Executive onboarding,
from offer to day 100.

There is a persistent myth that senior people do not need onboarding. The opposite is true: the more senior the role, the fewer people who will honestly tell the new executive what is going on, and the faster the organisation will read their opening moves as policy. Onboarding a senior hire is mostly about designing the flow of honest information. Here is the checklist we would run.

Before day one

• Write down the mandate as the employer sees it: what success looks like at day 100 and day 365, in one page, agreed by everyone who had a vote in the hire.
• Agree a day 100 review date before they start, so the checkpoint is a calendar fact rather than a threat.
• Prepare the practical kit: contracts, payroll, equipment, systems access, and a working badge on day one. Nothing says "we were not really ready for you" like a week of IT tickets.
• Assign one sponsor with authority, and name them. A committee of sponsors is the same as no sponsor.
• Handle family logistics early, especially for a relocation: schools, partner's work, healthcare. It is usually the family, not the org chart, that ends senior moves.
• Send a short internal announcement that explains the role, not just the name.

The first two weeks

• Book the new executive's first listening conversations for them, or at least help: direct reports, key peers, one sceptic, one or two customers.
• Keep the first calendar mostly unscheduled. A week of wall-to-wall intro meetings is a good way to guarantee they learn nothing.
• Have the sponsor check in weekly, in person if possible, for the first month.
• Brief them on the unspoken stuff: which meetings matter, who really holds influence, which landmines are load-bearing.
• Warn the organisation in both directions: the executive's early questions are curiosity, not verdicts, and the executive will hear opinions, not commitments.

Days 30 to 60

• Ask what they would change, then help them sequence it. First actions should be small, visible and reversible where possible.
• Protect them from the early reorganisation reflex. If they propose structural change before they have seen a full cycle, slow it down together.
• Start feeding external representation: introduce them to key customers, partners or investors personally, not via email signature.

Days 60 to 100

• They present a first draft of their priorities, and the employer reacts while adjustments are still cheap.
• Review the mandate against reality: what did everyone learn in the first season that changes the plan.
• Run the day 100 review honestly, against the date you set in week one. Two questions: is this working, and what support changes now.

The failure modes this checklist exists to prevent

Role ambiguity: nobody wrote the mandate down, so the executive and the board each hold a different job in their heads. Sponsor drift: the executive sponsor loses interest around week six, right when the questions get real. Family strain: everything on the work side goes well and the move still collapses. Each of these is cheap to prevent and expensive to discover in month five.

If you measure onboarding, measure two things: whether placed executives are still in seat and effective after a year, and how long until they made their first good decision. Time-to-contribution is a better metric than first-week satisfaction scores, which mostly measure the welcome pack.

For the executive's own side of the same season, the 100 day plan guide covers the five phases, with role versions for CEOs, managers and pastors. The resources page lists the books and courses we would hand a new leader.