She tried to work out if he felt guilty and whether his position make him feel that way. In her questions, she asked if his job was stressful. The Doctor managed to work out of her a way to get some personal information out of her. She wanted to know if there was a decision that he regretted.
Eventually, the Doctor decided to go back in time to ensure that Guilana's fiancé survived the attack. As a result, over the course of their sessions the details about her life would change. In the new timeline, she married her fiancé and had children with her office also becoming more decorated. When she deduced that the Doctor was time travelling to see the results of their sessions together she installed a security measure. Eventually, because of this she discovered that her life had been manipulated beyond recognition by the Doctor. After angrily confronting him, she cancelled their sessions. (AUDIO: Asking for a Friend)