Should I encourage my toddler to be more assertive or is this just a phase?

[bgmama]

My DS is almost 2 years old. He is an affectionate and friendly little boy. He has liked being around and interacting with other children from a very young age.
I have noticed that he is not very assertive in the playground. For example, when he is playing with a toy and another little child comes and takes it from him, he usually looks surprised and hurt but he doesn't know how to react. At the beginning I had put it down to him being the youngest in the playground, but things haven't improved and I have seen the same thing happening even with children who are younger than him.
What I usually do in these situations is get down to their height and ask them to play nicely/encourage them to share etc. My DH thinks that I shouldn't get involved because DS will never learn to stand up for himself and that he will eventually get the hang of it. What do you think is the right approach?
As a child and a young adult I have struggled with assertiveness myself and I don't want him to go through the same. If that makes any difference, he has been in full time childcare since a year old so he has had plenty of opportunities to interact with other little children.

Btw I know it all sounds pfb and boring but any advice from people with similar experiences will be appreciated

I’d rather this than my child hitting or pushing, which tbh mine went through a recently after seeing a friend do it and thought it was hilarious. No matter what they are both stressful situations, he is only little I’d maybe just encourage sharing/swapping rather as assertiveness. Only you know if your wee one will be receptive to that though.

I was and and still not that assertive and happily do without for others, no amount of pushing and prodding forced martial arts lessons made any difference to my nature. The scored out stuff actually left me really shook up but I was about 5 so have quite a strong memory of that.

How’s his communication can he say loudly share if someone takes a toy he was playing with?

Personally I found it was just a phase with my 2.

My eldest even went through a phase of refusing to play in the playground if there were any other children there - previously he'd been happy as larry and trying to play with everyone (even 9 year olds when he was 18 months...)

He grew out of it and gained a lot more confidence. Today he will happily play with anyone and although he still has a tendance to give away his toys as soon as someone asks, if we tell him in advance not to, he won't. He's now 6.

DS2 just used to burst into loud tears if someone took his toy which usually meant the other mum gave it back . He also went through a phase of refusing to take his beloved sit on motorbike to the park because he didn't want to share it. He is now 3 and happily shares his toys but also will grab them back if he doesn't want to share.

As for advice, I found that standing very near DS gave him the confidence to ask for something back. And if he didn't I asked him if he wanted it and if yes then I asked the other child to give it back.

My 2.5 yr old is the same. In fact, we were out last week and a little girl who couldn't have been more than a year old pinched a toy off him and he just stood there looking dejected!

I guess it's just not in his nature to be overly assertive at the moment and I'm not sure if it can be influenced?

I do think it's the responsibility of the other parent to correct their child if they've blatantly taken something from another child. That shouldn't fall to you. Most parents I've encountered are really good at that.

I think it's personality. I don't know how to teach assertiveness either. And I totally understand where you come from. DC1 was like this. In gymnastic class, all the children will queue up to join the next equipment and she'll be squeezed to the end of the queue. Getting a pompom from the bag and she'll be the last. I kept telling her she can tell others that she was queuing and that they shouldn't queue jump. But it's just not her.

DC2 is very assertive. She started nursery at 1 and they told me if an older, bigger child took her toy, she would follow until he handed it back to her. She won't hit other children but she'll talk back with a very angry and loud voice.

Thank you for sharing your experiences, it's good to know my boy is not the only one.
To answer some of your questions/comments:
His speech is a bit behind his peers, probably because we are a multilingual household. He definitely doesn't know the word "share" in any language
I agree that it's in his nature and I know from personal experience that it's not easy to change that. Still, I always worry I do too little/too much to role-model appropriate behaviour when something like that happens.
When the other mother is around I don't interfere as they are good at stepping in. However, the children usually ignore them and carry on, so I am not sure their intervention is helpful for either of the little ones

I've been teaching dd that she has a strong voice and we practise at home saying 'No' or 'Stop that I don't like it' She gets upset trying it but we make a game of it and she is getting braver. The best lesson to teach is that they are strong and can speak up for themselves and if that doesn't work then they get an adult.