Why collecting money is hard and how to get better at it
The reason that it's so difficult to collect money from people was best summed up by one of our late-paying users when we quizzed him on why he was such a lazy git and had taken so long to pay. He said (I may or may not be para-phrasing slightly): "Matt, unlike you I am a fundamentally lazy human being and not extraordinarily good-looking; when I see a reminder that I owe someone money or they ask me to pay I won't bother until the amount of guilt I feel about not paying exceeds my general apathy towards paying".
What does this mean for you? In short you've either got to work on ramping up the guilt factor or do something to minimise their laziness. I'm not going to lie, guilt is by far the easiest to effect a change. This might mean telling them you're struggling to make rent this month or that they're the last person to pay. A twist on the "I'm not angry, I'm just disappointed" line your parents have used on your for all these years can be particularly effective with particularly lazy mates.
The laziness bit is where we try to come in but you can apply the same principles we do to help yourself. The way we think about it is that the corollary of people being too lazy to pay is that the process is currently too difficult, it takes too much work for them to do it. So one thing you can do is make it as easy as possible to pay. This might mean making sure they get your reminder at a point when they can actually pay e.g., email is generally better than text because often when you get a text you're on the go and can't do anything about it right then, and by the time you can, you've forgotten what it was you were supposed to be doing. Another way is to minimise the deviation from their usual behaviours e.g., if they rarely use online banking there's no point demanding your money that way, let them pay by cash or cheque. This coupled with timing can be extremely effective. For instance if your naked wrestling group meet up at 6pm every Thursday and you know most people come after work which finished at 5pm you could contact them at 4.50pm reminding them to pick up the money on the way over.
One final way is to hit them where it hurts other than their wallet. If you normally use the money you collect for your football team to wash the kit you might see a level of improvement in the speed with which people pay after a couple of weeks of wearing the same kit (randomly assigning shirt numbers each week can help up the ante that little bit more). Admittedly, depending on just how lazy your team is, you might not, but as an incidental benefit you may also find this leads to increasingly lax marking from opposition teams at set-pieces. If only Arsene Wenger wasn't so prudent perhaps Arsenal might start scoring more headers! That or explaining to Nicklas Bendtner that whilst there is a certain irony in him hanging up balls at the back-post for Andrei Arshavin, irony tends to be an oft unrewarded quality when it comes to awarding points in the Premier League. I digress...
To return to the topic in hand, there's lots can you do but one final thing that might be worth considering is how much time you're spending chasing people for money and how awkward you find it. If it's too much obviously you could give up and pass the responsibility on to someone else. However, lets not be hasty and forget that this would also mean surrendering control of the drinks kitty at the end of season do; something we at GrouPAY refer to as the obverse spiderman scenario - "With great responsibility comes great power". So, I hear you say, what should I do? Well, I'm not one for telling people what to do, but imagine if there was a website which was free to use and really easy to set-up which would do all this for you...