10 Questions You Need to Answer Related to Digital Transformation Through Learning

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Digital transformation is a long journey, one that we have helped several organizations navigate. The first steps are uncertain, the unknowns are many, but the potential payoff is large. Answers to the following questions can help you determine whether or not you’re ready to take those first steps. We run through these questions very early in the "getting to know you" stage with the project champion as a way for the potential client to learn how Extension Engine thinks about projects.

Can you describe (even a short phrase or sentence) three specific options that you're considering (or that have just crossed your mind), no matter how preliminary or ill-formed?

Even if you feel that you’re not informed, simply thinking about this and presenting it to other people for their feedback can help you learn about your options. For us, knowing what is being considered helps us understand how we can talk about options, processes, and goals. 

What organizational goals do you have for 1yr and 3yrs?

The first time period determines what needs to be done in the short-term, while the second time period defines the long-term. Creating a custom learning experience that reflects your organization takes time, but the steps can be arranged in different ways so that more is available sooner...though this arrangement might cost more in the long run. 

Do you want to change your scale/reach, your cost structure for delivering your mission, or both?

COVID-19 has made many organizations face the question of how to deliver their mission without face-to-face contact. But there are bigger questions in play. Over the long term, does your organization want to grow, to go from delivering in 5 cities to 100 cities (or countries)? Or are you thinking about changing the cost structure from a high-touch, white-glove experience to one that can be more automated, more supported by technology? Or maybe it’s both. 

How much money is available, and when?

The answer determines both what might be done and the path to reaching that end result. The process of reaching your goals will definitely change if you have the money available and dedicated to the process up-front versus if you will be finding and allocating the money along the way with great dependencies on the visibility of interim deliverables. 

What's the decision-making process around strategic spending such as this?

The answer determines the flow of the engagement and what deliverables we might create to help you navigate your organizational reality. Sometimes “shiny objects” need to be available for decision-makers to help them understand what has been accomplished, or the cost structure or the project, or the organizational impact of the project, and so on. Every organization is different. Understand the flow of the decisions and what might be needed to support the decision-making process can help ensure that the project gets continued support. 

Who are the decision-makers (both strategically and financially)?

How can you help them buy into the vision for the project? Some of these people might be on the formal staff of the project; others might be unofficial advisors. It’s important to know who they all are and what they’re concerns are. You can build in the appropriate processes for addressing those decisions...but only if you know what they are. 

Who are the subject-matter experts who you would have access to for creating any learning and/or mentoring experiences?

The subject matter experts will need to provide a lot of time and effort in order to support the project’s success. Do you know who they are? Do they have the appropriate time cleared on their calendar in order to contribute? And, probably most importantly, is this project important to their personal success? 

What technology and Instructional Design personnel/expertise do you have on staff already?

These people are not required for you to start but, if they are on staff, they need to be brought into the project so that they will provide the appropriate support during the long gestation period. These professionals can also see the creation of a completely new type of learning experience as a threat rather than as an opportunity if they are not brought into the project in its early stages. 

Do you have commitments to education technology and customer relationship management software?

Again, this is not something that is required at the beginning of the project but, no matter what the answer is, the status of these two provides boundaries on what can be accomplished. Realize that the software used at the beginning of the project does not have to be the software used at the end—this can evolve over time, with the investment growing as your scale requires.

What personal goals do you have for 1yr and 3yrs?

Finally, you need to recognize that this work will take a major portion of your time and effort for the next several years. If you do not feel like this effort will pay off in your career, then right now you need to either bring your boss onboard or choose to do something else. This is a significant project, and it will affect your organization in myriad ways. You need to feel like it will pay off or you won’t be able to drive the change that is needed.


We have helped organizations large and small digitally transform themselves. Sometimes it has been seen as one big project; sometimes it’s a series of steps; sometimes it involves a deep dive into strategy and exploration even before the action-oriented steps are taken. Every one has been different.

Where are you in the process? Are you ready to talk about it?

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Dr. Scott Moore

Dr. Scott Moore is a former Principal Learning Strategist at Extension Engine. In this role, he led the global Custom Learning Experience practice. He worked with dozens of nonprofit, higher education, and learning business organizations as they considered using online learning to support their mission and margin, using his deep understanding of organizational dynamics, online learning, strategic differentiation, decision-making, and more. Prior to joining Extension Engine, he was a faculty member, administrator, and dean at Michigan Ross and Babson College for 20+ years. He holds an M.B.A. from Georgia Institute of Technology and a Ph.D. in Decision Sciences from the Wharton School of the University of Pennsylvania.

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