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Cloud Transformation Day: 5 Challenges of Cloud Computing

January 06, 2023

On December 8 2022, Pluralsight hosted the inaugural Cloud Transformation Day. For the last session, Pluralsight CEO and Co-founder, Aaron Skonnard, sat down with Google Cloud’s VP of Migrations, Stephen Orban, to talk about the evolution and challenges of cloud computing, and how organizations can make the most of their cloud investments in 2023.

Watch the on-demand sessions online now

How has cloud computing changed in the last decade?

If there’s one thing that’s changed in the last decade or more, it’s that the cloud has created a paradigm shift that’s transforming every industry. Cloud computing has come a long way from simple server and database capacities that you could scale up and down on demand. That’s still a quintessential use case that will continue transforming many businesses. 

But the cloud is also transforming the way people collaborate, use data and analytics, process enormous amounts of data, and generate business outcome predictions using machine learning models. Those types of capabilities didn’t exist five or six years ago, and it’s changing the way customers are doing business.

Home Depot is a great example. Their cloud journey started by migrating their data warehouse to the cloud because they couldn’t scale with the growth of their store footprint, and the supply chain dynamics that went along with that. It was just too expensive to keep racking and stacking servers and continuing to purchase licenses for their data warehouse. 

Now that they’re in the cloud, Home Depot is able to enter new geographies faster and stock their shelves with the right items at the right time. They’ve since taken it a step further, using machine learning capabilities for advanced inventory management and to make predictions about shopping behaviors.

Overcoming the top five challenges of cloud computing

But as the technology evolves, so too must organizations. The reality is transformation at this scale is easy to talk about, but hard to do. Still, most of the cloud computing challenges organizations face aren’t technical. 

Transformation at this scale requires three aspects of your business adapting at the same time: people, processes, and technology. And the primary focus for the last decade has been technology. Now, we’ve hit a point where many technology transformations stall or fail because technology came such a long way, but people and processes did not. The reality is enterprises have been building on and creating new systems without replacing old ones for more than a decade (hello, technical debt), which makes it increasingly difficult to meet new technology expectations. 

The cloud makes it much easier to develop, implement, and maintain these plan and scale systems. You just have to drop the technical debt anchor you’ve been dragging behind you to be able to make the change. That makes the path easier to follow, but there are still some obstacles to overcome once you leave your excess baggage behind.

Define a business case

The first challenge of cloud computing is getting executive buy-in. Executives are skeptical, and understandably so. It’s their job to look out for the financial stability of the organization. Cloud computing is a risk. It’s your job to put that risk in perspective by building a business case. This business case identifies a clear set of objectives the transformation project will fulfill over a one to three year period. Not only does it help remove the C-suite skepticism, but it gives you something to rally your troops behind.

Outline a skill development strategy

You already have the people you need to succeed in the cloud. You just have to train them. Computer science fundamentals haven’t changed. Physics hasn’t changed. Cloud computing just makes it easier to build these large scale systems. But saying you’ll provide the tools, and encouraging your team to build skills are two separate things. Some employees may be hesitant to follow this path because they’re afraid of what they don’t know. 

A skill development strategy outlines the steps and milestones to get from one role to the next, including the responsibilities and technical capabilities needed to move up through the ranks. This strategy works to remove the fear, as well as provide a structured environment for skill development that drives toward organizational objectives.


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Organize your team

Many organizations struggle institutionalizing change management and learning. You need a team dedicated to institutionalizing your learnings and enabling the rest of your organization. There’s no one right way to organize this team, but the only way to prevent knowledge silos is for one team to be held responsible for disseminating information and best practices throughout an organization.

Reevaluate your partners

Some partners are only meant to walk with your organization for a season. With cloud computing causing massive shifts in the way organizations are operating, you need partners that support your cloud transformation journey. If your current partners aren’t adapting or shifting to help you overcome your cloud computing challenges, it might be time to find some new ones. There’s a whole slew of born-in-the-cloud partners cropping up, and plenty more in the middle of their own transformations. It’s time to lose the mindset that your partners today may not be your partners of tomorrow.

Be maniacal about your metrics

It’s one thing to build a business case. But once you have everyone on board with your cloud transformation project, you need to solidify the main objectives and identify the key metrics that drive overall success. OKR (Objectives and Key Results) metrics are structured well for this type of transformation. The objective is the ambitious goal you’re trying to achieve. The key results support that objective and are measurable metrics you can quickly push in one direction or another. You should be monitoring these OKRs weekly to make sure they’re moving in the right direction.

What should leadership support look like in cloud transformation projects?

Top-down support is critical to overcoming the challenges of cloud computing. But support without enablement won’t get you where you want to go. Instead, it will leave you frustrated and confused over your lack of progress. Implementing skill development strategies is a great first step. You could take it a step further, though. 

One of the best forms of enablement is showing your team what good looks like. If you don’t, you leave it to their imaginations to decide. Unless you hire mind readers, their idea of what good looks like and yours probably differ. 

How do you do this? Shoutouts. Pick three projects that are going the way you want. In a quarterly town hall, celebrate the people running the project, point out what they’re doing well, and award the progress they’re making. What you’ll find is it’s easy for others to emulate what they see, as opposed to what they’re told. The result? More projects running the way you want, resulting in better key results.


Catch the full fireside chat with Aaron Skonnard and Stephen Orban for more of their take on the challenges of cloud computing.