digital transformation questions to ask

Digital Transformation Questions To Ask First

Digital transformation (DT) is now a necessity for all businesses. These digital transformation questions to ask will set you on the right track. 

Many businesses acknowledge the need for digital transformation. However, they still struggle to achieve the desired results. Around 66 to 84% of DT initiatives fail. However, such a high failure rate isn’t surprising. Why? Because many leaders attempt to install new digital technologies without getting rid of legacy cultures and operating models. 

Keep in mind that DT isn’t just a system update – it is a top-down cultural change that affects how a business operates. As mentioned, DT is now a necessity. Yet, it comes with tons of benefits such as streamlined operations and better customer service. 




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There are digital transformation questions to ask before embarking on the journey. These digital transformation questions to ask aren’t just “what talent do you need” or “how much is your budget”. The key here is to probe deeper. 

Is this a digital upgrade or a digital transformation? 

Most companies aim for digital transformation but end up with digital upgrades. These two terms are entirely different. A digital upgrade is the use of digital technologies to increase the efficiency of an existing process. For instance, upgrading internal communication systems or increasing your marketing spend. 

DT also uses digital technologies. However, it changes the way you operate and how you provide value to your customers. Identify what you are really in. If you discover that you’re on an upgrade instead of a transformation, ask yourself if that will suffice. However, business models based on digital networks create market valuations four times higher than the rest.

Are you really bought in, and is your team?

Most DT leadership teams are not really passionate about the process. They change just for the sake of changing and keeping up. However, everyone must be passionate about DT for it to succeed. 

Are you prepared to share value creation with your customers?

The latest technology-enabled business models give customers and other networks a share in value creation. For instance, Uber relies on a network of drivers; eBay relies on a network of sellers. Accessing external assets will enable you to achieve outstanding profitability. 

However, many leaders hesitate to give up a part of their control and rely on external networks. Indeed, you’ll need new, co-creative styles for this one. Yet, it allows your organization to discover and use enormous sets of capabilities and under-utilized resources. 

Do you know how to measure the value you intend to create?

It is up to you what you want to measure. Most organizations focus on physical capital by tracking inventory, productivity, and other traditional KPIs. Yet, it is also useful to track intermediate indicators such as sentiment and engagement as well as network co-creation and value sharing.

Are you ready to make the tough calls about your team?

Sometimes you’ll need a new set of people to create your vision. Many organizations decide to outsource to have their current staff dedicated to doing what they have always done. 

Hence, you must make the tough calls early on regarding your team and board. Moreover, if you need to turn over some team and board members, don’t feel bad. It’s really a good thing for the organization—creating a balance between the old and new.

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