AWS Cloud Enterprise Strategy Blog

What Makes Good Leaders Great?

“It’s a lack of clarity that creates chaos and frustration. Those emotions are poison to any living goal.” -Steve Maraboli

Leaders lead in many different ways. Some lead by fear, some by example, some with charisma, and some lead through others. And while every leader’s style is slightly different, experience has taught me one thing that stays the same: people are most likely to follow those they understand.

People believe in what they are able to understand. When it comes to change management, they’ll typically revert to what they’re comfortable with — the status quo — when they don’t understand the direction in which they’re being led. Leaders can resolve this dilemma by providing clear and concise direction. The ability to provide clarity of purpose separates the great leaders from the good ones.

I recently wrote that today’s technology executives should consider themselves Chief Change Management Officers (CCMO™) when leading their organization’s Journey to the cloud. In addition to handling the merging of business and technology, the CCMO is also responsible for providing clarity of purpose. That means being able to articulate your strategy, how your team fits into that strategy, where there is and isn’t flexibility, staying determined, and staying patient.

Organizations move to the cloud for different reasons — some to save money, some to expand globally, some to improve their security posture, and some to improve agility. Through my experiences I’ve found that companies begin to embrace cloud as a platform across the entire organization once they realize how it helps them devote more of their resources to what matters to the business. Those are the activities that matter most to your customers and your stakeholders. And unless you’re an infrastructure provider, these activities are not related to managing infrastructure.

Whatever your short or long-term motivations may be, I’d encourage you to make them known and make them measurable. Clearly articulate your motivations and goals to your team and your stakeholders, and hold everyone accountable for moving the needle in the right direction.

Early in my leadership tenure, I thought — naively — that just because I was the boss everyone would do what I said. I learned the hard way that this is, of course, not how leadership works. It wasn’t until I started to clearly articulate what was important about our strategy that the behavior of my team started to change. Before presenting a new idea or goal to my team, I had to consider how everyone fit into this strategy and how it tied back to the business and everyone’s careers. Then, I had to capitalize on every opportunity to reinforce these points.

This meant talking strategy at quarterly town halls, on internal blogs, during sprint planning sessions, and using every meeting as an opportunity to relate the work being discussed back to our strategy. Sometimes it felt redundant, but the bigger your team is, the less likely each individual regularly hears from you. Remaining determined and being consistent with your communication is key.

Fear of the unknown is one of the most common points of friction in any change management program. I’ll address this point in an upcoming post when I cover the Educate Staff best practice of the cloud Journey. It’s worth mentioning in this context that a great way for leaders to address this friction is to give everyone on the team clarity around what will happen with their roles.

Making it clear what everyone’s options are in light of the changing direction will give them a clear path to understanding how they can participate, and likely some peace of mind. When I was the CIO at Dow Jones, we gave everyone in the department training and gave them the opportunity to move to new roles within the company. We made it clear that we wanted everyone to be a part of the Journey, and sometimes that meant they had the opportunity to take on something new. It was in everyone’s best interest to take advantage of the wealth of institutional knowledge they held, and in many cases it became even more valuable when directed toward a different area or discipline. That knowledge is hard to replace, and I’d argue you should make every effort to keep it.

In almost any strategy that involves change, there will be some elements that you need to stick firmly to and some that may be more suggestive. Making it clear to your team which is which gives everyone the opportunity to continue pushing boundaries in the appropriate areas, and shows that the organization is still willing to learn.

At Dow Jones, we made automation a hard requirement for everything we did at the beginning of our Journey. Once we became skilled enough with our cloud operations, we were able to make financially appealing business cases to migrate dozens of data centers to AWS. At this point, a “lift-tinker-and-shift” strategy was better suited to move us toward these goals. This required some clarity of purpose — we had to communicate this several times — to get right, but once we relaxed our automation constraint and applied a spectrum of migration techniques our progress accelerated substantially.

Every enterprise’s cloud Journey will hit some bumps in the road. I wish I could say that everything is going to be perfect and that the industry has figured out how to prescribe what every company should do every step of the way. At AWS, we are committed to becoming more prescriptive based on what we see working for our customers, but it’s unlikely the whole process will be completely turnkey. I’ve found that it’s best to treat the bumps you hit as learning opportunities, not to chastise your team for making mistakes (although you shouldn’t accept the same mistake twice), and swiftly address skepticism that goes against your purpose. Don’t let those who would be more comfortable reverting to the status quo influence the potential of your vision. This isn’t always easy, but your patience and perseverance will pay off.

Remember, practice makes permanent. What’s worked for you? I’d love to hear about it.

Keep building,

Stephen Orban

Stephen Orban

Stephen is the GM (General Manager) of a new AWS service under development, and author of the book “Ahead in the Cloud: Best Practices for Navigating the Future of Enterprise IT” Stephen spent his first three-and-a-half years with Amazon as the Global Head of Enterprise Strategy, where he oversaw AWS’s enterprise go-to-market strategy, invented and built AWS’s Migration Acceleration Program (MAP), and helped executives from hundreds of the world’s largest companies envision, develop, and mature their IT operating model using the cloud. Stephen authored Ahead in the Cloud so customers might benefit from many of the best practices Stephen observed working with customers in this role. Prior to joining AWS, Stephen was the CIO of Dow Jones, where he introduced modern software development methodologies and reduced costs while implementing a cloud-first strategy. These transformational changes accelerated product development cycles and increased productivity across all lines of business, including The Wall Street Journal,, Dow Jones Newswires, and Factiva. Stephen also spent 11 years at Bloomberg LP, holding a variety of leadership positions across their equity and messaging platforms, before founding Bloomberg Sports in 2008, where he served as CTO. Stephen earned his bachelor’s degree in computer science from State University of New York College at Fredonia.