Skip to main content

DEAR GURU: Every month or so, I take my staff out for drinks. It's a way for them to let their hair down, and for me to make sure they know how much I appreciate their help. At the last outing, however, things got a little out of hand, and I may have drunk too much. Now a few of my staff treat me like I'm their best buddy, not the boss. How do I reassert my authority?

YOUR ANSWER: Socializing with employees is almost always a good idea. It helps everyone get along better, and diminishes the likelihood that your underlings are saying nasty things about you behind your back.

"It's a good way to level the playing field," says Chris Cook, president of Trevor//Peter Communications in Toronto. When Mr. Cook takes his staff out for drinks, hierarchies dissolve pretty quickly, and camaraderie goes up as the pints go down.

But when your staff starts thinking that the office is a frat house and that you're Bluto, well, you've got a problem. Just like the bartender who turns off the lights after last call when everyone is having fun, you need to shut the party down.

"Regardless of what you do outside the work environment, you're the boss inside it. And that entitles you to lay boundaries for how you should be treated, and you need to put those forward," Mr. Cook says.

In other words, lay down the law. Make it clear to your staff that, whatever happens outside of work, you're the boss and everyone has to behave professionally at the office.

DEAR GURU: One of my employees has asked if she can telecommute two days a week. I feel pressure to say yes, since she has always made it clear that she left a large company to improve her work-life balance. But I'm worried that working from home just means taking the day off, and that, if I let her telecommute, I'll have to let everyone work from home. What should I do?

YOUR ANSWER: First, know that you're not alone. Every manager who is uneasy about letting people work from home shares your concerns. Managers fear that people will just kick their feet up or go golfing, rather than get their work done, and that no one will be in the office if they're given an option.

This kind of thinking has haunted telework since it first became popular in the late 1990s. "You see the same kinds of barriers today as you did 20 years ago," says Bob Fortier, president of the Canadian Telework Association, an Ottawa-based group that promotes the benefits of telework.

That's a sad comment, considering it's 2010. But fear not. All the evidence suggests that employees who telecommute are actually more productive than those who are chained to a cubicle, Mr. Fortier says.

Besides, if you deny her request, she could head for the door. "That employee is going to bail if she doesn't get what she wants, because there are too many other businesses that do offer this type of flexibility."

As for the rest of your employees, explain to them that this is a new concept for you, and that you're going to start small with this "test case" before you make any decisions about expanding it. If the program is successful and you put a telework policy in place, you'll have a great recruitment tool to help you attract more talent away from large firms.

Of course, you need to feel confident that work is getting done, regardless of where it's being done, so start small. And remember, you can always call or e-mail people to check in on them.

Just don't do it too much. No one will be happy knowing the boss doesn't trust them.

This feature originally appeared in the November issue of Your Business magazine. Send Guru questions to