A useful 90-day plan moves from learning the business to delivering one bounded outcome and making it repeatable. Do not measure onboarding by meetings attended or presentations produced. Measure whether the hire can increasingly operate with clear ownership.
Before day one: agree the contract for the role
Choose one important problem with a reachable first milestone. For example, improving the handoff from sales to onboarding is more manageable than “fix customer experience.” Write the current situation, intended outcome, constraints and decision owner.
Prepare approved access, an organisational map and existing process documents. Name a functional partner, not just the founder. A new operator cannot learn the business if every answer depends on an unavailable CEO.
Days 1–30: establish a reliable picture
The first month should produce a baseline and an agreed problem definition. Ask the hire to speak with the people doing the work, review a small sample of actual cases and map where delays occur. They should distinguish observed facts from interpretations.
- Deliverable: a short current-state map.
- Baseline: a defined measure with a named data source.
- Decision: which problem to tackle first and what not to tackle.
- Founder input: priorities and permission boundaries.
Do not require a grand strategy before the hire understands how the company earns revenue and serves customers.
Days 31–60: run a bounded experiment
Choose an intervention that can be evaluated without disrupting the entire organisation. In the handoff example, test a minimum information checklist with one team. Agree who records missing information and how exceptions will be handled.
A suggested weekly review covers the baseline, current result, blockers and one decision needed. Do not confuse a favourable week with proof that the change caused the improvement. Record relevant changes in customer mix, staffing or workload.
Days 61–90: stabilise or change direction
If the intervention works, document it, name the long-term owner and explain how it will be monitored. If it does not, show what was learned and recommend whether to revise or stop. Ending a weak experiment can be a better outcome than forcing a success narrative.
The hire should finish with a handover that another person can use: triggers, steps, exceptions, access requirements and escalation contacts. Founder’s Office should not become a permanent single point of failure.
Review both sides of the working relationship
Assess the hire’s judgment, execution and communication. Also assess whether the founder supplied timely decisions, access and realistic priorities. A missed milestone caused by a month-long approval delay is not solely a candidate-performance issue.
This is a suggested structure, not a universal probation policy. Adapt it to seniority, sales cycles and contractual requirements. Use the final review to set the next mandate rather than quietly adding every unfinished task in the company.
FounderSide’s practical editorial guidance for startup hiring and operations. Examples and assessment frameworks are illustrative, not reported client outcomes. Adapt them to your company’s stage and needs.
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