A drilling system includes a drilling machine, configured to drill a hole in a work piece along a drilling axis, a deployment mechanism, attached to the drilling machine, a measuring probe, attached to the deployment mechanism, and a controller, coupled to the drilling machine, the measuring probe, and the deployment mechanism. The measuring probe is configured to produce a signal indicative of an actual geometric parameter of the hole when inserted therein. The deployment mechanism is configured to selectively align the measuring probe along the drilling axis. The controller is configured to cause insertion of the measuring probe into the hole, and to receive the signal from the measuring probe.