Amazon’s Stephen Orban on Five Diagnostic Questions to Evaluate the Health Of Your Cloud Migration Program

The cloud has become an omnipresent part of the enterprise technological landscape. As I continue my research into how companies are moving to the cloud, I always enjoy speaking experts who can provide unique insight into what make these transitions tricky, and what can make them successful.


Author and AWS General Manager, Stephen Orban

As part of this research, I spoke recently with Stephen Orban, a General Manager at Amazon Web Services and author of the new book, Ahead in the Cloud. I wrote about his perspective on the five biggest mistakes companies are making as they move to the cloud in a previous article, but in this piece, I asked him about another topic that I think is crucial to ensuring a smooth migration. Namely, when he is speaking with a CEO or CTO, what are the top five diagnostic questions he would ask to try to determine whether the company was going to be successful in the cloud? Here’s what he shared.

Question 1: What’s your business case and who has bought into it?

Read through the academic and business literature on change theory, and you’ll get a resounding theme: change can’t happen in an organization without thorough buy-in from key players. Orban emphasized this aspect as his most important question. “I’ve seen a lot of companies where there’s a really hard charging champion and they want to move fast, go, go, go, go, go. That’s great and they can create a lot of positive change but at some point if they don’t get buy in from the CEO, the CFO, the Board, and the non-kind of technical stakeholders, progress stalls,” he said. This makes sense — you need both top-down and bottom-up buy-in to implement cloud migration well and the only way this can happen is with a strategy to cultivate this buy-in at all levels.

Question 2: How are you measuring success?

Regardless of the realm of work or personal life, to succeed, we all now recognize it helps to have quantifiable goals. That is very true with the cloud. The goals themselves will vary depending on the company, and even within the business, there may be separate goals for different teams and individuals. But firm accountability standards and metrics are key.

“It goes deeper — not just how are you measuring success at a company level but how are you measuring individual team success? Hopefully the answers are specific,” Orban said. “You would hope that if you go to an individual manager, they would know how they are measuring success for their team and that the metric being used would hold laterally across the organization.  That has great aligning capabilities across an organization too.”

Question 3: What is your training plan?

Orban talked extensively about the need for thorough training plans in the previous article I wrote about our interview. This means having a strategy to train employees on the new technology and develop new skill sets, as much as selecting the right small projects to start adoption with before rolling it out to the company at large. Without such a plan, Orban doesn’t believe a company can succeed.

Question 4: How do you escalate issues?

This question goes back to the strategy and vision planning implied by question three and the development of a training plan. “The question you need to address is when stuff comes up and you need an answer quick, what is the mechanism for resolving that?” Orban told me. The cloud will bring about fundamental changes in hierarchies and business processes within an organization and if you don’t have a plan for how to overcome and solve these challenges, you’re destining yourself to failure before you even begin.

Question 5: How has your org chart changed?

The cloud is a transformational technology. It allows for collaboration to happen in a way that was previously impossible and if the business itself doesn’t respond to its capabilities, there will be a lot of internal struggles.

As Orban pointed out to me, if he asked a CEO how their org chart has changed in response to the cloud, the wrong answer would be “not at all.”

“Companies do best when they move away from siloed teams with highly specialized skills who are managing to capacity, to teams that have full ownership and accountability of some delivery product, service, or project, and a much more cross-functional teaming model. Your org chart and internal structure needs to reflect this,” he said.