Our long-term estimator is overwhelmed by our new AI-assisted bidding software and is quietly resisting it. How do we use a three-step coaching process to determine if this is an alignment issue with our core value of Grow or Die or simply a GWC problem?

Question

Tyler Smith · Accepted Answer

When an experienced team member resists technological change, it is easy to assume they are violating your core value of Grow or Die. But you must slow down and diagnose the root cause before taking drastic action. Use a three-step coaching process to separate character alignment from capability. First, have an open and honest conversation to evaluate their GWC for the evolving seat. Do they get the new workflow? Do they truly want to work with AI tools? Do they have the mental and physical capacity to learn the software? Often, resistance comes from a fear of looking incompetent, not a lack of core values. Second, provide targeted support. If it is a capacity or knowledge gap, assign a tech-savvy team member to pair-program or co-work with them for two weeks. Break down the software into simple steps and let them master one module at a time. This removes the overwhelm and builds their confidence. Third, set clear, objective milestones. Give them thirty days to run their bids through the AI assistant with help. If, after thirty days of intense support, they still refuse to use the tool or complain about the change, you are dealing with a core value issue. They are choosing not to grow. At that point, you must make a tough people decision. You cannot allow a single seat owner to hold back the operational leverage of the entire company, no matter how much historical knowledge they possess.