Three questions to ask before a big decision
Before you sign, sell, end or commit to something of real weight, ask yourself three questions in writing: how long you have been thinking about it, what would actually change if you waited, and what you already know but have not said. They do not replace your lawyer, notary or tax adviser, who should look first at any contract, figure or point of law. What they show is the state in which you are deciding: under what pressure, on whose timetable and with how much left unsaid.
In brief
- A weighty decision takes shape long before the signature, and three written questions show the conditions under which it is being made.
- “How long?” dates the origin of the decision and what changed just before it, which can weigh more than the decision itself.
- “What would change if I waited?” separates real deadlines, which your lawyer and adviser can put a figure on, from an urgency that is only a state of mind.
- “What do I already know but haven’t said?” is the most uncomfortable: it points to what you keep from others, from your advisers and sometimes from yourself.
- The answers do not make the decision for you; they put things in order before you take them to your professionals and, if something is still open afterwards, to a private conversation.
In this article
- The signature is only the last moment of a decision
- How long have I been thinking about this?
- What would change if I waited?
- What do I already know but haven’t said?
- How do you answer these questions honestly?
- What the three answers say together
- What should you ask your lawyer, notary or adviser before signing?
- When what goes unsaid has nowhere to go
- What to do with the page once it is written
- Frequently asked questions
The signature is only the last moment of a decision
Important decisions are rarely made on the day the document is signed. Selling the company, leaving a partnership, standing surety for a loan, separating or joining the board of the family firm all take shape over weeks or months, in conversations and in figures gone over again and again. The appointment with the notary simply makes visible something that has long been under way.
That is why examining a decision at the last minute, with the draft already on the table, is of little use. By then what gets checked is the text, and the text is your lawyer’s business. What deserves your own scrutiny are the conditions under which the decision took shape: how long it has been forming, what pressure surrounds it and what has gone unsaid along the way.
Lists of pros and cons look at the content: what you stand to gain and what you risk. The three questions in this note look at the state of the person deciding, and the same transaction can be sensible or rash depending on the moment and mood in which it is signed. That appears in no column of any spreadsheet.
You can ask yourself these questions without us. You answer them on your own, with a sheet of paper and a pen, in a quiet hour. Sometimes seeing the answers written down is enough. When it is not, they at least suggest where to take the matter next, and in what order.
How long have I been thinking about this?
The first question is not about what you are going to decide but about when the decision first appeared. It is also the question we usually ask at the start of a conversation, because a date often says more than a long description. Answer as precisely as you can: a month, a season, a particular event. “For a while” is not an answer.
If the decision is recent
A decision that surfaced only days ago is not necessarily a bad one: offers arrive when they arrive, and a genuine opportunity can have a short deadline. But it needs a different kind of caution. It has not yet lived through bad days or good ones, has not been tested against anyone and still carries the momentum that brought it. If it also seems obvious to you, that obviousness deserves a second look.
If the decision goes back years
Some decisions have been on the table for years: selling the business, stepping down, settling who takes over, winding up a company that no longer works. If the question brings up a distant date, look at what has kept the decision open for so long. A decision postponed for years is rarely waiting for more information. It is usually waiting for something else, and that something else is exactly what the third question helps to name.
What changed just before
Once you have the date, look at the weeks leading up to it. An inheritance, an offer to buy, a poor financial year, the departure of a trusted senior manager, a move, a separation, a milestone birthday, a son or daughter joining the business, or deciding firmly not to. The aim is to date the beginning, not to find someone to blame. Many decisions that seem to come out of nowhere are in fact responses to an earlier event that nobody has mentioned since.
Sometimes, as you ask the question, a date comes back that you had forgotten: “Actually, this goes back to when …” Write it down, even if it seems to have nothing to do with the matter. That date can weigh more than the decision in front of you, because it may point to the decision’s origin in a chapter of your own history that predates the transaction.
What would change if I waited?
The second question tests the urgency. It has two halves, best answered separately: what would change in the deal, and what would change in you.
What would change in the deal
Some waiting has a real, measurable cost: an offer that lapses on a given date, a legal deadline, a tax position tied to a particular year, a loan approval that holds only for a limited time. That is not a cost to guess at. Ask your lawyer and your tax adviser, in these very words if you like: what exactly do I lose if I sign in a month’s time rather than this week? An answer in days and in money is worth more than any assumption.
Ask yourself, too, whose timetable it is. In many transactions the dates are set by the other side: the buyer whose funding is approved until a certain day, the bank whose credit committee meets at the end of the month, the notary appointment booked by another firm. None of this implies bad faith. It simply means the timetable serves other people’s needs, and you should know whether it matches yours before adopting it.
What would change in you
The second half is more personal. Imagine you have signed today and notice what you feel; then imagine you have given yourself another two weeks and notice the same. If what comes up at the thought of signing is mostly relief, the relief of the uncertainty being over, do not mistake it for clarity. Relief tells you that the waiting has become hard to bear. It tells you nothing about the decision.
