The link LynnH provided already shares some of my thoughts about this, but I'll just add a bit more here.

I knew my role would be changing as my dc matured, and I was not sure how to embrace that. The meeting times I have planned in my school routine have been the answer to this transition.
A little background on how the "meeting time checkpoints" were added to my day in the first place...

I knew I should be doing the follow-ups in each of the boxes, checking my older ds's work more consistently, giving feedback to his work routinely, etc. I did not do a very good job of this when Wyatt started CTC. I sort of didn't do my teacher part, I guess.

I figured out the hard way that "Independent" work still requires my involvement in the form of checking it, informally discussing it, and making sure my ds did all he was supposed to do. Fast forward to RTR and RevtoRev - the midpoint meeting checkpoint was born.

Wyatt and I both LOVE this time together. We each get our favorite beverage (he usually gets hot tea and I have strong coffee), and I look at the boxes he has initialized to show he completed that work. He shows me the maps he did, and I spot check any 'trace this route', 'find this country', type things he did. He says his Bible memory work for me, and I look over his Bible Quiet Time written work, again informally commenting on this or that, as he does as well. I ask any questions in the box, help with any editing using the Appendix tips and sheets, listen to him read his written narrations and use the helps again to fix, hear his oral narrations - etc. I guess I am probably repeating some of what I said in the link already given. I just wanted to try to explain how I am completely in touch with what Wyatt is doing, how we really enjoy this time together, how he likes being treated like a more 'grown-up' person during his school time with me, and how our role has changed to be more on the same playing field. It's kind of like coming out from behind the teacher's desk, and pulling up a chair to chat and work through things collaboratively, team player fashion.

I also let him determine the order of what we'll go through, other than I first do my teaching lessons (i.e. math, R & S English, writing, etc.).
This kind of interaction has not only let me get a handle on what he is doing independently, it has also built our relationship to be a deep, loving, sharing one. He sees himself as a mature, active participant in his learning, and he sees me letting him embrace that new role, while still giving him support. This kind of together time and fashion of education goes so much more deep than reading history books together or constant formal assessment can go. I'm trying to explain this well, but not sure I am. Can you come over?!?

Seriously, HOD has helped me figure out how to help my ds grow up, how to hang onto our relationship through these rocky teen years, and how to navigate my changing role as his teacher. I think he loves me as his teacher in this capacity. I know I love him as my student in this capacity. It is just great fun to go from teaching Emmett phonics, to talking about how to do a written narration with Riley, to talking about primary source documents and why that person wrote what they did and what he must have been thinking and how that impacted history and isn't it so incredible we can still read those words today and wow his faith sure impacted his decisions, and so on and so on with Wyatt! His being older and me focusing just on him (as his younger brothers do not place in the same guide as he does) have helped us just really go deep sometimes and move quicker at others, to sort of have the ebb and flow of the day be ours as we want it. I hope something here helps, but you can probably guess my advice would be for you to add some meeting times, checkpoint type times, to your day with your older(s), and enjoy it to the hilt!
In Christ,
Julie