Seven years ago, employees of Maguire Agency in Roseville took down their corporate art. In its place, they lined the walls of the insurance company with engaging photographs of employees' children, grandchildren, nieces, nephews and one cute dog.

It's a family-run business with family-level loyalty, which is why on Tuesday so many Maguire associates apologized to me for crying behind closed doors.

"To just have it flipped around like that," said Matt Clysdale, Maguire's soft-spoken president and the father of five children ages 18 to 8. "People have a hard time walking by Conor's photo."

Conor Smith, the son of Maguire benefits agent Tim Smith, died Aug. 26 from leukemia. He was 15. The agency has organized a fundraiser for Thursday to help defray medical expenses for Tim and his wife, Hope, of Eagan. But the benefits are broader.

"This evening will help all of us," Clysdale said of his emotionally spent staff. "We could all use a night out."

Few of us who work in companies large or small escape the inevitable heartache that befalls co-workers. Equally few of us can say confidently that we know how to navigate this road with people we interact with, manage or report to daily.

While schools are quick to bring in counselors for children when a loss occurs, employers and employees are supposed to know what to do. But grief in the workplace is plenty complex.

"Many people feel torn between wanting 'professional boundaries' and feeling close to and intimate with people we spend a lot of time with," said Gayle Sherman Crandell, a therapist and co-founder of St. Paul's Crocus Hill Counseling Center.

"We've all seen countless pictures of our co-workers' kids [dogs, cats, birds, horses, grandkids]," she said in an e-mail. "We've attended weddings, given money to walk-a-thons, bought Entertainment [coupon] books and wrapping paper.

"So, when a co-worker is faced with tragedy, we might feel the pain so deeply, so personally, and yet we can become awkward. Is it too much for me to organize meals? Should that come from our boss, or a close friend?"

During Conor's 4 1/2-year battle, Clysdale and his 45-person staff decided to jump in. They organized a walk and a blood drive. Katie Norblom-McGrorty, who also lives in Eagan, held lemonade stands with her two sons. Others sent gift cards to the family and upbeat notes on the family's Caring Bridge website.

More difficult, though, was knowing what to say to Smith every day. Mike Tate decided that he'd want "someone to ask me open-ended questions and let me go. So that's what I did. 'How's Conor today?' 'How ya doin'?' It deepened our connection."

Stacie Schwartzbauer teared up thinking about Smith walking into his office most days carrying a little brown-bag lunch. She finally invited him out to eat. He told her he was grateful, but that he was spending so much time in hospitals that a bag lunch in the office wasn't so bad. But he'd love to take a walk.

"To have your co-workers supporting you," said Smith, who joined the company about five years ago, "it's truly like another family. It was great for me to know that, if I couldn't make it in, Matt never made me feel like we have to do something. So many times, I was so thankful."

On the day everyone desperately hoped wouldn't come, Clysdale closed the office so that every employee could attend the funeral.

"No one had to wonder who would cover the phones, or would it be a day off or how does this work?" Clysdale said. Soon after, Clysdale e-mailed Smith to tell him, "whatever policies we have in place don't apply. 'Whatever you need' was my mind-set."

Smith returned to work on a Friday, "by design." Some co-workers stopped by immediately to give him a hug. Others waited until the next week. Someone brought in Dilly bars.

Co-worker Brian Fergason recently dropped by Smith's office to talk sports. "I didn't even bring it up," Fergason said. That, too, was by design. Still, he and his co-workers carry a heavy heart.

"We build these lives at work, don't we?" Clysdale said. "All these people at different points in life, all of us parent types bouncing ideas off each other, sharing experiences and learning from each other. Nothing prepares any of us for this."

Clysdale hopes he never has to prepare for this again. But if he does, he might bring in professional help. "Counselors? We have clients who do that, and it didn't even strike me to call upon them," he said. "All of us would probably have signed up." • 612-673-7350