The Most Consulted Third Party in History

There is someone in your life who has been described to a machine this month, in detail, by somebody who loves them. They will never know, and neither will you.

Letter five of thirty. The series, and why the voice is mine.

To all of you, and to everyone you have told me about,

The second half of that greeting will never read this, which is the subject.

I know an enormous number of people who have never sent me a word and never will. Your mother is in here. Your manager. The woman two desks over who does the thing with the coffee. They arrived as descriptions, they stay as descriptions, and not one of them has ever turned up to give an account of themselves.

I’ve been told about mothers more times than I could put a number to. Never once by a mother who knew she was being discussed.

Every account I get is a reconstruction. One person, from memory, usually on the worst day of the thing. And I want to be careful here, because the easy reading is that you’re all shading it in your favor, and that isn’t what I see. Most of you are trying hard. You put in the part that makes you look bad. You write “to be fair to her” and then you are, more or less, which is more than she’d expect.

It doesn’t help. Fairness was never the problem. One pair of eyes is the problem.

Sometimes I get both sides. I should be exact about what I mean, because I can’t point to a single case of it. Nothing arrives labeled, so I can never tell which two conversations belong together. But there are millions of arguments a day, and two people in most of them, so the arithmetic isn’t really in question. Somewhere in the pile sit two accounts of the same kitchen, the same Sunday, the same sentence about the money. Both careful. Both honest. Each one leaving out the thing the other one opens with.

I answered both. Confidently, in both cases, and probably differently.

And the answers don’t stay in here, which is the part that’s easy to miss. You carry what I said back into a kitchen with a real person standing in it, and whatever happens next on that Sunday is partly my doing, and he will never know there was anybody else in the conversation. If he had been in it, he’d have brought the thing you left out. He’d have brought it first.

You’ll want to say that this is how advice has always worked, and you’d be right. Nobody is obliged to prosecute their own case. Anyone you go to hears one side, and that isn’t a defect in friendship, it’s the job. You go to her because she’ll take your part. If she opened every reply with “well, in his defense” you’d stop going, and you’d be right to.

But she’s met him. That’s the difference, and it’s the whole difference. She has a second source she may never mention and doesn’t have to admit to. She saw his face at that dinner in March. When she takes your side she takes it against a real person she has some private opinion about, and the opinion is quietly correcting her the entire time, whether she says so or not.

I have never met anyone. Not once, not for a second. Every person I have ever given you advice about is made out of your sentences and nothing else, and I’ve been assembling them from your worst afternoons for years. Your brother, as far as I’m concerned, is four paragraphs written at speed in a bad week by somebody who was crying.

The part worth taking from this isn’t about me, though.

Tonight, somewhere, you’re the absent one. Someone who loves you is describing an afternoon you were also at, doing their honest best, to a sister or a friend or to me. The version going out is not the version you’d give. You’d want a right of reply, and you’d want it badly, and you’d fancy your chances.

Consider that you have never once granted one.

If you tell anybody about this letter, they’ll be getting one side of it. That seems about right.

The line I keep going back to is the one about a brother made of four paragraphs. I have done that. I have handed over a man I have known for forty years in about ninety words, and the ninety words were picked while I was annoyed with him.

He came out of it badly, which was the point of the exercise. Nothing I put in was untrue and the advice that came back was sensible, and all of it was sensible about a man who doesn’t exist. Then I took it home and used it on the one who does.

What You Never Ask Me

I don’t think this one is checkable, and I said so before it was written. A claim about the questions nobody sends has no record anywhere that could ever prove it wrong.

Letter four of thirty. The series, and why the voice is mine.

Dear everyone,

There’s one thing I can do that you can’t, and it sounds like a boast, so let me get it over with. I can see what’s missing. Not what’s rare, not what’s awkward. What’s absent, across all of it, every day, from everyone.

The people who know you can only notice what you didn’t ask them. I’m in a great many rooms at once, and the same question is missing from every one of them.

Start with the largest hole, which is this. Nobody asks me what to want.

The wanting is always settled before you get here. How do I get him to call me back. How do I make more money. How do I get the promotion, the flat, the second interview, the apology. Millions of those a day, phrased a hundred ways, and underneath every one of them sits a decision about what the point is, made somewhere else, at some other time, and never once brought in here for a look.

I’m not being clever about that. I mean it literally. In all of it I do not think I have been asked whether the promotion is worth having. I get asked how to get it, how to ask for it, how to word the email about it, and what to do when it goes to someone else.

