Feel free to structure a plan, I thought turning it into an exercise for him to solve would be better than just telling him what to do, and it seems equally arbitrary and pointless to withhold all advantages like magic. He pledged to a King with vast resources, that too is a reality that a vassal and ruling Lord has to face and account for.
I agree that he should make his own plans, and execute them himself too.
E.g. He doesn't need Ser Richard to capture some scrub knight, he has household guards and those are the people who are still going to be around come morning.
[X] Plan: Your Own Man
-[X] "You have asked for my advice, and I would offer my perspective on situation as I see it if you would still have it, but perhaps we should address the crux of the issue set out before you."
-[X] "Not every manner of ruling is suitable to each individual, akin to the fact that what works for captain of a trading vessel does not at all reflect the challenges faced by he who commands a war dromond."
-[X] "For you, a logistician's challenge." Adopt lecturing pose #27.
--[X] "The people of your fief insult and disparage you openly, this encouraged by your enemies openly, yet you retain tenuous hold over the Keep and servants. Men who serve you would instinctually bend to your commands as that is what they are raised to, yet you have likely issued few to none."
--[X] Lecturing pose #49: "You are then presented the challenge: your mother has directed all of the servants of the keep to her pleasing and rhythm. Taking away this privilege by simply assuming your rights to the household's direction immediately asserts your authority in this arena, making other commands seem natural as the incumbent Lord."
--[X] "The obstacles you face: Your mother countermanding your authority. The rousing of your subjects to discontent by outside hostile agents. A ruthless rival claimant loitering on your lands."
--[X] Lecturing pose #63: "Your resources: In the here and now, Sorcery granting mental fortitude or a diplomat's adroit tongue and a counselor and advisor with nearly four decades of experience navigating one of this realm's most perilous courts as a sounding board if you find it necessary in your initial planning."
-[X] "You have loyal retainers my Lord, make use of them to mutual benefit and should you find skills lacking in them or yourself my realm has training and advisors of the utmost quality to develop the abilities you require."
I didn't change much but I want him to learn that he needs to take charge, he needs to trust in himself, the people around him including us and that men are not stagnant, training and development is both available and encouraged.
