--- title: "Episode 41: Family Office Recruiting: How to Hire Leaders for Trust — with Cheryl Grimaldi" description: Recruiter Cheryl Grimaldi explains how family offices hire for trust, discretion, and ambiguity, and why she tries to talk candidates out of the job first. --- [![Velocity Advisory Group](https://www.velocityadvisorygroup.com/wp-content/uploads/2026/05/Velocity-Logo-2023-Wide-1.png)](https://www.velocityadvisorygroup.com/) ☰ Menu - About - [Meet Our Team](https://www.velocityadvisorygroup.com/about/) - [Meet Our Coaches](https://www.velocityadvisorygroup.com/coaches/) - [Careers](https://www.velocityadvisorygroup.com/careers/) - [Speaking Engagements](https://www.velocityadvisorygroup.com/velocity-speakers/) - Solutions - [Culture & Engagement](https://www.velocityadvisorygroup.com/culture-engagement/) - [DISC Assessments & Training](https://www.velocityadvisorygroup.com/disc-assessments-training/) - [Employee Experience](https://www.velocityadvisorygroup.com/employee-experience/) - [Executive Coaching](https://www.velocityadvisorygroup.com/executive-coaching/) - [Family Business](https://www.velocityadvisorygroup.com/family-business/) - [Leadership Development](https://www.velocityadvisorygroup.com/leadership-development/) - [Sales Training](https://www.velocityadvisorygroup.com/5cs-of-selling/) - [Strategy & Implementation](https://www.velocityadvisorygroup.com/strategy-implementation/) - Resources - [Activating Greatness Podcast](https://www.velocityadvisorygroup.com/podcast/) - [Blog](https://www.velocityadvisorygroup.com/blog/) - [Case Studies](https://www.velocityadvisorygroup.com/case-studies/) - [News and Announcements](https://www.velocityadvisorygroup.com/news-and-events/) - [OrderDisc](https://orderdisc.com/) - [Upcoming Events](https://www.velocityadvisorygroup.com/upcoming-events/) - Industries - [Construction](https://www.velocityadvisorygroup.com/construction/) - [Financial Services](https://www.velocityadvisorygroup.com/financial-services/) - [Life Sciences](https://www.velocityadvisorygroup.com/lifesciences/) - [Contact](https://www.velocityadvisorygroup.com/contact/) Activating Greatness Podcast Episodes August 10, 2026 | Episode 41 # Family Office Recruiting: How to Hire Leaders for Trust — with Cheryl Grimaldi ## Make Them Sell You: Cheryl Grimaldi on Hiring Leaders for Family Offices **In this post:** *Family office recruiting veteran Cheryl Grimaldi explains how wealthy families hire for trust, discretion, and comfort with ambiguity. She also shares why every candidate needs a career wound and why she makes candidates talk her into the job.* Most recruiters spend the first call selling the job. Cheryl Grimaldi spends it describing the worst parts. "I am not going to talk somebody into going into this world at all," Grimaldi said on *Activating Greatness*, the leadership podcast from Velocity Advisory Group. "They have to talk me into why they think it's good for them." The world she means is family office recruiting for the private firms that manage the money, households, and reputations of the very wealthy. Grimaldi opened her recruiting firm, Tangent West, in 1995 to place executive assistants with C-level executives, many at Fortune 100 companies. As the CEOs she served retired and opened family offices, they came back to her with a question: How do we do this? Three decades later, her approach to that question holds a lesson for any leader filling a high-stakes seat. When trust is the job, the hiring process has to test commitment, not just credentials. ## A Market Still Forming Itself Grimaldi calls the family office space "the wild west." By the figures she cited, $100 trillion to $120 trillion will pass to the next generation over the next 50 years, and 65% of the recipients will be women. A family office typically begins at about $200 million in wealth. These offices handle investments, tax planning, estates and trusts, philanthropy, and lifestyle logistics such as aircraft, yachts, and residences. Risk management, including cybersecurity, legal matters, and reputation, has become a bigger piece of the work. The biggest job is family governance, which Grimaldi summed up as one question: "How does a family stay a family?" That question covers sibling disputes, different spending philosophies, inheritance, marriages, divorces, and blended families. Families often describe the pattern in generations. The first creates the wealth, the second preserves it, and the third usually loses it. Grimaldi said 90% of heirs will immediately fire the entire family office and everyone who advised the previous generation. That raises the stakes on every hire. The people she places will help guide the next generation, and plenty of others would guide them in the opposite direction, she said. ## Family Office Recruiting: Where Nobody Posts the Job Family office hiring looks nothing like corporate hiring. There is usually no HR department and little work-life balance. Many offices operate under code names from hidden locations, and most of their people are not on LinkedIn. Nearly everyone has signed a nondisclosure agreement. "It's kind of this world that you have to know people to know people to know people," Grimaldi said. The job descriptions do not look corporate either. Last fall, a family called her after a cybersecurity breach put its staff and houses around the world on lockdown. Families in this world also worry