Workday rollouts are big gambles. With licensing, consulting, and back-fill costs hitting seven figures, it is troubling that only 29 percent of enterprise software projects meet their targets.
When you bet on Workday, your critical HR, payroll, and finance operations depend on a single go-live date. Make the wrong moves—select the wrong partner, leave scope undefined, fail to staff properly, ignore dirty data, or neglect change management—and you will face cascading problems from pay errors to frustrated executives.
Here are eleven traps you can avoid to transform a risky implementation into a lasting advantage for HR, Finance, and IT.
1. Picking the Wrong Implementation Partner
Your implementation partner affects project success more than anything else. Select poorly, and you will encounter budget overruns, missed deadlines, and endless rework that erodes stakeholder trust.
Partners with proper certification and experience in your industry deliver predictable results and effective knowledge sharing. Those who staff projects with junior consultants or conceal their pricing create significant risks.
Apply this framework when evaluating potential partners:
- Identify Workday-certified consultants with three completed projects in your sector
- Ensure senior architects remain involved throughout the project, not just during sales
- Request transparent staffing plans and fixed-fee discovery sprints
- Complete at least two reference calls before signing anything
- Invest in a discovery sprint to test assumptions and build a shared project backlog
2. Poorly Defined Project Scope
Fuzzy boundaries eliminate more projects than technical challenges ever could. Begin a rollout without clearly stating "what we will deliver—and what we will not," and scope creep takes over:
- Additional integrations appear
- Optional reports become essential
- Each addition expands costs and timelines while undermining team morale
Vague requirements create persistent complications. You spend weeks configuring compensation plans, then discover finance expected different approval flows. The rework stalls everything and cascades into data migration, testing, and training, multiplying effort across the board. Warning signs include frequent change requests, conflicting success criteria, and constant debates about "what constitutes phase one versus future state."
To resolve this:
- Transform scope into a contract everyone honors
- Conduct workshops to identify every dependency, then document clear acceptance criteria that stakeholders must sign
- Establish a formal change control board so new requests come with visible cost and schedule impacts
- Divide features into phases—core HCM first, then payroll—so your team delivers value incrementally instead of pursuing moving targets
- Create an "out-of-scope" list; documenting what you will not do maintains project trajectory
3. Inadequate Executive & Cross-Functional Communication
Communication breakdowns halt implementation momentum. Implement this four-part communication approach to maintain alignment:
- RACI Matrix Publication - Assign one accountable owner for each deliverable. This reduces information hoarding and decision delays that damage projects.
- Weekly Cross-Functional Stand-ups - Conduct 30-minute meetings where issues must have documented actions before proceeding to the next agenda. This maintains priority clarity.
- Executive Steering Committee - Review budget and risk every two weeks. Maine's $35 million HR system failed because agencies worked in silos debating payroll rules, leaving conflicts unresolved and falling months behind.
- Centralized Communication Hub - Establish a dedicated Slack or Teams channel (hint: with Siit!) linked to your project portal. Everyone accesses the same status updates, files, and decisions. Research demonstrates transparent workspaces enhance team collaboration and communication.
Conduct monthly alignment sessions to verify scope, data quality, and change management plans. These checkpoints identify emerging conflicts before they threaten your timeline.
4. Under-Resourcing the Internal Project Team
Implementation failures frequently occur when organizations assume existing staff can manage rollout tasks alongside their day jobs. Data cleansing, testing, and change management may require longer than initially planned. Subject-matter experts face impossible choices: maintain payroll operations or validate new system configurations.
Monitor these warning signs:
- Missed deadlines
- Quality issues
- Same individuals in every late-night meeting
Resource your project methodically. Allocate 25-50% of key SMEs' time for project work, with temporary staff covering their regular duties to sustain service during rollout. Document these commitments in a resource loading chart before you begin—tools like Asana display utilization in real time. Evaluate capacity weekly to modify workloads before fatigue causes missed milestones.
5. Trying to "Do Everything at Once" Instead of Phasing
Deploying all modules simultaneously multiplies risk exponentially. When payroll, benefits, finance, and reporting change concurrently, a single workflow failure can immobilize your entire organization.
The deployment follows a staged approach: it begins with the implementation of Core HCM, followed by a data accuracy validation phase. Once the data is confirmed to be accurate, the payroll and finance modules are integrated.
This enables teams to refine integrations and enhance change management between waves. Complex organizations with unions or multiple locations require phasing for stability, while smaller groups might succeed with Workday's Launch program—a rapid, consolidated approach for simpler organizations.
Apply this framework to select your deployment strategy:
Treat your first wave as a Minimum Viable Product: deliver core functions, measure adoption, then enhance.
6. Dirty or Incomplete Data Migration
Bad, duplicated, or missing data causes immediate operational failures—incorrect paychecks, broken approvals, and reporting gaps that undermine trust in the system. Clean data migration prevents these errors and ensures smooth operations at go-live.
Common migration problems can arise in the shape of duplicate employee IDs, inconsistent date or currency formats, and orphaned fields from legacy systems with no clear destination. Each problem necessitates manual corrections and delays your go-live.
The City of Seattle demonstrates what is at stake — Payroll errors linked to flawed data mapping triggered a class-action lawsuit and millions in remediation costs—a documented failure that emphasizes the importance of solid migration planning.
Safeguard your implementation with a structured data-quality approach:
- Initiate data auditing before configuration begins
- Examine every source system
- Clean and standardize values
- Document mapping rules in detail
- Utilize ETL tools with automatic reconciliation that compares record counts and key fields after each load to detect discrepancies immediately
- Execute multiple test migrations with validation cycles, having payroll and finance experts verify results and approve accuracy
- Permit final cutover only when test loads balance to the penny
7. Budget Overruns & Timeline Slippage
Exceeded budgets and missed deadlines invalidate business cases. Scope creep, poor estimates, and overworked teams cause most overruns. Projects that miss schedules almost invariably exceed budgets too.
