When there is a large digital transformation project, as a decision-maker, the most difficult question is “Where do I begin?” In 2017, I got an opportunity to work on one such large project.

The CFO of this organization wanted to modernize her department’s processes. But her department is only a slice of the bigger pie. Everyone going into the project knew that this is a multi-year project with multiple departments involved and stakeholders who are within and outside the organization. But the CFO’s goal was very clear. She wanted to begin with the last step in the process: invoicing customers. So, why did she want to start with the last step?

Typical of what you hear when it comes to pain points of handling business in spreadsheets, the invoicing process was prone to errors; no visibility into who paid and who was overdue; customers can’t self serve; each check sent back was charged by a bank for using their lockbox service, etc. So, she wanted to eliminate all of those.

When we went in as consultants and analyzed the process from the beginning to the end, we realized that it would take two years or probably more to rip and replace the entire system. This meant that the CFO wouldn’t get value on her technology investment for another 2–2.5 years. So, we had to start with the last step—invoicing—but leaving enough room in our model for retrofitting business processes/departments that would come in later.

What benefits do you have when you think strategically as the CFO did?

—See immediate benefits of a modern system instead of having to wait for 2-3 years. Just the invoicing project took about 6-8 months.

—Appetite for change is manageable: When you are rolling out a big project think about how much change you are introducing for your IT to manage and also your end users. Remember that it’s not just lift and shift. You are changing people’s way of working entirely. Maybe your IT is used to .Net technology and now you need to upskill your team to manage a cloud-based solution when the consultants leave. So, all this calls for careful planning. If multiple departments are impacted by changes all at once, it’s hard to manage this. So, make sure you have great adoption by focusing on those few users who will manage their business process in the new system.

—Spread your risks: A 6-8 month project is much more manageable than multi-year projects. Everyone will have a better handle on budgets, risks, and scope. People will not burn out and pay attention to what needs to be done. If you think about the tactical steps, like data quality and data cleansing, it becomes much more manageable when you chunk it out as opposed to millions of records spread across different systems that need to be migrated.

With all this said, we went live with the invoicing system and it was very well received. In the meantime, it was heartening to see how great the user adoption was. Both internal and external stakeholders were using the system and came back with feedback to improve the system further.

But the bigger kudos need to be given to my mentor who was the architect, project manager, rollup his sleeves and code if necessary—basically the jack of all trades and master of them all—who built a solution that was flexible enough so that subsequent departments can be retrofitted into this model. And we did end up working with them for several years with successful and almost painless rollouts, one project after another, bringing in more and more departments, and sunsetting their legacy systems.

With all this said, it’s important to:

—Understand the business,

—Listen carefully to goals being articulated,

—Remove any fuzziness around requirements,

—Not be swayed by shiny new features and develop a roadmap that will give the client a quick Return on Investment (ROI).

In our situation in this wildly successful project, the CFO was one of the best decision-makers and had very clear intentions and made sure that everyone around her understood this too.