If I could hire for one trait in an estimator today, it would be a good listener.
Not the fastest writer. Not the most technical.
Estimating touches negotiation at every stage. You’re working through scope with the homeowner, submitting to the carrier, going back and forth with a reviewer. At every point, someone has a perspective you need to understand before you respond.
The estimators I’ve watched struggle are usually the ones who walk in with the answer already decided. They’ve figured out how to settle the file before the conversation starts. And sometimes they give up more than they needed to, because they never slowed down long enough to hear what the other side actually needed.
I’ve seen this play out on the contractor-carrier side too. What looks like an adversarial exchange is often just two people trying to get questions answered. When someone slows down long enough to understand what the other side is actually asking, the whole dynamic changes.
A good listener catches that shift. They realize midway through that the issue isn’t what they thought it was, and they find a different way through.
The technical skills are a lot easier to build around. Xactimate has a long learning curve. But the estimators who become truly strong at it are the ones who stay curious, use the tools available to them, and aren’t afraid to ask questions. They work collaboratively. They don’t assume they’ve got it figured out.
You can teach software. You can teach line items and carrier protocols. It’s a lot harder to teach someone to stop and actually hear what’s being said.
Look for that in your next hire.
Chris Tilkov is a Director at DocuSketch and the President and Founder of 
