To clear things up, I do both boxing and kickboxing. I have this problem in both styles with my coach. I can out kickbox the new guy pretty easily, just having more trouble with boxing/punching so that's what I was wanting to focus on. I typically like to instigate until I can incite a reaction and then counter off of that. I'll mix things up with jabs, crosses and hooks on the lead, going to the head and body, mixing in feints and looking for tendencies. I throw a 1-2, pull, and hook off of that a lot and that has been giving me trouble because when I pull, I'm still in the taller man's striking range but I can't hit him. I'm aware of the problem, I just revert back to the habit often. Wanting to add a few tricks to the tool belt to use during these occasions.
Another thing is that I will throw punches and they are able to just lean back and avoid them, so I'll usually work the body and then go upstairs. After a few misses at the head, I'll get more explosive in covering distance to find the chin. I have a hard time pulling punches when I do this and usually land shots that are too hard. That is another reason I'd really like to improve getting inside and working from there in a more controlled manner.
Something that helps me is find the sweet spot right before his punch (where he can't jab you and obv you can't either)draw an imaginary line and keep that distance at ALL times unless you are ready to attack, don't hang out in the mid range with your feet planted.
Now from this distance (right on the outside of his punch) you will try to time him stepping in.
if you time him stepping in you take that step in as well, and meet him in the middle (keep in mind hes most likely going to try and close that distance with a punch since your right on the edge. Move your head step in at a dominant angle fire your combo, stay all the way in or all the way out...repeat.
So your feinting from that line outside his reach, faking entrys, moving angles, draw him towards you, meet him in the middle, dont chase
I have short reach for my weight so it's nothing new to me, this shit seriously works, i don't know if i can explain it any better on my phone.
But just meet him, you can even pressure your opponent and cut off the ring from that distance, once HE trys to close, BOOM meet him in the middle he just made it easier for you.
You wont be taking unnecessary damge against a less skilled fighter with this basic concept in your mind, its a simple strategy that goes a long way.
I suggest watching rigo box, when he fights much taller guys it still appears as if he has the reach because hes moving them into his punching