While 401(k) rollover conversations are common for financial advisors, they also represent a major decision point for clients and come with investment, tax, and fee considerations. Rolling over assets into an IRA may offer valuable benefits for the client, but it can also create conflicts of interest for the advisor. Which means that a thorough evaluation of all options and disclosure of potential conflicts of interest and may not always be the best option for the client can both help an advisor fulfill fiduciary responsibilities while also buildng client trust. In this episode, Leo Rydzewski, General Counsel and Managing Director of Professional Ethics at the CFP Board, explores the fiduciary responsibilities advisors need to consider and how they can incorporate them when navigating rollover conversations.

Listen in as Leo explains the CFP Board's fiduciary standard and its new guide to applying fiduciary duty to rollovers, including how advisors can identify, disclose, and manage conflicts of interest. You'll learn about the seven-step duty of care process for analyzing rollover recommendations, what information advisors should gather about the client and their retirement plan, how to compare an existing employer plan with alternatives, and why cost alone shouldn't determine the recommendation. Leo also explains why it's important not to treat a rollover as the 'default' option, why some rollover-related decisions may be difficult to reverse, and how monitoring and updating advice can turn the rollover conversation into an ongoing part of a strong client relationship.

For show notes and a full episode transcript, visit: www.kitces.com/FAT10

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Clients sometimes come to the table with legacy investment positions, from inherited stock passed down from a loved one to large amounts of employer stock, that the client does not want to sell. Which can create a challenge for advisors in managing the client's total portfolio and raises questions about how (and whether) to charge fees on the legacy position.

In this episode, we are joined by Rich Chen, founder of Brightstar Law Group, to explore the fiduciary and compliance challenges advisors can face when working with legacy stock positions. You'll learn why simply accepting a client's decision not to sell may not be sufficient, how mismatched expectations between the advisor and their client can create legal and regulatory risk, and what duty of care and loyalty mean when an advisor is working around client-imposed investment restrictions.

Listen in to hear best practices for documenting these discussions with clients, why concentrated positions need to be reassessed over time, and what advisors should be prepared to explain during an SEC examination. Rich also breaks down the different options advisors have for charging on legacy positions and how there isn't necessarily one 'right' answer.

For show notes and a full episode transcript visit: www.kitces.com/FAT9

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What should an advisor do when a client insists on taking an investment action that goes against their advice? In this episode, we are joined by Shelitha Smodic to explore the compliance, fiduciary, and practical considerations advisors need to navigate when a client wants to make a trade or take another action the advisor would not recommend. You'll learn about the duty to follow client instructions, what makes a request lawful and reasonable, and how questions around authority, capacity, and undue influence can affect how an advisor responds.

Listen in to hear about compliance requirements and practical steps advisors can take in the moment, such as explaining potential consequences, offering alternatives, and thoroughly documenting the decision. We also discuss how to think about the client relationship after the immediate issue has been resolved, including when to revisit the investment policy statement, adjust the service model, change from discretionary to non-discretionary management, or consider ending the relationship.

For show notes and a full episode transcript, visit: www.kitces.com/FAT8

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What if the "best" account for an intergenerational gift isn't actually the one that produces the biggest (potential) tax benefit? In this episode, Kitces.com Senior Financial Planning Nerd Ben Henry-Moreland returns to explore how advisors can help clients consider their goals for the gift alongside tax efficiency considerations before selecting a specific account type when deciding how to give money to their children.

Listen in to learn how to identify the different goals behind lifetime gifting—from childhood expenses and education to home purchases, lifestyle support, retirement, and dynasty planning—and how they can influence the account type chosen. The conversation also takes a closer look at the new Trump Accounts (including where they fit within the broader landscape of intergenerational giving), and why the "return" on a gift shouldn't only be measured by how many dollars remain decades later, but also by how effectively the gift supports the life the parent wants their child to live.

For show notes and a full episode transcript visit: www.kitces.com/FAT7

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While some individuals are able to pay for long-term care expenses through savings and/or through insurance benefits, others end up relying on Medicaid benefits to fund these costs. While doing so allows them to access needed services, it can require that they first sharply draw down their assets. Which leads to a variety of planning strategies that allow an individual to preserve assets for a spouse or future generations while still qualifying for Medicaid benefits. However, such strategies come wtih tradeoffs and might not actually represent an individual's interests.

