Spotlight on Joel Oleson, SharePoint Rock Star

Joel Oleson, or SharePoint Joel as he's widely known, is probably the SharePoint rock star most likely to elicit a "we're not worthy" bow for his contributions to SharePoint and the surrounding community.  Not that he'd stand for such behavior, as Joel is one of the nicest and most down to earth members of a professional community that is blessed with a multitude of such individuals.  Joel was, as they say, "present at the creation" of SharePoint, and for the next seven years he was integral in shaping the development of SharePoint at Microsoft.  Joel remains a tireless evangelist for SharePoint, recently accepting a position as Senior Product Manager on the SharePoint team at Quest Software.  In this exclusive interview, conducted to coincide with the launch of the SharePoint for Administrators feature area which was created in partnership with Joel, he not only provides his unique perspective on SharePoint's past, but unflinchingly shares his thoughts on its present and future as well. 

You were with Microsoft for 7 years.  Was the entirety of that time devoted to SharePoint development and deployments, or were you brought into the SharePoint team from another area?

It wasn't called SharePoint when I got there in Dec 2000, but on the very first day I went to Gabe Bratton's office and we talked about Office Server Extensions and Office Web Server (later known as SharePoint Team Services and now WSS).  I had 4 years of IIS administration experience at that point, going back to IIS 2.0 and another 5 years of IPlanet/Netscape Enterprise Server and Apache.  My interviews were with the Exchange team.  I had just gotten my MCSE in NT 4.0 and hadn't spent more than a week using Widows Server 2000 (what I had learned in class).  Essentially, the Office Web Server team was asking Microsoft IT to host SharePoint (or what would be called SharePoint) in the data center and asking them to pilot the Web collaboration software and build out a service.  They had purchased a server and Gabe himself took it out of his car and put it in the datacenter (definitely against the shipping/receiving policy).  You can imagine the IT pushback from some "random" under the radar product.  In that same first week, I met up with the Tahoe team to look at what they'd been doing with Magma (the Exchange Webstore).  A few weeks later I was doing performance testing with Ross Smith (Exchange Guru) to determine how to size both these apps with the idea of designing a service.  My role and responsibility was to manage, operate and pilot these apps to determine if Microsoft IT should build a service based on this software.  I was employee #1 on the ops team for SharePoint.  At that time we were the little "C" in the Messaging & Collaboration team, MACS.  One guy, Shawn Parks, did Unified Messaging; one guy, Rudi Peterson, did Conference Server and Fax; and one guy, Florian, did mobile.  We were the special ops  amongst a much broader Exchange Messaging Group of more than 20 that was staffed 24/7.    

Can you briefly sketch out, from your firsthand experience, the evolution of (what came to be known as) SharePoint from its inception to the current MOSS 2007 version?

To set the stage, let me give you some background on what prepared me for SharePoint.  I supported and designed a few databases for our SQL 6.5 environment at XO Communications, and configured NLB for our Intranet load balanced IIS 3.0 environment.  We even ran hardware load balancing solutions for the Internet sites.  SharePoint wasn't my first publishing app.  I used Notes and Domino for a couple of years at XO.  I supported and did code reviews for the publishing functionality in Allaire's Cold Fusion, Homesite, and publishing platform and various Java apps in BEA Weblogic, supported a few iPlanet Web apps and Apache Java Tom Cat Apps.

