Having trouble losing against a friend

Tell him all your plans and comboes and give him tips every step of the way. Mention charge ranges and other such stuff.

Make sure he doesn't feel suprised and guide him with every step. For a newguy you need this sort of tutoring until you can get stuff memorized.

Circle might be the most difficult faction to play and is really tough on the beginner. Encourage your friend to go online and read a lot of Tacticas and watch battle reports. Focus on positioning of models and order of activations and how the combos stack. Circle is all about order, position, and combo stacking, more than any other faction.

If you really want to work together the best thing is to talk through order of activations, allow rewinds, do some quick dice averages, etc.

Warmachine is an easy game or learn but a very unforgiving to master. It takes time and you will lose a lot your first year.

It's a different mindset to play these armies. Khador is super durable and even if you tell him your entire game plan it will be hard for him to stop you. Now Circle has tricks and movement shenanigans so it is a lot harder to learn. Kharchev should probably not be used much if at all because he's such a beast in smaller games. At least until your friend gets a feel for his army and understands threat ranges. Stalkers are a great suggestion as well as a primaled feral with warped strength. That's two MAT9 P&S 19 attacks and a MAT9 P&S18 attack and he'll frenzy next turn. Pretty scary if you ask me.

Wormy is a very good scenario warlock. But he isn't that good at small point games.

Like I said, Circle find Khador hard to beat, we carry too much in the way of armour. Sure, Wormy can spit out boosted Hellmouths, but it only delays the inevitable, the argus light can't even scratch the paint on a Khador Jack. Whilst a stalker is able to do so provided he warps strength and Wormwood gets a curse of shadows off (he can get up to effective ps20 at that point.) that's still one heavy against 2. Cassius isn't going to be hunting down warjacks, and the Stalker is going to be within counter attacking range one he gets in to kill a heavy.

To want a chance, he needs a damage buff and he wants something else that can hit. Like a Gorax and a wolf of some kind.

I have noticed that strangelhold is easily the most powerful spell he has access to. It makes it very difficult to actually get a meaningful charge on his units. I have been relying on countercharge from Karchev and effective positioning to get my alpha.

Just to elaborate a bit on some of the other points. Wurmwood is a difficult caster to play in the first place due to the nature of some of the mechanics and also isn't particularly suited to small battle box games. One primary reason for this is that there are not a lot of bodies on the table and therefore Wurmwood is unable to get souls to help fuel a lot of spell slinging. This is amplified by only having two beasts because it means that they need to keep active to fuel Wurmwood's spellcasting. Apart from that, if you are playing Karchev with a Kodiak and juggernaut you are effectively fielding 3 heavies against his single heavy. That makes his single warpwolf such a linchpin to the list that any small mistake where he looses it means its pretty grim.

If your friend wants to continue playing Wurmwood then I would suggest playing some larger points games to allow some more models on the table and give him access to things like troops for souls and as hellmouth targets. If you want to continue playing battle box games then I might suggest Baldur 1, Tanith (since she is in the box), or even Kromac 2. Either way, playing at a points level where he can have two heavies (you can do this at battle box with something like a feral and gnarlhorn satyr depending on the casters warbeast point) would certainly help over a heavy and a light.