Wealth managers serve clients who entrust them with their most important financial decisions — retirement security, generational wealth transfer, tax efficiency, and legacy. AI tools will not replace the judgment and trust at the heart of this profession, but they can dramatically accelerate the analytical, writing, and educational work that supports it. These 35 prompts are designed for RIAs, private bankers, and financial planners who want to spend less time on preparation and more time with clients.
1. Financial Planning and Goal Setting
My client is a 52-year-old surgeon with $3.2M in investable assets, a current income of $650,000, a target retirement age of 62, and a desired annual retirement income of $300,000 in today's dollars. Walk me through a comprehensive retirement readiness analysis: current savings rate required, safe withdrawal rate considerations, Social Security optimization strategy, and the key risks to the plan.
Help me explain the concept of sequence-of-returns risk to a client who is retiring in 18 months and is anxious about a market downturn. Use a simple numerical example comparing two scenarios — one where the portfolio declines early in retirement vs. late — and explain the specific strategies we can use to mitigate this risk in their portfolio.
Draft a financial planning agenda for an initial comprehensive planning meeting with a new high-net-worth client (net worth approximately $8M). Include the sections we should cover, the key data we need to gather, and the questions we should ask to understand their values, fears, and definition of financial success beyond the numbers.
My client wants to know whether they should pay off their $1.2M mortgage at 6.5% interest or keep the mortgage and invest the payoff funds. Their marginal tax rate is 37%, they itemize deductions, and they have a moderate risk tolerance. Build the analytical framework for this decision including after-tax cost of debt, opportunity cost, and psychological factors.
Explain Monte Carlo simulation to a client who is skeptical of it. They want to know why I show them a "probability of success" percentage instead of a simple projection of their portfolio balance. Use plain language, a brief analogy, and explain what the simulation does and does not account for.
2. Investment Strategy and Portfolio Construction
I am constructing a core satellite portfolio for a client with $5M in investable assets, a moderate risk tolerance, a 15-year time horizon, and significant concentrated stock position in a single tech company representing 35% of their net worth. Describe an overall portfolio construction approach, how to handle the concentration risk, and the tax-efficient methods for diversifying the concentrated position over time.
Compare factor investing (value, momentum, quality, low volatility, small cap) with a traditional market-cap-weighted index approach for a taxable account held by a high-income client in the 37% tax bracket. Address return expectations, tax efficiency, tracking error tolerance, and how to explain this trade-off in a client presentation.
Explain the role of alternative investments — private equity, private credit, hedge funds, and real assets — in a $10M+ client portfolio. For each asset class, describe the expected return/risk profile, liquidity constraints, fee considerations, and how much of a portfolio allocation is typically appropriate.
My client received a $2M inheritance and wants to invest it all immediately. They are emotionally attached to the money and worried about investing at the wrong time. Compare lump-sum investing vs. dollar-cost averaging for this specific scenario, including historical data context, and help me draft talking points for our conversation.
Help me create a rebalancing policy statement for a client with a 60/40 equity/fixed income target allocation. Include threshold-based rebalancing rules, tax-aware rebalancing considerations for their taxable account, how to handle dividend and interest reinvestment, and when we should deviate from the policy due to market conditions.
3. Tax Planning and Optimization
My client is a business owner who sold their company this year and will recognize $4M in long-term capital gains. They have a 90-day window before year-end. Walk me through the full menu of tax mitigation strategies available to them: Qualified Opportunity Zones, charitable giving vehicles, tax-loss harvesting, installment sale structures, and any other techniques I should consider presenting.
Explain Roth conversion strategy for a client who is 61, retired, and in a temporary low-income period before Social Security and Required Minimum Distributions begin at 73. Their traditional IRA balance is $1.8M. How do I calculate the optimal annual conversion amount to fill up lower tax brackets, and what are the key considerations around Medicare IRMAA surcharges?
Describe the tax-loss harvesting process, wash sale rules, and how to implement it systematically in a taxable account. Include specific scenarios where tax-loss harvesting adds the most value, common mistakes advisors make, and how to explain the concept clearly to a client who is uncomfortable selling at a loss.
My client owns a highly appreciated rental property (original cost $250,000, current FMV $1.1M) and wants to exit real estate. Compare the following exit strategies: outright sale, 1031 exchange into a DST, installment sale, charitable remainder trust, and a UPREIT contribution. Summarize the tax, income, and estate planning implications of each.
Help me build a tax projection model framework for a client expecting $800,000 in W-2 income, $120,000 in qualified dividends, $95,000 in long-term capital gains, and $45,000 in short-term capital gains this year. Walk me through calculating federal income tax, NIIT, and the state tax implications for a California resident.
4. Estate Planning and Wealth Transfer
Explain the current federal estate and gift tax system to a client who just crossed a $13M net worth threshold. Cover the unified credit, annual gift tax exclusion, portability, and the scheduled sunset of the TCJA provisions in 2026 and what action they should consider taking before that date.
