Keep the Journey Going: Cloud Migration Conversation Starters for Your Leadership Team

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👋 Hi everyone,

Thanks for your interest in the Enterprise Cloud Migration: Journey Behind the Slides session.

We talked about how successful migrations are just as much about people, process, and governance as they are about technology. I wanted to share a simple checklist you can use to keep the conversation going with your leadership and transformation stakeholders.

Below is that checklist in full. Use it as a quick discussion guide in your next steering committee, planning session, or strategy review to confirm you’re aligned on outcomes, ownership, and what “good” looks like 12–24 months after your move to Atlassian Cloud.

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Journey Behind the Slides Checklist ✅

Use this as a quick discussion guide with your leadership team:

1. Outcomes
   [ ] Have we sat down for a migration planning session with our Atlassian team?
   [ ] Have we defined 3–5 clear business outcomes for moving to Atlassian Cloud?
   [ ] Have we shared our business goals with Atlassian to develop metrics?
   [ ] Do we know how we’ll measure success 12–24 months post‑migration?

2. Governance & Ways of Working
   [ ] Have we agreed on a governance model (central, federated, hybrid)?
   [ ] Have we defined what’s standardized vs. where teams can adapt?

3. Operating Model
   [ ] Is there a named owner for the Atlassian platform as a product?
   [ ] Is there committed funding for ongoing improvement, not just migration?

4. Change & Adoption
   [ ] Do we have executive sponsors beyond IT?
   [ ] Is there a change network/champions group in place across key business areas?

5. Training & Enablement
   [ ] Is there a role‑based enablement plan (execs, managers, teams)?
   [ ] Is onboarding to “how we work” part of standard new‑hire onboarding?

6. Risk & Compliance
   [ ] Have we clarified our risk posture and non‑negotiable policies?
   [ ] Is information architecture aligned to business structure and regulatory needs?

7. Continuous Improvement
   [ ] Do we have a recurring forum to review metrics and evolve our ways of working?
   [ ] Are we using Cloud data to guide process and org changes?

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If you’d like to share how you’re approaching these topics - or where you’re getting stuck - feel free to reply in the comments so others can learn from your experience, too.

Hope you see you at a future session!

Tyler Applebaum
Enterprise Technical Architect