Limits
When the Honest Answer Is to Stop Asking
Asking for the same document for the fifth time is not persistence; it is a signal that something other than willingness is in the way.
What nobody wrote down here, and what it cost
Judgement about when a client is about to leave
Nobody could write it and nobody tried
Three occasions, all of them noticed too late
Why the architecture is the shape it is
Attempted twice and abandoned
Both drafts described the result rather than the reasons
two things nobody wrote down · 5 occasions it cost somebody something
Two things, five occasions, and no mechanism proposed for either.
Before adding another required page, managers can explore its capabilities and check whether the underlying bottleneck is missing knowledge, overloaded authors, or unclear ownership.
Teams can compare this approach with the established material available from Adobe.
Five things one team asked for repeatedly over two years, and what asking produced
A full description of the billing reconciliation
Agreed six times, never written
Six requests, six agreements, two years
An architecture overview
Agreed four times, two drafts abandoned
Both drafts stopped where the reasons began
A glossary of internal terms
Written on the third asking
Opened once, by its author
Four lines on the deploy order
Written the afternoon it was asked for
Asked once, with a size and a name
Documentation standards for the team
Agreed five times, never written
Nobody could say what it would contain
five things nobody wrote down · 19 occasions it cost somebody something
Five things, nineteen occasions. One was written, immediately, because it was small and specific and addressed to somebody. Two were written about and never written. Two more were asked for so many times that asking had become the activity. One team's own two years.
Persistence is usually a virtue. In this subject it is frequently a way of avoiding a conclusion.
A document that has been asked for five times and not produced is telling you something, and the thing it is telling you is rarely that a sixth request will work.
What repeated asking costs
Not much time, which is why it continues.
It costs credibility: a manager who asks for the same thing six times and accepts six agreements has taught the team that agreement is the required response and completion is optional.
It costs the relationship with the person asked, who now has a standing failure attached to their name for something they never refused.
And it costs the opportunity to find out why, because each repetition is a replacement for the diagnostic conversation.
The four things it usually means
It is too big. The request is unbounded and the person has correctly estimated it at two days. Fixable by asking for four lines instead, which is the fourth row of the panel.
It requires something unsettled. Writing it means deciding something nobody has decided, as the third page of this collection described. Fixable by settling the thing, or by writing around it with the hole marked.
The person will not write. Covered earlier; fixable by removing the composing.
Nobody can say what it would contain. The fifth row — documentation standards — is this. A request nobody can specify is not a request, and it will be agreed to indefinitely.
The diagnostic question
Asked once, instead of a sixth request:
What would have to be true for this to get written? Not whether you will — what would have to change.
The answers are usually immediate and specific, because the person has been thinking about it for two years. "It would take two days and I don't have two days." "I'd have to work out why we did it, and nobody knows." "I would rather talk it through and have somebody else type."
Each of those has a different remedy, and none of them is another request.
When to stop
Three conditions, any of which is enough.
The answer to the diagnostic question is something the organisation will not change. If it needs two days and there will never be two days, the document is not going to exist and continuing to ask is theatre.
Nobody can specify the contents. The request is a wish.
It has been asked more than four times. At that point asking is the activity and something else is required.
What to do instead of asking
Three options, in descending order of cost.
Do it yourself, by the interview method: thirty minutes of their time, two hours of yours.
Reduce it until it is a thing that will happen. Four lines on the one question people actually ask, rather than the description of the whole system.
Accept that it will not exist, and record that: a note saying this is undocumented, who holds it, and what the risk is. That is a real document, it takes ten minutes, and it is more useful than a sixth agreement.
Saying it out loud
The conversation is short and is rarely had.
"I've asked for this five times and we've agreed five times. I don't think it's going to happen that way, so let's either do it differently or write down that it isn't going to exist."
Most people receive that with relief. The standing unfulfilled request has been uncomfortable for them too, for two years, and naming it ends a situation that neither side was enjoying.
What repeated asking usually means
Four diagnoses, and the fifth request distinguishes none of them while a single question distinguishes all four.
- It is too big. The request is unbounded; the person has estimated it honestly at two days.
- Something is unsettled. Writing it requires deciding a thing nobody has decided.
- They will not compose. The act itself is what is being declined, not the sharing.
- Nobody can specify it. "Documentation standards" is a wish rather than a request.
Each has a different remedy and none of the remedies is another request. The question that separates them is in the next section and takes about a minute to ask.
The boundary of this argument
Nothing here says to give up after one attempt, and the threshold above is deliberately four requests rather than two.
It is an argument against the specific failure where asking becomes the ritual that substitutes for the thing — which is the same failure as "we should document this", one level up.