Let’s get real about Digital Transformation

A talent shortage and an “all in” approach is a recipe for disaster in the era of modernization projects.

Kyron Baxter
Kyron Baxter
6 min readNov 26, 2019

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Change is coming. The question is, why do so many organizations struggle with technology change?

It does not matter if you blame millennials, GDPR or a more competitive global market place. Digital Transformation projects are all the rage.

They become an opportunity to resolve an organization’s technology missteps in one large swoop. Some organizations elect to take phased approaches, while others include every possible platform as a success metric for their transformation projects.

Organizations pay a premium for professionals to guide them in these projects. There are more transformation projects than truly experienced professionals in the market.

Why is this?

Photo by Helloquence

Training is deplorable. Many technical professionals work on digital transformation projects via contract roles. This is different from working as a full-time permanent employee (FTE), where training is provided. Companies are usually happy to provide their FTEs training because they receive more value from their employees, and vendors often include free training alongside software licenses.

Professionals working as contractors, meanwhile, typically do not have access to company-provided training or certification programs. As such, a contractor has to take time away from any projects they are working on or job hunting to partake in these certification programs.

Certifications for modern platforms are very expensive. An example is Jamf, the preferred device management platform for Apple devices (Mac, iPhone, iPad, etc).

Jamf Certification courses are popular among device management experts.

As shown above, it is $2,500 USD for the Jamf-200 level course. There are further courses and the 200 level is meant to be an entry point. This can get very expensive. These courses are four days long, which can be an issue as organizations are not fond of contractors taking time off in the middle of a project (sadly even if the certification is relevant to the project).

Jamf is just one portion of device management. While Google offers the Android for Enterprise certification for free, this only covers the devices and not the device management platforms. Popular platforms such as VMware’s WorkspaceONE (formerly AirWatch) and Microsoft’s Intune are a pain to be certified in.

VMware has WorkspaceONE training sessions in major cities on specific dates each year. These training sessions can run north of $1200 USD and are best for professionals who already have experience with administrating WorkspaceONE.

Microsoft’s approach to certification is not much better.

Microsoft does not offer such certifications for Intune. Microsoft now has a “Microsoft 365 Mobility & Security” certification track that requires working knowledge and experience with Exchange, SharePoint, Powershell and Skype for Business.

While this may be useful in a daily operations or BAU support role, this is very optimistic of Microsoft and is unrealistic to the average organization with hundreds or thousands of employees.

A consultant hired to work on an Intune project will likely not be engaged to work on a Skype for Business project, let alone given access or decision-making authority related to Skype.

There are still tons of job postings globally that ask for (in some cases require) candidates to have the Microsoft MCSE-Mobility certifications. This certification has been discontinued by Microsoft. In fairness, how would the average hiring manager, HR professional or recruiter even know this?

Even just the name changes to platforms will throw off uninformed recruiters and hiring managers. Many will assume people who have experience with AirWatch have not worked with WorkspaceONE, even though they are the same platform.

Transformation projects often represent a time of transition for organizations. It is common to see device management platforms being rolled out alongside Office 365 migrations.

Device security improvements are often followed by (or in parallel) to improvements in identity management. Fancy new Surface Pro’s and MacBook Pro’s come with the latest versions of Windows 10 and MacOS.

Here is an exercise for anyone in a hiring role. Try finding an expert who knows Jamf well enough to manage a large MacOS fleet and knows either Swift or Objective-C to make scripts. This person should also know Intune, Windows 10, Autopilot, Windows Hello for Business and Powershell.

This roughly translates to “find a professional with mastery of two competing platforms”.

Scarily, these are just the desktop platforms and do not include Android or iOS. Many organizations use WorkspaceONE or MobileIron to compliment Jamf and Intune.

With a mouthful of ever-changing platforms, there is zero likelihood of finding a professional who knows all of the aforementioned in-depth. This is why a professional who knows even a few platforms well is a hot commodity in the job market.

Organizations need to stop asking their plumbers to fix their blinds.

Apple releases a new major version of MacOS yearly. iOS usually has two large updates per year. Keeping track of changes to these platforms and their management tools, such as Jamf, is a commitment. To then ask this same professional to be an expert in all of the Microsoft platforms simultaneously is unrealistic.

Organizations (especially larger ones) should build a small bench of professionals — preferably one or two for each technology stack. If there is only budget for one consultant, the organization needs to prioritize which technologies to modernize then slowly make their way down the list.

This is in stark contrast to the “all at once” approach most organizations take.

Typically, there are FTEs within the organization who have knowledge of related platforms. If an Intune expert is hired for a mobile device management project, the employee responsible for packaging desktop apps should be asked to take on that portion of Intune.

Digital Transformation projects should be collaborative. The idea of paying a “hired gun” a premium to solve all of their modern technology platform pains is pure fantasy. General practitioners have wide, general knowledge of the human body. A neurosurgeon has different skills than a cardiologist.

Organizations should pay closer attention to the skills of each professional they already have and are considering hiring.

Complexities around certifications and unrealistic expectations aside, here is the REAL issue:

To gain experience with the aforementioned platforms, one must work for an organization that has already purchased them.

This is a huge problem. IT professionals typically have been able to setup test environments (labs) to learn new technologies. While this has transitioned from using old computers to making an at home server lab, to testing in the cloud with AWS (Amazon Web Services), these are still very affordable and relatively easy ways to gain practical knowledge.

With modern SaaS platforms such as Intune and WorkspaceONE, gaining access to these platforms requires owning an incorporated business and going through a sales funnel. This is assuming the software vendor will even sell you a license and provide an environment for you in the first place.

This creates a chicken and egg situation. Organizations tend to want experienced professionals as opposed to enthusiastic novices. Access to these platforms being limited causes a supply and demand issue with short supply of skilled professionals available in the market.

This will also cause consultants engaged on a specific portion of a transformation project to be more eager to venture out and gain more experience. This can be useful but can also create issues (conflicts with other SMEs, quality of work issues, dis-empowering FTEs). Consultants will feel the need to branch out to stay as relevant in the marketplace as possible.

Conversely, this means professionals who have access to training, certifications and test environments typically have a more narrow set of expertise. They are typically FTEs working in a specific role within IT. It is likely for an organization to send their Exchange administrator to an event to learn Office 365. It is much more unlikely that same employee will learn Jamf.

Until organizations can acknowledge the subtleties of dealing with such large and complex projects, they will continue to miss delivery dates and deliver less than desirable results.

More importantly, employees will become unhappy and money will be wasted.

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