5 Questions Every CIO Should Ask to Prepare for Digital Transformation

Robby Gupta

The business landscape is constantly evolving and is simultaneously creating new opportunities and challenges. It is redefining competition and putting forth a need to upgrade continuously.

At a time when technological disruptions are turning the competition more intense by the day, businesses need to transform their digital strategy to stay ahead. Rather than a choice, digital transformation is becoming an indispensable business need in this new age.

It would be only fair to say that it’s an unsaid imperative for organizations today to make digital transformation an integral part of their strategic vision.

Transformation helps them connect with their customer more effectively, bring in innovation at the workplace, create new opportunities and realize the potential of organizational data.

However, it’s crucial to remember that digital transformation is a complex exercise. It requires a clear vision, well-crafted strategy and all the right resources for the transformation to be a success.

Read: Common Roadblocks in Digital Transformation Journey

The CIO has a critical role to play in the entire exercise. To ensure the success of digital transformation, he/she needs to be on top of emerging technologies and determine what’s right for the business. But the digital transformation isn’t solely about technology.

The CIO is required to run the entire digital strategy, oversee the transition and drive agile practices across the organization, all the while managing the talent.

It requires a thorough clarity and preparedness, especially considering it’s a long-term exercise and requires precision in approach.

Here are top five questions that the CIO should ask to be better prepared to drive the transformation exercise effectively:

What is the objective the organization aims to achieve through the digital transformation?

This is the most important question to ask before starting off on a digital transformation journey. Review thoroughly the existing IT capabilities of your organization and identify the focal points. Determine the areas of your IT operations where there are concerning gaps. Once you’ve identified the areas, prioritize them and start planning. Hiring a digital consulting firm can also be helpful in this.

Remember, the transformation initiative will yield result only when it is relevant for your business. It has to be purposeful with actionable objectives. There are many organizations who rush to join the transformation bandwagon — considering it the latest trend. They often miss out on defining their strategic goals clearly; thus, failing to realize them.

Therefore, before you finalize your transformation initiative, make sure it has the potential to make a difference. An aimless venture with a poorly crafted strategy can be detrimental to your business.

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Are your IT strategies aligned with corporate objectives?

Evidently, the IT department has an important role to play in transformation. The long-term exercise involves the adoption of new technologies and the IT team facilitates these changes and ensures proper implementation. That’s why it’s crucial that the department understands the transformation vision and ultimate objectives.

CIOs should make sure that the IT department is working in alignment with all other business units. In addition to that, all IT resources should be working on high-value tasks and not invested in redundant jobs. Here, CIOs are required to take an agile approach while managing technology during the transformation phase.

As the role of IT in an enterprise evolves with the addition of new technologies, synchronization between IT and strategic objectives becomes more important than ever. To ensure the transformation’s success, it’s critical to ensure that IT strategies are aligned with business goals. Without this, it would be impractical to expect significant transformation benefits.

Do you have the right talent to drive digital transformation?

In a digital transformation, execution matters more than the solution; hence, talent matters more than technology. Lack of right talent is one of the biggest hurdles when it comes to driving transformation. And when we say right talent, it doesn’t mean technical expertise but strategic thinking to drive the process.

Online platforms and apprenticeship programs can prove effective in doing so. Also, employers can collaborate with educators to find the best resources and prepare them for a competitive career.

Competition in business also involves a race to find the top talent. In this scenario, hiring people with in-demand skills can be expensive. It’s recommended to review the existing team and identify resources who can be trained in specific areas. Give them the resources they need, share accountabilities with them and encourage them towards creative thinking.

The organization needs to establish a culture of learning where resources can not only learn how to tackle challenging assignments but also work with a diverse set of colleagues to develop new skills. It’s not just to address changing digital needs but also to prepare a workforce of the future.

To expedite filling up the talent gap, it’s always advisable to hire digital transformation services of an expert team who has executed this before to drive business goals.

Does your IT contribute to building strategic business partnerships?

IT holds a critical set of responsibilities in any digital initiative. Ideally, the IT function should have the right capabilities to interact with the business in a strategic manner. It should work as a trusted advisor for the business.

However, stakeholders in a business are generally not quite sure whether IT is able to build strategic business partnerships. There can be several reasons behind this general perception based on past experiences. For example:

  • ◙ Primary focus on technology rather than business objectives
  • ◙ Experience of working with people with insufficient or no understanding of transformation
  • ◙ Inadequate or inefficient IT infrastructure

IT function should be equipped with the knowledge of how the business functions, and how technology can support in its strategic initiatives. The CIO should ensure that there is adequate infrastructure and the focus continues to be on strategic objectives and not on technology.

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

Digital transformation is not a one-off instance. It’s an ongoing process over the course of years. Therefore, it’s important to measure its ROI so as to take timely corrective measures to ensure its success. Standards have to be set in place to avoid any confusion.

Businesses eventually want to cut down costs and increase revenue, profitability, and value to customers. So, ROI should include these metrics as well. However, it should not be limited to them as they represent short-term objectives.

Moreover, these are the metrics that the company must already be tracking. Instead, the focus should be on the metrics that give visibility of transformation progress. For example:

  • ◙ The contribution of each department to the transformation
  • ◙ New customer acquisition rate
  • ◙ Change in customer behavior
  • ◙ Profits generated due to the implementation of the initiative etc.

Broadly, you may want to divide the KPI between operational performance and customer experience.

There is a need to understand that mere proper planning is not sufficient to ensure positive outcomes of the digital initiative. Choosing the right KPIs to measure success is critical.


Rather than the leader of the IT department, CIOs are strategic partners of the business and their decision has a direct grip on the performance of the organization during the transformation process. The above questions can help them ensure an effective transformation of enterprise IT architecture.

Contact us if you have any questions related to digital transformation. We’ll be glad to assist you. We’re one of the leading digital transformation consulting firms helping our clients drive business efficiency and better customer experience.

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about the author

Robby Gupta

Robby Gupta is the head of US operations for TechJini, Inc. He has had varied experiences working in New York, Cupertino, and Bangalore with packaged & amp; custom web and mobile app development for an assortment of industries. His current focus is Immersive Technologies, IoT, AI bots and their applications in the digital enterprise.