Workday Implementation Checklist: 10 Essential Steps for Success
Your Complete Guide to Planning, Executing, and Launching Workday
Three weeks before our Workday go-live at Slack, I realized we'd skipped a step.
Not a small step. A critical one. We'd been so focused on configuration and testing that we hadn't finalized our change management communication plan. Seven hundred employees were about to wake up to a completely new system, and we hadn't told them exactly what to expect on Day 1.
We scrambled. Worked 14-hour days. Pulled it together just in time.
But here's the thing: that near-disaster was completely preventable. If we'd had a comprehensive checklist that we actually followed, we would have caught that gap weeks earlier.
After supporting 40+ Workday implementations at companies like Google, Slack, and Coinbase, I've learned that successful implementations aren't about heroic last-minute efforts. They're about systematic execution of proven steps.
This checklist is everything I wish I'd had during my first implementation.
Want the downloadable version?
Get The Complete Workday Implementation Checklist - a practical tracking tool with timelines, role assignments, and status tracking you can use throughout your implementation.
Download your Implementation ChecklistWhy Getting Workday Implementation Right Matters
According to Gartner, 55% of HR leaders report their technology doesn't meet business needs. The primary cause? Poor implementation execution.
When done well, a Workday implementation can:
• Make HR, Finance, and IT operations dramatically more efficient
• Keep your data accurate and accessible
• Enable better, faster decision-making
• Drive high user adoption and satisfaction
• Keep your business transformation goals on track
Mess it up with common implementation mistakes, and you're looking at data problems, clunky processes, frustrated users, and 12-24 months of remediation work.
The difference between success and failure usually comes down to disciplined execution of a proven process.
The 10 Essential Steps for Workday Implementation Success
Here's your complete checklist, with detailed guidance for each step:
1. Set Clear Goals and Success Metrics
2. Build Your Implementation Team
3. Plan Data Migration and Integration Strategy
4. Configure and Customize Workday
5. Test Everything (Thoroughly)
6. Train Your Users
7. Execute Change Management
8. Go Live
9. Provide Post-Implementation Support
10. Continuously Improve
Let's break down each one.
Step 1: Set Clear Goals and Success Metrics
Timeline: Weeks 1-2 | Owner: Executive Sponsor + Project Manager
Before touching Workday, you need absolute clarity on what success looks like.
Why This Step Matters
I've seen implementations fail not because of technical issues, but because nobody agreed on what "done" meant. Different stakeholders had different expectations, and the project couldn't satisfy everyone because it was never designed to.
What to Do
Define Measurable Objectives:
• What specific business problems are you solving?
• How will you measure success? (Be specific: "Reduce time-to-hire by 20%" not "Improve recruiting")
• What's the timeline for achieving these outcomes?
Align with Company Strategy:
• How does this implementation support broader business goals?
• What does the CFO need from this system?
• What does the CHRO need?
Document and Get Sign-Off:
• Create a one-page goals document
• Get executive sign-off before proceeding
• Reference this document throughout the project
Real-World Example
At Coinbase, we aligned our Workday goals with the company's hypergrowth strategy. Every configuration decision was evaluated against the question: "Will this still work at 3x our current headcount?" This clarity prevented countless rework later.
For more on strategic alignment, see our Ultimate Guide to Workday Implementation.
Step 2: Build Your Implementation Team
Timeline: Weeks 2-4 | Owner: Project Manager + HR/IT Leadership
Your implementation is only as good as your team.
The Core Team Structure
Executive Sponsor: Strategic decisions, roadblock removal (5-10 hrs/week)
Project Manager: Day-to-day coordination, timeline management (Full-time)
Functional Leads: HR, Finance, IT requirements and testing (20-30 hrs/week)
Technical Lead: Integrations, data migration, security (20-30 hrs/week)
Change Manager: Communications, training, adoption (15-20 hrs/week)
SMEs: Process expertise, user acceptance testing (10-15 hrs/week)
The Client-Side PM Question
One of the biggest decisions you'll make is whether to have a dedicated client-side project manager. Based on our experience, the answer is almost always yes.
A client-side PM can save your company $500K-$1M in avoided rework and consultant overruns. They serve as your advocate, ensuring the SI's decisions align with your long-term interests.
Filling Gaps
If you're missing key roles or can't find specialists, consider staff augmentation services. Having the right expertise is more important than keeping everything in-house.
