You've asked this question twice now, so I'll do a TL/DR on it even though I'm going to get destroyed for it.
Honest answers.
1. Are we playing well? Do you know what his plan/system/formation is?
I think we are playing pretty well. But more than that, I think there are very interesting signs on the pitch.
There are two types of managers: System managers (Wenger, AVB, Rodgers) and flexible/pragmatic managers (Pep, Jose, Fergie). Both approaches can work, but personally I favour the latter. Flexible/pragmatic systems can be either exciting/attacking (Fergie/Pep), or boring/defensive (Jose). I think Sherwood is one of these flexible types, and I think he's clearly at the attacking end of that scale.
For example, he doesn't seem dogmatically obsessed with DM's like so many are nowadays. It was so dispiriting to see so many Spurs fans - Spurs fans! - losing the head the other night against Sunderland because we didn't have a DM against the worst team in the league at home. Sherwood decided there was no need for it - just put decent footballers like Chadli and Paulinho in front of the back 4 and that's enough of a shield whilst also giving us loads more go-forward. And that's exactly what happened. Horses for courses, not systems and DM's who aren't needed. Sherwood owned GG in the tactics stakes on Monday night.
Nobody else agrees with me, but in my very strong opinion the loss to Liverpool had nothing whatsoever to do with tactics. We'll never know what the tactical game would have been because we were buried after 1 minute and then again on 25 (we all now why.) But the thing for me is that Sherwood rejected the clichéd, lazy tact of playing counter-attack. It sounds so tempting and obvious a thing to do, but is actually a TERRIBLE tactic against Liverpool, esp. with our defence. So instead, the plan was to attack their crappy defence rather than inviting them to attack our crappy defence. I really liked Sherwood's rejection of the easy, obvious option, and I'm sorry we never saw how it worked. The point is he was thinking.
We were good against Arsenal (we were played off the park at their place) and against Chelsea for an hour (they were in flying form at the time). In 16 games, only against Norwich have we been truly, irredeemably hopeless. (There's a good argument that judging Sherwood at all on his first 4 or 5 games when he hardly had a spare day to work on the training pitch is unfair).
I think we've been...interesting. I am very tempted to see how these experiments might progress.
2. Does it look like the football is improving?
Eriksen - Serious step up in class/performance in recent weeks. And how many of us spotted that wide left was his best position? Certainly not me.
Chadli - Who thought he'd be effective in the middle? He's doing the job we all wish Dembele would do, and all thought Pauli would be doing. Who knew?
Soldado - Injury came at terrible time because he was so, so good against Southampton. I'm not saying that's definitely down to something Sherwood did, but it might be.
Ade - The salute said it all.
Bentaleb - How many of the people abusing Sherwood the other night for not playing Bentaleb had never even heard of Bentaleb 6 months ago? Fair's fair for crying out loud. What does Sherwood's spotting, nurturing and trusting this guy say about Sherwood? And what does it say that he had the nuts to believe in what he saw and stuck him straight into the first team? (Note to Scara: Bentaleb is not Glenn Whelan.)
Paulinho - Did anyone see him SMILING on the pitch the other night? He's been dire all season, but the other night he looked a bit more like the player he surely can be. Again, may not be down to Sherwood, but who knows?
What players have gone backwards?
Vertonghen - I honestly don't think this has anything to do with Sherwood - Jan wants out and has done for some time, and I think at this stage many Spurs fans want him out too. If Sherwood was talking about Jan when he said there were some he doesn't trust, how many Spurs fans would argue with that? I don't want him at the club any more (barring a big mea culpa/humble pie eating).
Capoue - I don't like how Sherwood has treated Capoue at all. It has been disrespectful of a guy who I hear is very good. Black mark against Sherwood for sure.
Sandro - I honestly don't think he's fit. He was magnificent at CB in Lisbon, but picked up a knock there and then was out of the team because of rotation. I don't think there's a Sherwood issue here at all. Sandro still Tweeting like a good thing and talking positively.
Overall, I see more positives about fulfilling potential and progressing then negatives.
3. Are we an exciting side?
It's a work in progress. More exciting than under AVB? I can't believe even Sherwood's harshest critics would deny we're more attacking and are creating more chances.
p) out in, it became necessary because Ade (and Defoe) kept missing too many sitters; I can think of QPR away, West Ham away, Swansea away. I'm sure there were many others..