Amazon’s Stephen Orban on the Five Biggest Mistakes Companies Make When Moving to the Cloud

Recently, I spoke with Stephen Orban, a General Manager at Amazon Web Services and author of the new book, Ahead in the Cloud. Orban’s book is a fascinating look from someone with extensive insider knowledge about how companies can make the most of their transition to the cloud.

As I’ve written before, I see tremendous opportunity in the cloud, but also recognize that many companies are hesitant to take the first step towards migration until they’re forced to. Inertia is a powerful force, but companies can’t risk being left behind when it comes to figuring out what the cloud will mean to their business. There’s simply no denying that it’s a technology that will be an integral part of the enterprise in future, and they only way to understand what it will mean to you is to get started. That is the core of Orban’s advice.


Author and AWS General Manager, Stephen Orban

During our interview, I had two main questions for Orban pertaining to how companies can move to the cloud as smoothly as possible. I’ll document his ideas about analyzing how ready a company is technically in a separate article, but in this article, I want to outline his thoughts on the five biggest mistakes that companies are making in their journey to making the cloud useful for their business. While this is a topic upon which it is hard to generalize because each company’s journey is unique, I still think that there are enough commonalities for businesses to pay attention to.

Mistake 1: Analysis paralysis

Orban’s top mistake was one that I’ve pointed out before — analysis paralysis, in which the fear of doing the wrong thing becomes so strong that it leads companies to do nothing at all.

“I see a lot of companies that are so overwhelmed that they don’t know where to begin. There seems to be so many things that need to change, and the result is they can’t process what it would take to even begin moving to the cloud,” Orban said.

He and I agreed that the best course is not to try to move the entire organization to the cloud overnight. Instead, the migration should occur with an individual project. “Companies should just start with a project, get moving, prove the value, figure out what’s going to work well in your organization and what doesn’t and then grow at a rate from there,” he said.

Mistake 2: Forgetting about training

To combat the fear of change, Orban highly recommended that companies develop robust, and well-thought out training plans for their staff. “Training takes away the fear,” he said.

Many companies underestimate the amount of retraining and re-skilling teams will need to succeed with the cloud. They should instead overplan with a strategy that recognizes every person who will need additional training in the business. “I do believe that engineers, in particular, are in general innately curious and want to learn new things, yet folks who have been in roles for a long time can be afraid of what they don’t know and that fear will present itself as resistance to where the organization wants to head,” Orban said.  “Companies don’t take that seriously enough because they think that a top down edict will be good enough. But you have to have a training plan.”

Mistake 3: Moving too slowly

Orban’s third mistake draws on his first: fear leads to migrations that occur too slowly. “Cloud migration isn’t as always as difficult as people think,” Orban said. “Computer science fundamentals and physics and just general science constructs have not changed as a result. If anything it’s easier to build distributed systems at scale; you just need to learn some of the basics of it.”

Overcoming this laggard pace means that not everything can be planned perfectly in advance. The key is to just start with a few projects and then assess what works and what doesn’t. Not everything has to be ideal on the first go-around.

“I understand at a portfolio level that people have budgets and they need to manage those budgets. I get that, and they should continue to do that if that’s what their business requires. But most of the companies I’m talking about are big enough where there’s wiggle room to get a couple of projects started and not overthink it. Start with something that’s important enough that stakeholders care, but not so important that some failure is not an option,” Orban said.

Mistake 4: Failing to set a clear vision

Especially for companies that recognize the power that can come from going all-in on the cloud, Orban identified a lack of vision as a major pitfall. He emphasized that when a business is just getting off the ground with the cloud, the vision isn’t needed — but once the company is ready to expand cloud usage beyond just a few projects, that’s when a vision is essential.

He reiterated that the change to the cloud is not different than any other change process. “If you’re going to be leading some sort of significant change program where you’re going to be doing any kind of major migration or a change to your operating model where you’re moving to DevOps or Agile or scrum or whatever it is, you want to paint a vision for the organization about where you’re going, what good looks like, and, ideally, what are measurements you’re going to put in place for how you’re going to measure success and then hold people accountable to those,” he said. “You need a way to not just hold people accountable but also shine a light on them when they do the things you want them to do because it serves as a great positive reinforcement to the rest of the organization. You’ve got to have a plan for this.”

Mistake 5: Continuing to work only with existing partners

Orban’s final major mistake is that too often, when it comes to partner organizations, companies stick with what they know. Again, the fear of the unknown plays a huge role here in keeping companies from fully capitalizing on the cloud.

“Many companies just continue to work with their existing partners, particularly in businesses that have done a lot of IT outsourcing. When you have an opportunity to do something new and different, relook at the types of skills and people you want to obtain those skills from. There’s a whole new breed of system integrators and consultancies and digital capabilities that you can get, and companies need to take advantage of that.”

Change to the cloud isn’t easy. But it doesn’t have to be as fear-inducing or hard as some companies think. Orban’s advice is sound to keep in mind as companies begin their journeys.