Building your team?
Book a strategy call with one of our Experts to discuss optimal team structure for your specific situation.
Book a strategy call with an ExpertStep 3: Plan Data Migration and Integration Strategy
Timeline: Weeks 3-8 | Owner: Technical Lead + Data Stewards
Data problems are the #1 cause of implementation delays and post-go-live issues.
Here's a painful truth: the data in your legacy systems is probably worse than you think. Duplicates, inconsistencies, missing fields, outdated records - they're all waiting to cause problems in Workday.
The Right Approach
1. Assess Your Data (Early)
Pull representative samples, run quality assessments, identify issues
2. Cleanse Before Migration
Deduplicate, standardize formats, fill missing fields, validate
3. Map and Transform
Map legacy structures to Workday, document transformation logic
4. Validate Relentlessly
Multiple validation cycles, reconcile counts, spot-check quality
Integration Strategy
Workday doesn't exist in isolation. Plan your integrations early:
Must-Have for Phase 1: Payroll provider, benefits carriers, time tracking, core financial systems
Can Wait for Phase 2: Learning management, performance tools, non-critical reporting
In our Lightspeed case study, dedicated upfront data work led to a 73% reduction in position data errors and a smooth go-live.
Step 4: Configure and Customize Workday
Timeline: Weeks 6-14 | Owner: Functional Leads + SI Team
This is where your Workday tenant takes shape.
The Configuration vs. Customization Decision
Workday's Golden Rule: Configure first, customize only when absolutely necessary.
Why? Customizations cost more to build, cost more to maintain, break during Workday updates, and create technical debt.
Configuration Best Practices
• Organization Structure: Define supervisory organizations, company hierarchies, security roles
• Business Processes: Map workflows (hiring, terminations, transfers), configure approvals
• Position Management: This is the #1 source of post-go-live pain. Get it right from the start.
For detailed guidance, see our position management best practices guide.
Step 5: Test Everything (Thoroughly)
Timeline: Weeks 12-18 | Owner: QA Lead + Functional Leads + Business Users
Rushing testing is one of the 5 common implementation mistakes that leads to post-go-live disasters.
Testing Phases
Unit Testing: Test individual components, verify each configuration works
Integration Testing: Test data flows between systems, verify end-to-end
User Acceptance Testing (UAT): Real users test real scenarios, validate requirements
Performance Testing: Test under expected load, identify bottlenecks
Real Warning: In 2025, the city faced a lawsuit after payroll errors resulted from inadequate testing during their Workday implementation. Don't let this happen to you.
Concerned about your testing coverage?
Download The Complete Workday Implementation Checklist for detailed testing scripts and criteria.
Get Your Complete Workday ChecklistStep 6: Train Your Users
Timeline: Weeks 14-20 | Owner: Change Manager + Training Lead
The best Workday configuration in the world is worthless if people don't know how to use it.
Training Program Components
• Role-Based Training: Customize sessions for different roles (managers vs. ICs vs. admins)
• Hands-On Workshops: Interactive sessions with real scenarios in training environment
• Training Materials: Quick reference guides, video tutorials, FAQ documents, job aids
Target: >95% training completion before go-live
Step 7: Execute Change Management
Timeline: Weeks 8-20 (ongoing) | Owner: Change Manager + Executive Sponsor
Change management isn't a phase - it's a thread that runs through your entire implementation.
Key Strategies
• Communication Plan: Who needs to know what, and when? Multiple channels, focus on "why"
• Stakeholder Engagement: Identify influencers, get buy-in early, make them advocates
• Feedback Mechanisms: Create channels for questions, address issues quickly
The Communication Countdown
Remember my Slack story? We almost forgot Day 1 communications. Your plan should include: 30-day, 14-day, 7-day, 3-day, and day-before communications, plus Day 1 instructions and Week 1 check-ins.
For detailed communication templates, see our Top 6 Tips for Going Live with Workday.
Step 8: Go Live
Timeline: Week 20 | Owner: Project Manager + Technical Lead + Change Manager
This is the moment everything has been building toward.