In this episode, we are joined by David Haughton, Vice President of Estate Planning at Carson Group, to explore how Medicaid planning works in the long-term care context, why the "best" planning strategy might not be straightforward, and the ethical challenges advisors can face when adult children, powers of attorney, and aging parents have competing priorities. David also talks about proactive versus crisis planning and practical ways advisors can start these conversations well before a care need arises.

For show notes and a full episode transcript visit: www.kitces.com/FAT6

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What happens when one partner takes the lead on finances and the relationship with their financial advisor while the other stays quiet, disengaged, or simply operates on a different wavelength? In this episode, we welcome Sydney Squires, a Senior Financial Planning Nerd here at Kitces.com, to explore the challenge of working with "misengaged couples"—client couples who have different levels of involvement, communication styles, or priorities when it comes to financial planning.

Listen in to learn how advisors can identify different types of misengagement using an assertiveness and cooperativeness framework, understand the risks of only engaging with the more active partner, and apply practical strategies to ensure both clients feel heard. Sydney also shares actionable approaches for improving client meetings, setting expectations early, and helping couples build a stronger relationship with their financial goals.

For show notes and a full episode transcript visit: www.kitces.com/FAT5

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While the 'traditional' approach to retirement of working full-time until one's mid-60s before leaving the workforce entirely might be a good fit for many individuals, others might prefer tap into the freedom retirement offers earlier in their lives. In this episode, host Adam Van Deusen is joined by Michael Kitces, Chief Financial Planning Nerd at Kitces.com, to break down four alternative retirement paths (Financial Independence, Sabbaticals, "Coast FIRE", and Semi-Retirement) and to discuss how financial advisors can identify and support clients interested in them on an ongoing basis, model the financial trade-offs involved with these alternatives, and ultimately create "aha" moments that transform the way clients think about work, money, and the future.

For show notes and a full episode transcript visit: www.kitces.com/FAT4

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Sometimes clients will want to hold on to a particular portfolio investment or piece of real estate (or value it at much more than the market indicates) even though selling it might make financial sense. In this episode, we explore the endowment effect, a powerful behavioral bias that causes people to value what they already own more than what the market suggests it is worth. Joined by behavioral finance expert Meghaan Lurtz, we unpack three core drivers behind this bias (loss aversion, ownership identity, and reference price anchoring) and how each one shows up in real financial planning conversations.

Listen in to hear why logic alone rarely convinces clients in this situation, how emotional attachment can distort decision-making, and what advisors can do to guide clients toward better outcomes without dismissing their attachment to these assets. You'll learn practical communication tools and powerful questioning techniques that help clients reflect, reframe, and confidently move forward with their financial decisions.

For show notes and a full episode transcript visit: www.kitces.com/FAT3

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One of the great challenges of retirement planning is that an individual's exact lifespan is unknown. Given this uncertainty and the potentially severe consequences of underestimating a client's life expentancy (i.e., possibly exhausting their portfolio prematurely), it's common for advisors (and financial planning software) to use standardized, conservative lifespan estimates.

In this episode, Jeremy Ko, an economist and the founder of ShoreUp Retirement Solutions, explains how creating personalized lifespan assumptions can be easier than many might assume, allowing for more accurate retirement planning inputs (that can still be adjusted based on risk preferences if desired). He also discusses the key health and lifestyle factors that influence longevity, several free tools advisors can use to create more accurate lifespan projections, and practical advice on having sensitive conversations about life expectancy with clients.

For show notes and a full episode transcript visit: www.kitces.com/FAT2

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With consumers now able to open new 530A "Trump Accounts", financial advisors are likely to get questions from clients about how they work and how to actually open them.

In this episode, Kitces Senior Financial Planning Nerd Ben Henry-Moreland shares his firsthand experience opening Trump Accounts for his own children, providing practical insights into a process many advisors will soon be guiding clients through. Listen in to learn how Trump Accounts compare with 529 plans and custodial accounts, who stands to benefit most from them, and the unique rules around contributions, government funding, investments, and rollovers. Ben also explains how while the individual steps in the account-opening process are relatively simple, the proccess as a whole could trip up clients, suggesting a valuable role for advisors in supporting them along the way.

To access the related Nerd's Eye View blog post on this topic and to access this episode's trascript and show notes, visit: www.kitces.com/FAT1

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