The Question: How can I transition team members into new roles now that AI is doing their job?

(This question was submitted via Spec It Out.)

I’m watching AI change our workforce in big ways. Entire sets of tasks that people used to handle are now automated, which means some employees are losing their jobs while others are being reassigned into roles that are totally different from what they had before.

The shift means that instead of doing repetitive work, people are suddenly expected to think critically, analyze, and engage more directly with customers and strategy.

But many don’t yet have those skills, and they’re unsure where they fit. What should I be doing to help employees adapt when their old roles disappear and their new roles demand capabilities they haven’t developed yet?

My Answer:

You’ve described a challenge many leaders face: roles are changing rapidly as AI and automation reshape the workforce. Routine work is disappearing, and employees are being asked to perform tasks that require new skills, higher-level thinking, and more collaborative engagement with colleagues and customers. Naturally, employees may feel uncertain, unprepared, or even displaced during this transition.

Consider applying mindset engineering

One way to approach this situation is through mindset engineering, a structured framework I developed to help leaders uncover and shift the assumptions, beliefs, and organizational patterns that shape how teams operate.

I call these mindset constraints, which define your team’s feasible region — the range of behaviors that feel possible and acceptable in the workplace. Put simply, if a desired outcome (like employees successfully transitioning into new roles) isn’t happening, it’s because those actions aren’t currently part of the feasible region. Achieving this requires thoughtfully shifting mindset constraints so the behaviors needed can emerge naturally and be supported.

The process works in four steps:

1. Identify the constraints → Determine what organizational assumptions, rules, and beliefs are shaping behavior.
2. Understand the impact → Each constraint limits the feasible region, creating boundaries on what employees feel comfortable attempting. This can result in hesitation, fear, or disengagement.
3. Shift the constraints → Adjusting these mindset constraints expands the feasible region, making new, productive behaviors possible and expected. Employees gain confidence to develop skills, take on new responsibilities, and adapt to evolving roles.
4. Take action → Put in place supportive structures, resources, and practices that reinforce the shifted mindset constraints and help sustain the new behaviors.

For this scenario, these might be observed patterns such as:

• “Only highly qualified employees should take on new roles.”
• “Experimentation is discouraged and errors are punished.”
•  “Employees must find support and learn new skills largely on their own.”

Shifting the constraints

Here are some examples of shifts that help employees navigate role transitions:

• Moving from “Only highly qualified employees should be placed in roles” → “Employees are supported to take on new roles with guidance and learning opportunities.”
• Moving from “Experimentation is discouraged and errors are punished” → “Experimentation is encouraged, feedback is constructive, and learning from mistakes is valued.”
• Moving from “Employees must find support and learn new skills largely on their own” → “Resources, mentoring, and structured learning pathways are integrated into work to help employees develop necessary skills.”

Questions to guide your reflection

As you consider your current environment, think about:

• Which new skills and capabilities are required in the evolving roles, and how confident do employees feel in developing them?
• Where do existing policies, workflows, or mechanisms limit or discourage employees from experimenting or learning?
• Which behaviors, achievements, or learning efforts are currently recognized and reinforced? How could recognition shift to encourage growth in new areas?
• What mechanisms allow employees to ask questions, get feedback, and safely experiment in the workplace?
• How are workflows, expectations, and role definitions aligned (or misaligned) with the capabilities employees are being asked to demonstrate?

Big picture

This is about more than training or reskilling — it’s about shaping the environment and mindset so employees feel empowered to grow, experiment, and adapt. By surfacing and shifting mindset constraints, you create an environment where learning, experimentation, and role transitions are both feasible and supported.

If you’d like support working through this process (identifying mindset constraints, shifting them, and designing pathways where employees can adapt and thrive in new roles), I’d be glad to help.Reach out anytime.