Design a Ninety-Day Review for a New Executive Assistant

A ninety-day review is a decision point, not a formality

The end of a new executive assistant's first quarter is the first honest moment to ask whether the placement is working. By then the novelty has worn off, the executive has formed habits around the new support, and small misunderstandings have had time to become expensive. A review that consists of a friendly chat and a generic scorecard wastes that moment. The review should produce a clear decision: continue with a development plan, change the scope of the role, or end the placement before the cost of a bad fit grows.

Design the review before the assistant starts, not in the week it is due. Tell the assistant what will be assessed, who will be asked, and which examples will count as evidence. A process that appears suddenly feels like a test of loyalty rather than a fair assessment of work. Early transparency also gives the executive a reason to keep notes during the quarter instead of relying on a vague impression formed in the final week. The onboarding plan should name the review date from the first day.

Set checkpoints that produce evidence along the way

Use three short checkpoints rather than one large meeting. In the first two weeks, review access, tools, and the basic rhythm of the executive's week. Between weeks three and six, review ownership of recurring work such as calendar triage and meeting preparation. Between weeks seven and twelve, review independent judgment on travel, vendor communication, and confidential routing. Each checkpoint should end with one or two written adjustments, not a long list of impressions.

At every checkpoint, ask for a specific example of a task the assistant handled without prompting and one where they needed help. The pairing matters because it shows whether the assistant recognizes the boundary between initiative and overreach. An assistant who claims to have handled everything independently is not necessarily stronger than one who names a legitimate escalation. The review is looking for accurate self-awareness as much as for completed work. A cross-training coverage review can show whether the assistant can also cover a colleague's queue when the team is short.

Judge the work against the role brief

Return to the role brief that was agreed at the start. If the brief said the assistant would own calendar prioritization, then the review should examine calendar decisions, not just attendance or politeness. If the brief said the assistant would prepare board materials, the review should examine the last two board packs and the corrections they required. The federal O*NET profile for executive secretaries is a useful reference for the duties that belong in the scope conversation, though it cannot settle what a specific executive needs. Vague criteria produce vague verdicts, and vague verdicts make it impossible to defend a fair decision to the assistant or to the client.

Separate three questions that are often blended together. Can the assistant do the work with normal support? Does the executive trust the assistant with the scope that actually exists? Is the working relationship sustainable for both people? A yes on skill and a no on trust points to a different problem than a no on skill. Naming the distinction prevents the review from becoming a personality judgment when the real issue is training, authority, or unclear expectations.

Ask the executive and the assistant different questions

Ask the executive where the assistant reduced load, where the assistant created rework, and which decisions still feel unsafe to delegate. Ask the assistant which parts of the role were unclear, where access or information arrived too late, and what they would change about the working agreement. These are not symmetrical questions, and that is the point. The executive sees outcomes; the assistant sees the conditions that produced them. Comparing the two views exposes gaps that neither party would name alone.

If the assistant works through an agency, give the account manager the same evidence before the review meeting. The account manager can check whether a difficulty is specific to this placement or reflects a mismatch in the brief. That outside view is especially useful when the executive is frustrated but cannot articulate why. It also keeps the review from turning into an unsupervised negotiation about service charges, hours, or scope.

Make a decision and write down what changes

End the review with one of three written outcomes. A continue decision names the scope that stays the same, the development areas, and the date of the next check. A scope-change decision explains what moves to another person and what the assistant will own instead. An exit decision sets a transition date, a handover plan, and the access-removal steps. Each outcome should be signed or acknowledged by the executive, the assistant, and the agency where one is involved.

Do not leave the meeting with only verbal assurances. Write the two or three changes that matter, assign an owner to each, and schedule a follow-up within thirty days. A ninety-day review that produces a clearer role and a shorter list of unresolved issues has done its job. The goal is not to declare a permanent verdict on a person. It is to decide, with evidence, whether this working relationship deserves another quarter. For help structuring a review that fits your placement, speak with our team.