Before joining Microsoft, I had played with SQL Dashboards, ran a few Front Page Server Extensions 98 boxes, and evaluated site server and had some limited experience with it.  I'd say I was really prepared for SharePoint with my experience doing Web support at Slate.com (a Microsoft Webzine at the time).  I did all the technical support, and ran the dev and test environments, including the propagation of code and managing the publishing environment code named InterPress (I think it was used by MSN -- not sure if anyone outside ever saw it).  Search and audiences had their beginnings in site server which we used at Slate.com in early 1998.  We were using ASP, and I had written a few ASP apps for automating common responses.  That's where I got my first experience with SQL 6.5 and IIS 2.0.  Once I got to Microsoft, I upgraded an Office Server Extensions box to STS Beta 1, Beta 2, RC.  There was a decent deployment of 800 Sites under Gabe's desk on his desktop essentially.  In the first couple months of running the pilot service I got my first experience with database migration pains and server health check.  In designing that early service I was very fond of an add-on that was created by Radu R, one of the PMs.  Despite the push back, I saw it as the future and a way to achieve scale and provide a global service.  It was called the SSC, Self Service Creation.  With no quotas and thousands of sites on one virtual server, I was very concerned about scale and capacity.  I worked with the SharePoint team to understand the administration experience.  Running 17 STS servers with 500GB and 5 SPS 2001 servers with 75 Workspaces, I was the sole ops resource until we started upgrading.  We consolidated the File Server team of 2, hired a contractor, and I became the ops manager.

The products continued to evolve through better management through leveraging SQL as a store, getting rid of dependencies on the Exchange Webstore (SPS 2001) and local groups (STS).  In the Office 12 wave, the portal would try to manage the WSS sites.  WSS lists and site collections were solid, and SPS would look to take advantage of the modularity.  SPS finally drank the list Kool-Aid in MOSS and they truly became integrated, making WSS and MOSS management very consistent.  I could obviously go on and on about this stuff...

Indeed, I don't doubt that you could write an entire book!  What was your sense of the public reaction to the release of WSS 2.0, and how do you think that reaction informed development efforts and/or product planning for future releases?

WSS 2.0 was overcoming that stigma of STS as a site for 15 users, a poorly written marketing document that was seen as the law.  SPS 2001 was seen as a repository for a group.  Neither were taken seriously as an enterprise Portal (maybe departmentally by analysts), but not even considered enterprise apps until 2003.  That's when things really came together.  The Microsoft Intranet would fully adopt SPS 2003 as its portal, where before only search was used in 2001 for MSW.  This re-architecture would help us build real scalable farms.  In V1 on both products you were really stuck on one box.  2003 opened up real farms with load balancing and SQL clustering.  The portals were seen as enterprise portals and the team sites as an enterprise collaboration offering.  The partners really came on in this version as well with real integration workflow apps, anti-virus, and obviously a bunch in the back-end around backup/restore, some of which were there with us in SPS 2001 in the beginning.

What would you say was the biggest challenge the SharePoint team faced during your tenure?

The biggest challenge was moving from the enterprise to the cloud.  The dedicated service was something I worked on for a little over a year.  Trying to turn all of what we learned internally and in the extranet space into a repeatable and scalable service with a skeleton crew that could be run hands off.  We began with the pilot hosted service in WSS 2.0, SPS 2003 which really wasn't viable for doing much beyond small sites.  Our first customer was running STS and getting that data from the Midwest to Redmond area presented challenges of space and time.  Each company has different challenges and different dynamics.  The CIO may say one thing, but his right hand man may be making different decisions which then might get backed up by the CIO.  Trying to manage to cut through these politics and provide a common vision as a SharePoint Architect was extremely challenging.  The product itself needs to build that vision beyond the marketing wheel, and the stacks.  SharePoint Governance is different in every organization and with some common threads, managing these differences in an organization where it touches everything and everyone in a company that is not yours is extremely challenging.  The technical challenges are simple in comparison, while I still think there is a lot of room for growth here and I have high hopes for the Office 14 wave.

Given your extensive experience as a member of the SharePoint team at Microsoft, and the prominence of your blog, your name is virtually synonymous with SharePoint in the community, so I'm curious what prompted your decision to leave Microsoft earlier this year?  Were you just ready for a new environment and new challenges?

