How to Hire an Assistant: The Complete 9-Step Playbook

If you want to hire an assistant who frees your time instead of creating more work, follow a repeatable, low-risk hiring system. This guide gives you a clear job brief template, a practical test, a paid trial plan, and onboarding steps that actually stick. Skip the fluff — focus on structure and signals.

Why most hiring fails (and how we avoid it)

Hiring fails for three reasons: unclear role, poor vetting, and sloppy onboarding. Fix those and you get reliable output fast. The system below solves each one in sequence: define → test → trial → onboard → retain.

Step 1 — Define the role precisely (30–60 minutes)

Write a one-page brief that answers: daily tasks, weekly recurring tasks, tools (e.g., Trello, Gmail, HubSpot), target hours, timezone constraints, and KPIs for 30/60/90 days. Example KPI: “Schedule 15 qualified calls per week” or “Reduce inbox backlog to <10 unread business emails by EOD.”

Why: A crisp brief filters 70% of bad applicants before you ever speak to them.

Step 2 — Decide channel & budget (15–30 minutes)

Choose where to recruit: freelance marketplaces (flexible), VA agencies (vetted), LinkedIn (professional fit), or referrals (lower risk). Set a realistic budget range and expected commitment (hourly vs retainer).

Step 3 — Create a short, real task test (30–90 minutes)

Give a 20–40 minute task that mirrors daily work. Examples: write a 150-word listing description, create a 3-step email follow-up sequence, or schedule and confirm 5 prospect calls in a provided CRM demo account.

Scoring: Use a 1–5 rubric for accuracy, speed, communication, and attention to brief.

Step 4 — Structured interview (30 minutes)

Ask identical questions to top candidates: past relevant experience, a problem they solved, preferred tools, how they manage deadlines, and how they escalate issues. Rate answers numerically. Avoid chit-chat bias.

Step 5 — References & micro-portfolio check (15–30 minutes)

Request 2 references or client screenshots (data redacted). Look for consistency: repeat hires, multi-month engagements, and measurable outcomes.

Step 6 — Paid trial block (1–2 weeks)

Offer a paid trial: 10–30 hours depending on role. Give specific tasks and a daily reporting format. Sample terms: “10 hours paid at agreed rate; deliverables: (A) three appointment confirmations, (B) one updated SOP.”

Why paid trials: They ensure mutual commitment and reduce early churn.

Step 7 — Onboard with SOPs & tools (first 2 weeks)

Create short SOPs (5–8 bullet steps) for each task. Use shared boards (Notion/Trello) with checklists. Schedule daily 10–15 minute standups for the first two weeks.

Step 8 — Measure & adjust (30–60 days)

Review KPIs weekly. If output is under expectations, diagnose: unclear brief? missing tool access? non-native skill gap? Adjust tasks or train — don’t fire immediately.

Step 9 — Retain & scale (after 60+ days)

If the VA proves reliable, move to a retainer, add responsibilities, and create career incentives (bonuses for milestones, clear raise plan). Reliable people are cheaper long-term.

Templates I can give you now (pick one):

• Job brief + 10-minute real test.

• 2-week paid trial plan with deliverables and evaluation sheet.

• SOP templates for 5 common tasks (email, scheduling, CRM updates, social scheduling, invoicing).

Tell me which template you want and the single most painful task you want off your desk — I’ll draft the job brief + test now.