Breaking the “This is How We’ve Always Done It” Barrier

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Hi everyone! I’m part of the Onboarding Success Management team here at Atlassian. Every day, I help teams navigate the transition from on-premise setups to the Cloud.

Trust me, "But we’ve always done it this way," is a very common phrase I hear. It is a classic hurdle, and honestly, it is one of the top reasons digital transformations stall. But here is a secret from the front lines: most people are not actually afraid of the Cloud. They are just comfortable with their current habits.

If you are leading your team through a migration, your job is about being a technical expert and about being a guide. Here is how you can break down that barrier and turn your skeptics into your biggest fans.

1. Start with the "Why" (and skip the "How" for a minute)

When we talk about migrating, we often get bogged down in the logistics. But your teams probably don't care as much about user permissions or data mapping. They care about their daily frustrations.

Instead of just saying, "We are moving to Jira Cloud," try saying:

"We are moving to a version of Jira that automates those three manual reports you hate doing every Friday." When you frame the change as a solution to a known challenge, the old way of doing things starts to look a lot less appealing.

2. Find your "Early Birds"

You don't have to convince everyone at once. In every department, there is usually one person who is curious about new tech or always looking for a better way to organize their work. These are your Change Champions.

Give them early access to the Cloud sandbox and let them play around and discover what actually works best. When a peer says, "Hey, this new Confluence layout actually makes it way easier to find our meeting notes," it can carry a lot more weight than a formal announcement from leadership.

3. Leverage the Proven Blueprints

And don’t worry, you don't have to reinvent the wheel. We have built specific resources to help you guide your team through this exact transition. These aren't just dry technical manuals; they’re built to help with the "people" side of change.

For Champions to align teams and support adoption:

• For Jira: Use the Jira Adoption Guide to get templates, checklists, and communication tips to help you lead the charge and inspire your team

• For Confluence: The Confluence Adoption Guide helps you show your team the "what is in it for me" side of things, like how Cloud connects knowledge across the whole company.

For migration teams or change leads to create a plan:

• For Change Management: I also highly recommend checking out the Cloud Adoption Guide. Running a "Change Management Play" can help surface fears before they become blockers.

4. Acknowledge the "Messy Middle"

There is always a period right after a move where things feel a little clunky. People will click where the old button used to be. That is okay!

The goal is not to have a perfect Day One. The goal is to build a culture of continuous improvement. Encourage your team to call out what they miss from the old system so you can show them the new (and usually faster) way to achieve that same result in the Cloud.

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How is your team feeling about your upcoming move? Drop a comment below and let’s chat about how to handle the "but we've always done it this way" crowd!