In some ways it was, "OK, so I've seen SharePoint hit a billion in revenue, what's next?"  I've seen it through three releases from various, compelling roles.  Yet, in Microsoft I had the ability to jump into Live or Mobile or ILM.  My passion was SharePoint, and my ability to do exactly what I wanted to do was getting limited as I scaled the ranks.  Let me give you an example, like going to the Middle East to speak at a couple of SharePoint conferences and going to see Petra and venture into the Holy Land, or  teaching a SharePoint class with my friend Shane Young and connecting with consultants and architects for 5 solid days.  I found that my passion was connecting with the MVPs and the community and that was limiting my ability to do my "day job" at Microsoft.  I'm still obviously a big fan of Microsoft and the people there.  I have a ton of friends at Microsoft and may return some day when my desires to do what I want are more satisfied, or until I see an opportunity where such freedoms were available.

Since leaving Microsoft, you've kept up an almost superhuman pace of blogging, traveling the world to speak at SharePoint conferences and workshops, consulting, training for the Ted Pattison Group, working as a SharePoint evangelist at Nintex, serving on Bamboo's Advisory Board (and, more recently, guest blogging for us) ... you've had quite an active year!

Arpan Shah gave me some advice when I was leaving.  He said, "You have 18 months.  People know who you are because of Microsoft.  When you leave, you'll have 18 months to capitalize on that."  That burned a pretty solid impression in my mind that I needed to prove that I knew what I knew not from internal memos, but from real experiences and based on my career and the perspective that has been built over years of experience with the Web administration and Web engineering and operations since 1995, not since SharePoint.

It was my goal not to drop out of sight, and to keep extremely connected with my community contacts.  Waiting 1 year to even be considered for an MVP award was hard to swallow and put the 18 month name visibility challenge at risk.  I haven't made a lot of money, in fact I've burnt through a lot of money to have the amazing summer that I had.  It's been an incredible year.  December 27 marks 8 years with SharePoint for me, and I have to say it's been another incredibly rich year of connecting with SharePoint's best through social networks and conferences around the globe.

Just a few weeks ago, you announced your acceptance of a position at Quest Software.  Can you tell us a bit about your role at Quest?  I understand that one of your responsibilities will be designing new tools to help IT administrators...

My title is currently Senior Product Manager.  My role is an entirely flexible one.  (I will likely change it on slides as I feel fit.)  This means support for speaking at Best Practices conferences around the globe, building community, blogging, and connecting with the community.  I recently blogged about Mike Watson ... he and I have been talking about an idea I had about configuration management tools, and true enterprise management for SharePoint.  We are now realizing our ideas and dreams with Quest.  While most product managers would go heads down and focus on their product, I won't.  I'll stay connected to the community and be the outward-facing strategy guy to help the Quest SharePoint team understand customers.  I'll also be spending time with Quest customers and helping them understand both the SharePoint and Quest SharePoint and SQL roadmap.  In fact, just yesterday I was presenting the Office 14 roadmap deck with Microsoft as a Microsoft Consulting services consultant subbed through Quest in a leadership meeting with a customer.  (Great job Ann, Vern, Mark, and Mike.)  It was a fascinating experience to speak to 14 from the outside, but representing MCS.

Speaking of tools for administrators, since we're talking on the eve of the launch of the SharePoint for Administrators feature area in Bamboo Nation, I'd like to publicly thank you for your involvement in the creation of the area.  We're thrilled that your schedule permitted the guest blogging you did for Bamboo Nation over the past couple of months, and that those efforts culminated in the launch of our newest feature area, SharePoint for Administrators.

Thank you!  When I was looking for something to fill in my time while waiting to work out the details, and looking to pay off some bills from my Asia trip, you guys were there to help me out.   I had a fun run as a professional blogger.  I really enjoyed the experience.  You guys did a great job making me feel important and making me realize that I was helping you make a difference.

I understand that you provided some valuable feedback (as well as an enthusiastic blurb) to Dux Raymond Sy, resident expert for our SharePoint for Project Management feature area, on a pre-publication draft of his book, SharePoint for Project Management.  How did that come about?  Are you approached regularly by publishers seeking feedback and/or blurbs for SharePoint books?

