mrc's Cup of Joe Blog

Join us in exploring the world of modern development, evolving technologies, and the art of future-proof software

5 (more) questions to ask before starting a digital transformation project

EducationSummary: Digital transformation–the reinvention of an organization through the use of digital technology to improve performance–is a priority for many businesses these days. However, it’s a complex task. Many businesses dive in without truly understanding the process. In this article, we explore 5 more important questions to ask before you start.

photo credit: fancycrave1 via pixabay cc
photo credit: fancycrave1 via pixabay cc

Digital transformation is one of the top CIO priorities of 2017. More and more business leaders are recognizing the need to adapt their organizations to today’s digital world.

The problem is, it’s a complicated journey. Many businesses go into digital transformation without fully understanding the extent of the project.

How can you best prepare your business for a digital transformation journey? It starts with the right questions. In the first part of this article, we explored these 5 questions you must ask before starting a digital transformation process:

  • How will you measure the value of your digital transformation?
  • Have your key stakeholders bought into the project?
  • What talent do you need to successfully execute your digital transformation project?
  • What kind of team and resources do I need to sustain this new digital business?
  • How will you manage employee perception of and response to the change in approach?

These questions will help you start your digital transformation journey off on the right foot. But, these aren’t the only ones you should be asking. Today, let’s take it a step further. Here are 5 more questions to ask before starting a digital transformation project.

1. Are we just looking at our direct competitors or are we considering what people expect of digital experiences today, regardless of industry?

photo credit: Unsplash via pixabay cc
photo credit: Unsplash via pixabay cc

In the first part of this article, we explored the importance of setting a target for your project. After all, you can’t gauge success unless you have specific goals.

However, this is where many fall into a trap. They set their goals too low, or they aim for the wrong target.

Why? They base their goals off of their competitors. They try to match what the competition within their industry is doing from a digital perspective.

The problem: Some industries traditionally lag behind. The top player in your industry may be miles behind the rest of the business world. Setting that as your goal will limit your potential.

So, what should you do? As explained below, look outside your industry for examples of other businesses who are thriving in this digital world.

“Many companies start by looking at their direct competitors and just want to be on par with them or beat them, but they fail to look around,” says Antonella Pisani, CEO & Founder of Official Coupon Code. “If all websites in a given industry are behind, then they’re benchmarking against a sub-par set to begin with. It’s important to remember that people’s desires are based on their best digital experiences, not the best digital experiences in a given industry.”

2. What really needs to be digitized?

Digital transformation is an overwhelming topic. Some make the mistake of assuming it’s all or nothing. They think that they must rip out the old systems and replace everything with new, modern systems.

The reality is, digital transformation isn’t a “big bang” type of project. It’s a gradual process.

Before you dive headfirst into digital transformation, take a step back and ask this question: “What really needs to be digitized?” You’ll find that some areas are in dire need of replacing, while others are fine the way they are.

“Trying to digitise everything in a workflow without asking this question first can have nasty consequences,” says Kyle White, Co-Founder and CEO of VeryConnect. “By trying to encompass all rarely used features and examples within your new systems you risk extra expense, complexity, delays and ultimately lowering the quality of the core task that must be achieved. Very often the most successful digital transformation projects leave edge cases for later phases or to remain as manual tasks. Consider a pre-planned phased project approach that enables you to assess any edge cases after the core transformation has bedded in.”

3. How much do you know about your current systems?

photo credit: jurvetson via photopin cc
photo credit: jurvetson via photopin cc

This may sound like an obvious question, but it’s far more difficult than many businesses realize. For example, how easily can you answer these questions:

  • How many different systems are you using across your organization?
  • Where is your data?
  • Who has access to these systems?
  • What dependencies exist in your current systems?
  • What does your documentation look like?

As many are well aware, enterprise systems become increasingly convoluted as they age. Digitizing these aging systems and processes will lead to many unpleasant surprises if you don’t truly understand your current systems.

“How much do you know about your current systems?”, asks Anna Daugherty, Digital Marketing Manager, PITSS America. “Does documentation exist? Who are the IT gatekeepers? These questions are important because you need to have full access to understanding your system before you can embark on a digital transformation journey. Not understanding your system can mean risks in development time, scope, and project costs, as well as creating inefficient workflows for the people who interact with your systems, down the line.”

4. What if we’re wrong?

Now, I’m not saying that you should plan to cancel your digital transformation project halfway through. Rather, this question is all about adopting the right mindset.

The digital world we live in today requires agility. You need the ability to adapt to new information quickly, and change course if needed. You need the ability to deliver necessary solutions when the business needs them.

This often requires a fundamental shift in mindset and business processes. As explained below, the digital business requires a “fail fast” mindset. You must be able to pivot quickly and adapt as needed.

“One of the biggest advantages that digital businesses have is that they can evolve very rapidly,” says Skot Carruth, CEO at Philosophie Group, Inc. “The value chain for software delivery is much shorter than that of a physical product. This is why startups can afford to “launch early and often.” If a company is trying to move into digital, it must adopt the fail fast mindset. In other words, acknowledge your assumptions and change course as soon as there is evidence to the contrary.”

5. What is your “cross the street” plan?

photo credit: LoboStudioHamburg via pixabay cc
photo credit: LoboStudioHamburg via pixabay cc

The digital business brings many changes to your data. Specifically, it often changes where it’s stored, how it’s accessed, and who can access it.

For example, suppose your data isn’t currently accessible outside of your office. After a digital transformation, your data might be accessible via smartphones. That brings some advantages to your business, but also some risk if not properly addressed.

How will you control data access when your data is accessible from anywhere? How will you limit risk when employees leave your organization? As explained below, these are questions that you must address before you start.

“What is your “cross the street” plan?”, asks Pam Dingle, Senior Technical Architect at Ping Identity. “That is, if employment with anyone in your organization ends, what will they have access to if they immediately walk across the street to a coffee shop (or a competitor!) and try to login to resources? What about partners? Vendors?”

“This is a critical question for digital transformation, because so many of these kinds of transformations push corporate data to systems and devices that can be accessible from outside the organization. Your teams should be able to show you exactly how a change in status at the center of the organization ripples out to revoke access on native mobile apps, public SaaS apps, and any other digital asset, in an automated fashion.”


These are 5 more questions to ask before beginning a digital transformation journey, but the list could certainly be longer. If you would like to add anything to this list, I’d love to hear it. Feel free to share in the comments.

3 thoughts on “5 (more) questions to ask before starting a digital transformation project”

Comments are closed.