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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!

Author: Matt Sitomer

After earning a Master’s in Psychology, Matt Sitomer grew weary of the laboratory and abandoned his academic path. He began working with Gary Vaynerchuk in 2006 and boosted his wine knowledge, but also rapidly absorbed Gary’s approach to marketing and the social web. Matt loves jazz, independent rock, good wine, great beer, and baseball. Although he ran track in college, he is gradually coming to grips with the fact that he is no longer a Division I athlete.
  • Kmurph

    Good luck Phil!! It can be intimidating to take over for Matt and there will be mistakes made for sure (I speak from experience), but you'll get it! :)

  • mattsito

    hehe you did pretty well miss murphy :)

  • philtoronto

    Thanks, KMURPH! I'm looking forward to this, for sure!

  • Kmurph

    definitely! it'll be a fun one for sure!

  • Kmurph

    why thank you Mr. Sitomer. your shoes are hard to fill, but I've tried my best…

  • http://twitter.com/NeilSarkar Neil Sarkar

    Good post Matt, I'm kind of fascinated by the personal aspect of training as well.

    Specifically, how training another person exposes just how much you are leveraging your personal strengths and mitigating (or ignoring tasks that require) your personal weaknesses in doing your job.

    One thing to try to remind yourself of when training is that you're not developing a protocol for how to train anybody to do your job…you're developing a specific training program that is optimized to work from one specific individual (you) to another specific individual (Phil).

    At the end of the day the most important thing is to keep an open dialogue (obviously not an issue) and try to tailor your recommendations to his strengths and (constructively) make him aware of areas that may be trouble spots given his personal makeup.

    At the end of the day you're transitioning one custom, personal approach to another…so it's to be expected that the training process itself will be custom and personalized as well.

  • TheGreatWazu

    Phil being offered that particular job speaks volumes about how much Vaynermedia loves you. You're zeal for life is infectious and I'm really happy for you. You'll do a great job! Just be yourself. Congrats man. Oh hey….what's Matt gonna be doing I wonder….hmmmmm? Be well :)

  • TheGreatWazu

    Neil I don't know where your path will inevidibly take you in life but I know it will be a rewarding ride and a satisfactory destination.

  • http://wendyhopkins.net/ Wendy Hopkins

    Yay Phil! Congrats. Great post, Matt. Lots of good points. Basically: slow down and play nice.

    …oh and Rocky 4, FTW!!

  • http://wendyhopkins.net/ Wendy Hopkins

    I think VM needs to find a new phrase to replace “at the end of the day”. :)

  • http://htp://www.jamiesanford.com JamieSanford

    Why don't we all have life glossaries? I want to write one for myself, because it sounds like fun. If we all started making them now, they could be interesting biographical documents later.

    Good luck with new projects Matt, and good luck to Phil too!

  • http://www.DrinksAreOnMe.net Dale Cruse

    I don't know if I want to imagine what it says next to my name in the “glossary document of various people in Gary's world!”

  • mattsito

    oh, I better add that Dale Cruse entry STAT!

  • mattsito

    thanks Jamie, hope you're well :)

  • mattsito

    well put, Neil

  • http://www.DrinksAreOnMe.net Dale Cruse

    Matt's reply features notes of sarcasm on the sniffy-sniff.

  • mattsito

    Hi Sherry, thanks for the kind words. Not actually going anywhere, this will free me up to do other things for VaynerMedia and our clients. It has certainly been a fun ride holding down this position and I have learned a ton! Ready for new challenges :)

  • philtoronto

    Wow, thanks so much for all of this positivity!!

  • philtoronto

    Thank you very much, Wendy =)

  • philtoronto

    Thank you for the well-wishes, Jamie!

  • philtoronto

    Neil, this is excellent. Well said.

  • http://twitter.com/jbereklewis Jason Berek-Lewis

    Hey Phil, Congrats on the new gig. Go well.

  • philtoronto

    Thank you, Jason!

  • David Siteman Garland

    Matt – He is going to need it. :) Good luck with the training.

  • http://www.lifenotion.com Derek Jensen

    As always Phil, wish you the best! Be sure to top Matt's 'personal touch' and I could only imagine managing Gary's schedule is going to be some task. Why? Managing my schedule is somewhat tough and I no where near as busy as Gary. (don't think anyone else is)

  • mattsito

    thanks pal :)

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