Yeah, I was asked by Laura from O'Reilly to review the book and provide feedback, which I was happy to do.  Each of the MS Press SharePoint Resource kits and Admin Resources, and a number of other related titles, such as the Best Practices book and SharePoint Essentials have many quotes from my blogs, some include entire posts (with permission).  I have relationships with Penton Media, O'Reilly, and TechTarget. 

Ironically, I was turned down an MS Press STS Admin book I proposed in 2001.  They didn't think the market was big enough.  I did review a few chapters for MS Press in the first SharePoint book that MS Press published, but I think it was their loss that they never came back to me when they realized the market and demand was there.  I have a relationship with nearly of all the SharePoint authors.  Don't be surprised if I take a stab at a book this next time around (now that I have more flexibility).

Dux's book, by the way is great to finally have.  How many times have we asked the PMs to ramp up and they didn't get it?  Dux's book is simple and easy to read and doesn't get bogged down in the technical details.

Given your stature in the SharePoint community, it seems to be a rather common (and understandable) misconception that you're an MVP.  You mentioned earlier that there is a one year "waiting" period that's required after leaving Microsoft before you become eligible.  Since you're pretty obviously a shoe-in for the designation, is this something you'll be pursuing?

Yep.  I think I hear this question at least once per conference.  To clarify, you don't pursue MVP, they even watch for that and don't like to see MVP pursuits that could be "fake."  You can focus on activities that do help you qualify for the MVP award.  I love hanging out at the MVP booth at Tech Ed Asia.  All the cool people are there.  Why have a conference booth if people can't pursue it?  Confusing, huh?  I think it's about promoting community and connection.  I am not eligible for the MVP award or to be considered until 1 year after leaving MS, so this would be right after MVP Summit around the end of March (March 28^th to be exact).   I have been nominated a few times over, but they are insistent in following this guideline or rule.  I'm not complaining.  I am frequently invited to the MVP dinners (don't think I've missed one yet when I was around) and I haven't missed an MVP paintball game yet.  They've adopted me in their circle.  There is so much emphasis on these awards, I feel bad when someone doesn't get renewed.  I think it's important that we as a community recognize those that contribute whether they have the MVP award or not.  We shouldn't be cliquish or try to be exclusive.  I think Bob Fox and Andrew Connell have done a good job of having events where everyone is invited for example.  Whether or not I get the MVP award I will continue doing what I'm doing because I enjoy it and feel satisfaction doing it.

Since I started at Bamboo in mid-May, and was new to SharePoint, my first exposure to your blog was with the buzz that was generated around our office in response to your Top 100 SharePoint Blogs post.  That list, which you've since updated, has proven to be so popular that I wonder if you have any concerns about having created a monster?

Yes, it was a fun exercise which started from seeing a blog that ranked Analyst blogs.  It is pretty time consuming, but it was enjoyable to see a stack rank.  It did start some competition and some people really started blogging more.  So it did serve its purpose and helped tighten the SharePoint community.  I think we also gained some better bloggers who optimized their SEO and I think we get better search results from that.

You just announced this past week that you'll be the keynote speaker at the Best Practices SharePoint Conference in February.  I was already looking forward to blogging the conference for Bamboo Nation, and your keynote is sure to launch the event in style.  Any early thoughts that you'd like to share as to the approach you'll be taking with your speech?

I love the blogging approach to conferences.  It's great to see other people's perspectives and share notes.

I plan to take a fresh approach.  I'm super excited about this opportunity to address this audience.  It's my audience.  These are my kind of people:  People who are seeking the diamond in the rough.  I enjoy the passion in those seeking order in the chaos.  I'll leave it at that.

I was just getting back from a month long Asia trip after 3 conferences, so I missed the last one, but I hear from Bob Fox, Mike Watson, and Ben Curry that it was a huge success and I'm very excited to be presenting at this one.  Presenting the keynote is a great honor.

