If you can’t resolve a thorny conundrum, try asking the question backward.

In the United States we have an ongoing, unresolved question: What are society’s obligations to the poor? 90 years after FDR’s New Deal we’re still arguing about this, with plenty of programs but little in the way of a national consensus.

What if we asked the question backward — instead of asking what obligations, if any, we have to the poor, let’s ask what privileges should accompany wealth?

We might imagine a continuum. On one end are certainties: Wealth should entitle those who have it to more and cooler toys. Tastier meals. Freedom from having to pick up after themselves, vacuum their floors, and scrub their plumbing fixtures.

Terry Pratchett once pointed out that “privilege” means “private law.” On the other end of the continuum from better toys, food, and household hygiene I think most of us would agree that wealth shouldn’t entitle its owners to private laws, whether in the form of legislation passed to benefit the favored few, or better judicial outcomes because that’s what you get when you can afford the best lawyers.

For that matter, instead of asking if the poor should be entitled to free healthcare, question inversion leads us to instead ask if wealth should confer better health and longer lifespans for those who, through luck or skill, have more of it.

Keep the Joint Running isn’t the place for this conversation, although I’d be delighted if you decide to have it, whether in the Comments, at your dinner table, or in a local tavern accompanied by conversational lubricants.

What does fit KJR’s charter is a very different business question that looks much the same when you invert it.

The question: How can business leaders keep their organizations from turning into stifling, choking bureaucracies.

The inversion: Must all rules apply, all the time, to everyone, regardless of their performance, contribution to the bottom line, or where they rank on the organizational chart?

For example:

> In your sales force is a rainmaker — someone who’s exceptional at designing and closing big, profitable deals. He also has a volatile disposition and huge temper, which he aims at whoever is convenient whenever he feels frustrated. The question: Should his direct financial contributions result in, shall we say, a more flexible and nuanced response from HR than another employee, with a similar temperament who contributes far less to the company’s success should get?

> Your company has a well-structured governance practice for defining, evaluating, and deciding which capital projects to undertake.

Your CFO is championing a major capital project. While it seems to make sense she hasn’t run it through the process. Instead she’s schmoozed it through the committee, whose members trust her judgment … or might want her to return the favor come budget season.

The question: Should the CFO and her executive peers be allowed to skip procedural steps that lower-level managers are required to follow?

> Your company’s recruiting function has established specific procedures for filling all open positions. The CEO recently brought in a new CIO to straighten out the company’s IT organization, and the CIO wants to bring in “his team” — three managers he’s worked with in the past. He knows they share his approach to running IT and are the right people to lead the company’s IT turnaround.

Should he be allowed to bypass Recruiting’s procedures?

For most of us the instinctive answer is yes — the rules apply to everyone.

Except for most entrepreneurs, who tend to see the uniquenesses of situations as well as their similarities.

Take the case of the CFO and her capital project. Companies institute governance frameworks and procedures for reviewing capital proposals to reduce the risk of making poor investments. The CFO applies these frameworks in her sleep. Dragging her proposal through the procedure wastes a lot of her valuable time with little additional risk reduction.

On the other hand, insisting everyone follows these rules, from the top of the organization to the bottom, helps establish an egalitarian perspective that says nobody gets special privileges. It also ensures the company’s executives don’t get sloppy, mistaking arrogance for good judgment.

But on yet another hand, if everyone in the organization had the CFO’s level of financial sophistication, there might never have been a need for the rules in the first place.

“There are reasons we have rules,” is a phrase you’ve probably heard from time to time.

And I agree. There are reasons we have rules. And if we took the time to remember those reasons we’d all be better off.