Should I expect my waitress to rise to the occasion?

During the holiday season, every year for the past 14 years, A.L, a reader from the Northeast, accompanies her daughter and her two grandsons into the city for an outing. The outing regularly includes a theater production or movie, but always includes a meal at a downtown restaurant. Given her grandson's appetite, the tastier the food and the bigger the portions, the better.

For the past several years, the restaurant of choice for these outings has been an Italian restaurant that serves traditional Italian dishes and freshly baked bread that the boys consume with vigor. Last year, as A.L. and her family were finishing their meal, the waitress came over to the table with a small loaf of bread that she had wrapped up for each grandson to take home with him. "I have a teenage brother so I know how teenage boys are always hungry," the waitress told A.L. and her daughter as she handed them the bread. They hadn't ordered the bread and there was no charge for it. The boys devoured the bread on their walk through the city after their meal.

This year, A.L. and her family are planning to go to the same restaurant as part of their outing. She loved that the waitress offered the bread at the end of the meal the previous year, something that none of their previous waitresses had done. She'd love it if the meal ended with a nice freshly baked takeaway again this year.

"Would it be wrong for me to tell our waitress this year about our experience last year and see if she might do the same?" asks A.L. "But I don't want to get anyone in trouble by asking."

A.L.'s concern is that the prior year's waitress might have broken one of the restaurant's rules by giving them bread as they were leaving. She doesn't want to call attention to the prior year's offering if it would risk getting someone in trouble. Still, the grandsons do love the bread.

The restaurant doesn't charge customers when they ask for more bread with their meals, so it's unlikely that the prior year's waitress did anything wrong or that this year's waitress would say no. There would be nothing wrong with A.L. telling this year's waitress about their experience last year and asking if it might be repeated. The waitress might respond that she's not permitted to give them extra bread and then A.L. would have to decide if she wants to purchase it for the boys to eat on their walk.

The right thing would be for A.L. to decide how important it is to her to leave the restaurant with the bread snack for her grandsons. If she'd like to explore the possibility of it happening again, she shouldn't hesitate to ask the waitress for help in making it happen.

If A.L. believes that the simple gesture would make the traditional outing even a bit more special, then it's worth putting her concern aside and trusting her waitress to respond graciously and professionally to her request. A.L. shouldn't tip her waitress any less if she can't comply with the bread-to-go request, but if the waitress does come through, A.L. might tip her even better. 

Jeffrey L. Seglin, author of The Simple Art of Business Etiquette: How to Rise to the Top by Playing Nice, is a lecturer in public policy and director of the communications program at Harvard's Kennedy School. He is also the administrator of www.jeffreyseglin.com, a blog focused on ethical issues. 

Do you have ethical questions that you need answered? Send them to rightthing@comcast.net. 

Follow him on Twitter: @jseglin 

(c) 2015 JEFFREY L. SEGLIN. DISTRIBUTED BY TRIBUNE CONTENT AGENCY, LLC.

If my handyman did time, do I give him another chance?

For years, H.F. has helped out his childhood friend's stepson by hiring him for odd jobs around his house, mostly yard work. Even as he grew into adulthood, the friend's stepson had trouble holding down a full-time job, instead relying on his stepfather for support him. H.F. regularly employed him for the occasional odd job.

After H.F.'s friend died, he kept hiring his friend's stepson for the occasional job as a way of helping him stay on his feet. When the friend's stepson worked, he worked hard and did a good job.

But H.F. says that the stepson began to start asking to be paid before each job was complete. H.F. never agreed to do this, but he says he suspected something was going on in the stepson's life that made him a bit more desperate for money.

One weekend, H.F. got a call from the stepson's mother letting him know that H.F. had been arrested for trying to break into a store after it had closed and steal the cash register. Before he could leave the store, the stepson was caught by the police and arrested for burglary. He was convicted of a misdemeanor and sentenced to several months in jail.

Now that the stepson has served his time and is out of jail, he's been living with his mother and has been in touch with H.F. to see if he might have a few odd jobs he could do for him.

H.F. says that he always hired the stepson for the occasional job around his house out of loyalty to his old friend, and because he would have hired someone else anyway to do the same work. But now he is wondering whether he should continue to hire the stepson given his recent arrest and conviction for attempted burglary. All of the jobs H.F. hires him to do are around his house, and, if he's being totally honest, he wonders whether it's wise to risk having the stepson steal anything from him.

"In all the years I hired him to do work, he never stole anything from me that I know of," H.F. says. He says he has no reason to believe that that will change now that the stepson is out of jail.

H.F. says he's inclined to hire the stepson for the occasional job he needs done around his house. But he wants to know if it's wrong to trust the stepson given his criminal record.

While it was good of H.F. to give the work to his friend's stepson when he needed a job done, he was under no obligation to do so when his friend was still alive and before the stepson went to jail. He's also under no obligation to do so now.

But he's also not wrong to give the stepson the work and a chance to make some money now that he's served his time. The right thing is to decide if he's comfortable with the stepson doing work around the house, set up clear parameters about how much and when he will get paid, and to monitor the work the stepson does. In other words, to do business with the stepson exactly as he had in the past.

If H.F. needs the work done and feels comfortable having his old friend's stepson do the job, he should do it. 

Jeffrey L. Seglin, author of The Simple Art of Business Etiquette: How to Rise to the Top by Playing Nice, is a lecturer in public policy and director of the communications program at Harvard's Kennedy School. He is also the administrator of www.jeffreyseglin.com, a blog focused on ethical issues. 

Do you have ethical questions that you need answered? Send them to rightthing@comcast.net. 

Follow him on Twitter: @jseglin 

(c) 2015 JEFFREY L. SEGLIN. DISTRIBUTED BY TRIBUNE CONTENT AGENCY, LLC.