How will I know when is the right time to ask?

A very interesting point in Creative ambiguity, Scottish independence, and sudden death by Tyler Cowen.

In general we aspire towards clarity and transparency and I strongly believe that those ought to be the default position in almost all situations. But if look at it by areas of life, there are clearly shades of transparency and clarity.

Businesses tend to be the most vested in achieving greater clarity and transparency because they are under the greatest competitive pressure and need to constantly adjust and adapt to new risks and circumstances. Independent of that, in most OECD countries, and particularly in the US, such transparency is also encoded into law and regulations (for example Sarbane-Oxley). Constituent parts of a business, particular individuals or divisions, may be more or less enamored of transparency (depending on the consequences and just how much they have to hide), but overall there is a strong predisposition towards transparency.

In government administration there is a marked aversion to clarity and transparency. Too many vested interests, rent seeking, regulatory capture, backroom dealings, etc. Politicians are even less enamored for obvious reasons.

Marriages and personal relationships seem to have a schizophrenic relationship with clarity and transparency. In many ways there is much greater transparency but in some ways much less. Somebody once observed that a sustaining marriage is a wilful act of imagination.

Cowen is talking about what he refers to as "creative ambiguity". What the British used to refer to as "muddling through". His point is that there are significant benefits to clarity and transparency but that there are also costs and that we ought to be mindful of the benefits of non-clarity and non-transparency. He gives lots of examples.

Canada, Belgium, and indeed the entire European Union seem to be organized on this basis. It’s not quite that everyone thinks they are getting their way, but rather explicit concessions are not demanded for each loss of control embodied in the broader system. Certain rights are held in reserve, with the expectation that they probably will not be exercised, but they can nonetheless influence the final bargaining equilibrium.

Most international treaties rely on some degree of creative ambiguity, as do most central banks, with their semi-promises of bailouts but “not too much not too certain you know” as the default. You might like the mandated outcome (or not), but I doubt if it would improve political discourse in the United States to have an explicit thumbs up vs. thumbs down referendum on abortion.

Many partnerships and marriages rely on creative ambiguity too. Should the Beatles have forced Lennon and McCartney to specify who had the final say over each cut? That probably would have led to a split in 1968 and there would be no Abbey Road. Must parties to a marriage specify the entire division of chores and responsibilities in advance?

We find the same in many academic departments. Things can be going along just fine, but once the department has to write out an explicit plan for future growth and the allocation of slots across different fields or methods, all hell breaks loose.

There is great power in asking the right question. There is even greater power in asking the right question at the right time. Asked prematurely and it either precipitates an answer we are not yet ready to assimilate or it is dismissed as irrelevant and essentially innoculates against that question any time in the near future.

All praises of democracy must be embedded in a broader understanding that a) formal questions can be destructive, and b) we cannot be allowed to pose questions without limit, at least not questions which require explicit, publicly verifiable, and commonly observed answers.
Once a question is posed very explicitly, and in a manner which requires a clear answer, it is hard to take it off the table. There is thus an option value to holding these questions in reserve, which means that the expected return from the question has to be pretty high to justify changing the agenda in a hard-to-revoke manner.

The challenge, in a complex system, is that there are powerful benefits AND significant costs to both "Creative ambiguity" and to Clarity and Transparency. It is not possible, in advance, to discuss what is the right question and when should we discuss it. By planning ahead, you are inherently letting the cat out of the bag. The question cannot be unasked. So individually all parties have to arrive at 1) What is the right question?, 2) What are the consequences of asking it?, 3) What are the consequences of not asking it?, and 4) How will I know when is the right time to ask?