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TOP-30 Interview Questions About Digital Transformation

Facing interviews are an integral part of having a healthy corporate life. So in this post, we have compiled a list of TOP-20 digital transformation interview questions that you are almost certain to face in any job opening. The information is a good knowledge base that helps you gain a higher level for your future profession.

Questions on a digital transformation can be tough, especially when you face them in an interview setting. Some of these digital interview questions are relatively straight forward and basic, while the rest are open and require a bit of thinking. You can try to answer them on your own before checking the correct reply.

To open digital strategy interview questions, there are no right answers as it is where your creative thinking and analysis start working. Here we have compiled a list of digital transformation questions and answers that you would find helpful for sure.

Okay then, without further ado we present the first question.



1. What IS digital transformation to you?

Digital transformation is, in reality, a 2 phase process. The first part is about the usage of digital technologies like cloud computing and social networking. The second half, on the other hand, is concerned about changing how the organization works itself.

They complement each other in reality. If you think the first as ‘what’, the second is certainly about ‘how’. You cannot succeed without taking into account both of them.


2. Why do you think is digital transformation so important?

There are many reasons behind the necessity of business transformation. One of the key reasons is that an organization has failed to evolve naturally over time. Another slightly different reason is the change in consumer behavior over time. Whatever may the reason be, if you think it is going to benefit the organization it becomes important.


3. Is it equally important for all types of businesses?

Certainly not. Business to business industry, for example, is much more concerned about automation and cost reduction. So it all ultimately boils down to having an effective action plan.


4. What are the most important elements of digital transformation?

First, a clear vision – absolutely necessary. Having a clear vision of what your organization NEEDS and what doesn’t is in fact key to success. You certainly don’t want to waste your resources on things that simply don’t matter. Second, a well-tested strategy. And last but not the least, the technology itself. Knowing what you want is not enough, after all – you need to know how to achieve them.


5. What could create additional value if the employees were working together more closely?

An organization is not merely a machine, it’s a hierarchical social structure. There would be cases when an employee wouldn’t be able to make sense of the data. So pairing them with people who are using them could make a difference.


6. Which functions, according to you, would yield more value if there were more coordination?

Working in small groups can work wonders. Pairing peoples who normally do not work together can have a remarkable outcome in terms of productivity. The team members start to see newer opportunities and experience the situation in a new light.


7. How would/could you implement your action plan?

Collaboration is the key to any success. So keep testing your ideas. Share your ideas with others, maybe with someone from another team. Small experiments are a great way to break the ice.


8. Where do you think the change is taking place?

The start is always tough. You never know where exactly to start. The digital journey could be intimidating, and daunting at the same time. But as the spearhead of this transformation process, you need to understand the new frontiers where the changes are taking place. Moreover, you need to understand what aspects of the business is getting affected by it and what kind of foundation is needed to support that kind of transformation.


9. Where should BUSINESSES start?

It is one of the most common digital transformation leader interview questions that you would face. The starting point depends on the need of the specific organization. The goal ultimately is to optimize and coordinate resources more carefully. For some organizations, the top priority is to connect the internal resources more efficiently. For others, the coordination of internal operations is much more important.


10. What are the main obstacles in your opinion?

One of the main obstacles that the organizations face is the strategy – a well-thought, battle-tested strategy. The actual obstacle is the lack of an informed strategic view of the whole situation. Another very common hindrance is the lack of joined-up thinking. Often you would see a plan that is all-over-the-place, and the most probable reason behind such a mess is that the decision-takers have no idea as to what to expect from the new technology.


11. How are you going to take the budget into account? What role does the budget play in your plan?

Many transformation journeys come to their knees soon after they start due to having a rigid budgetary cycle. Your plan needs to have the steam to achieve the long-term goal while taking into account the short-term milestones. Studies suggest even less than one-fifth of the organizations are able to quantify the return on investment.


12. What do you think is a “digital business platform”?

A digital business platform (DBP) is a recombination of a variety of different tools in a single package. These orchestration and integration tools enable the organization to create new assets.


13. What is the need for an effective “digital business platform”?

The need for a “digital business platform” is multi-dimensional. But the key reason why an organization would need a DBP is simply the associated cost. Creating and maintaining the tools internally would be way too expensive, if also not time-consuming.


14. What makes a ‘digital business platform’ better than the others? What differentiates them?

Speed to market and ongoing work agility is of top priority when it comes to choosing a good ‘digital business platform’. You would also like to know if the platform offers cloud-based service and good API service. While not essential these are critical to pleasant and flexible user experience. Engagement is a good metric for gauging the usability as it helps measure to which extent it provides appropriate user experience to a wide variety of workers.



These are the type of questions which have no as such right or wrong answers. They are asked simply to judge your knowledge as well as your thinking capabilities.


