Onboarding
CAO onboarding questions: the first two weeks
A new CAO's first two weeks should be heavy on listening and light on commitments. The 90-day plan sets the broader rhythm; this guide is the diagnostic input that feeds it. Ask these questions early, write the answers down, and let the patterns shape what you propose later.
Updated 2026-10-029 min read
Who to ask
- The CEO
- Peer executives
- Direct reports
- Internal customers
The CEO
Questions for the CEO
The CEO conversation is the most important one in the first two weeks. Verbal alignment with the CEO drifts as soon as priorities change, so the goal is not just answers but a shared written summary you can both refer back to. Ask the questions below early, then send the CEO a one-page summary of what you heard and let them correct it.
Mandate and scope
- What does success look like at the end of year one?
- Which functions report to me on day one, and which are still being decided?
- Which decisions should I make alone, and which require partnership?
- Who do I report to functionally, and who reviews my performance?
Context and signals
- What problem made you decide to hire a CAO at this point?
- What part of the function works well today and should not be disrupted?
- What part has been frustrating you, and for how long?
- A year from now, what would tell you that hiring a CAO was the right call?
Peer executives
Questions for peer executives
Peer executives — COO, CFO, CHRO, chief of staff — will be your closest working relationships. The first conversations set the tone for the working relationship. Use them to map mandates, identify boundary disputes early, and signal that you intend to be a partner, not a competitor. The CAO vs COO, CAO vs CFO, and CAO vs CHRO guides describe the boundaries you are mapping.
Mapping the boundary
- What part of your function depends on the administrative side working well?
- Where has the line between our roles been ambiguous in the past?
- What decisions do you expect to make jointly with me?
- Is there a current dispute or open question between our functions I should know about?
Service experience
- Where have administrative services let your team down recently?
- What service would you most want improved in the next six months?
- Where does the current setup actually exceed expectations?
- What would you stop doing if you could?
Direct reports
Questions for the team
The team has answers no executive will give you. They have lived with the function under previous leadership and know what is real about the way it runs. Ask them as individuals first, then as a group. Resist the urge to promise anything in the first two weeks; you are gathering, not deciding.
The work itself
- What is the most important thing your team does that nobody outside it understands?
- Where do you regularly miss commitments, and why?
- Which of your services has the largest gap between what we promise and what we deliver?
- Which of your peers do you depend on most, and is that working?
The structure around the work
- What decision do you wish you could make without escalation?
- What decision are you currently making that probably should be escalated?
- Where does the cadence we run support you, and where does it slow you down?
- If you could change one thing about how we are organized, what would it be?
Internal customers
Questions for internal customers
Department heads and senior managers across the organization consume the services your function delivers. Their view of you is the view that will travel through the organization. Talk to as many of them as you reasonably can in the first two weeks — even fifteen-minute conversations are useful, and the pattern across them is more informative than any single answer.
Service experience
- Walk me through the last time you used one of our services. What worked, and what didn't?
- Which of our services do you avoid using, and what do you do instead?
- What would make the biggest difference to you in the next ninety days?
Trust and credibility
- What promises has the function made in the past that did not get kept?
- Whose name comes up when something we deliver actually exceeds your expectations?
- What do you wish you could ask of us but currently do not?
Board or governing body
Questions for the board or governing body
Not every CAO has direct board contact. In local government, nonprofits, and many health systems and universities, the CAO works closely with an elected council, a board, or a board committee. Where that relationship exists, ask the CEO how they want it handled first, then use early conversations with the chair or committee chair to learn what the board actually watches.
Expectations and oversight
- Which administrative topics come to the board, and how often?
- What information about operations do you feel you are missing today?
- Which risks in the administrative area worry the board most?
- How do you prefer to hear about problems — in scheduled reports or as they happen?
History and boundaries
- What administrative decisions has the board been asked to make that it felt should have been made by management?
- Are there open commitments from management to the board in my area?
- Which committee, if any, will I report to regularly?
- What did the board find most and least useful in past administrative reporting?
Keep the CEO in the loop
Board conversations in the first two weeks should never surprise the CEO. Agree in advance who you will speak to, share what you heard afterwards, and avoid any commitment the CEO has not seen.
The data
What to look at on paper
Conversations are necessary; they are not sufficient. In parallel with the interviews, pull the documents below. The pattern in the data often differs from the pattern in the conversations, and the gap between them is itself useful information. The metrics dashboard guide covers what good looks like once you have the documents in hand.
