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5 questions every Chief Information Officer should bring to Workday Rising 2026
For every new AI opportunity, CIOs are being handed a second set of questions, such as:
- What data will it access?
- How will it integrate?
- Who governs it?
- How do we secure it?
- What does it add to the architecture?
- What happens when a handful of promising experiments become hundreds?
That is happening while IT is already being asked to reduce complexity, improve employee experiences, modernize legacy technology, protect enterprise data, and help the business move faster.
At Workday Rising Las Vegas, technology leaders have an opportunity to step back and consider what role Workday should play in an enterprise architecture that is becoming more intelligent, connected, and complex.
Here are five questions a Chief Information Officer to ask at Workday Rising?
1. How do we scale AI without creating another layer of risk and complexity?
Starting an AI pilot is relatively easy but scaling AI across a global enterprise is a very different proposition.
As more AI and agentic capabilities enter HR, Finance, and other business processes, CIOs have to think about access, governance, identity, security, auditability, data permissions, monitoring, and accountability. Its important for a CIO to consider these questions:
- Who can an AI agent act on behalf of?
- Which data can it access?
- How do you know what it did?
- Where does human oversight belong?
- How do you avoid every function developing its own approach?
At Rising, look beyond what an AI capability can do and ask how it fits into the controls and architecture required to operate it at scale.
The strongest examples will show both the intelligence of the technology and the structure required to manage it responsibly.
2. Is our data foundation ready for what comes next?
AI is only as useful as the data it can work with. The same is true for analytics, planning, automation, and many of the experiences businesses are trying to create.
Yet in large organizations, critical data often spans Workday, legacy platforms, industry systems, point solutions, data warehouses, and countless integrations built over many years.
The real question is whether the right systems, people, and increasingly AI can use that data reliably.
At Rising, pay attention to conversations around data architecture, integration, governance, interoperability, and how organizations are bringing information together across the enterprise.
Ask where fragmented data is still slowing down decisions or creating manual work.
A stronger data foundation gives the organization more options as AI, automation, and analytics become more deeply embedded in everyday operations.
3. Are HR, Finance, and IT planning for the same future?
Technology decisions are increasingly business model decisions that have to align with each functions needs, such as:
- HR- may be planning for a different workforce.
- Finance- may be setting new productivity or growth expectations.
- Business leaders- may be looking at AI to rethink entire processes.
- IT- has to turn those ambitions into an architecture that actually works.
That makes alignment with the CHRO and CFO particularly important to answer key questions including:
- Does the technology roadmap reflect how the workforce is expected to change?
- Are Finance and IT aligned on where technology investments will create value?
- Are business functions adopting AI within a common enterprise approach, or one use case at a time?
Use Rising to understand what your HR and Finance peers are hearing too.
Some of the most useful conversations for a CIO may happen outside the IT track because those conversations reveal what the business is going to ask of technology next.
The earlier IT is part of that discussion, the more intentionally the architecture can evolve.
4. Where can we simplify instead of adding another tool?
Enterprise technology has a habit of accumulating to meet new business situations including:
- A new business requirement creates a new point solution.
- A missing integration creates another manual workaround.
- A process that does not quite fit creates another application.
Eventually, complexity becomes its own operating cost.
Rising is an opportunity to look at your Workday environment through a simplification lens to assess improvement opportunities such as:
- Where are employees moving information manually?
- Which integrations have become difficult to maintain?
- Where have point solutions multiplied around Workday?
- Could automation, Workday Extend, Orchestrate, or a different process reduce the number of systems or handoffs involved?
At the Strada booth, AI & Innovation and Optimize & Operate will both be core areas of focus, alongside HR, payroll, benefits, finance, and planning.
We will also be hosting smaller conversations in the Strada Lounge, including workshops around AI readiness, Workday Extend and Orchestrate, and ongoing Workday optimization.
This gives a great opportunity to explore those ugly processes that are unnecessarily complex with expertise to rethink how to approach that issue. Those conversations are often much more useful than another generic demo.
5. What should we build, buy, extend, or automate next?
CIOs rarely suffer from a shortage of ideas, the challenge is deciding which ones deserve to become part of the enterprise. These include ideas like:
- Does a requirement belong in the core platform?
- Is it better addressed through configuration?
- Should you extend Workday?
- Integrate with another system?
- Automate the process?
- Buy a specialist solution?
- Question whether the requirement should exist at all?
Rising gives you access to Workday, partners, customers, and peers who have made many of those decisions already.
Ask customers why they chose one approach over another. Find out what became more difficult at scale. Understand what they would do differently. Talk to people who have worked across multiple Workday environments, not just one.
Strada experts will be available through Braindates, the booth, our workshops, customer sessions, and conversations in the Strada Lounge throughout the week.
Bring the architecture decisions you are struggling with, alongside the technologies you are evaluating.
Leave Workday Rising as a CIO with a clearer view of what comes next
By the end of Rising, your list of possibilities will probably be longer than when you arrived.
The value comes from knowing which ones deserve to move forward, by assessing them with these questions:
- Which AI capabilities are ready to scale?
- Which data issues have to be addressed first?
- Where can the organization remove complexity?
- What decisions require closer alignment with HR and Finance?
- Where should Workday play a larger, or perhaps simpler, role in your enterprise architecture?
For CIOs, Rising should help bring the architecture, data, governance, and platform decisions required for what comes next into sharper focus.