Identify early warning signs—missed design sessions, vague deliverables, or increasing change orders. When these appear, activate contingency funds (10-15% of baseline) and reset the plan with phased milestones. An independent project management office provides unbiased status reports, while transparent budget dashboards shared in weekly steering meetings maintain executive accountability.
Process every new request through a change-control board. A five-minute approval meeting costs substantially less than reconfiguring payroll two weeks before go-live.
8. Insufficient Testing (Unit, End-to-End, Parallel)
Thorough testing prevents deployment disasters. Seattle's payroll crisis resulted from skipped scenario tests, leaving thousands of employees with incorrect pay and triggering lawsuits. Allocate at least 20% of your timeline for structured testing, progressing methodically from isolated components to live-data parallels.
Unit tests verify each calculation rule, integration, or report individually, capturing mapping errors before they propagate. End-to-end tests connect those components, confirming cross-module workflows—hire to pay, procure to pay—function without manual intervention. Parallel testing executes actual payroll or financial transactions in both systems until every difference is resolved; specialized consulting firms can help structure these tests.
Execute each phase in a fresh sandbox loaded with current production data. Automate high-volume regression tests and involve business users early so unusual cases surface before go-live.
9. Poor Documentation & Knowledge Transfer
Insufficient documentation is the hidden failure that manifests after go-live, when urgent questions reach the help desk and nobody recalls configuration decisions made months earlier. Comprehensive documentation becomes your fastest path to efficient problem solving and reduced dependency on expensive consultants.
Without a central knowledge base, support teams waste hours reverse-engineering processes while unresolved requests accumulate and user confidence diminishes. Organizations become permanently dependent on external partners who are the only ones who understand how the system functions.
To prevent these problems, document critical items before migration freezes, including:
- Configuration decisions and rationales
- Custom objects and calculated fields
- Integration diagrams and API mappings
- Data migration scripts and reconciliation reports
- Step-by-step guides for common problems
Maintain everything in a searchable system—Confluence, Notion, or a Git-backed wiki—and establish it as the project's definitive reference. Schedule recorded walkthroughs, shadow sessions, and hands-on workshops so your team learns not just how processes work but why they were designed that way. When updates arrive or staff changes, this living documentation enables rapid adaptation without compromising service quality.
10. Inadequate Training & Change Management
Workday appears intuitive, but users rarely master it independently. Insufficient training and change management reduces adoption, increases errors, and motivates employees to create workarounds. Inadequate training significantly contributes to deployment failures, especially when the system manages critical processes like payroll and performance reviews.
Most failures follow a predictable pattern: generic webinars scheduled months before go-live, overwhelming slide decks, and no follow-up plan. These approaches disregard that HR professionals, managers, and finance analysts require different workflows explained at different levels across various learning styles.
To provide proper training:
- Develop a role-based training structure—map each user type to their specific tasks
- Create multi-format content: short classroom demonstrations, hands-on practice, quick micro-videos, and searchable job aids
- Schedule sessions immediately before users need to perform tasks
- Collect feedback after each session to improve materials based on performance data
- Implement digital adoption platforms for real-time coaching—Iin-app guides from tools like Apty deliver step-by-step instructions, provide contextual help, and collect data showing where users encounter difficulties
Structure your program on disciplined change management: stakeholder analysis, communication plans, and two-way feedback loops. When users observe their input triggering immediate improvements, resistance decreases and the system becomes the preferred tool rather than an inconvenient detour.
11. Ignoring Workday Updates During Long Implementations
Workday releases two mandatory updates every year, each capable of altering configuration tables, retiring features, or adding new security requirements. Disregarding these updates during extended projects creates expensive rework when design decisions from previous quarters fail in updated preview systems.
Establish parallel release management using this three-person team:
- A system analyst to review impact assessments and configuration changes
- An integration architect to verify API changes and connection stability
- A testing lead to coordinate regression testing and output validation
Synchronize your project schedule with the bi-annual release calendar. Schedule regression testing immediately after each preview system refresh. Use this time to verify end-to-end scenarios, compare outputs against pre-update baselines, and repair broken integrations.
Monitor Workday Community closely for deprecation notices and inform stakeholders before design workshops commence. Release notes function as live requirements—treating them as optional reading predisposes projects to mid-rollout failures.
How Siit Helps Avoid These Pitfalls
Disconnected workflows, manual setup, and data gaps undermine implementations. Siit eliminates these problems by managing hire-to-retire processes directly within Slack or Teams, reducing administrative handoffs.
Our connector integrates employee records into unified 360° profiles—displaying role, location, devices, and access permissions—all accessible through one interface. Dynamic Forms and AI Powered Workflows help with asset and access management. During offboarding, Power Actions cancel SaaS licenses, schedule device returns, and generate IT checklists without manual intervention.
Attribute-based routing directs requests to the correct resolver groups within 60 seconds. AI Triage monitors onboarding and offboarding sequences, identifying problems like missing security badges or stalled provisioning before they become audit issues. Request management occurs where teams already work, eliminating portal switching and request tracking inefficiencies.
Analytics & Reporting presents real-time MTTR, automation coverage, and compliance status. The modern interface requires minimal training—teams configure workflows in minutes instead of weeks.
Workday only works when the right systems surround it. Siit turns Workday events into secure, automated IT actions—without requiring portal switching or custom scripts. Start your trial today and launch your first workflow in minutes.
