Many years ago, when I was watching a lot of television, there was a very funny commercial that was popular. It was a Miller Lite commercial, where a guy and his girlfriend were sitting in a bar. He had an arm around her and his other hand was wrapped around his beer.

Me in college

She asks him if she and his dog were about to go over a cliff, who would he save; he says her. She asks the same about his mother and he gives the same answer. She then asks about his beer; he pauses, then asks how high the cliff is. Thinking about it still makes me laugh; I have a weird sense of humor sometimes. 🙂

That certainly wasn't the answer she was expecting, but the commercial points out two things that happen in real life that people don't prepare themselves for. One is asking questions where there's only one correct answer, mainly because a different answer, which might be truthful, might cause a lot of disruption in someone's life. Two is the possibility that things aren't going as well as you thought, and now you have to do something about it.

On the first, I've always been specific in my personal life in telling people to never ask me a question where there might only be one correct answer because I was never going to answer it. I've stuck to that my entire life, never falling into the trap, and it's helped me avoid trouble here and there along the way.

On the second, I can only think of once ever, when I was in management, when I expected an answer that I didn't get, and wasn't sure what to do with the answer. That's not a bad record, I'd dare to say. I'd like to think it was because I had trained people well and thus never had any issues to worry about, but that wasn't the case.

I'd have to say that it's my propensity to think of both the good and bad things that could happen as a result of things I'd put into practice. If the bad thing happened, I'd have already reasoned out why it might happen and thus would have an idea of how to fix or alter it. I think most of us want everything to go perfectly, but also most of us don't look at the problems that could occur and plan on how to correct them if things go that route.

I tend to believe most people in leadership positions hate having to think of what could go wrong with an issue, which means they're totally unprepared to fix things if they fail. I always hope for the best but prepare for the worst. It doesn't mean I'm always absolutely correct on either one, just that I've realized that even the best laid plans can go off kilter.

I also think most managers have a sense of when things aren't going right, and therefore won't ask the question because they don't want to have to deal with the problem. That usually makes problems worse, and harder to correct later on. History repeats itself so often that you'd think most leaders would learn from these types of mistakes, but they don't. I guess if they did I'd have nothing to write about or consult on.

Never be afraid to think about potential problems, and always be prepared for an answer you're not hoping to hear. When it comes to business and leadership, you can't afford to "not" ask those questions you need to know the answers for.

When it comes to your personal life... sometimes it's better to leave it alone.