I have been advising people on international tax and corporate structures since 2006, when I set up in the UK, and since 2008 on the American side. That is roughly twenty years of first meetings. Thousands of them. And somewhere along the way I noticed something that I have never seen written down anywhere: I can usually tell within the first fifteen minutes whether an engagement is going to work.
Not whether the client is rich. Not whether the problem is solvable. Whether the relationship will function, whether the advice will be followed, whether we will still be on speaking terms in three years.
The tell is not the balance sheet. It is the questions.
Before I go further, one caveat. Every scene in this piece is a composite. I have merged people, changed industries, moved cities. If you think you recognise yourself, you do not. You recognise a pattern, which is rather the point.
The Questions That Make Me Sit Up
There are three questions that, when a prospective client asks them early and unprompted, tell me the engagement is going to be a pleasure.
"What does the mistake cost me?"
The best first meeting I can remember of this type went something like this. A manufacturing entrepreneur, mid-fifties, planning to leave his home country. He let me talk for ten minutes, took notes, and then asked: "Fine. Now tell me what happens if I get this wrong. Not the best case. The invoice for the worst case."
That question changes the entire conversation. Suddenly we are not discussing a brochure fantasy in which everything goes to plan. We are discussing exit taxation, audit risk, the cost of unwinding a structure that a tax office refuses to recognise, the years of correspondence that follow a badly documented departure.
A client who asks about the cost of failure is a client who understands that tax planning is risk management, not shopping. He will read the memos. He will keep the documentation. He will phone before he signs something strange, not after.
The client who never asks this question is often the one who later tells me that nobody warned him. Somebody did. He was not listening, because he had only ever priced the upside.
"What would you not do, in my position?"
This is my favourite question in the entire repertoire, and perhaps one client in twenty asks it.
Anyone can ask an adviser what to do. The answer is a product, and products are pleasant to present. But "what would you avoid" forces the adviser to reveal judgment rather than inventory. When someone asks me this, I talk about the things I have spent years helping people undo: the residency structure bought off a website that fell apart on first contact with reality, the five flags collected like stamps with no substance behind any of them, the company in a jurisdiction the client could not find on a map and never once visited.
A client who asks this question is telling me two things. First, he assumes that some of what is sold in this industry is rubbish, which is correct. Second, he is interested in my scar tissue, not my sales material. Those clients get my most honest hours.
"How long does it really take?"
Note the word "really". The question is not "how long does it take", to which there is always a polite official answer. The question is what happens between the official timeline and the lived one.
The clients who ask this have usually built something themselves. They know that every project has a published schedule and an actual schedule, and that the difference between the two is where all the pain lives. When I answer honestly (banks are slower than anyone admits, government offices have backlogs, a clean exit from a high-tax country is a project measured in months and sometimes years, not weeks), they nod. They budget for it. They do not phone me in a rage in week six because a bank asked for a third document.
The ones who never ask about time are frequently the ones who have already booked the farewell party.
The Questions That Make Me Reach for My Coat
Then there is the other category. Three openings that, twenty years in, function as reliable smoke detectors.
"How do I hide X?"
The verb is the problem. Not "reduce", not "restructure", not "plan". Hide.
A composite scene: a man with a successful online business, first meeting, third sentence. "I basically want to know how I make this invisible." Invisible to whom, I asked. "You know. Everyone. The tax office."
That meeting lasted another twenty minutes because I am polite, but the engagement was dead at "invisible". What he wanted does not exist in the legal world. Automatic exchange of information has been operating for years, banks report, registers connect, and the era in which secrecy was a product you could buy ended some time ago. What remains on offer under the word "hide" is either fraud with extra steps or an expensive placebo.
There is a legitimate version of this instinct: privacy from casual snooping, from competitors, from unstable jurisdictions. That is a real conversation and I have it often. But the client who opens with concealment from the authorities is not looking for an adviser. He is looking for an accomplice, and he will eventually find one, and it will cost him far more than tax ever would.
"Can you guarantee that this works?"
At first hearing this sounds like prudence. It is the opposite.
