Migrating from Legacy ITSM to Jira Service Management: Lessons Learned

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Introduction

Migrating from a legacy ITSM platform to Jira Service Management (JSM) is more than a technical upgrade, it's a strategic shift toward agility, collaboration, and cost-efficiency. Whether you're transitioning from tools like ServiceNow, BMC Remedy, or a custom-built solution, the journey can be transformative if approached thoughtfully.

This article outlines key lessons learned, offering practical insights to help you plan, execute, and optimize your move to JSM.

Phase 1: Planning the Migration

Lesson 1: Define Clear Objectives

Before touching any configuration, clarify why you're migrating. Common goals include:

• Reducing licensing and support costs
• Improving usability for agents and requesters
• Aligning ITSM with Agile and DevOps practices
• Expanding service management to HR, Finance, and Facilities

Lesson 2: Audit and Rationalize Existing Workflows

Legacy systems often accumulate clutter—unused request types, outdated SLAs, and redundant automation.

Phase 2: Designing in JSM

Lesson 3: Don’t Replicate—Reimagine

Avoid the temptation to copy legacy configurations into JSM. Instead, leverage JSM’s native features:

• Smart forms with conditional logic
• Automation rules using smart values
• Assets for lightweight CMDB functionality
• AI agents for ticket deflection and triage

Lesson 4: Build for Scalability

Design with future expansion in mind. Use request type groups, custom portals, and permission schemes to support multiple departments.

Phase 3: Execution & Rollout

Lesson 5: Pilot Before Full Launch

Start with a single team or service desk. Validate workflows, gather feedback, and iterate.

Lesson 6: Train and Empower Users

Migration success depends on adoption. Provide role-based training and self-service documentation.

Phase 4: Post-Migration Optimization

Lesson 7: Monitor KPIs and Iterate

Use JSM’s reporting tools to track:

• MTTR (Mean Time to Resolve)
• CSAT (Customer Satisfaction)
• FCR (First Contact Resolution)
• Ticket volume trends

Final Thoughts

Migrating to Jira Service Management is an opportunity to rethink how your organization delivers service, not just a tool swap. By focusing on simplification, scalability, and user experience, you can unlock the full potential of JSM and future-proof your service operations.

[Rick Westbrock]

We went through this process a couple of years ago and I cannot emphasize enough how important 

Don’t Replicate—Reimagine is. We had users asking us to replicate kludgy designs from our old tool and they were quite happy once we simply asked "What is your business requirement" and designed JSM to meet the requirement without any though to how the old system did it.

One thing I would add is that as an admin you should really push your users to be engaged during the design and testing process so that they have a chance to request changes and are not surprised by any behavior after go-live. We had one stakeholder who was not engaged nearly enough and we ended up having to do a fair amount of work to compensate after their agents were having troubles after we went live.