A good poker player is evaluated over the course of weeks, months, years, and a career or playing. You lose some hands and some games, but this doesn’t necessarily mean you made the wrong calls. With that said, each hand is a universe in and of itself. When you’re playing hand, your chip stack and the stacks of those around you may influence your play, but you’re mostly playing a hand. It’s the opposite of chess, where you’re supposed to be thinking many many moves ahead. In the poker hand, you consider your position, consider how your play may influence the perception of you in the game, but you’re predominantly playing the hand. I think it is poker and not chess that reflects the current realities of business today.

You need to play each product, sales, or business development decision as a hand that exists in the here and now. You can be influenced by the historic play of your partners, employees, and counter parties. You’re also smart to consider how your play in this hand will influence the perception of you by partners, employees, and counter parties in the future. So to drill the caveats: business and life is a multishot game, so you do need to play each hand with consideration of long term ethics and reputation. But with all those caveats, focusing on future hands and not the current hand is a misallocation of your mental energy.

The current hand is what matters, and last I checked, you only live in the present, not the past and future. The alternative would be to focus on moves ahead. Overly focus on how your current sales strategy or the business development deal that is on the table will play out moves ahead. Playing chess is a mistake because the board will be changed by the time the future arrives. Far from the hyperbole of the bubble in the 90′s (i.e. “if you have a business plan you’re too late”), this reality is one where partners and competitors enter, leave, and shift strategy so quickly, that the future you anticipate is never the one you are dealing with.

For example, had FourSquare looked moves ahead a year ago, it might have considered a merger with Gowalla or some high level multi-step strategy to compete. Ultimately such long term competitive theorizing would have been worthless, as the competitive dynamics for FourSquare are now shaped by a new platform entrant – Facebook. FourSquare wisely chose to just play hard poker, hand after hand, and I imagine will continue to do so.

In my day to day business, I focus on the deals and sales today that I believe will increase enterprise value. I ask myself, is this transaction good today and does it preserve my and the company’s long term position at the table. My typical decision process is: “Is this good, and if yes, does it do anything to hurt or long term position?” Which in poker terms would be, “can I win this hand, and if yes, are there any ways this hand could play out that would cause me to lose the game?” If it’s a “yes” followed by a “no,” I push chips in.

We focus on playing hands, and avoid analysis paralysis of thinking like, “Deal A is good but what is Company B enters our market and we would have preferred to do Deal Y.” With that said, we frequently fold on hands that we think we could have won, but didn’t like the pot odds.

Don’t even get me started on why business is not like golf…