From the advent of personal computers and the Internet to smartphones and sophisticated financial software, the profession of financial advice has always been in continual dialogue with technology. However, the rapid rise of artificial intelligence has brought a deeper wave of disruption to the financial advice profession. As clients increasingly expect seamless, automated financial solutions – what might be thought of as ‘self-driving money’ – advisors are left to consider how their roles are evolving and where they can continue to add value.

In this 169th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards discuss how AI will reshape the tasks advisors perform and the value they bring to client relationships. Looking back across the decades, the foundational elements of financial planning have remained surprisingly consistent – from discovery meetings to financial plan presentations – as advisors have striven to help people make sense of their financial lives. In fact, as technology solutions have become more sophisticated, some advisors now serve fewer clients more comprehensively.

AI will likely accelerate this trend – not by replacing advisors, but by automating some of the mechanical aspects of planning, including cash flow modeling, tax optimization, and investment rebalancing. As the mechanical side becomes more optimized, the human side of financial advice increasingly becomes the true differentiator. Clients rarely have clear, static goals; their values and priorities evolve over time. Helping clients articulate what matters, navigate trade-offs, and stay emotionally aligned with their plans is a task that remains uniquely human, since even with perfect data and perfect modeling, planning decisions must still be made within the messy context of real lives!

Technical expertise remains essential – not because it alone creates value, but because it underpins the confidence and judgment needed to evaluate outputs, catch errors, and guide clients through complex decisions. In our current era of financial advice, the internet and early iterations of AI can solve many prospective clients’ problems. However, a core segment of the population will always be delegation-oriented, while others will face financial situations so complex that they require an expert’s help. This dynamic may deepen over time; as ‘basic’ financial planning questions become easier to access, the bar for an advisor’s competency may continue to rise. Which means that deeper specialization – whether in a subset of clients or a specific set of financial problems – may help advisors differentiate themselves in the long term.

Ultimately, the key point is that as AI evolves, so will financial advice, stretching advisors to embrace both technical competence and human connection. In the years ahead, the advisors who stand out will help their clients better understand who they themselves are, what they want, and how to leverage their financial resources to get there!

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As the financial advice profession has matured, behavioral finance has become an increasingly important element of modern advice. This holistic approach to financial advice, often referred to as life planning, focuses on helping the advisor understand the client’s financial history, deep-seated goals, and overall relationship with money, which can allow for more targeted and comprehensive advice. However, for advisors who want to explore financial psychology with their clients, it may be difficult to determine when – and whether – to go deeper, and how to handle high-emotion conversations gracefully without overwhelming clients.

In this 168th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards discuss the pros and cons of holding financial psychology conversations early in the client (or prospect) relationship – and how to determine whether a deeper exploration of the client’s financial history is appropriate in the first place.

From the prospect’s point of view, it’s easier to not hire a financial advisor than it is to hire one (at least in the short term). Sifting through advisors’ websites, fee schedules, and other information can require substantial effort. While some prospects may seek an advisor’s behavioral coaching – especially if the advisor markets themselves as a behavioral finance expert – the majority are motivated by a specific event that propels them to begin the process. As such, a prospect usually comes to an advisor with one key stressor in mind, and it may feel jarring to hear questions like, "What is your first memory with money?" These questions, though intended to build trust, may inadvertently leave clients feeling disoriented or uncomfortable if they were expecting a more straightforward problem-solving approach.

Instead, advisors may find more success in leading with solving the problem that the client immediately presents, and then, over time, gradually exploring the client’s financial background as trust develops. This process of earning permission to go deeper can take months – or even years! – of consistent, high-quality work. Such an approach may also create a more organic environment for advisors to practice and hone their empathy and behavioral finance skills.

Ultimately, the key point is that starting a financial planning relationship with introspective behavioral finance questions may feel jarring to the client unless the advisor has an express specialty in life planning, and the prospect is expecting that approach. For many prospects, it can be more effective to start by addressing the immediately presenting problem and, once trust has been established, dive to gradually explore their money stories together. And in the meantime, it’s worth remembering that the so-called technical work of financial planning isn’t ‘just’ technical – it often involves an incredible amount of emotional support and can go a long way towards helping clients realize their most important financial goals!

