What to do to make this haircut much easier on my hair?

Ask the barber which he prefers.

I always used to wash my hair before going to the barber.
Now, I just wash my head and I am done.

In general, haircutters like to cut wet hair that has been shampooed and conditioned. Your barber needs to be able to run a comb easily through your hair without hitting tangles and snarls that will take him a long time to get out.

I am not sure what stiff hair is.

(The barber is coming to you?)

Finished! Thanks for the responses and yeah, he’s a friend of mines so he decided to just cut my hair at home.

Did he cut it wet or dry?

Generally washed hair make easier to comb and if you washed it with shampoo then really it will become more easier to comb and comfortable for both, you and barber while cutting the hair.

@gailcalled Sorry for the late reply, he cut it semi-wet because I was just finished taking a shower but I normally dry my hair a bit once out of the shower.