Hiring the Right Workday Project Leader: What Most Organisations Get Wrong
- Feb 16
- 5 min read
Updated: Feb 20
Deploying Workday is one of the most expensive and disruptive programmes your organisation will undertake. The technology is proven. The system integrators are experienced. But the single biggest variable in whether your programme succeeds or fails is the person you put in charge on your side of the table.
I've spent 25 years leading Workday and ERP programmes - first as an SI practice leader, now as an independent adviser to the organisations deploying them. I've seen what happens when the right person leads a programme, and I've seen the damage when the wrong person does. The difference is rarely subtle.
The Mistake Most Organisations Make
Most organisations treat the Workday project leader role as a project management hire. They look for someone who can maintain a plan, run status meetings, and produce RAG reports. That's not leadership - that's administration.
A Workday programme doesn't fail because someone forgot to update a Gantt chart. It fails because no one on the client side had the authority, experience, or confidence to push back when the SI proposed a change order that doubled the integration budget. It fails because the person leading the programme couldn't distinguish between a legitimate scope addition and a revenue play by the delivery partner.
This is the fundamental problem: most organisations hire for project management competence when what they actually need is programme leadership — someone who understands how SIs operate, how change orders are constructed, and where the commercial pressure points sit in a Workday delivery.
What to actually look for
Forget the generic competency frameworks. When I assess whether someone is the right leader for a Workday programme, I look for five specific things:
Direct Workday delivery experience, not just ERP experience.
Workday has its own deployment methodology, its own configuration logic, and its own integration patterns. Someone who led a successful SAP programme does not automatically understand Workday's tenant architecture, business process framework, or how Workday's phased update model affects testing strategy. The learning curve is real, and your programme cannot afford to fund it.
SI-Side Experience
This is the one most organisations miss entirely. The best client-side leaders are people who have worked inside a system integrator. They know how SOWs are structured, how margins are managed, how change orders are justified internally, and where delivery teams cut corners when they're under pressure. That knowledge is what gives a client-side leader the ability to hold the SI accountable - not from a position of suspicion, but from a position of understanding.
Governance instinct, not just delivery instinct.
A good project manager will execute the plan they're given. A good programme leader will question whether the plan is right. They'll challenge assumptions about timeline, resourcing, and scope before the programme kicks off - not three months in when the budget is already committed. They establish governance structures that create accountability, not just reporting.
The confidence to say No.
This sounds simple. It isn't. When your SI's engagement partner presents a change order with a tight approval deadline, supported by technical justification your internal team can't evaluate, the pressure to approve is enormous. A strong Workday leader has seen this before. They know which change orders are legitimate, which are commercial padding, and which are the SI protecting themselves against their own delivery risk. They can say no - and explain why - without damaging the relationship.
Stakeholder credibility at executive level.
Your Workday programme leader will need to present to your board, your CFO, your CHRO. They need to translate technical delivery status into business risk language. If they can only speak to project teams and not to executives, they cannot fulfil the role. The most common failure pattern I see is a technically competent PM who loses the confidence of the executive sponsor because they can't communicate programme risk in business terms.
Red Flags I've seen too often
In 25 years of ERP delivery, certain patterns repeat. Watch for these when evaluating candidates:
They've never challenged a system integrator.
If every programme they describe was a smooth collaboration with the SI, either they were lucky or they weren't paying attention. Healthy SI relationships involve constructive tension. If your candidate can't give you a specific example of pushing back on a delivery partner - and explain what happened - they're not the leader you need.
They talk about methodology more than outcomes.
Frameworks are tools, not achievements. The question isn't whether they follow PRINCE2 or Agile or a hybrid approach. The question is whether the programmes they led were delivered on time, on budget, and with the business outcomes the sponsor expected. If they lead with methodology rather than results, that tells you something.
They've only worked on one side of the table.
A candidate who has only ever been on the client side may not understand how SIs think commercially. A candidate who has only ever been on the SI side may struggle to prioritise the client's interests over the delivery partner's. The most effective Workday leaders have experience on both sides - they understand the incentives, the pressures, and the dynamics from every angle.
They can't explain a programme failure they were involved in.
Everyone in this industry has been involved in a programme that went wrong. The question is whether they can articulate what happened, what they would have done differently, and what they learned. If they claim a perfect track record across 25 years of ERP delivery, they're either not being honest or they weren't senior enough to be accountable when things went sideways.
The Internal Hire vs. External Partner Decision
Some organisations can hire the right person permanently. If you have ongoing Workday programmes - multiple phases, global rollouts, continuous optimisation - a permanent hire makes sense, provided you can find someone with the profile described above.
But most organisations deploying Workday for the first time face a different reality. They need senior programme leadership for 12 to 18 months. They need someone who can establish governance from day one, not someone who needs three months to learn how a Workday programme operates. And they need someone whose only incentive is the programme's success - not their next internal promotion, and certainly not their relationship with the SI.
This is where the fractional model works. An independent, client-side programme leader who has led dozens of Workday implementations, who understands how your SI operates because they've sat in those chairs, and who can be in place within two weeks rather than the two to three months a permanent hire takes.
How we approach this at 360 HCM
When organisations come to us, it's usually because they've already recognised the gap. They know their internal team doesn't have the Workday-specific programme leadership experience to hold the SI accountable. Or they've started the programme and realised that the person leading it - however capable they are in other contexts - doesn't have the authority or the knowledge to challenge what the SI is delivering.
We provide that leadership through COMPaaS - fractional, senior programme oversight that establishes governance, manages scope, leads steering committees, and ensures your SI delivers what they committed to. We also provide dedicated Workday project managers for organisations that need experienced, hands-on delivery coordination embedded in their programme.
Both services exist because of a simple truth I've observed across hundreds of Workday programmes: the technology works. The SIs are competent. But without the right person on the client side - someone with the experience, authority, and independence to protect the programme - budgets overrun, timelines slip, and executive confidence erodes..
Start with a Conversation
If you're about to deploy Workday and you're thinking about who should lead the programme on your side, we offer a free 30-minute programme risk review. We'll discuss your programme scope, your current leadership structure, and the specific risks you're facing. Within 24 hours, you'll receive a written findings summary with our top three recommendations.
No obligation. No sales pitch. Just an honest assessment from someone who has led these programmes from both sides of the table.
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