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In recent years, financial advice has expanded beyond spreadsheets and technical strategies to consider the behavioral and emotional factors driving clients’ relationships with money. Advisors today often serve not just as technical experts but also as thinking partners – helping clients process their money stories, explore values, and determine what they want their wealth to accomplish. Yet advisors also bring their own money histories, attitudes, and values into the relationship, which can influence not only how they interpret clients’ financial situations but also how they perceive their own financial standing.

In this 167th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards explore how advisors can productively navigate the personal and philosophical distance between themselves and their clients – particularly in cases where clients have higher income or net worth. As Kitces Research on What Actually Contributes To Advisor Wellbeing has found, advisor wellbeing tends to decrease as client net worth increases – while higher client income is associated with greater satisfaction. One possible reason is that advisors may subconsciously compare their own financial standing to that of their clients – especially when clients’ wealth is inherited or perceived as unearned.

Reflecting on their personal history with money may help advisors understand the formative stories and emotional associations with money throughout their lives. Even an exercise as simple as writing down a dollar sign and naming the first few emotions that come up can surface themes that shape how advisors think and respond around money, and how those beliefs show up in client work.

At the same time, advisors’ personal money stories may serve as a magnet for like-minded clients – and an asset to the relationship. For example, an advisor who sees money as a safety net may naturally attract clients who value security, while another who sees money as a means of freedom may resonate more with clients who prioritize flexibility. The similarities can foster trust, and the differences – when thoughtfully navigated – can lead to deeper conversations.

Ultimately, the key point is that comparison is a natural human impulse, but it doesn’t have to be a liability. With greater awareness of their own financial backstory, advisors can cultivate more meaningful client relationships and use their emotional insight to help clients connect more intentionally with their own values and goals. And by treating the emotional and philosophical distance as an opportunity for empathy and mutual reflection, advisors can unlock richer conversations and a deeper sense of purpose in the work they do!

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Every financial or business decision brings some amount of inherent risk. However, the consequences of those decisions – positive or negative – don't always align with the actual level of risk taken. As a result, when advisors are tasked with (re-)educating clients about the potential consequences of financial decisions, there may be a disconnect between potential risk and what a client actually experiences. So how can advisors help clients understand dangers they haven't personally encountered?

In our 166th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards discuss how advisors can bridge the gap between planning and a client's lived experience to guide better decision-making.

One helpful framework to contextualize financial decisions is the concept of 'wicked' versus 'kind' learning environments. Kind environments have clear rules, quick feedback, and consistent patterns, making them easier to navigate and learn from. Tax planning often fits the 'kind environment' model: The rules are relatively stable, outcomes repeat annually, and feedback is immediate (e.g., a tax bill or refund). By contrast, wicked environments feature ambiguous rules and delayed or misleading feedback, where individuals can 'learn the wrong lesson'. Investment planning falls into this camp; a client who makes a risky bet and sees strong returns might conclude the strategy is sound, even if it was more luck than skill.

For planners, kind environments tend to allow for systematization and consistent advice delivery. Wicked environments, however, require more narrative focus and concrete examples. Advisors can use historical context and stress testing to show clients how a situation might play out differently under less favorable conditions. And when clients persist in making risky decisions, advisors can help by constructing guardrails, allowing for some flexibility while protecting against catastrophic loss.

The wicked/kind framework also appears in business leadership. Those who thrive in kind environments may excel at optimizing systems and scaling efficiently but might miss warning signs when conditions shift. Leaders in wicked environments may excel in handling ambiguity and disruption but may struggle to maintain stability in calmer business environments. Both leadership styles offer value, but they manage different types of risk and opportunity.

Ultimately, the key point is that the results of a decision don't always reflect the risk involved. Advisors who recognize this disconnect – and who adjust their planning strategies to fit the terrain – can help clients and businesses remain resilient across a wide range of circumstances. That means knowing when to lean into systems and when to pause and reassess, when to simplify, and when to explore new possibilities. And by helping clients understand the type of environment they're in – and shifting between 'peacetime' and 'wartime' toolkits as needed – advisors can offer more than just technical guidance. They become trusted navigators in a changing landscape, offering clarity, perspective, and a steadier path forward in an uncertain world!

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Financial planning is inherently complex, especially when it comes to data gathering, analysis, and crafting well-reasoned recommendations. But delivering those recommendations in a way that clients can understand and act on is a separate skill. Advisors not only need to do the deep technical work, they also need to translate that complexity into clarity – a step that can be surprisingly time-consuming and cognitively demanding. And when an advisor is already managing a full schedule, carving out the time to make the message clear can be a real challenge. So how can advisors ensure that their advice is both comprehensive and simple enough to be truly actionable?

