AWS Cloud Enterprise Strategy Blog

Great Leaders Make New Rules

“I am free, no matter what rules surround me. If I find them tolerable, I tolerate them; if I find them too obnoxious, I break them. I am free because I know that I alone am morally responsible for everything I do.”
― Robert A. Heinlein

Good leaders enforce the rules. Great leaders know when the old rules no longer apply and that it’s time to make new ones. As Heinlein suggests in the quote above, sometimes this means actually breaking the rules. But before they do either, great leaders wanting to influence behavioral change across the organization must first know the existing rules and then decide the ifs, whens, and hows of altering them.

Leading an organization on its Journey to the cloud is one of the best opportunities technology leaders will have to make new rules. I would even argue that a technology executive-turned-Chief Change Management Officer(CCMO™) has an obligation to inspect his or her processes and determine which rules are still appropriate for governing a cloud-enabled enterprise.

New Rules for New Missions

Many of us are familiar with process-based frameworks such as ITIL, ITSM, and plan-build-run. These were developed over the last few decades in order to standardize the way IT was delivered and operated in large organizations. The creators of these various frameworks prided themselves on being able to improve some combination of efficiency, effectiveness, quality, and costs by clearly defining roles, responsibilities and processes in the organization.

These methodologies made sense when everyone used them to govern similar activities, like managing infrastructure. But today, companies are increasingly looking to focus on the activities that delight their customers and make their organization different: Talen Energy wants to focus on generating power from a fleet of power plants that use diverse fuel sources. Nike wants to bring inspiration and innovation to every athlete in the world. GE wants to build, move, power, and cure the world. Before, managing infrastructure would be the table stakes for such missions. Now, the cloud provides the table stakes, and so it follows that today’s CCMO should keep what makes sense from their existing process-based frameworks, but not be afraid to make new rules to govern their new, more modern and increasingly digital, operating models.

Look for Organizational-Wide Opportunities

Regardless of where you are on your Journey (or any change-management program), I urge you to consider what your roles, responsibilities, and processes will look like in the cloud-first world of tomorrow. This will take some exploring, and will be different for every organization. Operations, IT audit, and financial management are among the topics I frequently discuss with enterprise executives when it comes to changing the rules.

I should note that this list is by no means exhaustive — it would be impossible cover every angle and nuance here. I’d love to hear about some of the others you’re finding, and welcome your responses!

Operations. Earlier this year, I wrote a series of posts for enterprises considering switching to DevOps. These pieces include a number of rule changes to consider:

Focus on creating a customer-service-centric IT department that strives to understand what customers (internal or external) need and remains open-minded about what and how solutions are delivered.

The run-what-you-build concept, meanwhile, focuses on exactly what it sounds like. In my experience, this practice tends to be one of the most difficult changes for enterprises to make, perhaps because it is so far from the traditional IT process-based frameworks. There are many, many good reasons to adopt run-what-you-build and the inherent rule-changing that goes with it, and I’ve yet to come across an organization that didn’t reap plenty of benefits from the shift.

Finally, it helps to know what you can expect as you make these and other operational changes. Remember to remain patient — making changes to rules that have been around for decades or longer won’t happen overnight.

Auditing process. Auditors are an essential part of any enterprise’s Journey. Right now, many executives still associate the phrase “audit function” with negative thoughts and headaches because they believe an audit could delay their progress. But that isn’t a productive or progressive way of looking at the situation, especially when you’re trying to establish new rules. Audits are your friend, not your enemy. Use them to educate everyone that you’re better off with the new rules that you’re making and get feedback. Collaborate with your auditors early and often, and explain what you’re trying to accomplish. Get their input and I’m sure they’ll improve your thinking and your results.

When I was with Dow Jones, I was very anxious about explaining our plan to adopt DevOps and run-what-you-build to our auditors. This anxiety made us prepared, though the stress was somewhat misplaced. Once we illustrated that our controls were greatly improved because of the new rules we were employing around automation, our auditors became more comfortable with our future direction. By showing them early that we no longer had ownership spread across siloed teams sitting next to one another but communicating through tickets, and that the opportunity for human mistakes was much less, we were able to build the necessary confidence and trust of our auditors.

These same tactics apply when dealing with your security and legal teams. Involve them early and often, and partner with them to ensure that everyone’s needs are met. Make sure to be empathetic to your executive stakeholders, and find ways to address their needs with your rules.

Financial Management. In nearly all cases, moving from large up-front capital investments, where capacity is uncertain and often overbought, to a pay-as-you-go (and only for what you use) model leads to better cash flow. Having said that, managing variable expense may change the way you’re used to governing your finances. Typically, it’s best to work closely with your finance department to make new rules that allow you to capitalize on the levers cloud offers and get the most out of your budget.

At Dow Jones, our cloud expenses grew slower than our infrastructure investments declined. We may have been getting a lot done, but eventually our growing bill caught the interest of our finance team, and they became our partners in optimizing our budget.

As our resources became increasingly focused on product development, we reached a productive monthly cadence with our controllers around forecasting, Reserved Instances (RI) purchases, and capitalizing an increasing percentage of our labor costs. We learned that it’s best to stagger RI purchases over the course of several months as your compute needs evolve, and that there are a number of partners who can help with financial management. Cloudability is one of them, and they recently posted a great article on staggering RI purchases. This piece does a much better job of explaining this than I could here.

As I noted, these are just some of the rules worth scrutinizing on your Journey. I’d love to hear about some of the others you encounter. Whatever they are, don’t be afraid to make new ones.

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.