On Training
I have managed Gary Vaynerchuk’s schedule for the last several years, and I am in the process of turning over the reigns (don’t fret, I’m not going anywhere–just doing other things). As I prepare Phil Toronto (star of stage and screen) for his new role, I’ve been thinking about training in general and what makes this particular instance of it different.
I used to train new customer service reps in the order department at Wine Library. In that case, the job primarily consisted of procedures. Various people served the same role, and essentially needed to be interchangeable. If John Q. Customer called and spoke to Customer Service Rep A on Monday, then called again and got Customer Service Rep B on Tuesday, B needs to be able to pick right up where A left off and understand the status of an order, what the customer wanted, and so forth. The job required little in the way of specific product knowledge (trained wine consultants handle that part of the business), and had everything to do with understanding how the various back-end systems interfaced with each other, what company policy was in each situation, and standard procedures that everyone had to follow in the same way.
Training Phil for the assistant role is a very different kind of training. I have procedures that I use, but they are my own. There are certain things we’ve worked out over the years that will remain the same (for instance, how Gary expects things to appear in his calendar), but other than that, it’s the results that matter: making sure Gary is in the right place at the right time, making sure he takes the meetings and calls he wants at appropriate times, and etc. Some of that takes specialized knowledge, which I am teaching as best I can as things come up. Unlike for the Wine Library job training though, most of the procedural stuff is personal, just the way I keep myself organized. I am sure other people use different systems, and my system might not necessarily be the right one for Phil.
I basically showed him how I do it, but I don’t want him to treat that as gospel. He has to make it his own. At this point he’s spent a few weeks being cc’ed and bcc’ed on correspondence, with me explaining why I made this or that choice or who so-and-so is, but at a certain point he just has to get in the trenches and lean on me when he has questions. And that point has come! I’m creating a glossary document of various people in Gary’s world for his reference, and he’s off to the races. Now he’ll cc me and I can lurk and make suggestions and improvements, and Gary will provide feedback as well.
Wish him luck!











