10 Questions to Ask an Estate Planning Attorney

Estate planning may be the hardest professional hire to evaluate, for a structural reason: the work is graded long after you can do anything about it.

A tax return gets tested every year. A trust structure gets tested at a death, a divorce, an audit, or a sale — sometimes twenty years later, by which point the drafting attorney may be retired and the reasoning gone with them. That puts more weight on the interview than anywhere else, and the interview is exactly where charisma passes for competence.

Nothing substitutes for years of working with someone. Short of that, here are ten questions calibrated for an estate with entities in it: closely held businesses, partnerships, property in more than one state, and possibly a transaction ahead.

1. What kind of work do you actually do — planning, administration, or litigation?

Estate law splits into three practices that share a vocabulary and little else. Planning drafts the structure; administration settles it after a death; litigation fights about it.

Ask for the mix, then ask the better question: have you administered the structures you draft? An attorney who has settled estates knows which provisions fail at the worst possible moment — which trustee-succession language stalls, which formula clause becomes unworkable, which discretionary standard invites a fight. A pure drafting practice can be excellent. It is also working without that feedback loop.

2. What do the demographics of your client base look like?

Typical client net worth. What share of the book is taxable estates versus non-taxable. How many clients hold closely held businesses or multi-entity structures.

That taxable-versus-not question does more work than it appears to. The federal estate and gift exemption is $15 million per person for 2026 — permanent under current law, with no scheduled sunset — and the top rate is 40%. At that threshold, transfer-tax planning is a narrow specialty, and most estate practices are appropriately built around plans that will never owe the tax. Both are legitimate practices. Only one of them is yours.

3. How much of my work will you do personally, and who else is involved?

Which parts this attorney drafts. Who else works the file, at what experience level, and who reviews before you sign. Whether anyone in the office handles funding and retitling, or whether that lands on you.

4. What are turnaround times, and what should I expect on a call or email?

Ask explicitly: how long to return a call, how long from engagement to a signable draft. Estate planning is unusually prone to going quiet, because nothing external forces a deadline. There is no filing date, which makes the stated standard the only thing you have.

5. How do you work with other professionals, and who do you work with most often?

The plan touches your CPA's returns, your advisor's portfolio, and your company's governance documents. Ask how coordination works, what gets shared, and how often a joint conversation happens.

Then ask directly: have you worked with my CPA and my advisor before, and what's your read? A candid answer is informative twice — once about them, once about this attorney.

6. Do you use only conservative, proven techniques, or will you explore newer structures?

Ask it, but listen for the answer that reframes it, because the strongest attorneys will tell you the premise is slightly off. Nearly every structure in use is decades old. What determines outcomes is not a technique's vintage but whether it was executed properly: a documented non-tax purpose, arm's-length terms, defensible valuation, and timing not driven by a deadline nobody wants to explain to a judge.

The Fifth Circuit made that point in 2026, and it binds Texas. A conventional family limited partnership was formed and funded in the weeks before an elderly client's death. The court held the transfers were includible in the estate at full value — roughly $17 million — rather than as a discounted partnership interest, because the estate could not show a non-tax purpose, and it sustained a 20% accuracy-related penalty. It also held that merely having engaged tax and legal professionals does not by itself establish reasonable cause; the estate had to show they actually advised the position taken.

A good answer separates a structure's legal pedigree from its execution risk. A grantor retained annuity trust rests on statute and regulation. An installment sale to a grantor trust is widely used and generally respected, but rests on a 1985 revenue ruling rather than a statute, with material questions the IRS has never answered. An attorney who can articulate that difference is telling you something real.

7. What verifies your expertise in this specific area?

Three things, each with limits.

Board certification. The Texas Board of Legal Specialization, operating under the authority of the Supreme Court of Texas, certifies attorneys in Estate Planning and Probate Law — requiring years in practice, a minimum share of practice devoted to the specialty, specialty continuing education, peer and judicial references, and a six-hour written examination. Across all specialties, on the order of 7% of Texas attorneys hold a certification.

ACTEC. Fellowship in the American College of Trust and Estate Counsel signals peer standing — fellows are nominated and elected rather than admitted on application. Worth saying what it is not: a private membership organization of roughly 2,400 lawyers and law professors, not a licensing body, not a specialty certification, and no examination.

Discipline history, and its limits. The State Bar of Texas profile shows license status and public discipline. It does not show a pending grievance, a dismissed grievance, or a private reprimand. So the useful question isn't whether the record is clean — it's what does and does not appear there?

8. Who funds the plan, and who keeps it current?

This question is easy to skip, and the failure it prevents is mechanical rather than exotic.

A Texas trust cannot exist without trust property, and a will proves no title to anything until it is admitted to probate. So an asset never retitled into the trust passes only under the will — through exactly the probate the trust was built to avoid, on a public docket.

Beneficiary designations are the larger trap, because the form beats the will and the trust. For employer plans governed by ERISA, the Supreme Court held in 2009 that the plan administrator must pay the named beneficiary according to the plan documents even where an ex-spouse had waived the benefit in a divorce decree — leaving open whether the estate could pursue the ex-spouse afterward — and eight years earlier it held that ERISA preempts state statutes automatically revoking a spousal designation on divorce. Different rules apply to IRAs, annuities, and individually owned life insurance, which is itself a question to ask.

