Organizational Readiness: Is Your People Strategy Ready for 2027?

They covered everything from workforce planning and job architecture to AI, compensation, organizational design, and the growing need for HR and Finance to plan together.

Below are some of the biggest takeaways from the conversation.

Headcount is only one part of workforce planning

Chad shared that workforce planning at many companies still starts with a spreadsheet: current employees, open roles, planned hires, and next year’s budget. But simply carrying today’s organization into another year isn’t really workforce planning.

Kathryn put it simply: “Headcount is really just one outcome.” The bigger question is what work needs to get done, what skills it requires, and whether that work should be handled by employees, contractors, technology, or AI.

Your workforce plan needs more than one future

A spreadsheet usually gives you one version of what next year could look like. Chad argued that companies need to think beyond that and model different possibilities: higher growth, lower growth, new skills, or completely new ways of getting work done.

As Chad explained, scenario planning gives companies the ability to explore “different universes” rather than betting everything on one version of the future. The point isn’t to perfectly predict 2027; it’s to understand what happens when your assumptions change.

Don’t automatically backfill every role

Someone leaves, so you hire their replacement. It sounds obvious, but both Chad and Kathryn argued that this is exactly when companies should stop and reconsider the work.

Kathryn suggested asking whether the backfill is “intentional” or whether the company is simply “running the motion.” Chad added that turnover creates a natural opportunity to rethink the level, responsibilities, skills, and even whether the same role is still needed.

HR is becoming a work architect

Job architecture has traditionally been about organizing jobs, levels, and career paths. But AI creates an opportunity for HR to go one level deeper and think about how the work itself should be designed.

Chad described the shift perfectly: “This is actually a work problem, not just a job problem.” Instead of only defining jobs, HR can look at where work gets stuck, what creates unnecessary friction, what technology can handle, and where humans create the most value.

AI readiness starts with getting the basics right

It’s easy to jump straight into conversations about AI transforming the workforce, but Kathryn argued that organizations first need to understand whether their foundations are ready for it.

Do you know where your workforce data lives? Can you trust it? Are your processes actually working? Chad agreed that AI may dramatically change how work gets done, but companies still need solid data and systems underneath it. AI won’t magically fix a messy foundation.

The human skills may become even more valuable

As AI takes on more routine work, Kathryn suggested that adaptability, resilience, and learning agility may become increasingly important because employees will need to continuously learn rather than master one skill and rely on it for years.

Chad added another side to this: AI may make us more efficient, but efficiency doesn’t automatically create a better employee or customer experience. Communication, empathy, judgment, and other human skills could become even more valuable as more work gets automated.

Compensation still comes back to value

If AI changes jobs, does the way we pay people need to completely change too? Kathryn’s answer was essentially yes and no. The work may evolve, but the fundamentals of compensation remain focused on rewarding the value employees create.

Chad connected that back to performance and incentives: rather than rewarding people simply for doing something faster or using a new technology, companies need to stay focused on the actual business outcome being created.

HR and Finance need to plan together

Chad emphasized that better workforce planning requires HR and Finance to have an ongoing relationship, not a conversation that happens once during annual planning. Finance understands the cost and business assumptions, while HR brings context around people, skills, organizational design, and how work is actually getting done.

As business assumptions change, those teams need to be able to change the workforce plan together rather than discovering months later that they were planning against different realities.

Final Takeaway

The biggest takeaway from the conversation was that 2027 workforce planning can’t simply be 2026 plus or minus some headcount.

The work is changing, skills are changing, and AI is creating new options for how companies get things done. Being ready means understanding what the business needs to accomplish and then building the right combination of people, skills, structure, technology, and investment around it.

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Watch the webinar here

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