7 iPad Deployment Mistakes

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These are the slides from my presentation at the 2013 MacIT Conference and AirWatch Connect conference. Thanks to everyone who attended! A packed room each time!

I'm the CTO of Tekserve, NYC's largest Apple consultancy and integrator. Tekserve has been integrating Apple into the enterprise for 25 years.

Seven years ago I started a site called Xsanity, creating a community for administrators of Apple's Xsan storage area networking product. The community was needed because Apple was focused at the time on the consumer market and not business customers. If we wanted this interesting product to succeed, we needed to create our own solutions, as a community.

Sound familiar? A few of us noticed the same trends as iOS devices began getting traction in business. And in 2010 I launched Enterprise iOS, or "Xsanity for iPads." Back then nobody called themselves an "iOS Administrator." But the trend took off, and with it so did the community. Today Enterprise iOS sees over 24,000 visitors each month. This is a measure of Apple's incredible success with business mobility.

Apple's success has also been Tekserve's success. I've helped Tekserve roll out our iPads to hundreds of businesses. And it hasn't always been easy. I've made plenty of mistakes. And in the spirit of community, I'm going to share the seven biggest mistakes I've made with you.

The #1 mistake: Let's not tell IT about these new iPads.

There are good reasons to avoid involving IT. In some businesses, IT doesn't quite have a reputation for thought leadership. Brian Katz colorfully illustrated this on his blog.

But there are good reasons for keeping IT in the loop.

One of our first deployments was a modest 40 iPads for a luxury retailer's district managers. The iPads were to be presented at their national meeting. Tekserve put each in a fancy bling case, added a dozen apps, and personalized each with a Lotus Notes account. On the day of the unveiling, the managers were thrilled. But as each powered up her iPad and logged into email....

...we managed to crash the Notes server.

40 iPads aren't a lot. But the company's email infrastructure was weak enough that the new devices brought it down. IT was well aware of the issues with their servers, and had planned an upgrade. Had we coordinated with IT, we would have been able to change the timing of the iPad rollout and avoid the crash.

My Mistake #2: Succumbing to the temptation of controlling every aspect of the user experience. This is often done under the banner of "security."

In the beginning there wasn't much for us to control on an iPad. Today we have Apple Configurator, Mobile Device Management, Mobile Application Management, Sandboxing, VDI...

But it isn't in your best interest to use every possible security measure. Here's an example.

Cablevision, the cable TV and network provider, wanted to put iPads in the hands of their field service techs throughout New York, New Jersey, and Connecticut. These "cable guys" are the most public face of the company, and Cablevision saw the iPads as a way to upgrade the capabilities of their fleet. But instead of the traditional "technology lockdown," during the pilot project Cablevision decided to allow their techs to customize the company-owned iPads. They went so far as to hold a contest to discover the most useful apps to support the field staff.

The most surprising find was Google Translate. This simple app solved a tremendous problem: A field tech shows up at a non-English speaking household, and can't communicate. Previously, the company would need to cancel and reschedule the appointment with a translator, frustrating the customer and at significant cost to the company. But Google Translate, saves a visit and gets the work done the first time. That's fantastic customer service, and it was discovered by a user during the pilot.

What's more, the contest was a strong signal from IT that the iPads are something different, something we can trust you with.

You don't want to control too much, but you don't want to control too little. That's my mistake #3.

If you don't organize enough at the beginning, you get overwhelmed by inefficiencies and inconsistencies. If you want your deployments to grow larger (and who doesn't?) you need to plan for scale.

To illustrate let's return to Cablevision. The deployment was for 3,015 iPads. Each iPad had 6 accessories, and 30 apps to be installed. Can you imagine asking each end-user to install 30 apps? How far would you get before they gave up? Two? (MDM doesn't help much here because the user must authenticate for every app install.)

But the most time consuming task is often the most mundane: creating an Apple ID for each user. If you've ever tried to help someone create their first Apple ID you know how frustrating the process can get.

Now if you centralize this process you can get creative. At least that's what Greg Moore from the Hope Public School District thought. Greg created an AppleScript to automate the creation of Apple IDs.

Using the AppleScript, Tekserve was able to create the 3,015 Apple IDs in just a few hours.

