25 Questions to Ask for a Successful Digital Transformation

You have seen the statistics that 80% of digital transformations fail to deliver on expected outcomes. The reasons vary but often they come down to lack of stakeholder engagement, poor communications, and inadequate planning and budgeting for change management.

80% of digital transformation fail to deliver on expected outcomes.

The following are some of the questions that we ask clients to answer as they begin a digital transformation.

Who are our stakeholders ?
What problem are we solving?
What opportunity are we creating?
Will a change to technology be part of the solution?
What is our organizational capacity for change?
How will our people be impacted?
Who supports this change?
Who should be part of the project team?
What is our budget for the change?
Who are our resources and what is their capacity?
What is our time frame?
How will this project be socialized? What is our change management plan?
Do we have existing functionality within our tech stack? Or do we need a new solution?
Can we engage with current vendors? Do we need to investigate new technology partners?
Have we clearly defined our requirements in a format that can be shared with vendors?
Have we prioritized key functionality and required services?
If we require new vendors, how are we selecting them to respond to our RFP?
Do we have a decision matrix to effectively rank vendors responses?
What is the vendor implementation model?
What is the vendor service delivery model?
What do current clients say about our preferred vendor?
What is our FTE commitment for implementation and organizational adoption?
What is our communication strategy and plan?
Do we have internal project management resources or do we need additional support?
Do we need backfill in order to free up project resources?

While these provide a framework, the details of answering each of these questions are often complex. For example, Questions 2 & 3 involve discussing business requirements as they relate to human capital or finance functionality with a variety of stakeholders. Question 4 requires discovery and reflection. Often, clients seek a technology solution for a problem but the solution won’t be found in a new technology. Solving the problem requires an analysis of policies and processes to identify the root cause. The solution is often found by fixing a broken internal process, communicating more clearly, or better understanding the capabilities of existing technology.

Reasons for failure include lack of stakeholder engagement, poor communications, and inadequate planning and budgeting for change management.

We offer this list as a starting point for organizations as they consider undertaking digital transformations to support their human capital and finance functions. While the list will improve the probability of success, engaging an experienced advisor is the secret sauce.