In this 165th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards explore how advisors can simplify the delivery of complex advice and why doing so is such a critical (and often underdeveloped) skill. While clients don't necessarily need to understand the full depth of the analysis behind a recommendation, they do need to trust that the analysis has been done thoroughly and clearly understand what the advice is, why it matters, and what's being asked of them. Because when advice is clear and comprehensible, clients are more likely to act on it and gain peace of mind from knowing there's a well-considered strategy in place!

One way to simplify delivery is to build meetings around a single core takeaway. For example, if someone stopped a client in the parking lot after the meeting and asked what they talked about with their advisor, what would the advisor want them to say? That question can help clarify the central message and shape meetings around what matters most. From there, additional sub-points can be layered in, while reinforcing the main takeaway to ensure the client walks away with a clear understanding of what to do next.

Visual aids can also help advisors clarify complexity and reinforce key messages. Summary charts or graphics – especially for topics that come up repeatedly (e.g., investment strategies or tax planning) – can reduce cognitive overload for clients and keep meetings on track. And because these conversations tend to repeat across clients, visuals offer leverage: the upfront time spent finding or customizing a helpful chart can pay off many times over. Fortunately, advisors don't need to start from scratch. A growing number of FinTech companies – like Holistiplan, Income Lab, fpPathfinder, and Clearnomics – offer ready-made illustrations to help make advice more understandable for clients.

Ultimately, the key point is that simplifying financial advice is not a simple task – but it is a skill that can be developed over time. The goal isn't simplicity for its own sake, but clarity. By combining communication strategies with technology solutions and approaching each meeting with one clear takeaway in mind, advisors can deliver recommendations that aren't just technically sound, but truly understandable and far easier for clients to act on!

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Young advisors may feel – and face – an extra burden to prove their expertise to clients. After all, it can feel odd to create an estate plan that will impact a client’s grandchildren… when those grandchildren may be older than the advisor themselves! And while any advisor needs to determine how much detail to share when explaining strategic decisions, younger advisors may feel added pressure to prove their credibility. There is a definitive difference between actual and perceived capability, and young advisors may risk overcompensating by diving too deeply into the granular details of their recommendations.

In the 164th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards discuss how young advisors can strike the right balance between complex explanations and simplicity as they build trust and social capital. Clients don’t just need to be accurately diagnosed – they need to feel accurately diagnosed. But walking through every page of a financial plan line by line could take up an entire afternoon and often isn’t necessary. So, how can advisors strike the balance of communicating competence without overwhelming clients?

A helpful approach may be to start with a simple, high-level summary, and then let the client guide the conversation from there. Then, when clients respond with their own follow-up questions, the advisor can elaborate, demonstrating the thoughtful analysis and care behind the recommendations. Along the way, regularly checking in (e.g., "Do you want more detail here?" or "Do you have any questions about what we’ve covered?") ensures the advisor stays aligned with the client’s preferences and attention span.

Advisors can also offer the client options like, "Would you prefer to review the executive summary, or would you like to go through the full details?" This approach not only honors the client’s preferences but also signals that the advisor is prepared to explain the full scope if needed. For visual impact, advisors might also show a printed or onscreen version of a full-length plan, using it as a physical representation of the underlying work, even if the discussion focuses only on the highlights.

The reality is that a young advisor may be asked to explain their reasoning… at first. But with time and experience, those requests often decrease as credibility and trust naturally grow, and as clients internalize that the advisor is fully capable and competent. This reflects a broader truth in client communication: While technical knowledge is essential, the ability to adjust and simplify explanations based on the client’s needs becomes equally important over time. Knowing when to stop explaining – before overwhelming the client with more information than they need – can be just as important as knowing when to elaborate.

Ultimately, the key point is that deciding between complexity and simplicity is, itself, a complex and nuanced decision for young advisors. But by letting the client direct the questions and level of detail they want, advisors can showcase their competence while also building trust and credibility over the long term!

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Advisors spend a lot of time crafting their financial advice recommendations – and how they deliver those recommendations – for their clients. These ultra-personalized suggestions are central to what makes financial advice valuable and can have a significant impact on a client's life. So, what happens when a client doesn't act on that advice – especially when their inaction can compromise their financial and holistic wellbeing?

