [Manager] File all completed paperwork in the personnel file. Confirm the file contains: completed Form I-9 (filed separately per USCIS requirements), completed Form W-4, signed offer letter, signed policy acknowledgments. IRS Publication 583 (irs.gov/pub/irs-pdf/p583.pdf) requires employment tax records for at least four years. [No workflow: recordkeeping requiring direct handling.]
21. [Manager] Export the Dave by voolama audit log for the onboarding workflow. Navigate to Admin, then Settings, then Audit Log. Use the date range filter to scope events to the first week. Click the download button to export as CSV. Store the export in the personnel file. Only the Admin role can view the audit log. Sourced from the tasks help documentation, DEV v0.11.0, confirmed 2026-08-30. [Workflow: remind]

The companion guide at How to build a new hire onboarding workflow for a small business covers the step-by-step process for building the Dave by voolama (hellodave.ai) workflow that runs the items marked [Workflow: draft] and [Workflow: remind] on this checklist. This section summarizes which checklist items map to which workflow node types, grounded in the tasks help documentation (DEV v0.11.0, confirmed 2026-08-30) and verified on the voolama production tenant on 2026-09-22.

Items not in this table (Form I-9, Form W-4, policy acknowledgments, team introductions) require direct human action and should not be routed through an automated workflow. Federal forms must be completed by the named parties with original documents: an AI agent cannot complete or verify them.

This checklist covers the first five working days of a new employee's onboarding at a US small business from an operations standpoint. Four explicit boundaries:

• This is not legal or employment advice. The compliance items (Form I-9, Form W-4, IRS Publication 583) are cited at the specific federal document level so the reader can verify each requirement directly. Whether a specific onboarding process complies with federal, state, or local employment law requires a qualified employment attorney's assessment. The author's expertise is in infrastructure and financial operations, not employment law.
• This checklist does not cover state-specific requirements. Several US states require additional new hire reporting, specific written notices, or particular forms beyond the federal baseline. Consult a qualified employment attorney or licensed HR professional on your state's requirements.
• This checklist does not cover benefits enrollment. Health insurance, retirement plans, and other benefits have their own enrollment windows and federal requirements (ERISA, ACA). This checklist does not address them.
• This checklist covers onboarding a new employee to the business, not onboarding a team onto Dave by voolama. Setting up the Dave by voolama workspace, adding AI providers, and configuring tenant settings are covered in the Learn Dave quick-reference at Build Your First Workflow.