about kidnapping, she said, and this one had no backup plan. It happened around 3 a.m. on a Sunday. So Grimaldi looks for people who like the gray. She described them as the backstage crew, not the actors on stage, people whose reward is seeing a family at peace. One candidate told her recently she would not know what to do with her time if she was not on 24/7. ## Find the Career Wound With so many new family offices, Grimaldi cannot always recruit from other family offices. She often draws from investment banking, hedge funds, and venture capital, looking for people who want to be a big fish in a small pond and who have grown frustrated with red tape. Every candidate has to have what she calls a career wound: a concrete reason for leaving. "I always want to keep the door open" does not count. Frustration with management does. So does a candidate who says she wants a place where her ideas get implemented and who does not need a full job description to get started. Grimaldi reads more than answers. She listens for what candidates say and what they leave out, when their voice rises with excitement, and where they pause. Then comes what she calls the takeaway. She lays out the hardest parts of the role and makes the candidate sell her on it. > "I am not going to talk somebody into going into this world at all. They have to talk me into why." > > *Cheryl Grimaldi, Founder, Tangent West and Anton Everest* She rarely accepts an answer on the spot. "I want you to go home. I want you to talk to your spouse. I want you to talk to your family," she said. Sometimes she tells a candidate the timing is wrong. "I may say, I don't think you're ready to leave your current job yet." She sees that as her duty to the paying client. A candidate who is only half interested may last 12 to 18 months, which costs the family a hire and the recruiter her reputation. FREE ONE-PAGE CHECKLIST ### The Commitment Test Checklist Use it to screen any high-stakes candidate for a real reason to leave, describe the hardest parts of the role, and let them make the case. [Get the free checklist](https://coaching.velocityadvisorygroup.com/leadership-library/commitment-test-checklist) ## The Right Candidate, Not the Best One Grimaldi describes each search as a commission, closer to painting a piece of art than running a process. "We're not a staffing company," she said. She pushes back on the family, asks what happened before, and interviews the matriarch or patriarch. If the office already has a team, she interviews every member to learn their personalities and find the holes. Her model is Herb Brooks, the coach who built the 1980 U.S. Olympic hockey team. "I'm not looking for the best candidates. I'm looking for the right candidates," she said, paraphrasing his philosophy. She learned to ask different questions as a college senior at TCU, helping the admissions office recruit students. Counselors there told high schools they did not want the students bound for the Ivies or the service academies. They wanted "the kid that in five years, you're going to invite to your house for a barbecue." On *Activating Greatness*, Toni Burkard has explained [why great teams don't happen by accident](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-23-why-great-teams-dont-happen-by-accident-toni-burkard), and Terri Fleener has described [HR that moves the business](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-19-hr-that-moves-the-business-terri-fleener). ## A Vault With a Reputation Grimaldi's own business rests on the discretion she screens for. Her husband does not know her clients' names. The firm does little advertising, so new clients come from one family talking to another. That leaves no room to hide a miss. Every couple of years, she said, a placement does not work out. "That is my responsibility to get in there as fast as I can and make sure that we do get it right for them." She is also candid about the irony. She talks to people about changing jobs every day, yet at 55 she has not changed jobs since she was 23. ## Key Takeaways 1. **Test commitment, not just credentials.** Describe the hardest parts of a role up front and let the candidate make the case for taking it. 2. **Ask why they are leaving.** A concrete career wound, such as frustration with red tape or management, predicts staying power better than a vague openness to opportunities. 3. **Hire for the team you have.** Interview the people the new hire will work with, learn their personalities, and recruit to fill the holes. 4. **Look for comfort with the gray.** In unstructured environments, the right leader thrives on ambiguity and does not need a linear job description. 5. **Act faster on toxic people.