The Good Times & The Bad

In the eight years or so that I’ve been running businesses, and in the twelve years or so that I’ve been managing teams of people, I can wholeheartedly say that I’ve always been able to balance a leisurely work environment, one that’s bullshit-free, and one that’s productive as well as fun, with being a boss, a manager, and sometimes the bastard who doesn’t take any shit. I think the folks who’ve known me longest, and who’ve worked for me longest, know the kind of ship that I run. In fact, we just hired a guy here at CitySquares who worked for me at my previous company and part of the appeal was exactly that, “the type of ship I run.” As a manager, or a boss, or a CEO, sometimes you have to be the bad guy. It just comes with the territory. It’s hard being a manager, and anyone who says that being a manager is easy doesn’t really know management. As a manager, or a managers manager, or a CEO, you’re constantly being scrutinized. Everyone is watching and it can be a very tough crowd, with little forgiveness.

At CitySquares we have a hell of a good time. I’d say that about 80% of the time the mood in the office is good, music is playing, everyone is very productive, efficient, and everyone is communicating well. Everyone gets along well, they take their jobs personally, and they also hold themselves and each other accountable. These are traits in an organization that are extremely difficult, if not impossible, to simulate. It’s either there or its not, you can’t fake it. And that kind of morale, productivity, efficiency, etc, starts with management. We’re also fierce and extremely competitive. We’re relentless and we love the scent of blood. That comes with being a sales-oriented business. But we can be hubris too. That tone, and that mood, also starts with management.

For the remaining 20% of the time, the mood can range from stressful (i.e., the end month sales pressure) to downright high-anxiety and tense. Those are the times that you see how tough you are as a company, the times that you see how resilient your staff are, and who rises to the occasion, and who does not. It’s that 20% of the time that tests the will of the company and of those within it. Can it prevail? Can it stand back up, dust itself off, and get the job done?

Things can change very quickly in a startup. One day you can be flying high, rolling along and just steamrolling through goals and achievements, and laughing all the way, with a cigar in the corner of your mouth, and a bottle of champagne in hand. All that can change in an instant. In a startup, there is extremely little room for error. In fact, I prefer to take a no-room-for-error approach. Missing goals is not an option, and missing deadlines is not on the table. Mistakes can happen, they always will, and that’s OK, as long as we learn from them, and apply those lessons to the next day. When we fail to do that, to learn and then apply lessons, the mood can quickly change.

I hold this company, and its personnel, to very high standards. It’s those standards, I believe, that have gotten us to where we are today. Those are standards that everyone here understands and practices. The company can have all the fun in the world, listen to music, have a weekly happy hour, play games, go bowling, have company pools and contests, and eat, drink, be merry every day. But the moment that we stray from the plan, the moment we start to fall behind, that’s also the moment that the seatbelt sign goes on.

Often times people will ask how things are going at CitySquares. My answer, lately, has been the same: “Things are going very well. In fact, things are going so well that I’m uncomfortable.” That’s my take. I don’t want to be comfortable, and I want to be two steps ahead of where we should be. I want to see the clouds on the horizon, not caught in a hurricane, fat and drunk.

So it’s important that at a startup company that everyone keep perspective and remember, it’s a business. It’s OK to have fun, but at the end of the day, you have to take the good with the bad.