There are countless professionals holding Microsoft Exchange careers in New York City and the rest of the world who defy the introverted, pocket-protector stereotype. Jason Sherry, 7-time Microsoft Most Valuable Professional (MVP) in Exchange, is a leader of the pack.
A passionate professional who is as enthusiastic about music, dirt biking, skiing and travel as he is about technical excellence, Sherry was kind enough to sit down with Infusive to explain his route to specialization and why it’s been fulfilling for him as a highly social IT expert.
Infusive Solutions (Infusive): You describe yourself as a self-proclaimed “uber computer and Microsoft geek” who simultaneously has some badass outdoor hobbies. Can you comment on this duality?
Jason Sherry (Jason): I’m a bit of an anomaly among my geek friends. I haven’t found anybody who is as passionate about doing things away from the computer.
Growing up, I had severe asthma so I couldn’t do a lot of sports but I did have a dirt bike which I rode a lot where I grew up in the Virginia mountains.
So activities like dirt biking and downhill skiing helped me work around the things I couldn’t do with the asthma and have become big passions of mine outside technology. Those hobbies were actually primary reasons for relocating to Colorado where I live currently.
When I’m home, I’m definitely in front of the computer almost from almost waking until sleep but I really like going into the mountains to get disconnected. It’s kind of an odd contrast but it's kept the balance for me.
Infusive: What drove your decision to specialize in Exchange?
Jason: The main hook for me is collaboration, getting people communicating and working together better.
I got into it working for a Digital Equipment Corporation (DEC) as my first job out of college in Atlanta. After DEC, I took a contract helping to enable remote working during the 1996 Olympics in Atlanta because everyone was worried about the bad traffic from the events.
My next project was migrating 330 Microsoft Mail Postoffices all around the Southeast to Exchange (5.0 back then), which was a technology few people had worked with. But at DEC, I had deployed Exchange 4.0 for our internal communication to replace our green screen-based VMS email system. And being that we’re all Windows guys at this point, or becoming Windows guys, we got excited about Exchange since it had public folders for easy sharing of notes and the email that was much more functional and sexier!
It felt good to help our team and others to work better and more efficiently because that’s what ultimately helps a company run smoother.
And being a social creature who likes to help people communicate, it just fit.
Infusive: What led you to do the ‘above and beyond’ work necessary to get recognized as a Microsoft Most Valuable Professional (MVP)?
Jason: Really I started getting jealous of the people I associated with who were MVPs getting the inside scoop.
So that motivated me to start engaging with the community and going beyond doing only what it takes to get paid on Friday; answering questions on the Technet forums, speaking engagements, running user groups, mainly my blog.
But, undertaking those tasks requires having the time to do research, write articles, respond on the forums, to e-mails, to blog comments, etc. and most people don’t have the time or flexibility to do so without burning out. That’s the way I was in the late 90’s and early 2000’s … I was passionate but because my day job kept me so busy and the company didn’t put any priority on giving back to the community, I never had time to give back.
But when I moved to independent consulting, I had time because my bill rate enabled me to earn more per hour so I had more free time to give back to the community without compromising my income.
So while I currently put in about 50 technical hours per week, only 30 of those are billable while the other 20 are being spent keeping myself at a high bill rate by keeping my skill set sharp and blogging; big factors that help me keep my MVP status.
I now ask prospective employers what they enable their employees to do outside of just billable hours. Do you allow me to have time to work on my lab? To blog? To go do speaking engagements?
If they say you need to be doing billable hours 90 percent of the time, then it’s not a match because it doesn’t allow me to address my passion and to keep my skills sharp and stay in front of the paper MCSE crowd.
Infusive: So that notion of giving back was a major factor in your decision to become a contractor?
Jason: Ya, it definitely was. I could be on the bench for any number of consulting companies and have no time. But, as an independent contractor, I have the opportunity to keep my skills sharp and stay involved with the community while also creating a schedule that gives me time for my other passions like seeing live music, dirt biking and traveling.
Infusive: In what ways has your community involvement helped your business?
Jason: As an example, I’ve spoken at Tech Ed and a number of other conferences and have almost always gotten at least one contract engagement that pays for all the conference expenses and then pays the bills for several months in most cases.
Finally, you’re name and session details are posted in conference materials and posted on Microsoft’s website so then people can find you just through keyword searches.
Infusive: How’d you manage to get comfortable speaking in front of an audience?
Jason: My first non-sales speaking role was as a product manager speaking about what our product did. It was in a room with about 2,000 people and I had an hour and fifteen minute slot to fill. I finished in 45 minutes because I was so nervous that I went through my material really quickly.
So now when I’m speaking I just have a rough outline and a clock on the podium to keep track of time and consciously try to slow down, enunciate my words clearly and breathe.
The best way to get into speaking, is though local user groups looking for someone to speak on your area of expertise. Because it will likely be a small group of your peers and a topic you can speak on with authority, therefore should be comfortable with. Then you can submit your topics to different conventions like MEC and Exchange Connections, which are always looking for non-Microsoft speakers with a unique or interesting topic.
Infusive: Lastly, how do you stay informed?
Jason: A key source of information is the MVP email lists, which has all the Exchange MVPs on it as well as members from Microsoft’s Exchange product group; the people actually write or manage the people that do coding. I’ll see questions coming in and realize ‘Oh, this is a problem I didn’t know about,’ and I get the private, unfiltered response; under stick NDAs. That gives me a big edge
There’s also calls with the product group most weeks that are focused on product areas; like Hub Transport, Mailbox, Office 365, and Lync. So I try to jump on one of those calls because it’s a great way to learn about the issues coming into Microsoft support and future changes in the product. That helps me get early notifications of the issues so that I can address them at my clients, sometimes before that information has even gone public.
I also follow many blogs and Windows IT Pro Magazine, but really having my own lab and production environment - where I run Hyper-V servers, with clustered Exchange 2010 and 2013 servers – for hosting email for my friends and family has been the best way to keep my skills sharp.
About Infusive Solutions:
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