Law in the Marketplace: How to be a good boss

For the Monitor
Published: 6/18/2022 4:09:28 PM
Modified: 6/18/2022 4:09:08 PM

My wife and I are having our house repainted. Our painter, Keith Dalessandro, the owner, with his brother Craig, of KDD Painting, and the nine young men who are helping him repaint our house are doing a great job. I know they’ll make the house look good. For reasons you’ll see below, I’ll refer to these young men as Keith’s team.

But in addition, his team is not only working hard and doing a great job; they’re also obviously having a great time. My wife and I hear them as they labor away on our house, joking with one another, teasing one other, and laughing a lot. How they can get so much work done, and do it so well, yet also laugh so much, is a little hard to understand.

But not only are my wife and I impressed with Keith’s team’s work. We find them touching, because they remind us so much of our two grandsons Charlie and Will, aged 21 and 18. There’s something particularly charming, and yes, even touching about teenage boys and young men in their early 20s. For one thing, they have the vitality and good looks of youth. But for another, when my wife and I think of the world they have to look forward to as they become adults, we find ourselves feeling compassion for them. For their sake and for the sake of our grandsons, we hope the world somehow starts heading in a better direction.

But I’m not only a homeowner, a husband, a father and a grandfather; I’m also a business lawyer. So I find myself wondering what is Keith’s secret: How does he get such good work from his team when they’re also obviously having so much fun? So I asked him: Keith, what’s your secret? For starters, he told me that in a job he had when he was a young man (not a painting job), his boss treated him badly. It was not a happy experience. So he vowed that if he ever had people working for him, he’d treat them as well as he knew how.

And that’s what he tries to do.

But in addition, he played lacrosse for Plymouth State in his college years and later helped coach the Bow High School hockey team. He said that if anything can teach you the value of teamwork in your job, including your job as a boss, it’s teamwork in sports.

And he has two great supervisors — Derrick and Trent.

But beyond all that, he said he just plain likes the guys on his team (who wouldn’t?). And he enjoys their company. That’s a major reason why he hired them. And he takes them to ball games and has get-togethers with them from time to time to show them how much he values them.

If you read this column with care, you’ll see it’s full of lessons about how to be a good boss. I’ll leave it to you to figure them out.

John Cunningham is a lawyer licensed to practice law in New Hampshire and Massachusetts. He is of counsel to the law firm of McLane Middleton, P.A. Contact him at 856-7172 or His website is For access to all of his Law in the Marketplace columns, visit

Law in the Marketplace is a legal advice column. It runs every week in the Sunday Business section. The author is a lawyer in Concord and not a member of the Monitor’s staff.

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