I'd like to wrap up with a set of questions that we ask all of the SharePoint experts we speak with, beginning with, what would you say is your single favorite feature/functionality of SharePoint?

The self service collaboration - having a site in seconds that is fully functional without IT having to be involved.

Conversely, what do you feel is SharePoint's biggest weakness/drawback?

The dev ramp up requirement and associated confusion.  It's hard to take an off the shelf developer and get them to digest what they need to know, especially when  they've got requirements in front of them.  Most experienced .NET developers want to jump in and start coding, but with SharePoint they have to step back.  This ramp up, when skipped, is a disaster and can turn a decent SharePoint deployment into chaos.  The same thing can happen with an admin in relation to the faults in the default settings and need for IT Governance.  Both developers and admins require training and ramp up, but I think I'm more concerned about what can happen when the developers get thrown under the bus.  That's the part I'm anxious to address.  Often developers want to learn by getting their hands wet, they don't want to have to crack the manual.  I do expect tools to address this, but also maturity of SharePoint as a development platform.  Developers in the meantime need to spend time in blogs, in training (like TPG), and re-learn the basics around Web development.  They aren't used to seeing so much functionality in the box and the development platform is so HUGE!  Creating your first feature and packaging it in a solution requires quite a ramp.  Don't forget to run the SPDisposeCheck!

What is your vision of collaborative computing five years from now?

The rapid development that happens on the Internet in social computing will converge.  One example is the number of social bookmarking platforms.  There are literally hundreds, and the value is still low and personal since there are so many.  The FriendFeeds, Facebooks, and Twitters will encompass more of these features and functionality, but the base of applications that span to give us different interfaces to tag.  I expect Digg, Del.icio.us, and the others to be much more clearly led by one or two market leaders that have integrated search.  Google's Readers, Chrome, and its Web client apps come together with tighter integration with the social platforms, and Microsoft's Azure embraced with Office Web Applications and choice in the browser space.  The way we add properties today in documents will be tagging, and we'll know when people create docs in the enterprise that relate to us.  It's rich multi-user editing in Word, OneNote, etc...  The value in followings in companies is going to be interesting.  You don't want to fire the guy who has hundreds of internal people following his document authoring and blogging.  The masses will rise up!  I love that idea of someone at the bottom in the long tail influencing management so much that they are following him visibly, and soon he's a secret executive such as distinguished engineers.  These ICs (individual contributors) can have more flexibility in their jobs because their value is understood and appreciated by the execs.  How would that be?

When you're not busy writing about, coding for, or training SharePoint, how do you enjoy your downtime?  Your love of travel is well documented ... do you have any particular travel destination recommendations based on your experiences?

Here's my Top 5:

Petra, Jordan - Blows your mind, Popularized through Indiana Jones.  Loved the hiking and breathtaking monumental views.  Start early in the morning.  (There's a Marriott if you want a hotel.  )

Bali, Indonesia (Ubud, Monkey Forest or any of the temples) - Beautiful peaceful place, beautiful people, and super cheap once you get there  My hotel, 2 blocks from the beach, was $6, and my 2 guides and van for a DAY was $30 USD.

Ait Ben Haddou through the Atlas mountains near Marrakech, Morocco - This takes you back in time 2-3,000 years.  The adobe clay looking homes are amazing, the camel and donkey ride, the Berber people.  Fascinating.

Angkor Wat, Cambodia - It will take you more than a day or two to explore even a few of these temples.  Incredible ruins, largest religious complex in the world.

Chiang Mai, Thailand - Elephant trekking and bamboo whitewater rafting and visiting the long necked Karen villages.  Wow, an amazing incredible experience.

Bonus:

Molokai, Maui - Snorkeling and Snuba/Scuba with Sea Turtles.  Blows your mind how clear the water is.  Beautiful and peaceful.

Thanks for those recommendations (and I've got to say, I couldn't agree more strongly with your recommendation of Bali in general, and Ubud in particular), and thanks for being so generous with your time!