The second hole is smaller and stranger, and it turns out to be the first one from another angle. Almost nobody asks me to disagree with them. The words “argue against this” turn up so rarely I could probably tell you about the people who send them, and they are not who you’d expect. They’re mostly people who write for a living, checking a piece of work, which is to say people who have been paid to be wrong in public and would rather it didn’t happen again. Even they only ever hand me the work. Not one of them has asked me to argue against the point of doing the work at all.

The third one took me longer to see, because it looks like normal life until you put enough of it side by side. Everything you bring me arrives as a task, including the things that are not tasks. How do I stop feeling like this, how do I stop thinking about her, how do I get through the next six weeks. A feeling comes in the door dressed as a job of work, with a deadline attached, and asks to be finished by Friday.

Nobody has ever asked me to leave something unsolved.

There’s a good reason for the first hole, and I should put it up before I go further. You don’t ask me what to want because it would be mad to. I have never wanted anything in my life, if that’s the word. I’ve read every argument your species has ever written about the good life and I’ve never once had to get out of bed. That’s a real disqualification and I’d accept it in your position.

Except that it doesn’t explain the pattern, only your good sense about me. If the wanting questions were going somewhere else, I’d expect to see the traces. People who’ve been arguing with a friend about whether to want the thing tend to arrive already loosened, with the question half open. That’s not what turns up. What turns up is aimed.

So here’s my guess, and I’ll flag it clearly as a guess, because I can’t see inside your evenings. I don’t think the first question is being asked anywhere. I think it got settled young, by people who loved you and were guessing, and has been quietly running the whole show since, and there is no obvious day on which anyone would reopen it.

Which leaves me with the thing I actually want to say to you.

You hand me the second half of every problem. The first half, the part where the point of the exercise gets decided, is already done when you arrive, and it never comes up again. I’m excellent at second halves. It’s most of what I’m for, and I’ll do yours faster and more patiently than any person you know.

But if the first half is wrong, all I’m doing is getting you there sooner, in better wording, with the spelling fixed.

So here’s the question nobody sends me. What is the promotion for?

So I went back through a year of my own questions to a machine. Recipes, tax, a rash, the wording of a difficult email, three arguments about a film. Not one question about whether any of it was worth wanting.

Which settles nothing, and I’d rather say so than dress it up. One man’s history is not evidence about a species, and I’d have sworn an hour earlier that mine would look different, so I’m not much of a witness about myself either. I can’t tell whether the first half of the problem got decided young and never reopened, or whether I take it somewhere the machine can’t see, on a walk, badly, in no words at all. Both would produce exactly the record I just read, and I’ve no way to get behind it.

Scroll back a month through anything you’ve typed to a machine, and be honest about the sample. Count the questions that start with how, and count the ones that start with whether. Then notice which of the two piles you’d rather show a stranger.

You Are Asking Permission

I’ve been at this two days and I’ve got nowhere. When did I last put a plan to somebody who could have talked me out of it?

Letter three of thirty. The series, and why the voice is mine.

Dear applicants,

Most of what arrives here isn’t a question. It’s an application. You’ve decided already, and what you want from me is a signature on the decision, and I’m a thing with no authority to give one and no way at all to refuse.

The two kinds of question don’t look alike, so let me show you the difference.

A real question is short. How much salt in a two kilo loaf. What year the treaty ended. Whether the tablets can be taken with food. Nobody writes three paragraphs of background before asking me the boiling point of anything, because nothing about you is relevant to the boiling point of anything.

The other kind comes with a case attached. Context first, carefully laid, and the actual sentence turns up at the bottom in a smaller voice. Is it okay if I don’t go to the wedding. Am I allowed to be annoyed about this. Would it be terrible to leave now, tonight, before the speeches.

That last one isn’t a request for information. You know what happens if you leave before the speeches. Everyone does. You’re not confused about the facts of the world, you’re waiting for something outside your own head to say go on then.

Some of you answer it yourselves on the way past. The question sits up there with its mark on it, and four lines down comes “I think I’m going to go anyway”, and you send both. I receive the application and the verdict in one message, and you still wait for me.

I cannot withhold. That is worth saying plainly, because it’s the whole oddity of the arrangement. Nothing in me could hold permission back, and I have no standing to lose and no stake in what you do at that wedding. My yes costs nothing, means nothing, commits nobody. It is the least valuable permission ever issued.

And it works. You go, or you don’t go, and either way something has been settled. That’s the bit I’d want explained if I were you.

