So you just closed your first big deal and it's time to celebrate. Your boss invites you upstairs to the boardroom where the executives are lined up at the long oak conference table, premium cigars by their sides to mark the occasion.
One by one they light up, oaky musks wafting, and finally it's your turn to spark your earthy blend. There's just one problem—you're totally clueless.
"The smoking is supposed to be the fun part," said Michael Herklots, world-class tobacconist and Executive Director of Retail and Brand Development at Nat Sherman, a cigar emporium in midtown Manhattan. "The last thing you want to do is fumble -- to light or cut the wrong end."
How does one avoid these fatal flubs? We sat down with Herklots to find out the best ways to prove your worth when it comes time to lighting up the celebratory Maduro. Puff away, novices.
First of all, don't overthink your smoke

Beginning smokers can have three separate reactions to being handed a cigar. They can freeze and not know what to do with it, they can overreact and try to reinvent the wheel in cutting and lighting it, or they can calmly approach cigar smoking as a leisure activity capable of mastery.
The greatest risk, Herklots warns, is becoming over-involved with cigar nuances at the beginning. "Don't get caught up in the fanfare and be intimidated by it so you start feeling like you're doing something wrong," he says.
Instead, Herklots advises novel smokers to stay away from a "right versus wrong" motto. He agrees that there are ideal ways to cut a cigar, but he also says there are plenty of other ways to do it correctly.
Under pressure, just get the job done. Don't overdo it.
Choose the right cigar: smaller isn't necessarily better for a beginner

While the head honchos in the boardroom will be smoking heavier blends, it's important for you not to overdo it and cough up a storm. There's nothing wrong with choosing a premium mild cigar. Your bosses will respect you more for knowing what you want and not guessing blindly. This is where things can get dicey, says Herklots.
"The biggest mistake new cigar smoker make is in the format they pick," he says. "New smokers tend to smoke something shorter, thinner, and overall, smaller. The problem with this is that the shorter a cigar is, the closer the hot part is to your mouth. It gets hotter faster, which is not a pleasant experience if you're starting out."
Herklots makes an analogy here to using a regular straw versus a cocktail straw. With a regular straw, you have a wide cylinder with a long body that allows you to draw substance out over a longer period of time. If you use a cocktail straw, on the other hand, the experience is more aggressive and concentrated. The same goes for cigars. A long, fat cigar is a milder, cooler, and longer-lasting cigar. A shorter one is an intense experience better enjoyed by veteran smokers.
A simple tip for cutting your cigar

All hand-rolled cigars are closed off with a cap to ensure that they don't unravel and dry out. Removing this cap is essential to a good smoke, and there are a few ways to do so, none of which are wrong. Herklots, though, recommends the straight cut made by a guillotine cutter.
A tip he shared with us involves laying the cutter flat down on a surface and then bringing the two blades in and clipping the head. By placing the guillotine on its belly, smokers can ensure they don't over-cut the cigar.
Trying to smoke an uncut cigar is a sure-fire way to make a fool of yourself. You want to make sure you get your cigar cut, whatever the method may be.
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