Bruce knew all of his children's weaknesses. They were all unique and had their own fears and insecurities. Sometimes, when they were having a hard time, Bruce came to comfort them and dispel their fears.
Dick's greatest fear was of losing all of his loved ones. Of being left alone after everyone died. This often made Dick irrational when it came to family, he would sacrifice anything to keep them safe and feared not being there to save them. Always he was trying to be everywhere at once, checking up on everybody and making sure they were safe and sound. It was at times like that, when Dick was stressed and looking twice his age as he concerned himself over everyone else's wellbeing but his own, that Bruce put his worries to rest. Discretely, he'd call a family gathering and have everyone stay over at the manor. Dick would call those who couldn't make it and have a chat with them, reassuring him that they were okay. These nights were the times where Dick could completely relax and let all his worries go, sending Bruce a knowing smile that let Bruce know that Dick knew what he was up to.
Jason's fear was the hardest to pin. Bruce would say that he was afraid of going through life unnoticed and of no one ever being there for him. Before he became the Red Hood, Jason had always been insecure as Robin about his place in Bruce's life since people had often considered him to be a cheap knock-off of Dick. It was one of the reasons he taunted Tim by calling him replacement, he was really using something that had always bothered him against Tim. It was also because by saying that, it asserted that Robin had also been his. When Jason rebelled and became the Red Hood, it was his way of declaring his independence and showing that he could be his own person. Being on the street so long had left him constantly unnoticed and unappreciated, so being able to actually make a difference meant a lot to him. His second fear, of no one being there for him, most likely came from dying on his own. On the streets he had been forced to look after himself, being alone had been natural to him. But then he had gotten a taste of what having a family could be like and then had it forcefully ripped away from him. Though he could still tolerate being alone, Bruce could tell how it bothered him to have no one there for him, for having no one to stand up for him or have his back. He was scared that no one loved him. Bruce rarely got the chance to comfort Jason anymore. Their contrasting perspectives lead to fighting when he did talk to him. But on the occasion when he could, he'd use every chance to apologize. He'd tell Jason how he missed him and how he wanted nothing more than for Jason to be safe; even if Jason was didn't believe him. When Jason was in danger, Bruce made it his priority to save him despite the fact that Jason was a criminal. He refused to fail Jason a second time. While this did not fix everything, Bruce knew it helped keep Jason from crossing the line between sanity and madness.
Tim, while complicated to figure out, had pretty basic fears. Tim was afraid of failing his loved ones. He was afraid of letting people down and of disappointing them. This stemmed from his childhood; Tim's parents had put a lot of pressure on him growing up. They raised him with impossible expectations, often looking down on him when he failed to meet their standards. Tim had been forced to work hard in order to make a name for himself; always scoring perfect grades and working hard in everything he did. Nothing ever seemed to make his parents happy, the most acknowledgment he got was a small nod or an approving glance. This continued on even when Tim became Robin, Bruce realized belatedly. Batman had set up impossible standards for Tim. He had made the training as hard as possible and did everything in his power to get Tim to give up. The determined boy had given his everything, achieving each goal Bruce set before him. Yet Bruce was never really good at showing his emotions. So when Bruce finally realized just how insecure Tim was, the reason he spent every spare minute overexerting himself and straining to become better, he tried his best to let Tim know that he was appreciated. He would complement Tim after telling Tim things he could do to become better and tell Tim that he was doing well in training. He would comfort Tim by assuring him that he is perfect the way he is. This seemed to keep Tim from working to death, just knowing that he was meeting Bruce's expectations. When Tim beat himself up after making a mistake, Bruce would assure him that he was doing enough. That he was making a difference. But the best thing Bruce could tell Tim was that he was proud of him.
While Damian's fears were complicated, it hadn't taken long for Bruce to figure them out. Damian was afraid of showing weakness and of failing or not being accepted by Bruce. Weakness was condoned by Damian, Talia had made sure of that. He would always put up a façade of absolute strength, refusing to let down his barriers and admit his flaws. This also resulted in him never letting out his feelings, instead releasing his anger through violence. While Damian wasn't afraid to be rebellious, he was also scared of Bruce not accepting him. Gaining Bruce's approval was like a ray of sunshine in his life. In that aspect, he was similar to Tim; Bruce telling Damian he was proud of him was the best complement he could give. Talia used to hold this place, but it transferred to Bruce when Damian became Robin. Bruce knew that the central reason Damian didn't kill was because his son respected his wishes and wanted to gain his approval. This tied to weakness, Damian seemed to think that by showing it, Bruce would disapprove or get angry. So on the rare occasions that Damian admitted to weakness, Bruce was careful not to seem angry or judgmental. He encouraged Damian to open up and share his emotions; he would sometimes share stories of his own mistakes, again like Tim, to let Damian know that it was okay to open up sometimes. Because all Damian really wanted was to be loved and accepted by those that mattered most to him.
Alfred wasn't tricky to figure out, his fears were similar to Bruce's own. He was afraid of his charges getting hurt and of them, one day, not returning from patrol. Of this, Bruce couldn't do much, because in their line of work it was bound to happen. The only thing he could really do was try his hardest to see to that he returned home safely with his children, something he would strive to do no matter what.
Bruce thought about his own fears. Bruce supposed that he was afraid for his children and for his city. He was afraid that he was raising his children wrong and of not being there for them when they needed him. He was afraid that Gotham could never be saved, that crime would never stop and would eventually take over after he died. He was afraid of disappointing his parents and dishonoring their memory. Nothing could sooth these fears, nothing but giving his all and doing his best for his family and for his home.