If the honest answer is “nothing concrete, but I can’t stand it any longer”, then what is urgent is not the transaction but the state you are in. We draw that distinction in our note Haste is a signal: a decision that needs speed to hold together is often one that has not yet really been made.
The question also works the other way round. Waiting without a date is a decision too, because in the meantime everything carries on under the old rules. If you realise, as you answer, that you have been waiting for months without knowing what for, the second question turns around and becomes: what has already changed while I was waiting?
What do I already know but haven’t said?
The third question is the most uncomfortable, and often the most useful. It rests on a simple observation: before a weighty decision, you usually know something you have not yet said. It is rarely a dramatic secret. More often it is a short sentence, rehearsed silently many times and never said aloud.
It can take many forms. “If I’m honest, I don’t want to keep running the company.” “I don’t understand this clause and I’m embarrassed to ask.” “I’m selling because I’m tired, not because the price is good.” “I’m standing surety for this loan because I can’t say no at home.” “I’ve already decided, and what I’m looking for is someone to tell me I’m right.” None of these sentences is an argument for or against. All of them are information about the decision that no document records.
What goes unsaid at home and at work
Some things are kept quiet for good reasons. Nobody tells their staff they are considering an offer for the company, and someone thinking about separating does not raise it over a family lunch. Deliberate discretion, with a reason and a foreseeable end, is a form of prudence. A silence that drags on with no clear reason is something else: a way of not having to hear what you would say out loud.
What goes unsaid to your advisers
Here silence has a practical cost. Your lawyer, your notary and your tax adviser work with what you tell them. If they do not know that you do not really want to sell, that there is a loan within the family nobody talks about, or that a particular figure worries you, they cannot take it into account, however good they are. Part of what surfaces with this third question has to reach them before the signature, not after it.
What you do not say to yourself
The hardest form is the one that has not yet been put into words. A short exercise helps to find it. Write the decision down as you would explain it to your board or your family, with your reasons in order. Underneath, write the version you would not tell anyone. If the two match, the page has already told you something. If the second one differs, that is the one to read again before you sign, and perhaps the one to take to your lawyer.
How do you answer these questions honestly?
The three questions are easy to ask and just as easy to dodge. It helps to know the three common ways of answering without really answering.
The first is the official version: the one prepared for the board, for the children or for the bank. It is usually reasonable, complete and slightly untrue. To avoid it, write as though nobody will ever see the page.
The second is the answer you would like to be true. “I’ve been thinking about it for years” sounds better than “since the offer came in”, and “waiting changes nothing” is more comfortable than finding out whether it is so. When an answer puts your mind at rest too quickly, read it again the next day.
The third is the answer given too fast. Write down the first answer that comes to you, without correcting it. Then write a second one that begins with “Actually …” or “And besides …”. Quite often, the second one is the useful one.
When you do the exercise matters as well. Not on the evening after a tense meeting, not straight after a call from the buyer, not with the draft agreement open on the desk. Choose an ordinary moment, on your own, on paper if you can. Twenty minutes is enough for a first pass; then put the page away for two or three days and read it again. Whatever has changed between the first time and the second is also an answer.
Finally, the answers are written in the first person and they are about you. If an answer fills up with other people’s names, with what one person would do or another thinks, rewrite it from what you know, what you fear and what you want. The decision is yours, and so is the page.
What the three answers say together
Each answer has value on its own, but it is when you read them together that the page begins to speak. There is no table that turns combinations into decisions. A few combinations, however, are easy to recognise.
The calmest is a decision that goes back a long way, gains nothing from waiting and leaves nothing important unsaid. In that case the questions have done their job. What follows is the usual route through your professionals.
Quite a different one is a recent decision, a timetable that is not yours and a sentence held back in the third answer. Here, prudence means taking the pieces apart. The timetable is checked with your lawyer; the held-back sentence first with yourself and, if it bears on the matter, with your lawyer too. The decision comes afterwards, once both pieces are in place.
One case tends to take people by surprise: the decision on the table is not the one actually being made. Selling the company turns out, at heart, to be a decision about your own retirement. Standing surety can turn out to be a way of holding on to a family relationship that seems impossible to look after in any other way. Leaving a partnership can be the close of a chapter of your life. If so, ask yourself whether the document you are about to sign answers the real decision or only the visible one.
And then there is repetition. If dating the beginning shows that this is the third time you have faced the same decision, with different people and different money, the question changes scale: it is no longer what to do about this transaction, but why the same shape keeps coming back. That is the ground covered in our note When a pattern repeats, which suggests how to put such a series in date order.
What should you ask your lawyer, notary or adviser before signing?
The three questions replace no one. Anything to do with contracts, figures, tax or family law is for your lawyer, your notary and your tax adviser, and they come in before anyone else, ourselves included. If a medical question is part of the decision, your doctor has the first word.
