Our customer support director has been with us since we started ten years ago and is a cultural pillar, but we are upgrading our tech stack with automated ticketing and AI tools. She is completely overwhelmed and struggling with the technical side. How do we run a GWC assessment on a long-tenured leader when the seat has outgrown her?

Question

Tyler Smith · Accepted Answer

Running a GWC evaluation on a loyal, long-tenured leader is one of the hardest things a founder has to do. However, if your business is transitioning to modern tech stacks and automated tools, you must make objective decisions for the health of the company. A culture fit in the wrong seat still holds the entire organization back.

Evaluate your customer support director using the GWC tool.

- Gets It: Does she truly understand the underlying logic of automated ticketing and tech tools, or is she just memorizing steps?
- Wants It: Does she wake up excited to optimize these digital workflows, or is she resisting the change?
- Capacity: Does she have the mental capacity and technical aptitude to lead an AI-assisted department at scale?

If she lacks the capacity to master the new technology, she does not pass GWC for this seat. It is that simple. Keeping her in a seat she cannot handle will lead to burn out and operational failure.

The solution is to keep the human separate from the seat. Since she is a great culture fit, look at your Accountability Chart to see if there is another seat where she does pass GWC. This could be a high-touch client relations seat or a cultural leadership role. If no such seat exists or if you cannot afford it, you must make the tough call to let her go so she can find a seat where she can succeed.