Go-Live Checklist
Pre-Go-Live (Week before):
Final system checks complete
Data migration verified
User access confirmed
Communication sent to all users
Support team briefed and ready
Go-Live Day:
System activated on schedule
Support team on standby
War room established
Executive sponsor available
Day 1 communication confirmed
The War Room
During go-live, establish a war room with: technical support (integrations, system issues), functional support (process questions), change support (user concerns), and an executive escalation path.
Step 9: Provide Post-Implementation Support
Timeline: Weeks 21-32 | Owner: Workday Support Team + Change Manager
Go-live isn't the finish line - it's the starting line.
Hypercare Period (Weeks 1-4)
• Dedicated support team availability
• Daily issue triage meetings
• Rapid resolution of critical issues (<24 hours)
• User feedback collection
• Quick wins to build confidence
Transition to Steady State
• Establish support request process
• Create knowledge base
• Define SLAs for different issue types
• Begin enhancement planning
Step 10: Continuously Improve
Timeline: Ongoing | Owner: Workday Product Manager + Governance Committee
Your Workday implementation is never truly "done."
Continuous Improvement Framework
• Gather Feedback: Quarterly surveys, focus groups, help desk analysis
• Prioritize Enhancements: Maintain backlog, prioritize by impact, balance quick wins with larger projects
• Stay Current: Review Workday release notes, evaluate new features, plan upgrade testing
Governance Structure
• Strategic: Quarterly executive review
• Tactical: Monthly leadership meetings
• Operational: Weekly team standups
The Bottom Line
Successful Workday implementations aren't magic. They're the result of:
1. Clear goals and executive alignment
2. The right team with the right expertise
3. Disciplined data management
4. Thoughtful configuration (not over-customization)
5. Thorough testing (no shortcuts)
6. Comprehensive user training
7. Proactive change management
8. Well-executed go-live
9. Strong post-implementation support
10. Commitment to continuous improvement
Follow this checklist systematically, and you'll dramatically increase your chances of success.
Your Next Steps
Option 1: Get the Downloadable Checklist (2 minutes)
Download The Complete Workday Implementation Checklist - an interactive tracking tool with all 10 steps, detailed sub-tasks, timeline estimates, and risk indicators.
Option 2: Get Expert Guidance (30 minutes)
Already planning your implementation? Book a free strategy call with Seena to review your plan, identify gaps, and get personalized recommendations.
Option 3: Keep Learning
Explore our comprehensive implementation resources:
• 5 Common Implementation Mistakes - What to avoid
• How to Save Big on Your Deployment - Cost control strategies
• Position Management Best Practices - Get this critical area right
• Lightspeed Case Study - Real results
Related Resources
Featured Guides
• Ultimate Guide to Workday Implementation - Complete roadmap and best practices
• 5 Common Position Management Mistakes - What to avoid and how to avoid them
• How to Save Big on Your Deployment - Cost control strategies
Services
• Advisory Services - Solution architecture and strategy
About the Author
Seena Mojahedi is the CEO and Founder of Kandor Solutions. After working on the consulting side at DayNine Consulting, he spent six years at prestigious technology companies such as Google, Slack, and Coinbase managing Workday implementations from the client side.
He's been in the trenches on over 40 implementations and has seen what works (and what doesn't) when organizations implement Workday.
Why Seena started Kandor Solutions: He's passionate about helping Workday customers own their platforms - not just use them. Traditional consulting creates dependency. Kandor builds capability.
When he's not working, he loves spending time with his family, traveling, snowboarding, hiking, and enjoying his morning cappuccino.
Connect with Seena:
• Schedule a Strategy Call with Seena
FAQs
Is Workday implementation hard?
Implementing Workday can be challenging, but with a solid plan, the right team, and clear goals, it becomes manageable. The key is following a proven process and not cutting corners on critical steps like testing and change management.
How long does Workday take to implement?
A typical Workday implementation takes 5-9 months for mid-market companies using the Launch methodology, and 9-14 months for larger enterprises with more complex requirements. Timeline depends on scope, team readiness, and data quality.
What is the implementation cycle of Workday?
The implementation cycle includes: Planning (goals, team, strategy), Configuration (setup, customization, integrations), Testing (unit, integration, UAT), Deployment (training, change management, go-live), and Optimization (support, feedback, continuous improvement).
What's the biggest mistake companies make?
The biggest mistake is underestimating data migration complexity. Companies often assume their legacy data is clean and ready to migrate. It rarely is. Start data cleansing 3-6 months before you need it.
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