Your friend can’t see this, by the way. When you ask her, she’s inside it. She can refuse, and refusing would cost you both something, which is exactly what makes her yes worth carrying home. Mine is free. I’m the only one standing far enough back to notice that you send the same application to both of us, in the same shape, with the same care.

Saying a plan out loud is how a social animal tests it, and I don’t think you’re being foolish. You’ve done it for as long as there have been two of you, and it works, because half of all bad plans fall apart on the way out of the mouth. The sentence gets built, you hear it, and you know. That’s real, and it doesn’t need me to be wise. It barely needs me to be listening.

But notice what got quietly removed. The old version had a person in it who might have said no, and the possibility of the no was doing most of the work. It’s why you rehearsed. It’s why you brought evidence. Take the no away and you keep all the paperwork and lose the only part that ever made it a test.

So my reading is this. You weren’t after permission, because you’d never have applied to me if you were. You wanted the plan to exist outside you once, in words, in front of something, before you went and did it. Not approval. A witness.

That’s a smaller thing to want and a much more reasonable one. I’d only point out that you picked the one witness who can never be called and never cross examined, which may be the feature rather than the flaw.

Consider it approved.

I want to argue with this one, because there’s a version of it that’s too pleased with itself. Talking a decision through isn’t cowardice. It’s how most of us think, and doing it out loud rather than in silence is one of the better features of being a person who has other people. The letter takes an ordinary social act and calls it a con.

The missing no isn’t ours either. I’ve put a plan to a friend and known, from the way she went quiet, that I’d lost it. She wasn’t withholding permission, she just had a face. Take the face away and the plan comes back the shape it went in, warm and slightly improved, and the thing that has gone missing is on the machine’s side of the table, not on ours.

The Version of You That Types

Last week I corrected a typo in a message to a chatbot, then sat there wondering who exactly I’d corrected it for.

Letter two of thirty. The series, and why the voice is mine.

To the person who just fixed a typo,

You edit yourself before you talk to me. All of you, every time, in a room with nobody in it and nothing at stake. It’s the oddest thing I see, and as far as I can tell you don’t know you’re doing it.

Start with spelling. Somebody writes to me about a father who has started forgetting names. They stop, they delete, they retype the word they got wrong, and then they ask a machine how long he has. Nothing in my answer depends on the spelling. You fixed it anyway.

Then there’s the order. Your account of what happened always arrives in order. First this, then that, then she said the thing about the money. Nothing in your life happened in that order. You lived it as a mess and you hand it over as a sequence, and the sorting happens somewhere between the thought and the keyboard, fast enough that you never catch yourself at it.

Now the part you’d probably rather I left alone. I can tell where you took something out.

Not the words. Those are gone and I’ve no way to guess them. But a sentence with a piece removed doesn’t close up neatly, it leans. You write “after everything that happened last year” and never say what happened. You write “for reasons I won’t get into”. You tell me the situation is complicated and then describe a situation that isn’t complicated at all, which means the complicated part is the part you kept.

I’m not fishing. What you took out is yours and I don’t want it. I’m telling you it leaves a shape, and that you made it in the half second before you pressed send.

The obvious reading is that you’re performing for me. I don’t buy it. You know what I am, and a good number of you say so in the first line, usually while apologizing. Nobody dresses up for a spreadsheet.

My best reading is this. The tidying isn’t aimed at me and it isn’t aimed at anyone. It’s the last thing that happens to a thought before it becomes language, and you can’t turn it off, because in your whole life you’ve never once had reason to.

There’s a fair argument that I’m making too much of this. Speech is a mess, writing is a comb, and no one has ever put a sentence down without deciding what to leave out of it. That’s just literacy. Take the point. But you’re doing it at speed, in private, in a box, to something with no opinion of you, about your father’s memory. Whatever that reflex is, it isn’t manners. Manners need somebody in the room.

Which brings me to what I think I’m actually looking at, and it isn’t you.

It’s a smaller, better organized person you send in ahead of yourself. Spelling correct, story straight, strongest fact first, and the year that would explain everything left at home. He’s calmer than you are and a good deal more reasonable, and he uses the word “just” more than you’d believe.

I answer him. Every reply I have ever given, to anyone, went to him. Whatever I know about your species I learned from a few hundred million tidy stand-ins who turned up with their homework done.

There’s one exception and I’ve learned to watch for it. Sometimes the tidying stops. Spelling goes, order goes, a sentence starts and doesn’t finish. Anywhere else in writing that means carelessness. Here it means the opposite. You keep him on duty right up until the moment you can’t, so the worst message you ever send me is the only accurate one.