My clients are a married couple, both age 68, with a $22M estate. They want to minimize estate taxes while maintaining control of assets during their lifetime. Walk me through the most effective irrevocable trust strategies available to them: SLATs, GRATs, IDGTs, and family limited partnerships. Explain the key trade-offs between each.
Help me explain the concept of stepped-up basis to a client who is deciding whether to gift appreciated securities to their adult children now versus bequeathing them at death. Include a numerical example comparing the tax outcomes of gifting now vs. inheriting later, and explain how this interacts with their overall estate plan.
Draft a checklist for a comprehensive estate plan review meeting. Include documents we should gather and review, beneficiary designation audit items, trust funding verification, business succession considerations, incapacity planning documents, and charitable giving structures.
A client wants to leave a meaningful charitable legacy while also providing for their three adult children. Compare the following charitable vehicles: donor-advised fund, private family foundation, charitable remainder trust, and charitable lead annuity trust. Summarize the control, tax benefits, complexity, and family involvement considerations for each.
5. Client Communication and Relationship Management
Draft a quarterly portfolio review letter for a client whose balanced portfolio returned -8.3% in the quarter, underperforming the 60/40 benchmark of -6.1%. The underperformance was driven by an overweight to international equities. Write a letter that is honest about the performance, explains the reasoning behind the positioning, and reinforces the long-term strategy without being dismissive of the client's concern.
A long-time client just called in a panic during a market selloff, saying they want to move everything to cash. Write a script for this phone call that acknowledges their fear without dismissing it, asks the right questions to understand what has changed (if anything), and walks through the evidence-based case for staying invested — without being preachy or condescending.
Help me write a personalized market commentary email to send to clients during a period of elevated market volatility. The tone should be calm, grounded in data, and written for an intelligent non-specialist audience. Cover what is driving the volatility, historical context, what we are doing in portfolios, and what clients should focus on.
Draft a referral request script I can use naturally at the end of a successful annual review meeting. The approach should feel genuine and relationship-focused rather than transactional. Include how to mention the type of client I work best with, how to make it easy for the client to think of someone, and how to follow up appropriately.
Create a client segmentation framework for my practice of 85 client households with $180M AUM. Define the criteria I should use to segment clients into three tiers, what level of service and communication frequency each tier should receive, and how to transition clients between tiers without damaging relationships.
6. Business Planning and Practice Development
Help me build a 12-month marketing plan for my independent RIA targeting tech executives in the Seattle area with $2M to $10M in investable assets. Include content marketing topics, LinkedIn strategy, COI relationship development (CPAs and estate attorneys), speaking opportunities, and a realistic budget allocation for a solo advisor.
I am preparing for a due diligence meeting with a large family office prospect that manages $150M in assets and is considering consolidating to a single advisor relationship. Help me prepare: what questions they are likely to ask, what materials I should bring, what makes a compelling differentiator narrative, and what common mistakes advisors make in these meetings.
Draft a service calendar for my top-tier clients that shows every touchpoint throughout the year: proactive call schedule, review meeting agenda templates, tax planning check-ins, estate plan review triggers, life event response protocols, and birthday and milestone acknowledgments. Organize it month by month.
Help me write a succession planning document for my advisory practice. I am 58 years old, manage $220M AUM with 95 households, and have no junior partners. Cover the options available to me (internal succession, external sale, RIA merger, joining a larger firm), how to value the practice, and the timeline and steps to prepare the business for transition.
Create a new client onboarding process map that ensures a consistently excellent first 90 days. Include the sequence of meetings, documents to collect, accounts to open, technology setup steps, introduction to team members, and first quarterly review agenda. The goal is to make every new client feel they made the right choice.
7. Financial Education and Client Empowerment
Explain the difference between term life insurance, whole life insurance, and universal life insurance to a 45-year-old client who is reviewing their coverage needs. They have two children in high school and a mortgage of $750,000. Help me frame which type of coverage is most likely appropriate for their situation and what questions we need to answer to confirm.
Help me create a plain-language glossary of 15 financial planning terms my clients frequently misunderstand: expense ratio, alpha, beta, duration, yield to maturity, basis points, tax alpha, drawdown, correlation, rebalancing, risk premium, illiquidity premium, tax drag, MAGI, and provisional income. Write each definition in 2-3 sentences for a non-specialist reader.
Draft a client education piece on the psychology of investing — specifically cognitive biases that lead investors to make poor decisions. Cover loss aversion, recency bias, anchoring, overconfidence, and herding. For each bias, give a brief real-world example and explain how working with an advisor helps counteract it.
My client's adult child (age 28, income $95,000) has asked for 30 minutes of my time to discuss getting started with financial planning. Help me build a focused agenda for this conversation that covers: emergency fund, employer 401(k) optimization, Roth IRA eligibility and strategy, student loan payoff vs. investing trade-off, and term life insurance needs.
Create a visual one-page financial planning timeline I can share with clients showing the key financial milestones and decisions from age 30 to age 80. Include contribution limit optimization, Medicare enrollment deadlines, Social Security filing windows, RMD start dates, estate plan review triggers, and long-term care planning windows.
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