Documents to read in week one
- The current administrative service catalog, in whatever form it exists.
- SLA performance for the last twelve months by service.
- The most recent budget and the variances against it.
- Open audit findings, regulatory items, and risk register.
- Recent staff or employee survey results, where available.
Documents to read in week two
- Major vendor contracts up for renewal in the next twelve months.
- The board materials covering administrative topics from the last two cycles.
- Any consultant reports on the function commissioned in the past three years.
- The previous CAO's transition memo, if one exists.
- Open executive commitments your function owes other parts of the organization.
Schedule
A sample two-week onboarding schedule
The sequence matters more than the exact days. Start with the CEO so you understand the mandate, move quickly to peers and the team, and leave enough time in week two to read documents and write up what you heard. Adjust the timing to your organization's calendar and the availability of the people involved.
| Days | Focus | Who or what | Output |
|---|---|---|---|
| 1–2 | Mandate | CEO; your executive assistant or chief of staff | Draft one-page summary of the mandate, sent to the CEO for correction |
| 2–4 | Peer relationships | COO, CFO, CHRO, CIO, general counsel, chief of staff | Map of boundaries, joint decisions, and open disputes |
| 3–6 | Your team | Each direct report one-to-one, then a group session | List of commitments being missed and decisions people want to make |
| 5–9 | Internal customers | Department heads and senior managers, in short conversations | Recurring service complaints and strengths |
| 1–10 | Documents | Service catalog, SLA data, budget, audit findings, contracts, board materials | Notes on where the data and the conversations disagree |
| 8–10 | Board, where relevant | Board or committee chair, with the CEO's agreement | Board expectations and open commitments |
| 10 | Synthesis | You | Private memo: patterns, open questions, early hypotheses |
After the two weeks
What to do with what you heard
By the end of the second week you should have enough to write a short memo for yourself: the three or four patterns you keep hearing, the questions you do not yet have answers to, and the early hypotheses about what to change later. Do not share this memo broadly. It is your map, not your plan, and it should evolve quickly.
Patterns worth naming
- Stakeholders who consistently surface the same complaint — usually a real signal.
- Gaps between what the data says and what people describe — usually a measurement issue worth investigating.
- Areas where everyone agrees something is broken — easy to act on, but verify the diagnosis before the fix.
- Areas where opinions diverge widely — often where the most consequential structural change will eventually need to happen.
Things to resist
- Making promises in the first two weeks — you do not yet know what is realistic.
- Naming bad performance publicly before you have spoken to the people involved.
- Accepting a "quick win" pitched to you in week one — it is almost always more complicated than presented.
- Skipping the people you do not naturally gravitate toward — they often know the most.
FAQ
New CAO onboarding questions, answered
What should a new CAO do in the first two weeks?
Listen more than you decide. Meet the CEO first to confirm the mandate, then peer executives, your direct reports, and internal customers, and read the key documents in parallel. Finish by writing a private memo of the patterns you heard and the questions you still need to answer.
What is the most important question to ask the CEO?
Ask what success looks like at the end of year one. The answer defines the mandate, shows how the CEO will judge the role, and gives you something concrete to write down and confirm in a one-page summary.
Should a new CAO make changes in the first two weeks?
Generally not, apart from urgent risk or compliance issues. Early changes are usually based on incomplete information, and promises made before you understand the function are hard to keep. The first two weeks are for diagnosis; decisions follow in the rest of the first 90 days.
How many stakeholders should a new CAO meet in the first two weeks?
As many as you reasonably can without rushing the important conversations. Give the CEO, peer executives, and direct reports proper time, and use shorter conversations to cover a wide range of internal customers, because the pattern across many conversations is more useful than any single one.
What documents should a new CAO read first?
Start with the service catalog, recent service-level performance, the current budget and variances, open audit findings and the risk register, and any recent employee survey results. In week two, add upcoming contract renewals, recent board materials, past consultant reports, and any transition memo.
How do onboarding questions fit with a 90-day plan?
The two-week questions are the diagnostic input to the 90-day plan. What you hear shapes the priorities, early wins, and structural proposals you put forward later in the first quarter.
Related guides
Move from listening to planning
Use the 90-day plan to translate what you heard into a structured rhythm, and the operating model guide to anchor the structural decisions you will eventually make.
Browse CAO resources