When Kevin Dillon started working for JPMorgan in March 2008 as a “client processing specialist,” everybody liked him just fine. Better than fine, in fact. He was praised by his superiors, he received glowing reviews and in just a few months time, he was slated to receive a bonus and a promotion. This was all, however, before he filed a report citing “highly questionable accounting and management practices” at Highland Capital Management LP and recommending that JPM cease “facilitating Highland’s improper practices.” In doing so, Dillon was forcing his bosses to make a decision re: how to deal with the findings. They could 1) follow his suggestion and cut the hedge fund loose or 2) acknowledge the findings and decide to do nothing about them. In this case, Dill’s bosses decided to go with the second option, telling him they were “aware of Highland’s improper practices [but] that nothing would be done to remedy the issue.”

As I’m sure many of you know, however, when you’ve got a situation like a Kevin Dillon situation, it does not end there. Because if there’s one thing I’ve found in my multiple decades long career on Wall Street is that a guy like Dillon is gonna be trouble. He won’t just accept your decision to look the other way, which is admittedly annoying but something you can deal with if you’ve got the skills or someone coaching you from the sidelines (me).

First off, you can’t fire a Dillon-type straight-away, because it’ll be too obvious. This is something that requires a more subtle touch. You will want to, of course, make work life unpalatable for the employee in question, so taking away his bonus, promoting incompetents over him and offering negative but purposely vague reviews is a given. That’ll go a long way in psyching out said problem employee. But if you really want to break him…if you really want to leave your mark…if you really want to, in the event this thing ends up a lawsuit, make a name for yourself, give the readers something to aspire to and have people say “that guy may be a whack-job and potentially a racist but he knew how to deal with people,” you’ll try something like this. Continue reading »