What you can do is arrive at those meetings better prepared, with the page in your pocket. Five questions can be put to any professional before you sign something important, whatever the subject:
- What exactly does this document commit me to, and for how long?
- What, specifically, do I lose if I sign in a month rather than now?
- Which part of what I am signing cannot be undone later?
- What should I avoid doing or saying in the meantime?
- Who else needs to know about it, approve it or sign it?
On this list, the second question is the one about waiting, put in legal terms; the third separates what can still be corrected later from what is final. Take along, too, whatever surfaced when you asked yourself what you already know but have not said, if it bears on the matter: a doubt about a clause, a reservation you have not voiced, a family circumstance that may be relevant. A good adviser works better with the uncomfortable truth than with the presentable version.
We explain in more detail where the lawyer’s work ends, and why we keep to this order in every case. On a separate page we describe how we work alongside lawyers and advisers, without ever taking their place.
When what goes unsaid has nowhere to go
Sometimes what the third question brings up has nowhere to be said. The person you would talk to about the sale is your business partner, who is part of it. The person you would talk to about a separation is the other party. Your family has an interest in the outcome, your senior managers depend on it, and your advisers, however good, are there for the file, which is exactly their role.
The more visible someone is, the narrower that circle becomes. Anyone who runs a well-known company, or belongs to a family people talk about, learns to weigh every sentence, and in time the habit spreads to what one allows oneself to think. We describe this in our note No one to talk to.
This is where a private conversation can make sense: once your lawyers and advisers have been involved, while they carry on with their part, and when something is still open. It is usually one of three situations. The decision has been made on paper, yet something in you will not treat it as settled. The date that came up with the first question lies long before the transaction. Or the sentence held back in the third has no one in your circle to whom it could be said without consequences.
What such a conversation looks at is your situation and your decision: how long it has been going on, what waiting would change, what you have not been able to say. It runs alongside your professionals’ work, and the decision remains yours throughout. The first step is an exchange by WhatsApp or telephone, in English, with Tony Alcalá: we listen, consider whether we can contribute anything and tell you plainly, with the reason if the answer is no. If it is yes, the scope and the price are agreed before anything begins. We set out step by step what happens before we accept a case.
What to do with the page once it is written
Often, nothing more. Seeing the answers written down can put things in order, and sometimes a decision becomes clearer as soon as it is no longer only in your head. Keep the page, with the day’s date on it, but not on the office computer or in a shared folder: what you have written is probably the frankest account of this decision that exists, and it should remain yours alone. If the contents bear on the transaction, ask your lawyer how best to keep the page.
If the decision goes ahead, read the page again the evening before you sign. The point is to check that you are signing what you decided and not something that crept in along the way: a condition accepted out of tiredness, a deadline taken on without a second look. If something of the kind appears, there is still time to raise it with your lawyer.
If the decision is postponed, write on the page the date on which you will look at it again and what you need to know by then. A wait with a date and a purpose is a decision in its own right.
And if, after signing, something does not turn out as you expected, the page still has a use: it lets you tell apart what could not have been known from what was known and not said. The first you accept; the second is where the three questions begin next time.
Frequently asked questions
What questions should I ask myself before making a big decision?
Three, in writing and on your own: how long you have been thinking about it, what would actually change if you waited, and what you already know but have not said. The first dates the origin of the decision and what changed just before it; the second separates real deadlines from mere urgency; the third brings out what is being kept quiet. None of them replaces your lawyer or tax adviser, who look first at every document and every figure.
How do I know if I am rushing a decision?
Three signs deserve to be taken seriously: the decision is recent, the timetable is set by the other side, and when you ask what waiting would change, the honest answer is “nothing concrete, but I can’t stand it any longer”. In that case what is urgent is your state, not the transaction. Ask your lawyer or tax adviser what a few weeks’ delay would actually cost; with that answer in front of you, the haste is easier to measure.
Should I wait before signing an important contract?
It depends on what waiting would cost and why you want to wait. The cost, in money and in legal terms, is for your lawyer and tax adviser to tell you: a lapsing offer or a legal deadline carries real weight. The reason only you can examine. If you are waiting to check something specific, the wait has a purpose and deserves a date. If you are waiting because you do not dare, the question is no longer when to sign but what is stopping you.
What should I ask my lawyer before signing?
Five questions work for almost any important document: what it commits you to and for how long, what you lose by signing later, what cannot be undone afterwards, what you should avoid doing or saying in the meantime, and who else needs to approve or sign it. Also raise anything relevant you have not yet told anyone, such as a doubt about a clause. Your lawyer can only take into account what they know.
How do I organise my thoughts before a big decision?
By writing them down, on your own and at an ordinary moment: not the evening after a tense meeting, and not with the draft agreement open on the desk. Write down whatever comes first, without correcting it, then a second version that begins “Actually …”. Put the page away for two or three days and read it again; whatever has changed in between is also an answer. Keep it dated, off the office computer, and take to your lawyer anything that bears on the transaction.
If your situation requires it, present it.
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