Interview questions for a family office CEO

Built on Chapter 2 of The Single Family Office by Richard C. Wilson. Full chapter text: FamilyOffices.com.

Hiring a family office CEO is one of the biggest decisions a wealthy family makes. This person will run the office as a business, oversee the investment team, and sit close to the family's most private matters. A polished resume is not enough. These are the questions I would want answered before making an offer.

Start with the three hiring questions

Before any interview, I suggest the family answer three questions about the role itself. Will this person return a multiple of their pay, or bring the family real peace of mind? Will they bring deep skill in at least one area? Will they fit the team and the family's goals?

Then use the interview to test each one.

Questions about running the office

Walk me through how you set up or improved the operations of an organization like ours.
How do you choose and replace outside vendors and advisors?
What systems would you put in place in your first 90 days?
How do you keep costs lean in the early years?

Listen for specifics. Good CEOs talk about processes and decisions they made, not just titles they held.

Questions about leading experts

How have you managed senior people who know more than you in their field?
How would you oversee a CIO without second-guessing every decision?
Tell me about a time you had to let someone go. How did you handle it?

A family office CEO often leads a small team of specialists. The best ones guide without micromanaging.

Questions about the family

How have you handled disagreements between family members or owners?
What would you do if a family member asked you to bend a policy?
How do you protect the family's privacy day to day?

These questions test judgment and discretion. Look for someone who can say no politely and stick to the rules the family set.

Questions about results and pay

How should your success be measured here?
What would you want to see in your pay structure, and why?
What is the worst decision you made in a past role, and what did you change afterward?

A candidate who welcomes clear measures and pay tied to results is usually a better fit than one focused only on base salary.

Questions about commitment

Where do you see yourself in five to seven years?
What would make you leave a role like this?

It takes a long time for a new leader to learn a family's portfolio and priorities. You want someone who intends to stay.

Beyond the interview

The interview is only one step. Check references thoroughly, including people the candidate did not list. Run a background check. If possible, have the candidate meet several family members and senior staff in a relaxed setting. How they treat junior people and assistants tells you a lot.

Some families also give finalists a short paid project, such as reviewing the office's current budget or reporting. The work shows how they think far better than any answer.

Red flags

Watch for vague answers about past results, blame placed on others for every failure, a casual attitude toward confidentiality, or pressure to make a fast decision. Any one of these deserves a closer look.

What to take from this

Define the role and its measures before interviewing.
Ask for specifics about operations and leadership.
Test discretion with questions about family conflict.
Use references, background checks, and a short project before deciding.

This page is general information, not legal or employment advice. Some interview questions are restricted by law, so have an employment attorney review your interview guide.

Questions and answers

What should a family ask a family office CEO candidate? Questions about running operations, leading experts, handling family dynamics, and measuring results.

How can a family test a candidate's judgment? Ask how they would handle a family member asking them to bend a policy.

Should finalists do a work sample? A short paid project can reveal how a candidate thinks.

What are red flags in a CEO candidate? Vague results, blaming others, casual confidentiality, and pressure to decide fast.