06/13/2017 12:00 EDT | Updated 06/13/2017 12:00 EDT

There's A Good Chance You're A Horrible Boss

Mad boss yelling at employee on megaphone
grinvalds via Getty Images
Mad boss yelling at employee on megaphone

Do you work to live or live to work? And how about your employees? While some (though not enough) of us are lucky enough to be fulfilled by our work, there are very few of us who would choose a laptop and an office over a white sand beach and unlimited Piña coladas.

But for most of us, it's a necessary evil. While schlepping into an office will never be more enjoyable than cocktails on a beach, there are ways to make life a little better for your employees--and for yourself.

Since I've been both an employee and an employer, I know rules are needed to help a company run smoothly. Yet, many (too many) are for (as corporations love to say) "optics." It's always amazed me how little wiggle room there is in big companies. Employees typically work more hours than they're supposed to, and while not all employers have the ability to reward their hard work monetarily, they can certainly thank them in other ways.

Here's what I've learned (most of it from bad bosses) and committed to implementing in my businesses:


There is definitely a place for hierarchy (somebody has to make the tough decisions) but too much leads to too much beaucracy (and politics). Somebody needs to be in charge, but diplomacy is critical. Your employees need to feel heard. They need to know that their opinions matter to you and that they matter to you. This becomes more difficult the bigger your company gets, but try to maintain some of the practices you established when you were just starting out.

For instance, I used to reserve a few hours in my schedule each week for "Tea with JT."(I'm not a coffee person). It meant that any employee (from intern to director) could book time with me to have a tea and a talk. It allowed me to stay in touch with what was happening throughout the company, and gave my employees a forum to share their thoughts with someone who could really effect change, or just to get to know me better as a person, not just a boss.


I'm not saying that everyone can do whatever they want, whenever they want, but too much rigidity makes employees feel imprisoned. Where situations allow, there should be some flexibility in work hours and work environments. (Obviously not if you have to open a store, but if someone wants to start work at 8:30am instead of 9am and leave a bit earlier, what's the big deal?)

It always shocks me -- especially in the digital world, where pretty much everything can be done remotely -- how many corporations are rigid when it comes to work hours and environments. As long as they're in the office when they need to be (I'm talking big meetings, presentations, and department-wide events), what's the big deal if they work from home a day or two each week? Or come in early and leave early? Or for that matter, come in late and work late? If you can do something small that doesn't affect your bottom line or your efficiency, and it'll make an employee's life a little easier or more enjoyable, why say no?

I can already see some CEOs rolling their eyes (yes, even from here) thinking, "But if they're not in the office, who knows what they're doing?" Which leads me to my next point.


A mentor once told me, "once the trust is gone, it's over." It's like the boyfriend you want to break up with and suddenly everything they do is wrong. If you can't trust your employees and vice versa, you will never relax (and neither will they).

Of course the trust needs to be earned, but you need to give your employees the opportunity to earn it. If you don't trust the people who work for you, then they shouldn't be working for you. And that goes both ways. You need to trust them and they need to trust you. It's the only way to build a solid foundation.

With the rise of personal devices and social media, set work hours are rare. The days of the 40-hour work week are slowly fading away, for better or for worse. Don't get bogged down with start times and end times -- 'cause really, they don't exist.

When it comes to retaining your top talent, give them space. Trust them to get the work done and to do it well. Whether they get it done in a boardroom, a bar or on a beach should be up to them.

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