You know that guy. You work with him. You hear him working the phone. Sometimes I’m that guy too. Who is that guy? He’s the guy who’ll spend 2 hours fighting a $20 fee. His time measured by how he’s paid might be much closer to $70 an hour. He might be worth over a million dollars, but he’ll fight tooth and nail to get a surcharge removed, or a fine forgiven. He might even spend hours bargaining for an extra $50 when purchasing a car. The question is, do we want to be that guy?

Yes:
There’s no question that the squeaky wheel gets the grease, and grease is good. I probably spend a few hours a year trying to fight extraneous charges. Sometimes it’s quite easy as it was when I rented a car in St. John and I was double charged my $100 deposit.  All it took was two phone calls, and I got the extra $100 credited back to my card. There are low hanging fruit that need to be plucked.  It’s always worth asking, the question is do you relentlessly pursue?

No:
Sometimes you can spend hours and have countless exchanges to no avail. The best example of this was a telephone bill I received after I canceled service about 5 years ago. I spent at least 1 hour on the phone.  Sent around 6 emails.  Sent two physical letters.  I never paid my bill, but the company never admitted it’s error.  For all I know I was sent to collections on a $9.37 charge. I would gladly trade $9.37 for the two hours of time I spent on the whole endeavour, and the potential damage to my credit score.

Maybe:
Obviously there’s no one answer on if you should spend your time fighting the Man or the Woman. Every situation is different, but from what I’ve learned it’s important to go into every situation with a preset of idea of how much time and effort you want to spend.  Like anything, it’s also important to both understand the specific dynamics and have an exit strategy.  For instance my biggest problem when dealing with the Telecom company was my inability to get a hold of anyone who had any real decision making power.  That’s also why it’s never an effective strategy to get mad.  Anger is rarely effective.  Getting mad at a poor customer service representative rarely leads to results. This is not to say that you shouldn’t clearly make your needs heard, but do so nicely. Ask for a manager nicely. Don’t make threatening demands. Representatives are trained to block, but instead of getting irate, just ask how it’s possible to get around those blockades. Also with my disputed telecom bill, I failed by not having an exit strategy. I should have paid the bill to avoid any potential credit damage. Had I wanted to continue to the fight I still could’ve done so even after paying the bill. Risk vs reward always needs to be gauged.