In our 163rd episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards explore how to engage more meaningfully with clients who don't implement the financial advice they receive – by asking what the advisor may have missed the first time around.

Many advisors receive training to overcome objections from prospects when learning how to sell advice and gain clients. However, they rarely have access to training that addresses the objections – or silence – from long-term clients. And these objections can often show up differently: Some clients will voice disagreement openly, while others may appear to agree with the advisor's recommendations and reasoning in the moment, only to quietly fail to follow through.

Inaction can be a sign that the advisor misunderstood the client's real priorities. For example, an advisor might assume a client would prioritize long-term financial stability, when in reality, their focus may be on supporting loved ones in the present – even at the expense of their own future financial security. While both perspectives stem from good intentions, the mismatch can lead to recommendations that technically make sense but don't resonate emotionally. The key is to uncover this disconnect – not by asking, "Why didn't you implement?", which can feel accusatory and cause the client to react defensively, but instead using open-ended questions like, "What did I miss?", "What's going on?", or "How can I be helpful here?" These kinds of questions set the stage for collaborative conversations that make space for mutual investigation and problem-solving.

Often, the issue isn't a lack of clarity or explanation – it's that the advice may have focused on a goal the client wasn't truly prioritizing. When a client nods in agreement during a meeting but takes no action afterward, it may signal that the recommendation didn't reflect what truly matters to them. Shifting the conversation to explore the client's underlying values – rather than repeating the recommendation with greater emphasis – can open the door to a more meaningful dialogue and a more accurate diagnosis of the client's needs.

Ultimately, the key point is that when clients don't act on financial advice, it can be an indicator that a deeper – and different – conversation is needed. By extending curiosity and empathy, advisors can uncover clients' deeper priorities that may not have been previously articulated. In other words, advisors can use inaction and objection as an opportunity to have deeper conversations and build trust as they learn what clients truly value most!

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Hiring a contractor is an exciting step for many advisory firms. It represents a chance to delegate tasks, step away from day-to-day operations with more peace of mind, and pass a key milestone of (traditional) firm growth. However, hiring contractors isn’t without its complications. Even outsourced support requires some oversight, and delegation doesn’t always go as far as some might hope. So, how can advisors best leverage contractors, and how can they evaluate the value of such work (especially against the prospect of hiring a full-time employee)?

In the 162nd episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards explore how to master delegation, measure success with contractors, and weigh the cost of outsourcing versus hiring full-time to determine what’s actually ‘reasonable’.

Before an advisor can truly evaluate a contractor’s value, they must challenge themselves by looking inward. Delegation can be deceptive: Advisors may believe they’ve delegated more than they have, or that tasks only they can do are more essential than they really are. Taking time to interrogate those assumptions – by asking what can be delegated or even eliminated – can help free up more time than expected.

From there, an advisor can focus more on the art of delegating well. Creating style guides or video tutorials can streamline both training and follow-up questions. Advisors can also use these materials to communicate the firm's values and purpose – both for conveying firm culture and reducing the time advisors need to spend reviewing and correcting work done by others.

Eventually, advisors may wonder if it’s still worthwhile to ‘just’ hire a contractor, or if it’s time to bring on a full-time employee. There are certainly different ways to evaluate the all-in cost of a contractor versus an employee; both approaches will be the ‘right’ answer for different firms depending on the unique circumstances and challenges faced by advisors. While a contractor's hourly rate is often higher, the firm foregoes the additional cost of benefits, downtime, and in-depth people management. In fact, when considering the real cost of a full-time team member – including salary, oversight, and overhead – a contractor can be more cost-effective, especially when an advisor only pays for what they need. And, if an advisor is looking to manage costs more precisely, they may want to segment tasks by outsourcing low-cost work to one contractor and higher-skill work to another – without needing a single full-time hire.

Ultimately, the key point is that outsourced contracting can be a great tool to better leverage and reclaim an advisor’s time – when used well. With thoughtful and continual delegation, clear communication of the firm’s ‘why’ and unique values, and an eye toward iterative improvement, advisors can focus their energy where it’s needed most: on the work that only they can do!

