Stealing Pre-Flop

Stealing pre-flop is an art and a science at the same time. 
On one hand, you need to be able to carefully select the spots
where stealing is likely to be profitable, but on the other hand
you'll need to know how to execute.  Some players will blindly
make attempts to steal pre-flop without any real reason or
strategy in mind.  As is the case with most poker plays, any move
that's without reason and motivation is going to end up failing
more often than it succeeds.  The truth is that stealing pots
pre-flop is actually quite simple and systematic, and many
players end up making it way more difficult than it needs to be. 

There are three different spots where you are going to be
stealing pre-flop: from late position, in the small blind, and
in the big blind.  There's little to no reason why you should be
gunning for blind steals when you are in early or middle
position.  The reason for this is that you'll end up getting
way too many calls and re raises to ever make this move
profitable.  The very reason that steals work is because raises
don't have to fight their way through that many players.  When
you start raising from early or middle position, however, you
are now being forced to get folds from the majority of the
table.  If you are raising from EP or MP, you should have a
strong hand. 

Hands

The first thing that you need to understand about stealing
pots pre-flop is what types of hands are going to carry the
highest success rates.  Since you are stealing and don't desire
to actually see the flop, you would think that your hands are
largely irrelevant.  While this may be the case, you can't
discount all of the times where you are going to get calls and
will have no choice but to play your hand post-flop.  When you do
get calls, your opponent will frequently be putting you on a
reasonable hand.  They might give you credit for a pair, two
broadway cards, or something else along those lines.  As a
result, a deceptive range of stealing hands will go a very long
way towards winning big pots when you really were only hoping to
take down the blinds. 

The most ideal hands for steals pre-flop are big suited cards
like K3, Q4, etc.  These types of hands play well in these
situations, because they either flop hard or miss hard.  You'll
hit some big flush draws, random trips, and even two pairs on
occasion.  Since your opponent is unlikely to put you on K3
suited, a flop like K3x is going to look harmless to their QK or
AK, for example.  The beauty in these hands is that you can fire
a c-bet if you miss and promptly give up if you face further
resistance.  Or, you'll have an easy time laying down K3 when
you miss and your opponent leads out.  These hands are exactly
what you should be looking for when stealing pots pre-flop. 

Types of Players to Steal Against

One thing that will remain universal when stealing pre-flop
is that you need to target the right types of opponents.  If you
are gunning for players who never fold, you are just asking to
fail.  If you raise way too much against players who are super
tight, you are going to waste a lot of money.  Even if you are
playing otherwise tight players and have a super loose image,
you are going to get called more often than you would like. 

Whenever you make a steal attempt from any position, first
make sure that the other players are capable of folding.  This
should all go without saying, but one of the main reasons why
players fail at steal attempts is because they were trying to
procure folds from players who never had the intention of
folding, regardless of the action in the hand, your image, or
anything else. 

Stealing from Late Position

Late position is the best time to steal the blinds.  You'll
have no money already invested in the pot, have position on your
opponents, and there's always a chance that you actually have a
strong hand.  With that said, it's also the most obvious time
for a steal in the eyes of your opponents.  Regardless, this
doesn't mean that you shouldn't be shooting for the dead money
in the blinds whenever you can. 

Bet sizing for late position steals is going to be different
than what you will implement in the blinds.  If you are one off
the button, a good raise size is 3x the big blind.  This assumes,
though, that your standard raise is to 4x.  By raising to 3x
instead, you are still using aggression and will put your
opponent to a decision, but you aren't putting a lot of your
money at risk.  When you shift to the button, you can now trim
that raise size down even further to 2.5x. 

Depending on the game and your opponents, sometimes you'll want to adjust
these raises to 3.5x and 3x accordingly.  Also remember that
these figures apply almost exclusively to online play.  In live
games, you'll need to make normal sized raises, but stealing
pre-flop in live poker isn't usually advisable at all simply
because so many players hate folding any hands regardless of
strength or position. 

Stealing from the Small Blind

The small blind is an interesting spot for steals because you
are fighting for two blinds, but one of them is your own money. 
Once you post the blind, however, that money becomes worth
fighting for.  You'll get a lot of folds from the small blind,
but you should be wary of the times where you get called or are
raised.  The small blind is forced to play every pot out of
position, so you should be intent on winning pre-flop.  If you
feel like there's a good chance that you will get called,
mucking is the better play.  It's important to remember that the
value in a small blind steal increases when there's a late
position limper.  This is some added money that you can now win,
and it's unlikely that the limper is all that strong. 

If you are making steal attempts from the small blind, you
have to be prepared to make post-flop bets.  Don't steal in the
small blind, get called, and then check fold.  This is exactly
what your opponents (should) want and it will unnecessarily
cause you to bleed money from your stack.  Give up pre-flop or
continue with your aggression post-flop, but don't fall
somewhere in between. 

Stealing from the Big Blind

The big blind won't only enable you to make open raises
when attempting to steal pre-flop, but it will also give you
opportunities to re-steal.  In late position, most steal attempts
will be open raises, and the case tends to be the same in the
small blind as well.  In the big blind, however, you'll be able
to re-raise those late position and small blind raises as a
re-steal. 

If you are re-stealing from a late position player, you'll
need to be armed with a lot more aggression than if you are
aiming for the small blind.  The reason for this is that the late
position player will have position on you, and it's possible
that they actually have a strong hand.  If the small blind opens,
they are very likely to be weak and will also need to play out
of position post-flop. 

If the pot limps to you with only the small blind in the
hand, you should be raising with an extremely wide range of
hands.  You don't need to even have exceptionally playable hands
in these spots, because you have so many other advantages going
for you.  Some players even argue that you should raise the big
blind against a small blind limp every single time regardless of
hand strength. 

Stealing from the big blind will get an awful lot
of folds, but you also have to get ready to fire out many
continuation bets.  The aggression should slow down drastically
at this point, however.  Don't go crazy trying to double and
triple barrel in pots where your original intent was to simply
steal the blinds.  Being sucked into a small pot where you have a
weak hand is one easy way to hand over money to your tighter
opponents.