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I'm currently training a student (rating: ~1350 ELO, Age: 16) in my local chess club, who has been making quite some progress in his rating and playing style lately. Nevertheless, when he is playing against me or another much higher rated opponent (1700+ ELO), he always plays quite cowardly and defensively and isn't going for an attack even if it is objectively good for him. Therefore, he is quite happy when he draws a game against a higher rated player instead of taking a little risk to win a game.

How can I access this psychological problem in my training sessions and teach him some courage?

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Possible reasons

Strictly speaking to content oneself drawing a much higher ranked player in tournaments, when not having a clear understanding of what the exact counterpart for aggression might be, is not a bad idea at all. This said, I would look at two main sources for this to happen:

  • Playing style: not all chess players encourage attack: there are many examples of ultimate GM who are notorious for their positional solid play who dismantle the opponent only one bit at a time, very often just going into endgames where they convert tiny positional advantages into wins (promoting that f pawn after 30 moves preparation). Above all I would mention Karpov and Kramnik, not ultimately known for their attacking fantasies but for sure almost impossible to win against exactly due to the hard discipline and strong knowledge of theoretical positions.
  • Knowledge of enough lines, variations and continuations: it is by all means true that one is more comfortable attacking in positions where one knows already many (if not all) the standard outcomes, because "well, the worst that can happen is that I will be left with a doubled pawn on the g file..."

Possible exercises

I myself am part of the above category and generally dislike attacking only for the sake of it; since it is however true though that this characteristic has sometimes held me back from better results, I tried to address the problem in two ways, so far:

  • chess puzzles: looking and solving chess puzzles helps giving you the "feel" of a given position, showing how tactics can help winning a piece on the short run or combining together bishop and knight for a vortex attack (or the like).
  • better preparation of openings and position: preparing all (well, not all, but many) possible outcomes of a given opening helps minimising the "risk" of a blunder attack; it can be helpful to practice only one-two openings and defenses to be more secure about the continuations.
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The simple solution is to teach him to not look at his opponents' ratings until after the game. Seeing that he played well against a player who he did not know had a high rating will boost his confidence.

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Play the board, not the rating.

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Give your student a particular responsibility, for example finding out as much about a particular opening, in this case an assertive or attacking opening such as the King's Gambit, and ask him to use the opening in his training with you.

Praise any positive changes in his play, even if it is only a mildly attacking move or series of moves.

If these ideas don't work, start playing games by giving your student the advantage of a minor or major piece, as appropriate. He will be forced to attack because you will have more work to do to develop your fewer pieces.

Finally, turn things around: tell your student you want to develop your defensive skills, and ask him to attack more to help you do this.

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You can't solve this person's problems, or teach them courage really, they might have complex psychological issues that go beyond chess. Best you can do is just do the best you can with the mechanics of chess and leaving the rest up to the person himself.

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