15 Blistering Digital Transformation Questions Your Boss is Too Afraid to Ask You

Digital transformation remains at the forefront of every CIO's agenda, with multiple surveys and reports indicating that it's a top priority for IT leaders worldwide. The 2024 State of the CIO survey by Foundry revealed that 88% of surveyed CIOs believe their role is becoming increasingly digital- and innovation-focused. Similarly, the 2024 State of Digital Transformation report by TEKsystems found that 84% of respondents consider digital transformation as a core pillar of business strategy.

However, despite its growing importance, many organizations continue to struggle with getting transformation right. Some still view it as a project with a start and end date, while others see it as a technology initiative rather than an organizational change. So, what can CIOs do to avoid common pitfalls and steer their organizations towards successful digital transformation?

To answer this question, we've compiled a list of 15 critical digital transformation questions that every CIO must answer. These questions cover various aspects of transformation, from strategy and metrics to talent and cybersecurity.

1. Is this initiative about optimization or about growth and disruption? According to Anant Adya, executive vice president and head of Americas delivery for Infosys, digital transformation is about helping the company grow and disrupt. To achieve this, CIOs need to be clear on the business outcomes their initiatives will deliver and articulate outcomes in top- and/or bottom-line figures.

2. Am I using data to drive my transformation strategy? Data is essential for making informed decisions and measuring the success of transformation efforts. CIOs should leverage data analytics to identify trends, gain insights, and optimize their transformation initiatives based on data-driven evidence.

3. Is the organization's data ready to drive transformation? The 10th Annual B2B Data Report by Dun & Bradstreet found that only 57% of surveyed senior decision-makers believe their data can help them achieve their business goals. CIOs must ask if the state of enterprise data and data infrastructure is ready to support transformation.

4. Is my strategy organized around problems to solve, or technologies? David Rogers, a faculty member at Columbia Business School, advises CIOs to organize transformation workstreams around problems to solve. This approach helps to avoid the fascination with technology for technology's sake and focuses on solving real business problems.

5. What enterprise capability gaps will this transformation initiative close? Brandon Germer, a senior director analyst with research firm Gartner, recommends that CIOs ask and answer specifically what enterprise capability gaps a particular transformation initiative will close before pursuing that initiative.

6. Will my AI strategy solve a problem or address a gap? Greg Taffet, managing partner of Taffet Associates, advises CIOs to ask if their AI strategy will solve a problem or address a gap. This helps to ensure that AI is used to drive real business value rather than just for its own sake.

7. Who leads transformation with me? Krishna Prasad, chief strategy officer and CIO at UST, emphasizes the importance of collaboration in transformation initiatives. CIOs should not go it alone and should work closely with other business leaders to drive transformation.

8. Am I engaging people on the front lines to formulate DX plans? David Rogers advises CIOs to engage people on the front lines to formulate DX plans. This helps to ensure that transformation is driven by business needs rather than just by technology.

9. Am I identifying and using the right business metrics to measure progress? Most CIOs have moved beyond using traditional IT metrics to measure progress. However, it's essential to use the right business metrics to measure the success of transformation initiatives.

10. Do I have a DX budget and/or completion timeline? Transformation is not a project with a start and end date. It's an operational and strategic imperative that should be woven into all aspects of the organization.

11. Is transformation companywide? CIOs should examine whether transformation is happening across the organization or if it is occurring only in pockets. A holistic approach is essential to drive successful transformation.

12. Is all my talent ready? CIOs should ask if their talent is ready to drive transformation. This includes not only technical skills but also the ability to work collaboratively and make decisions based on data.

13. Is our workforce primed for digital success? Workers throughout the organization need skills to enable successful transformation. CIOs have a key role to play in ensuring that the workforce is equipped with the necessary skills.

14. How much time do I have to be successful? Laserfiche CIO Thomas Phelps advises CIOs to ask how much time they have to be successful. This helps to determine the resources and budget required to drive transformation.

15. Am I adequately addressing cybersecurity risk? Cybersecurity threats are continuously evolving. CIOs should ask if they are keeping their cybersecurity frameworks up to date with the risks that are continuously evolving.

In conclusion, digital transformation is a complex and multifaceted process that requires careful planning, execution, and ongoing evaluation. By asking these 15 critical questions, CIOs can ensure that their organizations are on the right path to successful transformation. Whether you're just starting your transformation journey or are already well underway, these questions will help you to refine your strategy, optimize your approach, and drive real business value from your transformation initiatives.