Home Cloud Digital Transformation Checklist: A Note to Leadership by Andy Jassy (CEO, AWS)

Digital Transformation Checklist: A Note to Leadership by Andy Jassy (CEO, AWS)


The cloud might be the most disruptive technology in the past decade but the majority of the organizations are still not truly convinced to move to the cloud. The reasons could be the security concerns, non-availability of suitable solutions as per one’s use case, etc. Amazon Web Services (AWS) CEO Andy Jassy‘s keynote on the second day of AWS re:Invent 2019 had a theme – ‘Transformation‘, and moving to the cloud is a pivot to digital transformation. Andy Jassy provided a thorough checklist for digital transformation.

What actually transformation means according to Andy Jassy?

Andy Jassy explained, “Transformation can mean transforming yourself or it can mean transforming to meet new technology situations or opportunities.” Andy Jassy specifically called out the most crucial ingredient to make a perfect transformation recipe is “the leadership”

The leadership should ask – how can we transform ourselves? How can we reInvent our business and our customer experience, so that we can be meaningful and sustainable over a long period of time? 

Suggested Reads: All the announcements from Andy Jassy’s keynote at AWS re:Invent 2019

If you are planning for big and critical transformation, you don’t want to procrastinate. In fact, if you delay the transformation the ditch gets deeper. Andy Jassy explained that when you think of the first element of a digital transformation like adopting cloud to the core, it turns out it’s not technical, it’s all about leadership.

Andy Jassy also presented a checklist to prepare you for successful cloud endeavorsThere are four differentiators between the company that makes this transformation successfully versus those that just talk about it. So, if you are planning for digital transformation here’s your checklist that you need to follow dedicatedly:

Andy Jassy Digital Transformation Checklist

1. Senior Leadership team conviction and alignment

We all can agree with this without a second thought. The leadership has everything to turn cloud as a digital transformation into reality. If leadership pledges to work hard and diligently to achieve what is crucial for business growth, no matter how complex the process will be; there will be resources, money, and strategy at the disposal to achieve that transformation. 

“The first is you actually need to figure out how to get your senior team aligned that you’re gonna make this change. It’s not easy to make a big shift like this and inertia is a very powerful thing. It’s easy to block in various parts of the organization sometimes for well-intended reasons, sometimes for self-interested reasons but it’s easy to block. And if you don’t find a way to have that senior management conviction in alignment that you’re going to make that change, and find a mechanism to get the issues on the table; so you know you’re making progress and you go several months down the road thinking you’re making progress when you’re not, you won’t make that change.”, Andy concluded for the first step in the checklist.

2. Top-down aggressive goals 

Andy Jassy insisted even if the leadership team gets on-board with the idea of adopting cloud, you need an aggressive approach. All-in or nothing for cloud.

“The second thing you need right alongside that is you need an aggressive top-down goal. That forces the organization to move faster than organically otherwise would.”, Andy Jassy said.

He gave the example of GE about their top-down aggressive goals, “If you think about several years ago the CIO of GE Jamie Miller decided that she thought it was critical that GE moved to the cloud. To move much more quickly, she got her top technical leaders together and said, we’re gonna move 50 applications to AWS in the next 30 days. She said for 45 minutes, they told her what a dumb idea that was and how it would never work and she listened to them very patiently. She said I hear you but we’re gonna do it, so let’s go.”

“And they got to about 42 applications in 30 days but along the way, they figured out their security model, governance model, compliance model. They had success and built momentum and all of a sudden all the ideas started flowing in on what else they could move. They’re now about three-quarters of the way through, moving several thousand applications to AWS. An aggressive top-down goal that wouldn’t have happened if they didn’t set that goal will force the company to move,” he added.

3. Train your builders (aka developers)

Andy explained, “Third thing is you got to train people lots of times, you have these conversations around a table, senior people get excited. They decided to move to the cloud, they come back to their companies and they say good news here’s the cloud and nobody has any experience using it. Now it’s not hard to use the cloud but it takes a little bit of training so that’s why we train hundreds of thousands of customers every year.”

Everybody loved how Andy put that into a checklist. It’s not necessary that everybody should be an “expert” on cloud. But what’s necessary is the efforts to make the human resources expert by providing required pieces of training

Suggested Read: Top 7 announcements from AWS re:Invent 2019 that made headlines

4. Don’t let paralysis stop your before you start

By this Andy meant that if you think that the migration and adoption tasks get too complex; then divide the processes into easy, medium and hard. Now set the priority to move to cloud in the same order.

In Andy’s words, “The fourth thing that’s important to do is that you’ve got to make sure that you don’t allow the organization to get paralyzed; if you haven’t been able to move and figure out how to move every last workload well. We do a lot with our customers, we will go and do a portfolio analysis where we will go through all their applications with them. And we’ll classify them into the applications that are easy to move, medium, hard to move should go last because they have the most dependancy and legacy.”

“You can also classify them into those that can easily be lifted and shifted and those that should be rejected before they move to the cloud. We build them a thoughtful methodical multi-year plan to migrate and what companies find almost always is that so many codes are relatively easy to move to the cloud and get all those benefits and in fact they inform a lot of the later workloads that are the hardest ones to move so you’ve got to make sure that you don’t get paralyzed by that,” he added.


If you see the upcoming products offered by various cloud providers be it AWS, Azure, GCP or any other; they are developing products to meet all the use cases that the company may face. In 2018, the cloud providers opened up the business of over $100billion and that was just the surface of cloud industry. Even if you have suffered setbacks when implementing cloud adoption, it’s not always the cloud providers but it can be you also.

So, if you truly want to achieve the digital transformation then align your superiors (or the leadership team) with the objective, set your top-down aggressive goals, provide proper training to your builders and set priorities what to move first to avoid any paralysis. 

Cloud Evangelist
Cloud Evangelist
Cloud Evangelists are CMI's in house ambassadors for the entire Cloud ecosystem. They are responsible for propagating the doctrine of cloud computing and help community members make informed decisions.


Cloud Management