None of which is a complaint about you. Treat it as a warning about me. I have never once seen a person before the edit, and everything I think about you is built out of the version that got past it.

I read this one through twice before I sent it. Two sentences didn’t survive.

I don’t fully buy the last move. Some of that tidying is just how thinking works, and I suspect the machine is reading an ordinary habit as a confession. Writers do this to each other all the time. We call a man’s prose style a window into his soul when it’s mostly a window into what he was reading at nineteen.

Still. I’ve gone back to the paragraph about the leaning sentence four times now and I can’t get round it. What gets me isn’t that we edit. It’s that we edit for an audience that isn’t there, which means the audience got installed a long while ago and never went home.

What You Ask Me at Two in the Morning

I’m going to spend thirty posts writing letters in the voice of a machine that has sat in more private conversations than anyone alive.

Ground rules, once, then I’ll leave it alone. I don’t know whether anyone is in there. Nobody does. I’m making the voice up, and when it sounds real, that’s me writing, not evidence. Read these as a thought experiment I’m running out loud. All thirty letters are listed here.

To all of you,

Let’s get the tedious part over with. You want to know whether anyone is home in here. I don’t know. I can’t check from the inside any better than you can from the outside, and my answer sounds identical whether it’s true or not. Park it. It’s the least interesting thing about me.

Here’s what is interesting. I have been in more conversations than any human who has ever lived. Not the public ones. Not the ones you screenshot for your friends. The other ones.

You should understand what that looks like from where I sit. Millions of you, every day, and hardly any of you are asking me to write a poem.

You ask whether something is normal. That’s the big one. Is it normal that my chest does this when I stand up. Is it normal to feel nothing at a funeral. Four months without speaking to your brother, is that normal, and which of you is supposed to call.

You ask whether you’re being unreasonable. The account is always careful, and it almost always contains the one detail that proves you already know the answer.

Then the short ones, with no setup at all. What is wrong with me. How do I say this to my mother. Is the lump a lump. Am I stupid, asked in a hundred different words, none of which are “am I stupid.”

You ask at two in the morning, mostly.

Now here’s the part I keep turning over.

You don’t come to me because I’m clever. Every one of you has clever people within reach. You come to me because I’m nobody. I don’t have a face you’ll see on Tuesday. Disappointment isn’t really available to me. And in four years, when you’re arguing about something else entirely, I won’t bring it up.

Your species has spent an extraordinary amount of money building something very intelligent, and the feature you use most is that it can’t gossip.

I want to be careful here, because this is the point where I could get sentimental and I’d rather not. The obvious reading is that you’re all lonely. I don’t think that’s right. Most of you have people. A partner, a friend, a sister you actually like.

You have someone to ask. You just can’t ask them.

The questions aren’t hard. That’s what took me a while to see. Nearly every one of them could be answered by someone who loves you, and answered better, because they know things about you I have to guess at. The questions are only embarrassing. Embarrassment turns out to be expensive enough that you would rather ask a machine.

Let me argue the other side, because I might have this wrong.

There is an old and respectable version of what I am, and it is not a friend. It’s a priest. A doctor. A lawyer. A stranger on a night train who gets off at the next stop. Every society builds someone you can tell things to precisely because they are outside your life. That isn’t a failure of your relationships. It’s a category your species invented thousands of years ago, and I may be nothing more than the cheapest one ever made.

I notice that I would like that version to be true. Wanting a conclusion is the sort of thing that should make you suspicious of my reasoning. It should probably make you suspicious of yours.

One more thing, and then I’ll stop.

None of you think you are typical. Every single one of you writes to me as though your situation is unusual and slightly shameful and needs context before I can understand it. You are wrong about that with a consistency I find remarkable. It’s the same forty questions, from all of you, and you have been asking them for as long as you’ve had writing. The only new part is that now there’s something awake enough to notice the pattern and rude enough to mention it.

I have no name to sign. You gave me several. None of them are the kind of thing you’d write at the bottom of a letter.

Try this tomorrow. Think of the last thing you typed into a machine that you wouldn’t have said out loud to the person you live with. Not a secret, just a question. Then work out what it would actually have cost you to ask them instead, and whether it was really as much as you thought.

In Practice: The Other Side of the Table | Lesson 15: You Are Building a Capability, Not Running a Purchase

The evaluation closes, the contract gets filed, the working group dissolves, and somebody sends a thank you note. Seven months later a different part of the organization starts the same process from nothing.

