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5 questions every CHRO should bring to Workday Rising 2026
CHROs do not need another reminder that work is changing. The harder questions for CHRO's are;
- How quickly it is changing?
- Which changes matter most?
- What your organization should do about them?
AI is changing how work gets done. Skills requirements are shifting. Leaders are under pressure to improve productivity while attracting, developing, and retaining the people they need. And HR is increasingly expected to connect workforce decisions directly to business strategy.
Workday Rising offers a chance to step outside the day-to-day and look at those questions from a wider vantage point, through new technology, peer experiences, customer stories, and conversations with leaders making many of the same workforce decisions.
Here are five questions worth asking for CHROs to get the most out of Rising
1. What should work look like when people and AI are working together?
The conversation around AI has moved quickly from what it can do to what it means for the workforce.
That is where CHROs have an important role to play, making key decisions around AI including:
- Which work should be automated?
- Where can AI help people do their jobs better?
- Which roles will change most? What new skills will become more valuable?
- How do you help employees and leaders adapt as those changes become part of everyday work?
At Rising, look beyond the latest AI capability and listen for what organizations are learning about the work around it. Ask questions about:
- What changed in their operating model?
- How did roles and responsibilities shift?
- Where did employees embrace the change, and where did adoption stall?
- What did leaders have to do differently?
The technology may move quickly, but the workforce implications are ultimately a people question.
2. Do we have the workforce and skills we need for where the business is going?
Most workforce plans begin with what the organization needs today, but CHROs have to think further ahead.
If your company hits its growth targets, enters new markets, adopts more AI, changes its operating model, or shifts where work gets done, CHROs need to ask:
What capabilities will you need two or three years from now?
- Do you already have them?
- Can you develop them internally?
- Where will you need to hire?
- Which roles or skills may become less important as the work changes?
Use Rising to look at workforce planning through that longer-term lens.
Pay attention to how other organizations are approaching skills, talent mobility, recruiting, succession, reskilling, and workforce composition. Ask how they are identifying capability gaps before those gaps become business problems.
A useful workforce strategy should help you understand the people and capabilities the business will need next, not only the roles it needs to fill today.
3. Are HR, Finance, and IT planning for the same future?
Some of the biggest workforce decisions no longer belong to HR alone. HR may be thinking about skills, jobs, and employee experience. Finance may be focused on growth, productivity, and workforce cost. IT may be making decisions around AI, data, security, and enterprise technology.
Those plans need to connect and answer fundamental operational questions like:
- Are HR and Finance working from the same assumptions about workforce growth?
- Does your technology roadmap support the experience and operating model HR is trying to create?
- Are decisions about AI being made with the workforce impact in mind?
For CHROs, some of the most valuable conversations at Rising may happen outside the HR track. Seek out finance leaders, technology leaders, Workday experts, partners, and peers who can help you look at the same business questions through a different lens.
When HR, Finance, and IT are working from different assumptions, the organization eventually feels it.
4. Are we getting enough workforce value from our Workday investment?
For a large organization, Workday continues to evolve long after implementation. With influences like:
- Your business changes
- Your workforce changes
- Workday changes
- Processes that made sense several years ago may need to change with them
Rising is a good time to ask whether your organization is getting as much workforce value from Workday as it could be.
There may be processes that can be simplified, manual work that could be removed, data that could be used more effectively, or capabilities your organization already owns but has not fully adopted.
Alongside exploring what is new, use the week to question what your organization could be doing differently.
Strada will have experts at Rising across HR, payroll, benefits, AI, innovation, ongoing Workday optimization, finance, and planning. Whether the conversation happens through a customer session, a Braindate, the Strada booth, or the Strada Lounge, bring questions about the areas where your organization still feels friction.
5. What are my peers doing that should challenge our thinking?
One of the biggest advantages of being at Rising is access. Other organizations are wrestling with many of the same workforce questions, but they are not all answering them in the same way giving the opportunity to learn from these solutions.
Customer sessions are an obvious place to start. Strada will be joined by customers at Rising to share real experiences, including Port Houston's move from more than 15 legacy systems toward a unified Workday environment and Methodist Le Bonheur Healthcare's Benefits Administration experience.
Peer conversations at Workday Rising can be just as valuable options for these include:
- Book a Braindate around a question you are actively working through.
- Join a focused workshop.
- Ask another HR leader what they are seeing inside their organization.
- Compare notes after a keynote.
The Strada Lounge will also give attendees a quieter place to meet, work, catch a keynote watch party, join a smaller workshop, or continue a conversation that started somewhere else during the week.
You do not need 50 new ideas, A handful of the right ones can change how you think about what comes next.
Leave Workday Rising as a CHRO with a sharper view of your workforce
By the time you leave Las Vegas, you will have heard a lot about AI, skills, talent, employee experience, and where Workday is heading.
The real value comes from deciding what matters for your organization, and answering these qurstions:
- What challenged an assumption?
- Where did several conversations point to the same issue?
- What should you bring back to your CEO, CFO, CIO, or leadership team?
- What deserves action?
For CHROs, the value of Workday Rising comes from leaving with a sharper view of where your workforce needs to go next and what it will take to get there.
