I’ve written about poker a few times in this blog (Leader/Manager Aces, Jackals, Mice and Eagles) related to both subjects of ‘Turning Adversity to Advantage’ and ‘Leadership and Management’. Given its rise in popularity, it is a dynamic and context with which many are familiar that helps making illustrative analogies to it. More importantly, poker entails a strong element of ‘risk’ and how people respond to which for me is at the heart of both of these subjects.
Poker is a game of maths and psychology and many books on the topic focus on either the maths or else the psychology of different types of opponents (eg. Jackals, Mice and Eagles). Larry W. Phillip’s book ‘Zen and the Art of Poker’ focuses entirely on the ‘mental’ side and in so doing, focussed not on the opponent, but instead on the mindset of the competitor themselves.
He captures why I think poker makes an interesting analogue to many dynamics in business:
“Imagine a chess game in which the pieces suddenly became worthless, or a hockey game in which the puck suddenly went against everything the players were trying to do. With poker, this additional factor sometimes exists. And this makes it more than just a simple game – your skill versus your opponents’ skill. The cards can go cold for you and hot for them, or start doing all manner of crazy things…It is sometimes difficult even for an expert player to fully grasp the concept of a game that requires a large degree of both skill and luck. The fact is, very few other sports or games in life work this way. Most competitions require either one or the other, not both.”
This description could just as easily apply to business as it does in poker – an interweaving of ‘both skill and luck’. Neglect either at your peril. Leadership view the upside assesses the opportunity to steal pots, make hands, slow play extra bets into the pot and ‘go all in’ none of which are certain, but with luck become lucrative manoeuvres. Management assesses the downsides skilfully calculating the outs, the pot odds, the scenarios at each board card. No one can survive at poker with just one of these approaches, but the deft combination of leadership and management can be overpowering and profitable.
My experience at Microsoft provides plenty of examples of this interplay. Most notorious was Microsoft’s original manoeuvring to secure the original contract to provide DOS to the IBM PC with the rights to sell it to other OEMs. The many accounts of this pivotal chapter always underscore the chain of fortunate events (eg. Gary Kildall not following up with IBM to offer his CP/M OS) which at any time could have broken and led to an entirely different outcome. At the same time, Gates’ and Ballmer’s savvy in negotiating, securing needed technology, etc. were all critical and skilful contributions to the end result. A tight interleaving of skill and luck laying the foundations to one of the great business franchises of all time.
Curiously, most biographical accounts of Gates start with stories of his prolific poker playing in his dorm when he attended Harvard College including a mention in his own book ‘The Road Ahead’:
"In poker, a player collects different shards of information – who’s betting boldly , what cards are showing, what’s this guys pattern of betting and bluffing – and then crunches all that information together to devise a plan for his own hand. I got pretty good at this kind of information processing. The experience of poker strategizing – and the money – were helpful when I got into business.”
Leadership and Management / Turning Adversity to Advantage 
I’ve always like the phrase: "Luck is when Opportunity meets Preparation".