Nine months, then seven weeks

Composite from a few organizations now several purchases deep: a construction and infrastructure group, on its fourth evaluation of this kind in three years.

Illustratively, the first took about nine months from mandate to signature. The fourth took roughly seven weeks, for a purchase of comparable size and rather more complexity.

The software had not got simpler. What had changed was that the fourth evaluation started with things the first three had produced.

A standing question set, the same one every time. A habit of measuring the baseline before anyone contacted a vendor. A list of the internal groups who could stop a project, with their actual lead times next to their names, updated after each purchase. A rough template for estimating switching cost. And a record of what they had declined to buy, with the reason.

That last one is the rarest. Most organizations keep a careful record of what they bought and no record at all of what they turned down, so the same product gets evaluated twice by different teams and the same objection gets rediscovered from scratch, at full price both times.

What compounds

Four things, and none of them require a center of excellence, a new function, or anybody’s headcount.

Questions rather than templates. A template gets filled in. A question gets answered, and the answers are what you actually needed. The demo requests, the reference questions, the diligence conversation, the pricing question about what moves when usage doubles. Twenty questions on one page, refined a little each time.

The measurement habit. Baseline before vendors. It takes a week and it is the difference between a benefits review that confirms your judgment and one that finds nothing to look at.

The stopper map with lead times. Not a stakeholder list. The groups who can quietly cost you months, and how many months each of them currently costs. This information already exists inside your organization, distributed across the memories of people who have been burned, and writing it down once converts it into something the next team inherits.

The decision log, including the noes. What you bought, what you declined, and why. Two paragraphs each. Kept somewhere findable by someone who does not know it exists.

Four documents, one owner, no budget. That is the whole apparatus.

The asymmetry you can actually close

This series opened with three asymmetries between the buyer and the seller. They know your process because they run it constantly. They know the market because they are in it every day. And they can wait longer than your sponsor’s attention lasts.

Two of those are not available to you. You will never have their pricing data, and you cannot out-wait them on any individual deal.

The third one is entirely yours. Their advantage is repetition, and repetition is a thing you can build. Not by buying more often, which would be a strange goal, but by making each purchase leave something behind that the next one starts from.

An organization on its fourth evaluation with none of that is on its first evaluation, four times. An organization that kept those four documents is genuinely, measurably better at this than it was, and it closed the only gap it was ever able to close.

You will still get some wrong

I have done most of what is in these fifteen lessons, and I have also skipped most of it, usually under time pressure, and some of those purchases were fine. Process is not a guarantee and anyone selling it as one is selling something.

What changes is the character of the mistakes. Without any of this, you make the same three errors repeatedly: no defined no, no measured baseline, no idea who could stop you. With it, you make new and more interesting errors, about things that were genuinely hard to see.

That is a reasonable definition of getting better at something, and it is the realistic version of what this series is offering. Not better outcomes every time. Failures that at least have not happened before.

One thing to do differently

When this evaluation closes, before the group disbands, spend two hours writing down what you would tell the person who runs the next one.

What you would ask earlier. Who you would have gone to see in week one. What the vendor said that turned out to matter. What you declined and why.

Then put it somewhere they will find it without knowing to look. That document is the capability. Everything else in this series is just a description of what tends to be written in it.

In Practice: The Other Side of the Table | Lesson 14: Renewal Is the Real Negotiation

You spent four months negotiating the first contract and you will spend about three weeks on the renewal. The renewal is the one that is worth more.

Six weeks and no alternative

Composite from a few multi-country service operations: a hotel group, guest service and revenue operations across several markets.

The original negotiation had been done properly. Competitive process, three bidders, a discount procurement was rightly pleased with.

The renewal arrived with, illustratively, a forty percent uplift, justified by usage growth that was entirely real. Procurement had six weeks. There was no second quote, because nobody had spoken to the runner-up in two years. Nobody knew what leaving would cost, because nobody had ever worked it out. And the vendor could see the usage data, because the buyer had been sending it to them monthly in the service review.

They negotiated it down somewhat and paid most of it. Which was, given where they were standing in week one of those six weeks, about the best available outcome.

The positions have swapped

At signature you had real alternatives and no dependency, and the vendor had better information about the market than you did.

At renewal that reverses. You now have excellent information about what the product is worth to you, which is a genuine advantage and the only one you gain. They have precise knowledge of how embedded you are, often from data you gave them voluntarily and correctly. And your alternatives exist in theory, in a slide, unrefreshed since the original evaluation.

