MAYOR CHARLIE HALES walked into council chambers late last month ready to improve the lives of Portlanders with criminal records.

After months of discussion with advocates and business owners, Hales was raring to expand a city policy that dictates when employers can ask about applicants' criminal histories—a suggestion many agree will help ex-convicts get jobs. An ordinance was all drawn up, and Hales parried the suggestions of Commissioners Amanda Fritz and Dan Saltzman, who thought a workgroup should be convened to tweak the law.

"It's a fairly straightforward policy call," the mayor told Fritz at the March 25 hearing. He figured the minutiae could be worked out once the "bare outlines" were enshrined in city code.

Then something interesting happened. One by one, a group of business representatives started criticizing the proposed ordinance. In particular, staffers at the Portland Business Alliance (PBA) and Oregon Restaurant and Lodging Association (ORLA) thought the city had pushed back criminal inquiries too far—after an applicant had already been offered the job.

"We are growing more and more concerned, frankly, with what we see before us," said Marion Haynes, head government affairs staffer at the PBA. She went on to cite problems with the ordinance's timing, and said the verbiage was overly protective to applicants.

And now? We're getting a workgroup.

Hales closed the meeting by announcing he'd take a month or so to let interested parties hash out the "ban the box" law, so named because similar policies around the country prohibit the boxes that applicants must check if they have a criminal past.

It's a foregone conclusion that Portland will adopt some form of the law. Everyone agrees it would help applicants shed the stigma of past mistakes long enough for an employer to get an honest take on their qualifications.

But there are questions. In particular, the workgroup Hales convenes might want to look at these four things.

Can Portland actually "ban the box?"

The Portland City Attorney's Office doesn't think so. Because of Oregon's free-speech protections, the city's lawyers say Portland can't forbid employers from including the checkbox on job applications.

"If someone wants to bring us a legal opinion that says it's possible to actually require an employer to ban the box, then I'll be interested in hearing that," said Hales. "But it is our understanding, and our city attorney's understanding, that it is not legally permissible. That's why our ordinance is written differently."

Rather than an outright ban, the city's draft ordinance sort of sidesteps any mention of the nefarious "box," making it a violation of city code "if an employer accesses or inquires into a person's criminal history" prior to making a job offer.

When should employers be allowed to ask about criminal past?

This is shaping up to be the central struggle of the "ban the box" discussion.

As drafted, the law says employers in most cases can only access an applicant's background after making a job offer. Then, if it turns out there are past convictions, the employer has to assess the nature of those convictions, when they occurred, and how they will apply to the job in question before turning the applicant away.

Failure to follow the procedure could result in a $1,000 fine.

In their testimony before council, Haynes and ORLA Executive Director Steve McCoid said the city had gone too far. They want to be able to ask about an applicant's background during job interviews to better screen potential problems.

Haynes, in particular, sought to paint Portland's proposed plan as an outlier that outstripped similar laws around the country.

But that's not the case according to people who study ban the box laws. Of roughly 100 policies around the country, nearly a third allow background checks only after a job offer, according to research by the National Employment Law Project (NELP). It's true many of those policies apply only to public entities—not to private businesses as Portland is considering—but not all.

Advocates argue waiting for background checks until an offer is made is the strongest possible policy. NELP attorney Michelle Natividad Rodriguez says it clears up what can be a muddled issue: If applicants are offered a job, they know they're the most qualified candidate. If they are then denied employment after a background check, it's obvious their criminal past is to blame.

"By no means is Portland going out on a limb," Rodriguez says.

What if applicants volunteer the information in an interview?

The first draft of Portland's law gives employers permission to talk about criminal history if a person volunteers it during a job interview. That's a provision business interests are pleased with, but that advocates at NELP and Urban League of Portland would rather see eliminated.

The problem, they say, is that people with past convictions are conditioned to offer up that information.

"What they're told is 'you need to be upfront and transparent,'" says Rodriguez. "It actually sidesteps the entire law."

How are we going to enforce it?

That's unclear. Right now, the city wants the attorney's office to field and investigate complaints. Then, if it turns out there's evidence a business broke the rules, the office would bring the employer before a code hearings officer.

The problem is, the city's not incredibly well staffed for that task. City Attorney Tracy Reeve told city council her office lacks the staffing of other cities.

"We have not historically had good enforcement of investigation capacity," she said. The city attorney's office has requested $180,000 for a new "equity and civil rights enforcement" position in next year's budget that could improve matters.

Hales, meanwhile, hopes the city won't need to bring the $1,000 hammer down very often.

"Most people support the goal," he said. "I think we won't be doing a lot of enforcement."