How to Talk to Your Boss about Atlassian Cloud Migration

Published: January 3, 2022

You know Cloud is the future. But how do you talk to your boss about cloud migration? How do you convince him/her it is worth investing in? And, most important, how do you explain the reasons to migrate as soon as possible? This blog will give you pointers on how to have this conversation. Read ’til the end for bonus content that is the icing on the cake!


Perhaps don’t start by telling her or him cloud is inevitable. (Atlassian is no longer selling perpetual server licenses, switching to subscription licensing only February 2, 2021, for example.) Nobody likes to be forced.


Instead list some benefits:

  • Work anywhere, anytime with anyone
  • Worldwide data management at scale
  • Power seamless teamwork
  • Move from idea to execution in an instant, without extra clicks
  • Pay-as-you-go flexibility instead of upfront fixed investment
  •  Scale rapidly without having to invest in hardware
  • Outsource the grunt work to someone better versed and able to enjoy economies of scale.


Maybe a metaphor is the easiest way to slide into this all-important conversation.


Telephones once were fixed communications terminals plugged into a wired network. When you traveled outside of your office or home and wanted to make a call you had to find a public terminal. Airports and train stations had banks of terminals you could rent. Payphones were seemingly everywhere: street corners, restaurants, bars and so on.

Then on April 3, 1973 Motorola engineer Martin Cooper called Germany from a portable device while sitting in his car on 6 th Avenue, NYC. Telephones became cloud terminals. No wires required. The communications network is now available everywhere. (Well nearly everywhere.) You pay a subscription fee for access.

Who wants to go back to wired phones?

How about Zipcar?

It’s a network of on-demand cars. Why invest in your own car? You subscribe and then pay only for the Zipcar time you use. A “cloud” of cars is available in select cities, neighborhoods, college campuses, etc. An app your phone locates, unlocks then pays for your car time. Zipcar maintains the fleet, updating “hardware” as needed.


Movie distribution was initially static. You accessed them only in movie theaters. Then movies were broadcast to your home via network TV. But your choices were limited. You could see “The Wizard of Oz,” but only once a year, and only when the network deemed to offer it. Next, you could buy or rent a hard copy of a movie to show on your own device at home. But you had to buy, and upgrade the player. Remember ditching your VCR for DVD and then BluRay?

Now you stream movies to your TV, computer, tablet or phone whenever you want, wherever you are. You just pay a subscription to a service that hosts the movie on its servers attached to the internet. Movies are now in the “cloud.” The movie service takes care of necessary upgrades, keeps up with new technologies, continually delivering better picture and sound fidelity. Betting your movie watching future on a fixed media option makes as much sense as owning a Blockbuster store.

Digitization and electronic distribution of information is the fundamental change of our time!

Information once was recorded on paper stored in file cabinets. Sharing information required physically moving the document, or a copy of it, via mail or courier or Pony Express. Then fax machines allowed transmittal of documents over phone lines. But they only generated another paper copy on the receiving end. Now information resides on computer servers connected to the internet. You simply log-in to access information you need. You can pull whole libraries from “the cloud.” And sharing is as easy as a click.


How about referring to the Harvard Business Review? An article titled “What Every CEO Needs to Know About the Cloud” states, “How important is cloud computing? I would argue that it’s a sea change—a deep and permanent shift in how computing power is generated and consumed. It’s as inevitable and irreversible as the shift from steam to electric power in manufacturing, which was gaining momentum in America about a century ago. And just as that transition brought many benefits and opened up new possibilities to factory owners, so too will the cloud confer advantages on its adopters.”

Maybe CIO Magazine holds weight? Its article “How to Explain Cloud Computing to Your CFO” cites a Forrester report. “First, Forrester emphasizes the fact that use of cloud computing matches cash flow to system benefits more appropriately than the packaged software use model. In the old way of doing things, a large investment is made early in the project prior to system build out, and well before the business benefits (presumably financial in some shape or form) are realized. By contrast, cloud computing is a pay-as-you-go (aka pay by the drink) approach, in which a low initial investment is required to get going, and additional investment is incurred as system use increases.
In this way, cash flows better match total system cost.” it writes.

“. . . the (Forrester) report makes the argument that cloud computing provides a way to outsource non-critical applications to organizations better suited to run them, allowing IT to focus on critical applications. For example, many companies use outside service providers to run their mail rooms and copy centers. Other companies use fleet management services to run their vehicle fleets. Cloud providers, according to the report, are more efficient at IT operations, using fewer man-hours for standard tasks.”


Certainly, citing someone else helps. Here are some quotes from Atlassian Cloud and Jira Service Desk for Cloud customers.

Moving to the cloud helps us move forward faster and focus on innovation.” Peter Grube, Software Engineer, Homegate

“Now I use Atlassian programmatically through the API to search, organize, and filter tickets at scale. It’s easily saved 25% of my time, and it’s a way better way to organize information.” Michael Slocum, Software Engineer, Fair

“The backend automation has freed up our time so we don’t have to worry about troubleshooting and can focus on setting up new dealers and processing inventory.” Ashley Provencher, Inventory Operations Manager, Fair

“Atlassian Cloud saves our team time, which saves us money.” Evan Lerer, Director of Engineering, Redfin


Working with an experienced cloud migrator like e-Core ensures consistent and reliable results. Migration can be estimated and controlled with predictable outcomes, time frames and investment costs. Multiple migration path options can be designed by e-Core to match your company:

  • All at Once
  • Project by Project
  • Merge/Consolidate
  • Atlassian Cloud enterprise SLA is 99.95%.


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