Nobody serious guarantees outcomes in this field. Laws change mid-project. Case law shifts. A bank can decline an account for reasons it will never explain. An officer at a residency desk can interpret a rule differently on a Tuesday than his colleague did on a Monday. An honest adviser gives you probabilities, structures the downside, and tells you where the residual risk sits. A salesman gives you a guarantee.
So when a prospective client demands a guarantee, I hear two things. First, he has not accepted that he is making a decision under uncertainty, which means every future surprise will be, in his mind, my fault. Second, he will eventually meet someone willing to give him that guarantee, because the market always supplies what people insist on buying. The guarantee will be worthless, but it will be confidently worded.
The engagements that end in acrimony almost never fail on the technical work. They fail on this: a client who wanted certainty, an industry that cannot honestly sell it, and somewhere a signature on something that promised it anyway.
"My YouTube guy says..."
Let me be careful here, because I publish content myself and I am hardly against people educating themselves. The best clients arrive well read. That is not the problem.
The problem is the client who arrives with a conclusion. A composite again: a young consultant, clever, profitable, who had absorbed forty hours of content from a personality whose entire catalogue amounts to "zero tax anywhere, tomorrow, no substance needed". He did not want advice. He wanted me to notarise the video. Every caveat I raised was met not with a counter-argument but with a citation: "but he says that doesn't matter any more."
What the videos systematically omit is the part that generates no views: substance requirements, management and control, the tax authority of the country you left caring deeply about where decisions are actually made. The gap between content and law is where the penalty notices live.
The distinction I draw is simple. A client who says "I saw this claim, is it true?" is doing research. A client who says "I saw this claim, implement it" has already hired his adviser, and it is not me.
The Questions You Should Be Asking Us
Fairness demands the mirror image. Advisers audit clients in the first fifteen minutes, but the traffic should run both ways, and most clients ask far too little. After twenty years on this side of the table, here is what I would ask any adviser, including me.
"Where are your conflicts of interest?" Every adviser has some. Perhaps I prefer structures I know well over structures I know less well. Perhaps a firm earns more from incorporation than from telling you not to incorporate. The question is not whether conflicts exist but whether the adviser can name them without flinching. An adviser who claims to have none has just failed the question.
"Who pays you, apart from me?" Commissions, referral fees, kickbacks from banks, developers, insurance products. In parts of this industry the advice is free precisely because the recommendation is the product. There are legitimate referral arrangements, but you are entitled to know that the residency programme you are being steered toward pays the person steering you. If the answer is evasive, the fee structure is the business model, and you are the inventory.
"What happens when we disagree?" Nobody asks this and everybody should. Which jurisdiction governs the engagement letter. What happens to your files if you leave. Whether you get the working papers. How a fee dispute is resolved. You are entering a relationship that will hold your most sensitive information for years; ask about the divorce before the wedding, the way you would in any serious long-term plan.
"Can I speak to someone who has been through this with you?" And then, crucially, treat the answer with realism. References are a curated sample; no one offers up their angriest former client. Confidentiality also genuinely limits what a tax adviser can share, unlike, say, a builder. So the useful version of this question is not "give me three happy names" but "describe, without names, an engagement that went wrong and what you did about it". The adviser who claims nothing has ever gone wrong in twenty years is either brand new or lying, and you can check the basics yourself: regulators and tax authorities publish sober guidance on vetting advisers, from HMRC's notes on choosing a tax agent to the IRS's checklist for choosing a tax professional. Dull reading, but dull reading is underrated in this field.
The Checklist, Both Directions
So here is the whole essay on one card.
If you are the client, ask: What does the mistake cost me? What would you avoid in my position? How long does it really take? Where are your conflicts? Who pays you besides me? What happens if we fall out? Tell me about one that went wrong.
If you are wondering how you sound to an adviser, avoid: hide, guarantee, and "my guru says". Replace them with: reduce, probability, and "is this true?"
None of this is complicated. That is rather the uncomfortable part. The first fifteen minutes of a consultation are not a mystery; they are two people revealing, through their questions, whether they want reality or a story. After twenty years I can promise you that reality, though it makes for a worse video, makes for a much better decade.
Work with Sebastian
If you want a conversation where the hard questions are welcome from both sides of the table, that is exactly the kind of first meeting I enjoy. Bring your list. Book a consultation.
