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What’s the secret to creating a good relationship between a CEO and a board of directors?

“The secret is there are no secrets,” says Michael Naufal, managing partner of Boyden, an executive search firm. His job involves matching CEOs with boards and then monitoring the results. “It’s like being a therapist,” he jokes. He fosters traits familiar to anyone in a successful relationship: respect, communication, appreciation and so on. What stands in the way of achieving those goals isn’t malice—it’s ambiguity. “A CEO can easily falter just because expectations aren’t clear,” says Naufal. Trust takes time and effort to build, yet it can be shattered in an instant. “A CEO who tries to hoard information or keep secrets will ultimately fail,” he warns. Endeavour to use inevitable moments of disagreement to find a consensus and strengthen the relationship for the next conflict, just like you would when squabbling with a spouse. Naufal compares the CEO-board relationship to a pair of chopsticks: One is much more effective with the support of the other.

One of my employees was working in England for three months and wants to expense dry cleaning done at the hotel. It seems very pricey. Should I approve it?

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Great news, cheapskates: “The employer should absolutely not pay the bill,” says Lisa Orr, a business etiquette expert. A fat reimbursement cheque could prove even more costly once the rest of the office finds out. “You’ll be in a ‘so-and-so got theirs covered, so why not me?’ situation,” cautions Orr. Saying no is awkward, but not for you. “It’s inappropriate for the employee to ask,” she says. Unfortunately, dealing with it is your problem just the same. Orr suggests a polite email to begin: “Let’s touch base by phone.” When you do talk, ask for the circumstances and start the dialogue you should have had with them months ago. If the situation sounds reasonable and you can afford it, then consider helping out just a bit. “Tactically, you might offer to cover a few extraordinary expenses under special circumstances—the waitress spilled wine on them, for example.” Then clearly set out the expectations for next time with something like, “In the future, this is not something we cover.”

My assistant keeps asking for advice about his family life. It makes me uncomfortable. Can I tell him to stop?

You can and should, but before you do, put yourself in his shoes. His job by nature is personal—grabbing dry cleaning, arranging travel, fielding calls from your kids and spouse—so it’s only human to forget the intimacy flows but one way. He probably doesn’t realize he’s crossing boundaries, but you can embrace this pseudo-friendship and address the issue in a way that’s not so bad. “You need to have a frank, transparent conversation that’s also honest and empathic,” says Wendy Giuffre, an HR consultant. Admittedly, this isn’t easy, so you might as well say so. “Often an awkward conversation is best started with, ‘This will be awkward,’” she suggests. Then counteract it with kindness: “I empathize with your situation and would like to help, but because of our working relationship, I’m not comfortable giving you advice.” You could make a joke if it feels right. But most important is offering a referral to HR or another employee assistance program that can provide help if your assistant actually needs it.

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