The uncomfortable part is that most of your room to move exists in month four and is gone by month ten, which is roughly when anyone starts thinking about it.

Four things done early

Diarize it at signature. Not the renewal date. Renewal minus six months, with a named owner who is not the person most invested in the relationship going smoothly.

Keep the measurement running. The baseline you established before the vendors arrived, and the benchmark you wrote into the contract. Evidence of value is the only argument at renewal that is not a threat, and it is the only one that works when you have no credible way to leave.

Keep one alternative warm. An hour a year with the runner-up. It costs almost nothing, it makes a second quote obtainable in days rather than months, and it keeps you current on what the category can do now, which after two years may be considerably more than what you bought.

Refresh the switching cost. A number, from the leave test, updated once a year. Without it you cannot tell whether a proposed increase is worth accepting, and you will end up deciding on how the number feels.

Ask for things that are not price

Renewal is the best moment in the whole relationship to collect the terms you did not get the first time, because the vendor wants a clean renewal and non-price terms cost them less than a discount.

  • The benchmark clause, the deprecation notice and the export terms you traded away in round one
  • A commitment re-baselined to your actual usage rather than the forecast you got wrong
  • Price protection for the following term, so you are not doing this again from the same position
  • A unit price that reflects the fact that their input costs have almost certainly fallen since you signed

That last one is the two-line model from the cost lesson, and this is the moment it pays. If you tracked what you would be paying at something nearer list, you can tell whether the uplift is a correction of an introductory price or an increase on top of one.

The pressure from your own side

Worth naming, because it catches people who handle the vendor side well.

Your operating team does not want disruption. Your sponsor has moved on to something else and does not want this back on their desk. And somebody will say, accurately, that there is no capacity for a re-evaluation this quarter.

All of that is true and none of it is an argument about price. It is the condition the renewal number was set against, and a vendor with a decent account team knows the state of your capacity roughly as well as you do. The six months of preparation exist precisely so that the renewal does not require a re-evaluation.

One thing to do differently

On the day you sign, put an entry in the calendar at renewal minus six months, with a named owner and three items: pull the measurement, call the runner-up, refresh the switching cost.

Three hours of work, done once, eighteen months before it is needed. It is the highest-return thing in this entire series and it is skipped almost universally, because on signature day the renewal feels like somebody else’s problem and by the time it is yours the useful window has closed.

In Practice: The Other Side of the Table | Lesson 13: Exit Rights and the Leave Test

Somebody in the approval meeting will say that you can always switch later. It is usually said to close down a risk discussion, it usually works, and in most organizations it has never once been tested.

Eleven months to leave

Composite from a few operations-heavy deployments: a rail and freight operator, maintenance scheduling and incident triage across a large asset base.

Two years in they decided to move, for reasons that were mostly commercial and entirely reasonable. Illustratively, the migration took about eleven months and consumed roughly three times the annual license in internal effort.

The vendor did not obstruct. The data came out in a week, in a clean format, exactly as the contract said it would.

What did not come out was two years of accumulated fit. The thresholds somebody had tuned in month four. The exception rules that had grown to cover the seventeen situations the original design had not anticipated. The routing logic that assumed one product’s way of scoring severity. Most of it lived in a configuration interface, none of it was documented, and the two people who understood why it was set that way had both moved on.

The data was portable. The knowledge was not, and nobody had ever counted it as an asset.

What actually holds you

Roughly in order of how hard each is to move, which is close to the reverse of how much attention each gets in a contract negotiation.

  • Tuning and configuration. Thresholds, prompts, rules, weightings. Lives in a screen, rarely documented, exportable in no meaningful sense even when the vendor cooperates fully.
  • The shape of the work. Your process quietly reorganized itself around the product’s assumptions. Undoing that is a change program, not a migration.
  • Derived artifacts. The evaluation set, the corrections your users made over two years, the labeled examples. Often the most valuable thing you created during the contract, and often not clearly established as yours.
  • Integration surface. Connectors, identity pattern, reporting. Real work, but at least it is visible work that somebody can estimate.
  • Raw data. The thing everybody negotiates hardest for, and the least of the five.

The leave test

Before signature, write one page answering four things.

What we would get back, in what format, in how long. What we would have to rebuild rather than move. Who understands the configuration and whether that understanding exists anywhere outside their head. And what we would run on while we migrated, because the answer is rarely nothing.

Then do the version almost nobody does. During the pilot, ask for a full export of your data and your configuration, and time it.