15. How important do you think it is for the teams to collaborate across functions?

The digital transformation journey is not a separate thread of execution. It is an organization-wide process. As an expert, you need to put emphasis on internal collaboration. No doubt, leaders put teams that integrate functions across the organization at a premium.


16. Tell us how you have cultivated the RIGHT MINDSET to deliver the promise of the technology?

This is a question designed to assess your strengths and weaknesses. The evaluator is trying to understand your mindset, how well you perform as a part of a team, how open are to new and novel ideas no matter where they are coming from, and obviously how well you can deliver the business value of a technology. Having the right mindset and an open attitude towards embracing changes is, in fact, the secret to success.


17. How does communication take place inside an organization?

Communication is an effective way of provoking new thoughts as well as encouraging new behaviors that can add value. So communicating and exchanging ideas with your colleagues and superiors can make the change. Communication is not limited to only having dialogues; they can come in many other formats. In a nutshell, you should be ‘listening for’ (some useful idea) rather than simply ‘listening to’.


18. How can you leave your impression on the digital investments that can sustain value?

It is a rather tricky question. There are certainly no wrong or right answers. The evaluator might be trying to get a hold of your thought process. They are trying to gauge how innovation played its part in your strategy.


19. What do YOU need to do differently? What are the things that you would like to change about yourself?

The feeling of ‘superiority’ is possibly the most common hindrance in learning something new. As soon as you start thinking that you know enough of it you are doomed. It has to be changed, sooner rather than later. In this fast-moving, ever-changing world you are simply going to fall behind if you do not keep learning.


20. Tell us how you have helped an organization achieve the goal through digital transformation?

A very important question. The evaluator is looking for certain aspects of the transformation in your answer. First, do the candidate even have the vision that is suitable for the company? Second, is he/she a leader material? Third, How much do you deserve the position? The following two questions are often followed by this question.


21. What were the things that went according to the plans?

This is very common among the digital strategy interview questions and needs special attention. Try not to boast too much, while keeping the good parts intact. Needless to say, try to be as honest as possible. The scent of dishonesty can be tracked from miles afar.


22. What did NOT go according to the plans?

This is most probably even more vital than the earlier question. Never, ever say: “None!” (yes, even if that was the case which is very unlikely). Get ready to be bombarded with a question like, “how would your plans be different if you were assigned the same task NOW?”.


23. Where do you think the company would find itself after two or three years? How do you think the transformation is going to affect the organization?

It can be a bit hard to answer. You cannot be too optimistic, else you would sound like you are being wishy-washy. That being said, you should not be too critical either. That might show that you are not confident about your plan of action. The best thing to do is to place a realistic-looking future plan, be it a bit on the conservative side.


24. How would you make your strategy future-proof? Any opinion?

The evaluator is probably looking for an honest answer. Really! Nobody knows about the future. Nobody knows how the events are going to turn out. So it would be better if you try to deliver your suggestions (no matter how hilarious they might sound) and mention that the future is uncertain.


25. What is the most influential technology for digital transformation to you?

The evaluator is most probably trying to gauge your thought process. What he/she is expecting to hear is more of a categorical answer e.g DevOps and not some very specific solution. Whatever you decide to tell be sure not to sound too outdated. That can be an immediate no-no. That being said, keep in mind that technology itself is not the solution. It’s just a part of the whole process, and that is ultimately the point of digital transformation.


26. How do you think your previous experience is going to be relevant for the current opening?

You need to prepare beforehand to handle this type of question well. The best thing that you can do is to study the organization and try to frame out your relevant experience inside your mind. Keep it short while trying to cover as much ground as possible.

Make a list of all the important and necessary points inside your mind, write them down if possible. Filter out the non-relevant ones, and obviously put the emphasis on your actions, not yourself.


27. How are you going to test ideas?

Not every idea is the same. Some are good, some are great, and some are simply dreadful. There is no hard and cold rule of testing new ideas. It ultimately is a game of experience. This is precisely why many organizations have advisory boards consisting of experienced and pro players. This way you can incorporate external voices and opinions into consideration.


28. Why do you think digital transformation is so important for businesses?

This is the type of question where the evaluator would certainly try to measure your grasp in your subject. Again, try to keep it short while sticking to the point.


29. If businesses really need to transform digitally, why do you think so many organizations are struggling to get going with business change?

The main reasons are two: either the higher-ups have next to zero experience about the transformation process, or the organization simply lacks leadership. The question aims to see whether you can think out of the box.


30. Why should anyone be led by you AT ALL? Why should others follow you?

There is no silver bullet for this question specifically. Instead, think about the things that you want to do, how you want to achieve it, and, last but not the least, your relationships and rapport within the organization. At the end of the day, you need to show how much YOU are willing to learn. How much you believe that change can bring success.


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