I recently discovered that one of my live-in nannies has a serious gambling problem. Now I know why she always comes home way past curfew and is always short of money. I have never witnessed her stealing anything from us, and our children are very attached to her, but she is four years away from retirement, and I fear the day will come when she realizes she has no savings and will do something drastic.

My friends are telling me to fire her, that it’s not worth the risk. But I feel I would be penalizing her for something she hasn’t done, and I know it will be nearly impossible for her to get another job at her age. On the flip side, we have had some discipline issues with her, and she is responsible for her own retirement. I don’t owe her a living. Should I keep her on or should I let her go? Name Withheld, Singapore

My response: How did the world get to where grown adults resort to asking permission on whom they employ to take care of their children?

You’re an adult. You can figure this out for yourself. If you do, you’ll get closer to where you can handle similar situations—a valuable skill, since they’ll come up many times. You’ll make mistakes and regret some decisions. That sting of regret is how we learn, but I predict you’ll find what you gain in independence worth it.

I don’t want to lose in stressing the value of taking responsibility for figuring things like this out the equal value in involving the people affected by your actions in the process. I think of handling situations like this in a few ways, including

• One of my top principles for business relationships: No surprises
• Surprises are for birthdays and competitors. Nothing else.
• How do you decide when your decision affects other people? Involve them in the process.

Applying those lessons here, why don’t you talk to woman? My guess is you don’t have the skills to make the conversation productive. Unskilled people see things as black and white, unable to see nuance or subtlety, as in “Should I keep her on or should I let her go?” as opposed to a question I’d ask in your position, “When I talk to her about this issue that affects myself, my family, and her, what might I forget to consider or say, and how might I practice before talking to her to increase the chances of a productive outcome?”

The New York Times response:

If you were writing from the United States, I would want to know about your nanny’s immigration status and her family situation and whether you are paying the employment taxes you should be paying. Those are common issues here. I know that Singapore requires permits for foreign domestic workers and doesn’t allow them to retire there. But I still have questions. Does she reasonably expect to be employed until retirement? Have you talked to her about her gambling problem and suggested she get involved with an organization like Gamblers’ Anonymous?

These are some of the things I don’t know. Here’s what I do know: You have someone living in your house and looking after your children whom you don’t trust. While you have an established relationship with her that entails obligations, they don’t extend to solving her problems or ignoring the fact that she isn’t keeping to the terms of her employment. But aside from whatever legal requirements are set by your country, she does have morally legitimate expectations that you’ll give her reasonable notice; or that you’ll pay her for a period in lieu of that notice, so she may find somewhere else to live.

Before you go all ‘‘Minority Report’’ on this pre-pilfering employee, though, you owe her a candid conversation about your concerns. Talk to her about her current problem and make it clear that you can keep her around only if she addresses it. Given your family’s established relationship with her, this would be the decent and compassionate way to proceed.

I own a small clothing store with a business partner; we have two employees. Recently, four people came into the shop and made off with a few items from a particular brand. We’ve had other attempts at theft and credit-card fraud involving items of the same brand. In all these incidents, the individuals were black.

My business partner and I would like to speak to our employees about these incidents as neither of them were present when the theft occurred. Of course, we’re going to encourage them to be vigilant about any interactions involving this particular brand. But is it appropriate for me to mention that every individual who has stolen or attempted to steal items of this brand has been black? My intent is only to point out a pattern, but can I do so without encouraging discriminatory practices or profiling? Or does noting the race of the individuals render moot my message that anyone asking for this brand should be watched carefully?

I am Chinese, my business partner and one employee are Caucasian and the second employee is Ghanaian. I don’t think our racial makeup matters, but I thought I would mention it. Name Withheld

My response: You’ve removed any information whatsoever from these incidents except their skin color and ask if you should mention the skin color. We don’t know the type of clothing, the store location, your typical clientèle, what was stolen, how you know who stole it, or anything else.

If you only consider skin color, you’ll only see skin color. We can’t tell if other products are being stolen by people with other skin colors, how many people of various skin colors aren’t stealing things, or other relevant correlations that help determine what’s going on. You only tell us one correlation with no evidence. You say you don’t think your racial makeup matters but imply someone else’s does.

Even without considering context, which you’ve stripped your story of, or how you know who is stealing things, which you ask us to take on faith, I suggest you consider the consequences of what you say more than a newspaper columnist’s opinion on its appropriateness. That is, how you say something can be as important as what. Do you intend to imply that someone being black causes them to steal? Are you stating relevant facts without drawing unfounded conclusions? How will the people you share the pattern you see react? If they don’t agree on the pattern, will they get angry? What if they will agree on the pattern? How will it affect your store’s relationship with its customers?

We can’t answer without the context you’ve stripped the story of. Only you can.

The New York Times response:

Your question reminds us how salient racial identities are to the way we respond to strangers. If the offenders had all worn nose rings or wristbands, you might not have stored that information. And I would guess that wearing those things goes with certain brand preferences in clothing as much as race does. Still, it’s great that you don’t want to be unfair to your black customers. After all, most of them, like most of those who aren’t black, are not thieves. Treating a whole class of customers with extra vigilance means you’ll mostly be focusing on innocent people. In a society where black people already face extra burdens, it’s especially unfortunate to add to them if you can avoid it. So you’re weighing two issues: You want to avoid adding to that burden, but you also want to help your employees do their jobs.

To think about this, let’s start with the fact that shoplifting (and credit-card fraud) are pretty common. One study suggested that United States retailers lost nearly $18 billion to shoplifting in 2016. Keeping an eye on customers is, sadly, a necessity. But as you say, you could encourage your employees to do so with or without adding information about the color of the offender. So what would be gained by mentioning it?

You say that one brand of clothing has been the focus of attempts at theft by some number of black customers. But it could turn out that, given the general incidence of shoplifting, hypervigilance when it comes to one brand and one kind of customer could expose you to greater losses in others. If it’s a brand that is particularly popular among African-Americans, it could turn out that you’re discouraging regular paying customers, and losing sales, by making them feel that they’re receiving excessive scrutiny. You noticed the race of these people because noticing race is a social habit. Did they have other distinctive attributes that would be more helpful to your employees? Conversely, could you deter theft by focusing on the brand, not the customer?