What good looks like at day 90
By day 90 the assistant runs a defined set of recurring tasks end to end without you reviewing each one.
Success measure: Number of recurring tasks the assistant completes without a clarifying question, tracked weekly.
Where this role usually goes wrong: The common failure is under-delegation. Managers hand over small tasks, keep the judgment calls, and then conclude the assistant is not adding value. Assign whole outcomes, not fragments.
Before day one
- Shared inbox or delegated mailbox access, with a written rule for what they may send without approval
- Calendar with scheduling permission and a stated policy on who can book your time
- Password manager entry rather than credentials pasted into chat
- A single task queue, one tool only, so nothing is tracked in two places
Week 1: August 10, 2026 to August 16, 2026
Working, connected, and shipping something small. Access problems in week one cost more than any other week.
- Record three screen captures of the tasks you plan to hand over first, narrated as you work
- Agree the working window and the response time you expect inside it
- Give the assistant one live task on day two, not day ten, so the loop starts early
- Set a 15 minute end of day check in for the first week only
- Confirm every account and tool works before the start date, not on it
- Send a written welcome that states the working hours, the payday, and who to contact when something breaks
- Book the recurring one to one now, inside the overlap window, for the full 90 days
Days 8 to 30: August 17, 2026 to September 8, 2026
Producing real work under review. The goal is a correction loop that runs daily, not a training course.
- Hand over the first three recurring tasks in full, including the decision that ends each one
- Have the assistant write the standard operating procedure for each task in their own words
- Move the daily check in to twice a week once two tasks run clean
- Name the tasks you are deliberately not delegating yet, so the boundary is explicit
- Hold the first written feedback conversation by day 21, while corrections are still cheap
- Confirm the first payment landed correctly and on the expected date
- Ask what is unclear and treat the answer as a documentation gap rather than a knowledge gap
Holidays in this phase: Assumption of Mary on August 17, 2026.
Days 31 to 60: September 9, 2026 to October 8, 2026
Owning defined areas with review at the edges rather than on every task.
- Add inbox triage with a written rule for what gets answered, escalated, or archived
- Let the assistant own calendar defense, including declining meetings against your stated rules
- Review the procedures they wrote and correct anything that drifted from how you actually work
- Introduce them directly to the two or three people they will coordinate with most
- Run a structured mid point review against the success measure, in writing
- Ask for feedback on your onboarding and fix the worst item before the next hire
- Check the working hours are holding in practice and adjust the schedule if they are not
Days 61 to 90: October 9, 2026 to November 7, 2026
Independent inside the agreed scope, and evaluated against the measure you set on day one.
- Hand over a project with a deadline rather than a recurring task, and let them plan the steps
- Ask them to propose two tasks you have not delegated that they believe they should own
- Move to a single weekly review of exceptions instead of a review of the work itself
- Write down the scope you expect at month six so the next quarter has a target
- Hold the formal evaluation before the probation window closes
- Put the next quarter's scope, targets, and any compensation review in writing
- Ask the hire what would make them stay two years and write down the answer
Holidays in this phase: Day of the Races on October 12, 2026; All Saints' Day on November 2, 2026.
Evaluation checkpoint
Hold the formal evaluation on October 1, 2026. The statutory trial window closes on October 8, 2026. Hold the evaluation a week earlier so a decision to end the engagement still falls inside it.
Statutory trial period in Colombia: 2 months. The trial period must be agreed in writing and caps at 2 months for indefinite contracts. On fixed-term contracts it caps at one-fifth of the term, never exceeding 2 months. During a valid trial either party can end the contract without notice or indemnity.
Employer notice after probation: None (indemnity instead). Colombia has no statutory notice period for ending an indefinite contract without cause; the exit is priced through the Article 64 indemnity instead, and many employers simply pay and end the same day. Fixed-term contracts are different: skipping 30 days of non-renewal notice renews the contract for the same term.
Holidays in the window: 3 total, 2 on days your office is open
- August 17, 2026 (Monday): Assumption of Mary (your office is open, the hire is off)
- October 12, 2026 (Monday): Day of the Races
- November 2, 2026 (Monday): All Saints' Day (your office is open, the hire is off)
Planning baseline only, not legal advice. Confirm probation, notice, and holiday rules for the specific contract with qualified local guidance.