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Launching a new business venture is often a creative – and somewhat vulnerable – act. Whether it's opening a new firm, publishing a book, or even just posting on social media, each public-facing offering reflects many hours of ideation, refinement, and effort. When preparing to launch, advisors must typically answer two core questions: "Who will show up for this?" and "Will the people who do show up like it and get it?" A good way to address both questions is to ask for feedback – but the real challenge is knowing who to ask,  and when.

In the 161st episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards discuss how and when to ask for feedback, how to use it constructively, and when it's better to simply act and launch.

As a starting point, gathering a sufficient volume of responses is crucial when asking for feedback. Negative feedback often feels ‘louder' than positive feedback, but a single critical opinion may not reflect a broader sentiment – people simply have a variety of preferences. Advisors can mitigate overreacting to one-off responses by ensuring they collect enough responses to identify real patterns, which can also prevent an advisor from rebuilding everything in response to a single opinion. Furthermore, ensuring that feedback is coming from the ‘right' people is just as important. For example, if a firm launches a new offering for its core clientele – dentists near retirement – then it may not be helpful to ask newly minted doctors what they think of the offering. The doctors may not find the offering helpful or relevant… and that's okay. Feedback from outside the target audience may be interesting, but it isn't always relevant!

In some cases, behavioral data may also be a helpful source of useful feedback. Observing the topics and offerings that clients actually engage with may offer better clues about what they find valuable. Doing more of what connects – and less of what doesn't – can be an easy, effective way to refine offerings over time.

Finally, there may be times when the best audience to build for is the advisor themselves. Many advisors build firms with fee service models that resonate with them. At times, what's needed isn't feedback – it's confidence. For example, there may come a point where an advisor may not need feedback as much as a rallying cry to move forward. Then, once something is launched, the advisor can watch for how prospects and clients react to their offerings and take that as implicit (or explicit) feedback.

The key point is that feedback can be a powerful tool to refine offerings and creative ventures, but only when it comes from the right people at the right stage of the process. When thoughtful feedback comes from a core part of the audience, it can be a helpful resource for advisors to shape services that resonate with their target audience. And, ultimately, those points of feedback can help advisors build a stronger, more relevant product – amplifying their impact in the long term!

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Whenever the markets become ‘scary' due to current events, advisors can anticipate calls from anxious clients wondering what to do next. These clients are often in fight-or-flight mode, which can make it difficult to have a rational discussion or a productive conversation about their financial plan. And if an advisor jumps straight to data – trying to ‘prove' why staying the course is the right decision – the client may become even more frustrated and reactive. So how can advisors navigate these conversations in a way that helps clients regain a sense of control?

In our 160th episode of Kitces & Carl, Michael Kitces and client communication expert Carl Richards explore how empathy-centered conversations can help clients emotionally reset before engaging in rational decision-making. They discuss a structured five-step framework that financial advisors can use to guide clients from fear back to confidence – helping them feel heard first before introducing logical reasoning.

When a client calls in distress, the first step is to greet them with empathy. If the client says they are worried, it can help to reflect that concern back to them with a simple acknowledgment, such as, "You sound very worried. I feel worried when I watch the news, too." Next, creating space – such as taking a minute to grab a glass of water or introducing a natural pause – can help slow the pace of the conversation and ease tension. Once the client feels more at ease, the advisor can affirm their goals by reinforcing what truly matters to them, such as ensuring they can continue spending a certain amount in retirement. From there, the advisor can remind them that their portfolio was built to support the client's long-term goals and designed to withstand market hiccups, declines, and corrections. Finally, once the emotional intensity has subsided, the advisor can introduce data and historical patterns to provide reassurance.

Still, some clients may insist that "this time it's different". In these cases, it can help to acknowledge that while the cause of each scary market downturn is unique, the market's pattern of recovery has been remarkably consistent. Walking the client through how their individual portfolio would perform in a recession can also be reassuring. Often, the worst-case scenario isn't financial ruin – it may instead be a matter of weathering a few years without an increase to their year-over-year spending. These conversations can also be a great opportunity to affirm why portfolios are structured for risk management, especially since the same client who fears a downturn today may, in a strong market, wonder why they have to rebalance when they could be chasing higher returns!

Ultimately, the key point is that scary markets feel scary – but advisors don't need to rely solely on data to convince clients to stay the course. While historical patterns provide perspective, no one truly knows what will happen next. By leading with empathy and curiosity, advisors can guide clients through market volatility with confidence and care, ensuring they leave conversations feeling heard, understood, and reassured!

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