6 Estate Planning Questions High-Net-Worth Clients Forget to Ask
Sam's List Editorial | 2026-06-06
Most estate plans were built to solve the problem that existed the year they were drafted. A life insurance trust set up in 2015 was solving for a different federal exemption, a different family situation, and a different tax landscape than the one you're living in now.
The federal estate tax exemption, retirement account distribution rules, digital asset ownership, and remarriage law have all moved materially in the last four years. For individuals with estates above $5M — and especially those with business interests, inherited IRAs, or significant digital assets — a plan that hasn't been reviewed since 2020 may have gaps that look small on paper and enormous at the worst possible moment.
These are six questions worth bringing to your estate planning attorney and financial advisor. Not because they're easy, but because not asking them is how expensive surprises happen.
1. What Happens to My Estate If My Spouse Dies Before Me and I Remarry?
Most estate plans assume the current spouse survives and that the family structure stays intact. That's a reasonable base case. It's not a comprehensive one.
Without specific planning provisions — a remarriage clause, a QTIP trust, or a spousal lifetime access trust (SLAT) structured to protect children's inheritance — assets that pass to a surviving spouse can flow directly to a new spouse in a subsequent marriage. Children from a first marriage can be unintentionally disinherited. This isn't an obscure scenario: second marriages are common among high-net-worth individuals who divorce or become widowed in their 50s and 60s. If your estate plan treats "surviving spouse" as a permanent category rather than a role that could be filled by a different person, ask your attorney how your documents address that scenario specifically.
2. How Does the Federal Estate Tax Exemption Interact With My State Estate Tax?
The federal estate tax exemption is high — historically high, in fact, though that may change. Twelve states and Washington D.C. still levy a separate estate tax with their own exemptions, some as low as $1-2 million.
A client with an $8 million estate may have zero federal estate tax exposure and a material state estate tax bill — depending on their state of domicile. Massachusetts has an exemption of $2M. Oregon's is $1M. A client who assumes "my estate is below the federal threshold so I don't have an estate tax issue" may be wrong about their state obligation by six figures. If you own real property in multiple states, the analysis gets more complicated: most states tax real property located within their borders regardless of the owner's domicile. Ask your advisor to run the state-level analysis explicitly, not just the federal one.
Note: Estate tax provisions under the One Big Beautiful Act (OBBBA) may affect federal exemption levels. Verify current law with your advisor at the time of your review.
3. Is My Buy-Sell Agreement Funded, and Does the Valuation Reflect Current Fair Market Value?
A buy-sell agreement that isn't funded by life insurance is a contract that promises an outcome it can't necessarily deliver. If a co-owner dies and the surviving owner or the business has to come up with the buyout proceeds from operating cash, the business may not survive the transition.
The valuation question is equally important. Buy-sell agreements often use a formula or a fixed dollar amount set at the time of signing. If your business was worth $1M when the agreement was drafted and is now worth $5M, the insurance coverage is woefully inadequate — and depending on how the agreement is structured, the underfunding may create a taxable event at the decedent's estate. A buy-sell that was set up once and never updated is a common problem in businesses that have grown significantly. Ask your advisor when the valuation was last reviewed and whether the funding mechanism is adequate at current enterprise value.
4. Are My Digital Assets Accessible to My Executor — And Have You Documented How?
Most estate plans predate meaningful digital asset accumulation. For clients who hold cryptocurrency, NFTs, or other digital assets, this is a material oversight.
An executor who can't access a hardware wallet holding $500,000 in Bitcoin has no legal mechanism to recover the funds without the seed phrase. The assets exist on the blockchain; without the private key, they're permanently inaccessible. This isn't a hypothetical: a meaningful amount of Bitcoin is estimated to be permanently lost to forgotten passwords and inaccessible wallets belonging to estates that didn't plan ahead. The solution involves a combination of proper documentation (seed phrases stored in a physically secured, legally accessible location), clear instructions for the executor, and potentially a digital asset custodian arrangement. If you hold meaningful digital assets, ask your attorney whether your current estate documents address them — and whether your executor would actually be able to access them if you died tomorrow.
5. How Does Step-Up in Basis at Death Interact With My Lifetime Gifting Strategy?
Assets gifted during life transfer the donor's original cost basis to the recipient. Assets transferred at death receive a stepped-up basis equal to the fair market value on the date of death.
For highly appreciated assets — a stock position purchased at $50,000 now worth $500,000, or a business interest with a low basis — dying with the asset rather than gifting it can eliminate capital gains taxes on the appreciation entirely. The "right" answer depends on the size of the estate relative to the estate tax exemption, the recipient's tax situation, and the expected holding period after transfer. For clients with both estate tax exposure and highly appreciated assets, the interaction between gifting strategy and step-up in basis should be modeled explicitly. Gifting to reduce the taxable estate may create a capital gains bill for the recipient that exceeds the estate tax savings. That math needs to be run.
6. Has Your Plan Been Reviewed Since SECURE 2.0 and the OBBBA Changed Retirement Distribution Rules?
Inherited IRA rules, required minimum distribution ages, and Roth account treatment have changed significantly since 2019. SECURE 2.0, passed in late 2022, and subsequent legislative changes have altered how beneficiaries take distributions, when RMDs must begin, and how certain trusts interact with inherited retirement accounts.
An estate plan that names a trust as the beneficiary of an IRA — a common technique — may now be structured in a way that produces a significantly worse outcome than it would have before the rules changed. The 10-year rule for inherited IRAs eliminated the "stretch IRA" strategy for most non-spouse beneficiaries. If your plan relies on an inherited IRA strategy designed under pre-SECURE rules, it needs to be reviewed by someone who knows how the current rules affect the specific trust language you have in place.
Ask the Questions Now, Not When It's Too Late to Adjust
These aren't abstract planning exercises. They're specific scenarios that create specific outcomes — some of them expensive, some of them irreversible.
Ian Weiner, CFP, CEPA, works with high-net-worth clients and business owners on the kind of comprehensive planning that integrates estate, tax, business succession, and retirement.
General educational content only. Not investment advice. Past performance does not guarantee future results. Consult a qualified financial advisor for guidance specific to your situation.