Tag Archives: succession planning

Ep. 115 – The Three Discovery Questions Every Advisor Should Ask with Jeff Thorsteinson

Creating Advocates, Practice Management, Prospecting, , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

What if the problem you’re trying to solve isn’t the real problem at all? How might that damage rather than help your business?

Jeff Thorsteinson argues that advisors often look for better answers when they should be asking better questions.

  1. A growth challenge may actually be a capacity problem.
  2. A referral problem may point to weak positioning.
  3. A full calendar may signal over-reliance on the advisor.

In this episode of Top Advisor Podcast, Bill and Jeff explore why questions are “the operating system of leadership.” The questions advisors ask shape their strategy, hiring decisions, client conversations, and plans for growth.

They discuss Jeff’s “stop, flip, expand” framework, a four-part test for deciding what belongs on an advisor’s plate, and three questions that can transform a discovery meeting.

As Jeff puts it, “The next breakthrough in your business may not require a better answer. It just simply requires a better question.”

3 Key Takeaways:

  • Reframe the problem before solving it. (03:35)
    An advisor who says, “I can’t grow the business,” may actually have a capacity problem. If the team is overwhelmed and every decision depends on the advisor, more clients will create more chaos.
  • Move from pursuit to attraction. (07:03)
    Instead of asking, “How do I get more affluent clients?” ask, “What would make affluent clients chase me for a meeting?” That shift changes positioning, niche marketing, authority, thought leadership, and client experience.
  • Use “stop, flip, expand.”  (31:45)
    Stop and identify the real problem. Flip the question into a more useful form. Then expand it to uncover the larger issue underneath. “How do I get more referrals?” might become, “What kind of business will naturally attract clients?”

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About Jeff Thorsteinson 

Jeff is the co-partner in the firm Advisor Practice Management.

Jeff has spent more than thirty years helping financial advisors build stronger, more profitable businesses.

He’s co-founded several advisor-focused companies, including The Newsletter Factory, YouFoundation, Agora Wealth, and Agora Dealer Services, and has worked on thousands of marketing and practice management projects with advisors across North America.

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#101 – Becoming the First-Call Advisor: Insights from Family Office Expert Rich Wolkowitz

Client Experience & Loyalty, Generational Wealth, , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

What can financial advisors learn from those guiding the world’s wealthiest and most complex families?

And how can you position yourself as the advisor your A+ clients call first?

In this episode of the Top Advisor Podcast, Bill Cates interviews Rich Wolkowitz – attorney, advisor, and founder of Xylogenesis. From White House counsel to family office insider, Rich shares unique lessons that every financial professional can use to deepen trust, expand value, and strengthen client relationships.

3 Key Takeaways:

  • Advising ultra-wealthy families is about more than money. The right brain side –  trust, relationships, and emotional dynamics – is often where true value is built. 
  • Being the “first call” advisor sets you apart. Learn how to position yourself so clients rely on you first – for both financial strategy and unexpected family challenges. 
  • Legacy requires alignment. Rich’s brilliant tree rings metaphor shows families (and their advisors) how to connect future aspirations with present-day decisions in a meaningful, lasting way.

Bill and Rich Discuss:

  • Why speaking truth to power is essential for advisors who want lasting influence  
  • Rich’s personal journey – from next-gen family business member to White House attorney to trusted family office advisor 
  • Real-life examples of the unexpected roles a family office advisor can play – from finding rare medical specialists to supporting a cat with cancer 
  • Why building a strong advisory team and collaborating across disciplines keeps you off the “replace” list 
  • How to help families build sustainable, purpose-driven offices with the right people and plan 
  • … And more!

Connect With Rich Wolkowitz:

Resources: 

Connect With Bill Cates:

About Rich Wolkowitz:    

Rich Wolkowitz is the Founder of Xylogenesis® | Family Office Advisory, bringing more than 25 years of first-hand experience working inside and alongside family offices of every type. 

A third-generation member of his own family’s enterprise, Rich grew up learning about stewardship, responsibility, and the values of family leadership from his father. That early foundation shaped his career in law, business, and family office management.

Rich began his legal journey at the White House before joining an AM 100 law firm, where he became an Equity Partner and Chair of the Hiring Committee. He specialized in international and domestic mergers and acquisitions, serving as outside counsel and trusted consigliere to public companies, private equity- and venture-backed firms, and family enterprises. He later stepped into his own family’s business and went on to lead two different single-family offices as a non-family executive. 

Prior to founding Xylogenesis®, Rich managed a global family business consulting firm.

Known for his ability to “speak truth to power.”  Rich now advises multigenerational families, their family offices, and teams of trusted advisors on the complex continuum of family, business, and legacy needs.

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