So ask: is funding, retitling, and beneficiary-form review inside the engagement, or carved out of it? These are among the tasks most often carved out, and among those most likely to determine whether the plan actually works. There is no credible measured research on how often plans go unfunded; attorneys who administer estates report that it happens often enough to be the first thing they check.

9. How does billing work, and what is excluded?

Flat fee or hourly. What triggers a shift. What the quote covers, what it excludes, who bills at what rate. Whether ongoing maintenance, trustee coordination, and annual review sit inside the fee.

One thing worth knowing: Texas does not require a written fee agreement for a flat-fee or hourly estate planning engagement — for a new engagement the rule asks only that the basis or rate be communicated, “preferably in writing.” So insist on a written engagement letter with a defined scope, precisely because the rule doesn't make anyone give you one.

10. Who is your client — me, my spouse, or my company?

The conflicts question, and it is easy to leave unasked.

If the same attorney or firm also represents your business, understand what that means: under the Texas rules, a lawyer retained by an organization represents the entity. Where the entity's interests and yours diverge, conversations between the company's lawyer and you individually may not be privileged as to you. For an owner whose estate plan runs through the company — buy-sell terms, transfer restrictions, recapitalizations, valuation — that may be the most consequential fact in this list, and it is among the least understood.

Joint representation of spouses has its own version. Texas permits it where the lawyer reasonably believes neither representation will be materially affected and both spouses consent after full disclosure. On confidentiality itself, no Texas authority settles the question; the leading practitioner commentary describes two competing models — one in which the attorney may hold nothing back from either spouse, and one in which separate confidences are possible. Ask which, and get the answer in writing.

Three more questions if a transaction is ahead

Does the letter of intent actually matter? You will be told planning must happen before the LOI. As a heuristic it is sound; as a legal rule it is folklore, and an attorney who knows the difference is worth finding. Two doctrines are measured on the transfer date: value is fixed as of the date of the gift, with the hypothetical buyer deemed to know the relevant facts including a pending transaction — and the transferor stays taxable on the proceeds if, by that date, the right to receive them had already ripened in substance into a fixed right. In a reviewed Tax Court decision, an LOI had been signed six weeks before a transfer of warrants to charity and the taxpayers still won — the charities could not be compelled to sell, and the IRS was held to its own published ruling. In a later memorandum decision, persuasive but not binding, the transfer came two days before closing with terms fully negotiated and the donor was taxed anyway; that taxpayer separately lost the deduction outright for want of a qualified appraisal. The two are in genuine tension. So the real questions are whether the recipient can be compelled to sell, and how many contingencies genuinely remain.

When was our buy-sell agreement last reviewed? In 2024 the Supreme Court held unanimously that a corporation's contractual obligation to redeem shares is not necessarily a liability reducing the corporation's value for estate tax purposes. Corporate-owned life insurance earmarked to fund a redemption counted as a company asset; the decedent's block was valued at $5.3 million rather than roughly $3 million, and the estate owed $889,914 in additional tax. Many entity-redemption buy-sells funded with corporate-owned life insurance and drafted before June 2024 assumed the opposite, because the question was contested rather than settled. Whether yours did is worth asking.

What is this plan for, now that the deadline it was designed around is gone? From 2022 through mid-2025, an enormous amount of gifting was marketed against a 2026 exemption sunset that was repealed before it took effect. If a structure was recommended on urgency grounds, ask what the case for it is now — including the trade-off between keeping appreciation out of the estate and preserving a basis step-up, which cuts differently than it did before the July 2025 law. Ask too how your attorney reads the IRS's 2023 position that assets excluded from the estate get no step-up: it is a revenue ruling rather than a court decision, it has never been tested, and it expressly left the leveraged-trust case open.

When your advisor already works with someone

If a financial advisor is in the picture, there is a practical case for hiring professionals the advisor works with regularly, and three reasons it isn't just convenience.

They know the field. An advisor who has sat through years of engagements with the same attorneys knows which one is genuinely strong on closely held business structures and which on multi-generational trusts, roughly what a piece of work should cost, and how long it should take. That comes from outcomes rather than presentations.

It changes what you can ask about scope and rates. An advisor who has commissioned similar work many times knows what a comparable engagement has cost and how it was staffed — a reference point you would not otherwise have when a quote arrives. Ask for it, and ask the attorney to account for any material difference.

The technical benefit is the real one. Most of what goes wrong in an estate plan goes wrong in the gaps between advisors: the trust nobody funded, the beneficiary form nobody updated, the buy-sell nobody re-read after the law changed, the entity nobody valued before the gift. A group that has worked together has built the habits that close those gaps.

The honest limitation. A referred attorney is not automatically the right one, and a group that always agrees carries its own risk. There is also an incentive running the other way: a professional who expects continuing referrals from an advisor has a reason to keep that advisor comfortable, which is not always the same as telling you what you need to hear about the advisor's own recommendations. Ask the ten questions anyway, ask whether anyone is compensated in either direction, and ask your advisor the same question. If the answers are unsatisfactory, the fact that your advisor likes them is not a reason to proceed.

The Bottom Line

You are hiring for judgment you cannot verify and will not test for years. So evaluate what an interview can reveal: whether this attorney has administered what they draft, who their clients really are, what they will and won't put inside the engagement, whether they can separate a structure's legal pedigree from its execution risk, and who their client is when your interests and your company's diverge.

Then choose carefully once, and let the relationship do the rest of the work.

If you are assembling a professional team around a business, a transaction, or an estate that has outgrown its current documents, we're glad to talk it through.