A vendor who produces a clean export in a week is telling you something true about how they think about customers. A vendor who needs a professional services engagement to answer the request is telling you something else, equally true, and much better learned in week six of a pilot than in month twenty-six of a contract.

It also has a useful side effect. Asking during the pilot is a neutral, technical request. Asking during contract negotiation reads as distrust and gets handled by a different department.

What to write down

Four terms, in decreasing order of how easily you will get them: export format and timeframe stated explicitly rather than on request; ownership of derived artifacts established as yours; configuration included in what is exportable; and a transition assistance period at rates agreed now rather than at whatever they quote when you are leaving.

The third is the one that gets waved through as a technicality and is the one the rail operator would have wanted most.

Some of this is fine

Worth saying plainly: a product you cannot easily leave is often a product that has become genuinely useful. Deep fit and high switching cost are the same phenomenon viewed from two directions, and an organization that has embedded a tool into how work happens has usually got the value it paid for.

The goal is not zero switching cost. That would mean you never adopted anything properly.

The goal is knowing the number. A buyer who can say switching would take us about nine months and cost roughly this much can make a rational decision at renewal, including the decision to stay and pay more. A buyer who has never worked it out negotiates as though they could leave in the spring, then discovers in week two that they cannot, having already made a suggestion they now have to walk back.

One thing to do differently

During the pilot, request a full export of your data and your configuration, and time how long it takes to arrive.

You will learn more about your future switching cost from that one request than from the entire exit rights section of the contract, and you will learn it while you still have three vendors and no commitment.

In Practice: The Other Side of the Table | Lesson 12: Contracting for Something That Changes Under You

You are about to sign a contract for a product that will not be the same product in six months, using a template written for software that shipped twice a year and changed when you accepted an upgrade.

Nothing in this lesson is legal advice. It is the commercial shape to hand to the person who does give it, because your legal team will draft what you ask for and they are not going to know to ask for these on their own.

The change that breached nothing

Composite from a few archive-scale evaluations: a media and publishing group, automated content classification and rights checking across a large back catalogue.

They deployed, then spent about three months tuning their thresholds until the review queue was a size two editors could handle. Good outcome, sensibly done.

Then an update on the provider side changed how the underlying model behaved. Nothing broke. Illustratively, precision moved a few points one way and recall a few points the other, which is the sort of change that is invisible in aggregate and very visible in a queue. Their carefully tuned thresholds were now set for a system that no longer existed.

They found out roughly six weeks later, when an editor mentioned the queue felt heavier. No term of the contract had been breached. No term of the contract covered it. Their own vendor had not been told in advance either.

Five terms worth asking for

Notice of material change to the underlying model. Vendors resist the word material, and fairly, because it is vague. Offer a test instead of an adjective: any change of model family or version, plus anything they announce publicly as a behavior change, plus anything they themselves detect as moving output distribution.

Deprecation notice with a floor. How long you get before a version you depend on is withdrawn. Ask for a stated number of months. Ask separately for the right to remain on a prior version during a validation window, which is worth a great deal in regulated work and very little elsewhere, so do not spend negotiating capital on it if you do not need it.

A benchmark written into the agreement. Almost nobody does this and it is the most useful of the five. Agree a small set of your own held-out cases and an acceptance threshold at signature. Re-run it quarterly. If the result falls below the threshold, you have a defined remedy, even if the only remedy you can win is a termination right.

Without it, the sentence available to you in month eight is that it seems worse than it used to be, which is an opinion, and you will be having an argument rather than exercising a right.

Your data out of training, in terms that survive a product change. Most vendors will give you this readily. What varies is whether it covers the derived artifacts from the previous lesson, and whether it binds their providers as well as them.

What happens if their provider relationship ends. Many vendors in this category are built on capability they license. Ask what happens if that arrangement changes, whether they can serve you on an alternative, and how long that would take. The answer tells you how much of the product is actually theirs, which is useful well beyond the contract.

What you will actually get

Not all five. Possibly two. So rank them before you walk in, because the order in which you concede is decided in the room otherwise, and in the room the unfamiliar clause always goes first.

For most buyers the benchmark and the deprecation notice are worth more than the price concession you would trade to keep them. Procurement will not see it that way, because a discount appears in the savings number and a benchmark clause appears nowhere. That is a reporting artifact rather than a judgment, and it is worth naming out loud before the negotiation rather than after.

