Migrating to Jira: 10 Critical Considerations for Jira Enterprise Teams

At 4G Technology Solutions, we help enterprise teams evolve their tooling to match the pace of modern Agile development. If your organization is planning to migrate from a legacy project management system to Jira, you’re not alone. You’re on the right track.

Make no mistake: Moving to Jira is more than a software switch. It’s a strategic transformation, especially when scaling to Jira enterprise.

In this guide, we break down the 10 essential considerations that will set your Jira migration up for long-term success.

1. Set Clear Migration Objectives from the Start

Before touching a single configuration screen in Jira, get clarity on the why behind your migration.

• Are you aiming for stronger Agile support?
• Do you need better reporting and traceability across teams?
• Is integration with DevOps tools (Bitbucket, Jenkins, etc.) a priority?

🎯 Pro Tip: Avoid a pure “lift and shift” approach. Migrating your legacy tool’s exact setup to Jira defeats the purpose. Instead, rethink what your teams actually need to work faster, collaborate better, and scale smarter.

2. Audit and Analyze Your Current Data Landscape

Your existing system is likely full of custom fields, workflows, attachments, and tangled linkages.

Start by creating a full inventory of:

• Work item types and their relationships
• Custom fields and usage frequency
• Historical data and compliance retention requirements
• Workflow complexity and exceptions

🛠️ Use tooling (e.g., APIs or data extractors) to pull metadata and usage stats. This gives you a clear picture of what should and shouldn’t make the leap to Jira.

3. Engage Stakeholders and Power Users Early

Migration isn’t just an IT project. It’s a culture change. Involving champions of Jira project management early helps adoption stick.

Bring in cross-functional stakeholders from:

• Development and QA
• Product and Project Management
• Business Analysis and Compliance

🗣️ Involve power users early. Create working groups or Jira “champions” who can stress-test designs, socialize changes, and provide real-time feedback throughout the process.

4. Design Jira Enterprise for the Way You Want to Work

This is where you architect your new world in Jira. But proceed with caution.

Key areas to configure:

• Issue types and sub-tasks
• Custom workflows and transitions
• Field schemes, screen layouts, permissions
• Notifications, automation, and integrations

⚠️ Pro Tip: Don’t recreate your legacy tool inside Jira. Simplify. Jira’s strength is in its flexibility — especially when configuring Jira agile project management to support Scrum, Kanban, or hybrid workflows.

🧩 Consider plugins like:

• Xray for test management
• R4J for requirements traceability
• ScriptRunner for automation and scripting

Test everything in a sandbox environment before rolling it out to production.

For efficiency in navigation and speed when customizing screens or managing issues, you might use the 17 essential Jira keyboard shortcuts that many of our users swear by.

5. Plan for Smart Data Mapping and Transformation

Data rarely moves cleanly from old systems into Jira. Expect a messy middle.

Build a detailed field-by-field mapping plan. For each item:

• What’s the Jira equivalent?
• Does the data require transformation?
• Should it be renamed or deprecated?

📦 Handle unmapped data with care, especially if it affects compliance, traceability, or team workflows.

6. Be Selective About What You Migrate

Not all data needs to make the move — one of the most overlooked aspects of Jira data migration is deciding what to archive versus what to carry forward.

Decide early:

• Will you migrate full history, or just active work?
• Are attachments, comments, and links important?
• What’s your archival strategy for legacy data (PDF snapshots, data lakes, backups)?

🧹 Pro Tip: Cluttering Jira with outdated tickets, deprecated custom fields, and irrelevant history will only frustrate users and slow performance.

7. Tailor Training to Every User Role

No matter how intuitive Jira is, change is hard. Your users need support.

Deliver role-based training:

• End users: how to create, transition, and manage issues
• Admins: how to maintain and troubleshoot configurations
• Testers & QA: how test management is handled (especially with tools like Xray)

📚 Build Confluence documentation with:

• Quick start guides
• Short training videos
• Use case-specific walkthroughs

🔁 Don’t forget post-go-live feedback loops. Listen, refine, and improve continuously.

8. Validate, Test, and Pilot Before Launch

Before going live:

• Run test migrations with real data
• Confirm field mappings, workflow behavior, permissions
• Pilot with a small team or project first

🧪 This minimizes risk, surfaces surprises early, and builds confidence before full rollout.

9. Don’t Skip Change Management

Communicating the “how” is just as important as the “what.”

Keep communication clear and consistent:

• What’s changing?
• Why now?
• How does it benefit the user?

💬 Use demos, open Q&A sessions, and internal champions to keep users informed and engaged.

In training, avoid pitfalls by reviewing the common Jira mistakes that slow down Agile teams, especially for team leads and Scrum Masters.

10. Establish Post-Migration Governance

Migration isn’t the finish line — it’s the starting gate.

Put governance in place to avoid chaos:

• Review usage metrics and adoption after 30–60 days
• Revisit workflows, field usage, and permissions
• Set up a change control process for future config requests

🚀 The goal is to keep Jira clean, scalable, and aligned to your evolving business needs.