I've written about planning before but mostly from a theoretical point of view; most of the practical planning advice I've come up with went into the books I write with Tim.  I did tuck some away some how-to-do-it in an ancient handout about what's wrong with club players, and had a reason recently to dig it out and have another go.  Here it is with a worked example:

Planning (level 1):

If someone were to ask you what you are trying to do at any stage in the game, you should have an answer.  (I'm trying to swap off pieces... I'm attacking the opponent's King... I'm picking on a weakness... I'm trying to make a mess...).

If you don't know what to do, pick out your worst placed piece and do something to get it working harder for you (Anderssen's Rule).

Planning (level 2):

...systematic planning comes down to: Ready, Aim, Fire!

Ready - Notice and assess the positional elements (see below),

Aim - Form a realistic plan based on an appraisal of the chances for each side, then

Fire! - Pick the move(s) which best meet your needs.

Planning (level 3):

Let's try and bring a bit of system to the sketch above.   I came up with the mnemonic To Know What Plan to Follow Look Carefully , standing for:

  • T actics (usually trumps other considerations),
  • K ing safety (again, if you're getting mated, it trumps other issues),
  • W eak squares&weak Pawns,
  • P iece position (good and bad),
  • F orcing moves (initiative, pawn breakthroughs, sacrifices),
  • L ine control (files, ranks, diagonals),
  • C entre and space.

The WPFLC are in no particular order, of course. 

This may be time-consuming to go through at first, but after doing a couple of dozen test positions this way (pick up a chess magazine!) you find it becomes automatic.  

Having identified the features of the position using this list, you should have a view about who is better and (more importantly) what you should be trying to do. Silman advises dreaming up a fantasy position to decide this.

Once you have an aim (or two) in mind, think about what you would need to achieve that aim -- which pieces need to move where, in what order...  This way you build up a set of candidate moves.  Work your way through the 'candidate' moves, calculating the likely consequences and assessing the resulting positions.  If no clear favourite emerges, just go for one. 

I think the relationship between your aim and your method is a dialogue: because you are interested only in achievable plans, your thinking may wander between aims and methods (moves) as you consider the position and conclude that some moves or sequences are impractical.  But the number of different aims you have in mind should be kept to a minimum. 

Again, this may all seem time-consuming, but you don't come to a position 'cold', you were looking at a very similar position just a move ago!  Every so often (coming out of the opening, say) you might need to take stock and make a plan from scratch, and this is worth 15-20 minutes of your clock time to get it right and guide your play over the next few moves.

Moulton L.
Scott R.

Exeter Tigers vs. Isca

w - - 0 17

Here's a position I had the misfortune to watch being played.  White came up with Kh1 "because I didn't know what to do".  Groan... Well, how could you decide what to do?  Have a go before reading on: listen to all your pieces:

Suggested aim based on this feature
K ing safety?  Both more or less OK: the moved f-Pawns make each a little weaker than usual (weak squares and possible pawn levers).
Plan: maybe we can attack the Black King by g2-g4: move h3, Kh1, Rg1, g4. Slow, but important if works! Generally, short-term plans are better than long-term ones which get upset by events.
W eaknesses?  White has a weak Pawn on d3 and a weak square at d4; Black has unprotected Pawns on d6 and e6.
Get rid of weak d3 Pawn by d3-d4. We would have to exchange e4 Pawn first, but even then e4xf5, Ne7xf5 improves Black's position and we will never play d3-d4.
P iece placement?  Na4 is doing nothing (I suppose it is co-operating with the Be3 in attacking c5). White is a little better mobilised.  There is a strong Black Bg7, and a poor Be2.  Rb1 and Rf1 aren't doing much.
Move Be2-f3 (although that's not doing anything until the e-pawn moves).  Or Rf1-e1 (can't see a better square for the Rb1).  Or play Qd2 then Nb2-d1-f2... A couple of reasonable one-move plans there that fit Anderssen's recipe, but our worst piece is difficult to bring to life.
F orcing moves? Apart from g3-g4 (see above) there is e5 and exf5.
The capture on f5 will force a recapture, and there is a natural break with e4-e5. 
There aren't any other forcing moves, so do we play e4-e5 straight away or prepare it? Does either move achieve anything?  exf5 doesn't appeal but e4-e5 undermines c5... a point we already mentioned.
L ines?  No open files, strong long dark diagonal for Black.
Bc1-b2 challenges control... ...but that's our good Bishop.
C entre?  White has more space.  Centre is unfixed, so can be opened up.  Black has space on the Queen's-side. 
Play in centre or King's-side, use the extra space to attack? If we want to open lines we can do it with e4-e5.