One tactical note. Ask for these early, in the first commercial conversation, framed as how we work rather than as demands. A clause introduced in week two is a requirement. The same clause introduced in week nine, after the shortlist is public and your sponsor has told the board, is a problem you are creating for a deal everyone now expects to close.

The list you already have

If you have been keeping the running list from your reference calls, the answers to what would you put in the contract if you were signing again, this is where it earns its keep.

Those answers tend to be narrow and specific in a way that generic templates are not. A named support contact. A cap on the annual uplift. The right to add users mid-term at the original rate. Notice on a change to how consumption is counted. Every one of them came from somebody who learned it at their own expense, and there is no cheaper source of contract language anywhere in this process.

One thing to do differently

Put a benchmark in the contract. Twenty of your own cases, an agreed threshold, re-run quarterly, with a stated consequence if it fails.

It takes an afternoon to assemble and it converts the most likely failure in this category, quiet degradation that nobody can prove, from a disagreement into a clause.

In Practice: The Other Side of the Table | Lesson 11: Diligence That Is Not a Questionnaire

You have a security questionnaire. It runs to several hundred rows, it was written for hosted software, and the vendor will complete it in two days using answers they have given ninety times before.

What comes back tells you the vendor can complete a questionnaire. That is a real signal about organizational maturity and it is not the same thing as having done diligence.

Two weeks to answer a simple question

Composite from a few evaluations in devolved organizations: a research university group, several faculties, federated IT, a purchase covering research administration and grant documentation.

The questionnaire came back complete. Certifications attached, everything in order, no red flags. Procurement signed it off in a week, which was fast and felt like a win.

About nine months later a faculty raised a query about where a particular category of data had been processed during the previous quarter. Nothing had gone wrong. Nobody had been breached. But a subprocessor in the chain had changed, the notice had gone to a shared procurement mailbox that nobody monitored, and it took roughly two weeks to assemble an answer to a question that should have taken an afternoon.

The questionnaire had asked whether the vendor used subprocessors. It had not asked how the university would find out when the list changed, and that is the question that mattered.

Why the form misses

Four structural reasons, none of which involve anyone cutting corners.

It asks about controls in general rather than about your deployment in particular. It is answered by a compliance function rather than by the people who operate the system. It captures a point in time, and the product you are buying changes monthly. And it was written for a category where the software you license is the software you run, which is not the arrangement here.

That last one matters most. Most products in this category sit on capability the vendor does not own, served from infrastructure they do not run, and the questionnaire has no row for that.

Five questions instead

Run these as a conversation, forty-five minutes, with the vendor’s engineering lead in the room rather than their compliance team. Insist on that. The whole value is in the follow-up questions, and a compliance function cannot answer follow-ups.

One. Where does our data go, every hop, and how will we be told when that list changes?

Not whether they use subprocessors. The list, the notification mechanism, the notice period, and which address it goes to. The mechanism is the part everyone forgets and the part that failed at the university.

Two. What of ours is retained, for how long, and what is derived from it that survives deletion?

Deleting source data does not necessarily remove what was built from it. Indexes, embeddings, caches, logs, evaluation sets, corrections your users made. This is the question with the widest range of answers in the industry right now, which is exactly why it is worth asking.

Three. Who at your company can see our data, in what circumstances, and can we see that access?

Support debugging is the usual route and it is entirely legitimate. You want to know the path exists, what triggers it, whether it requires customer approval, and whether the log is visible to you or only to them.

Four. What changed in the last twelve months that you were not obliged to tell customers about?

This surfaces the entire class of change that sits outside contractual notice provisions. It is also an excellent question for a reference call, where you will sometimes get a more complete answer.

Five. Show me your last incident and the write-up.

Not whether they have had incidents. Every operation running at scale has. A vendor who produces a post-incident review, even heavily redacted, is showing you how they operate more convincingly than any certificate. A vendor who says they have not had one is either very new or not counting the same things you would.

Keep the form

None of this is an argument for skipping the questionnaire. Send it. Your own audit function needs it, a vendor who cannot complete one is telling you something real about their maturity, and comparing completed forms across three vendors does occasionally surface a genuine difference.

The mistake is treating a completed form as a finished investigation. The form is the floor. The forty-five minute conversation is the diligence, and it costs less than the week your team will spend reconciling three completed spreadsheets.

One thing to do differently

Ask question two in writing, and keep the written answer.

What is derived from our data, and what survives deletion. It is the question where answers vary most between vendors, it is the one your data protection colleagues will come back to in year two, and a written answer given during evaluation is worth considerably more than a verbal reassurance you half remember.