** Grimaldi said leaders hold on to them too long, and she pointed to one company that lost 1,000 people because of one toxic employee. HOW VELOCITY HELPS ### Velocity Family Business Grimaldi described family governance as the work of keeping a family together when significant wealth is involved, and she warned that most heirs replace the advisers who served the generation before them. Family enterprises face the same pressure when leadership passes to the next generation. Velocity's Family Business work helps families and their leaders prepare for those transitions, including the succession planning and strategic planning host Alec McChesney described, so the right people are in place before the handoff. See how Velocity works with [professional services firms](https://www.velocityadvisorygroup.com/professional-services/). [Explore Family Business](https://www.velocityadvisorygroup.com/family-business/) ## The Takeaway: Purpose Shows Up in Others The best leadership advice Grimaldi has received reframes how she thinks about her own work. "Your purpose is not the thing you do," she said. "It is the thing that happens in others when you do what you do." For a recruiter, that means measuring success by what the people she places go on to build. For any leader making a critical hire, it means slowing down. Tell the truth about the job, ask the harder question, and let the right candidate talk you into it. ## Listen to the Full Episode Hear Cheryl Grimaldi's full conversation with host Alec McChesney on *Activating Greatness*. [Find it on YouTube](https://www.youtube.com/@VelocityAdvisoryGroup), or listen on [Spotify](https://open.spotify.com/show/4LcgAut0KyYiGyDhFvMjPD) and [Apple Podcasts](https://podcasts.apple.com/podcast/id1868386871). FREE GUIDE ### The High-Trust Hire A recruiting framework with three interview questions that test whether a candidate can handle real discretion and fit your specific environment, not just whether the resume looks strong. [Get the free guide](https://coaching.velocityadvisorygroup.com/leadership-library/high-trust-hire) Share: [facebook-f icon](http://www.facebook.com/share.php?u=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi) [linkedin-in icon](http://www.linkedin.com/shareArticle?mini=true&url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi) [Twitter icon](https://twitter.com/intent/tweet?url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi) [pinterest-p icon](http://pinterest.com/pin/create/link/?url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi) [envelope icon](mailto:?body=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi) [HR & People Strategy](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/hr-people-strategy) [Professional Services](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/professional-services) ## Ready to activate greatness on your team? Velocity Advisory Group helps leadership teams build the culture, strategy, and systems that let good people do their best work. [Book a discovery call](https://www.velocityadvisorygroup.com/contact/) ## Related posts [Construction](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/construction), [HR & People Strategy](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/hr-people-strategy) ## [Episode 32: Strategic HR Leadership: Scaling HR From 4 to 30-Plus — with Krista Robinson](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-32-strategic-hr-leadership-krista-robinson) [Alec McChesney](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/author/alec-mcchesney) Jun 8, 2026, 4:00:00 AM The Business Told Us So: Krista Robinson on Scaling HR From a Team of 4 In this post: Weitz Vice... [Read more](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-32-strategic-hr-leadership-krista-robinson) [HR & People Strategy](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/hr-people-strategy), [Financial Services & Insurance](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/financial-services-insurance) ## [Episode 49: Recruiting Financial Advisors: Hire Entrepreneurs First — with Chad Foster](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-49-recruiting-financial-advisors-chad-foster) [Alec McChesney](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/author/alec-mcchesney) Sep 21, 2026, 4:00:00 AM This Career Is Not for Most: Chad Foster on Recruiting Entrepreneurs in Financial Services In this... [Read more](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-49-recruiting-financial-advisors-chad-foster) [Culture & Engagement](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/culture-engagement), [Leadership Mindset](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/leadership-mindset) ## [Episode 36: Employee Engagement: Fixing the Survive Work Problem — with Patrick Manigault](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-36-employee-engagement-patrick-manigault) [Alec McChesney](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/author/alec-mcchesney) Jul 6, 2026, 4:00:00 AM We Have a Survive Work Problem: Patrick Manigault on Fixing Employee Engagement In this post:... [Read more](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-36-employee-engagement-patrick-manigault) --- [![](https://coaching.velocityadvisorygroup.com/hs-fs/hubfs/Velocity%20Logo%202023%20Wide-2.png?width=1025&height=267&name=Velocity%20Logo%202023%20Wide-2.png)](http://velocityadvisorygroup.com) Copyright © 2026, Velocity Advisory Group ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Alec McChesney", "url" : "https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/author/alec-mcchesney" }, "dateModified" : "2026-10-20T14:57:17.261Z", "datePublished" : "2026-08-10T08:00:00.000Z", "headline" : "Episode 41: Family Office Recruiting: How to Hire Leaders for Trust — with Cheryl Grimaldi", "mainEntityOfPage" : { "@id" : "https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-41-family-office-recruiting-cheryl-grimaldi", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://coaching.velocityadvisorygroup.com/hubfs/Velocity%20Logo%202023%20Wide-2.png" }, "name" : "Velocity Advisory Group" } } ```