Greg has generously made the Batch Apple ID Creator open source, and we host the project on Enterprise iOS. The code is in GitHub -- please fork and improve!

The iPad has been called the most intuitive computing device in history. So who needs training, right? More people than you think.

Without training many users feel uncomfortable, but they will be too embarrassed to ask for help. So that iPad will just sit unused in a box.

Under the leadership of Sara Clarke, SVP for Corporate Strategy, our customer Showtime Networks has developed a model training program for their BYOD users. Over the last three years, they have developed newsletters, instructional videos, and even an entire intranet dedicated to training. Sara's mantra is "measure, measure, measure." Measure your user's baseline knowledge and measure how much they improve. This isn't your last iOS deployment. So measure to learn how to do it better next time.

I'm not alone making my mistake #5. I see company after company repeating this mistake. You want people to be able to use the iPad, but you don't want them to break it or steal it.

Unfortunately, some companies react with a solution like this: This is a pilot deployment for OTG Management in New York's Kennedy Airport. OTG installed iPads for free Internet access and (not free) ordering of meals and snacks. It is a very cool system. But the case, which they call the "doghouse," limits the use of the iPad. Plus, are you sure you want to treat your customers like criminals?

So they unleashed the iPads.

This is the refinement OTG implemented, in the Delta terminal at New York's LaGuardia Airport. The iPads have a thin case, and several feet of standard white USB cable. Customers can pick up the iPads and spend as much time with them as they like, while waiting for their flights.

The iPads, which are pre-configured by Tekserve, do have some security measures, but these are designed to be very minimal. It's a regular iPad, running the regular iOS.

Every seat in LGA Terminal D has an iPad. Every waiting area and every restaurant. iPads include a dozen apps, and are integrated with flight statuses and the terminal concession stand. Tap a button, swipe your Amex, and someone brings you an Asian salad with fresh market greens. Tap another button, and someone brings you the Wall Street Journal.

OTG has worked with Tekserve to expand this system to airports in Minneapolis-St. Paul and Toronto.

And here's the best part: by simply allowing the customer to pick up the iPads, OTG increased sales by double digits. Damage and loss remain close to zero. And when customers are finished using the iPads, they carefully replace them back into their stands.

When you respect your users, they will respect your iPads.

Mistake #6 is overconfidence. iPads themselves may be solid-state, but deployments have many, many moving parts. Tekserve gets help from others when needed, and you should too. And the best help is help that makes you look awesome.

New York City's Institute of Culinary Education provides a good case study. ICE is training the next generation of top chefs. For years, ICE distributed their proprietary course materials in thick 3-ring binders, with new pages Xeroxed and added each week. Then last year, they decided to try issuing iPads to the students, using electronic textbooks to automate the content delivery while allowing for beautiful illustrations of food prep and plating.

But ICE's IT department had a problem. The small department had previously only supported the Institute's 70 faculty members. Adding 700 student iPads would increase their responsibilities literally 1000%!! Not only did they not have the staff, they didn't even have a free closet to store the iPads. So ICE reached out to Tekserve for help.

Now, when a student enrolls at the school, she receives a set of knives, a chef hat, and a voucher for an iPad from Tekserve. The student brings that voucher, which is uniquely tied to that student, to our retail store one block from the school. On the spot, Tekserve's staff picks a new iPad from our stockroom, personalizes it with the student's Apple ID, enrolls the iPad in AirWatch's Secure Content Locker, and does a short training. The whole process takes around 15 minutes.

Tekserve also provides faculty training, content management, phone support, and even end-of-life trade-in. With our help, the Institute is able to run a student BYOD program with almost zero burden on IT.

But before all of that, we needed to have a pilot.

This mistake is last because it has been the hardest for me to learn. It is very easy to underestimate the importance of your pilot.

Shortcuts can be very tempting. You can't wait to be done with the pilot and get into your first deployment, right?

But realize this: your pilot is your first deployment. A good pilot is always a great learning experience. The lessons you learn during the pilot are the keys to helping you scale. The better the pilot is, the more it teaches you. This is why you need to devote real resources to your pilot, including time, money, and experience.

So I offer to you these mistakes I've made. Please don't repeat them. Instead, make new ones! And tell us about your experiences at Enterprise iOS.

Aaron Freimark

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