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May 6, 2021

5 common roadblocks to cloud migration success

By now, most organizations have moved some of their applications or workloads into the cloud. But there is a big difference between migrating and running some of your services there and achieving the full benefits, such as speed and scale, offered by moving as much as you can into the cloud.

Considerations like repeatability, governance, budget, timelines, and control can pose significant delays and obstacles to a fully-optimized cloud program. So how can you maintain a rapid pace without the risk of your wheels falling off?

Our cloud migration experts spoke to others from AWS and Slack to discuss five ways to speed up your cloud migration program without blowing your budget, changing your timelines, or losing control of governance.  

The expert panel consisted of:

  • Marcus Wildsmith, Chief Product Officer, Cutover
  • Kieran Gutteridge, Chief Technology Officer, Cutover
  • Ron Melanson, Global Lead, Control Services Field Enablement, AWS
  • Richard Whitehurst, Senior Solutions Engineer, Slack

Here’s what they had to say about the challenges that come with cloud migrations:

Customer challenges and cloud adoption

Every successful cloud transformation starts with a bold vision and goals set by senior leaders. However bold and exciting the strategy, there can be execution challenges that occur. A few of these are:

  1. Trying to move all or nothing

The first stage of a cloud migration is deciding exactly what it is you need to move. According to Ron, often AWS customers try to move too many things at once and end up getting bogged down in the minutiae. Sometimes they can worry about a particularly complex system that will be difficult to move, and worry that they shouldn’t start at all until they’re comfortable moving that.

In AWS’ experience, companies sometimes get paralyzed if they can’t figure out how to move every single application. Ron said that he spent a lot of time working with customers through deep application portfolio analysis, sorting applications from the easiest to hardest to move, and deciding which ones needed to be rearchitected. It turns out that many applications are pretty easy to move and getting those early workloads in the cloud teaches invaluable lessons to the team on how to eventually move the hardest workloads. 

2. Not wanting to retire old systems

In most mature organizations there’s going to be some old systems and tools that are embedded and will not work on the cloud. There is often a reluctance to retire these as people are used to using them - but if there’s no better reason to keep a system other than “it’s what we’ve always done” and if it’s holding back your cloud strategy, it’s probably time to let it go. 

3. Planning

A cloud migration plan needs to be nimble, resilient, and compartmentalized, so you can iterate upon it and create a highly repeatable migration factory. You need to be learning, optimizing, and tuning the process so when you get to the harder-to-migrate applications you have developed the right knowledge based on the real-world experiences that got you to that point.

4. Communications

Communications are often overlooked but are a critical part of a successful and rapid migration. Not spending the time to research and adopt best practices around orchestration, automated testing, runbook creation, and communication amongst the team and stakeholders is a common mistake when it comes to cloud migration. 

5. Exceeding timelines and budgets

90% of organizations are currently trying to move to the cloud and of those that have already started the journey nearly half exceed timelines and budgets. Despite strong buy-in from senior management, most traditional organizations are not even sure what’s out there in their IT landscape because it's evolved over many years and the people that built and maintained the setup have usually left the organization. Customers are just trying to make sense of it all and then when it comes to delivering the project they typically don’t have the right expertise or resources to do so.  

In addition to all these common problems, the effects and pressures caused by COVID-19 have compressed timelines for full cloud adoption even further. As teams, infrastructure, and processes shifted to remote-first many organizations looked to the cloud for a solution. But as we've explored, in order to get the best out of the cloud, you need to have a clear understanding of your needs and the planned approach.

In our next blog post we learn from the experts at Cutover, AWS, and Slack how controls, automation, and governance can help to solve some of these challenges.

Watch the "5 ways to make your cloud migration faster" webinar to discover our top five ways to speed up your cloud migration and get migration advice from Cutover, AWS, and Slack.
Chloe Lovatt
Cloud Migration
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