White has two good-looking plans:

a. move across to King's-side and play g2-g4.  Good idea, bound to worry Black.  It is rather slow, and the centre is not yet fixed so Black's natural defence would be to blow up the centre. 

b. play in the centre: e4xf5 is poor (...Nxf5), but e4-e5 is possible.  In fact, e4-e5 undermines support by Pd6 of Pc5, and suddenly makes our 'lost' Na4 look like a useful piece.  Also, later we might play Be2-f3, using the opened long diagonal. Looking good!

[No obvious plan emerged for Black, who is rather passively placed; sometimes your best plan is to work out how to survive your opponent's best plan!]

So, after some thought, we come to the plan e4-e5, which has the ideas e5xd6, Na4xc5, and Be2-f3.  Does it work?

Don't play a good-looking move in vague hopefulness: consider what your opponent's reply might be. 

Black has four sensible replies which we must look at in turn:

A) 1. e4-e5 d6-d5, avoiding the attack on d6

B) 1. e4-e5 d6xe5, capturing the attacker

C) 1. e4-e5 Nb8-a6, defending c5

D) 1. e4-e5 Qd8-c7, defending d6 and c5

How should White react to each of these moves?

A) 1. e4-e5 d6-d5 2. Nxc5 because 2...d5-d4 just loses the Pawn.

B) 1. e4-e5 d6xe5 2. Nxe5 when the undefended Pawn on c5 is attacked twice.

C) 1. e4-e5 Nb8-a6 2. exd6

D) 1. e4-e5 Qd8-c7 2. exd6 Qxd6 3. Bxc5 wins the Knight on e7

One last look around for anything we may have missed – nothing, so, 1.e4-e5 is our move.

I promise you that, after a while, e4-e5 is the sort of move that jumps out at you as one to look at first.

[Event "Exeter Tigers vs. Isca"]
[Site "?"]
[Date "1998.??.??"]
[Round "?"]
[White "Moulton, L."]
[Black "Scott, R."]
[Result "0-1"]
[ECO "B21"]
[PlyCount "94"]
[EventDate "1998.??.??"]

1. e4 c5 2. f4 d6 3. Nf3 Nc6 4. Be2 g6 5. d3 Bg7 6. Nc3 a6 7. Be3 b5 8. Nd5 e6
9. Nc3 b4 10. Na4 Bd7 11. c3 a5 12. c4 Nge7 13. Rb1 O-O 14. b3 f5 15. O-O Nb8 {
#} 16. Kh1 (16. e5 Bxa4 (16... Na6 17. exd6 $16) (16... dxe5 17. Nxe5 $14) (
16... d5 17. Nxc5 $18) (16... Qc7 17. exd6 $18) 17. bxa4 Nbc6 $11) 16... Nc8
17. h3 Qe8 18. Kg1 Bxa4 19. bxa4 Nb6 20. Bc1 Nxa4 21. e5 Nc3 22. Qc2 Nxb1 23.
Qxb1 Nc6 24. Bd1 dxe5 25. fxe5 Nxe5 26. Qc2 Nxf3+ 27. Bxf3 Rd8 28. Re1 Qd7 29.
Rd1 Bc3 30. Bg5 Bf6 31. Be3 Bd4 32. Kf2 Bxe3+ 33. Kxe3 Qd4+ 34. Ke2 Rd6 35. Qb1
Rfd8 36. g3 a4 37. Qc2 Qe5+ 38. Kf2 a3 39. Be2 f4 40. g4 Qe3+ 41. Kf1 Qxh3+ 42.
Ke1 Qe3 43. Kf1 f3 44. Bxf3 Qxf3+ 45. Ke1 Rxd3 46. Rxd3 Rxd3 47. g5 Re3+ 0-1