By Evan Rabin, CEO of Premier Chess
In May, I kicked of a Premier Chess Program at a middle school at an impoverished neighborhood in Brownsville, NY by asking “Why Play Chess.” I got some typical answers, including “It’s Fun.”, “It helps you think” and “Competition is fun.” They were shocked how I explained the white and black plastic pieces could be used as a vehicle to help them get into high school, college and a good career. I then explained to them how chess has influenced me to become a critical thinker, get into enterprise sales at Oracle and Rapid7, cofound a sales outsourcing startup Pillar Sales and ultimately form Premier Chess, which teaches life lessons through the game for all ages and levels for organizations ranging from Thistlewaith Early Learning Center to Grace Church School to the law firm Kramer Levin to the nursing home Village Cares. If you’ve met with me recently, I’ve probably showed you my copy of Jim Egerton’s Business on the Board (2016), which illustrates the tactical and strategical lessons business leaders could learn through the game. Here are some of the highlights:
“Contextual leadership is ….Transformational in the Opening (Andrew Gove of IBM)…. Situational in the Middlegame (military leaders)…. Results-Basedin the Endgame (Bill Gates)”(15).A good leader has a blend of these qualities and could adapt to all of these qualities. The opening of a chess game is like a brand new startup that is innovative and changing the marketplace. In the middlgame, one has to evaluate the position given his success or lack thereof in the opening and determine whether he should keep the status quo or go for complications. Finally in the endgame, one has to take his advantage and convert it to a win as a sales rep needs to close a deal.
To demonstrate the importance of transformational leadership, one could compare the first two months of my stints at Oracle and Rapid7. At Oracle, it took me 2 months to get a territory and another to get an official . To the contrary, at Rapid7, I knew on my interview process that I was going to be on the State, Local and Education team and a few days after I started that I was going to cover the Northeast. Rapid7 used the basic opening principle of “creating an organizational environment with every piece contributing in fewer than twelve moves.”(24).
One also learns that each piece needs to have its own job and that every move needs to have a purpose. Every single move in the opening should be related to developing a piece, controlling the center or castling to make the king safe. My team at Oracle (which covered Infrastructure sales in Eastern Canada) illustrates this concept well as we divided and conquered with our expertise of sales. Another young sales rep Jake and I were the team experts on prospecting. We looked up to Mike for operations advise. Herb, who became promoted to our manager, was the expert on legal and pricing conversations. Diane was the “go to” for teaming agreements.
Situational leadership occurs as chess players orchestrate their strategic plans and related tactics. Grandmaster Alexander Kotov says, “ It often happens that a player carries out a deep and complicated calculation but fails to spot something elementary right at the first move”(60). This is exactly why we tell students before making a move, they should also do a blunder check, making sure they don’t miss anything that is obvious. Sales people will often get “happy ears” and invest a lot of time into a deal thinking it would definitely come in without doing any basic research. I made this mistake when working a non-existent deal with a bio-tech company in Ontario while at Oracle. Without doing enough research about BANT in the beginning (Budget, Authority, Need and Timeline), I built great rapport with my champion at the company and decided to give them a loaner unit for a month. Towards the end, my engineer and I realized he was just trying to spin our wheels and use our engineered system for R and D.
In World War II, Stalin and Roosevelt famously allied because they had the common enemy of Hitler’s Nazi Germany. Likewise, “In 199 Elon Musk’s X.com and Peter Thiel’s Confinity were locked in a heated battle to be the first company to supply eBay with an electronic payment system…. Rather than risk the possibility of losing it all, its perfectly acceptable in chess to offer your opponent a draw.” Rather than neither party getting the solution first, Musk and Thiel decided to merge their companies.
One of the craziest aspects of working at Oracle is the internal competition you face as a sales rep. In addition to competing with IBM, Dell, HP, Cisco, etc. Oracle servers reps have to compete with many of Oracle’s product lines, including the storage team, cloud team, etc. One of the biggest deals I closed at Oracle was for the 407 ETR, a privately owned highway, which goes from Ontario to Quebec. The client ws looking into one of Oracle’s flagship products, the Oracle Database Appliance, which has an option for additional storage capacity, and ZFS storage, which was sold by another team. Many of my colleagues thought I should work independently and try to sell the client the additional storage capacity so I would get a bigger deal size but in the end working closely with the storage rep proved to be valuable as we closed a deal for $600,000 CAD in servers and $400,000 CAD in software.
“Strategy is all ways there; it’s the tactics that come and go.” (60) In chess, it is not only important to understand all the different types of tactics but its important to be able to intuitively feel positions and see when tactics are in the air. Likewise, most professionals need to be able to develop a strong intuition and judgement skills. A sales person needs to know how to respond to surprises on the phone, a lawyer needs to know how to respond to a judge in a trial, a managerial accountant needs to give quick advice on decisions like build vs. buy. Similarly, in a chess game, the player needs to decide whether he is going to develop his pieces normally or “buy” a lead in development by gambiting a pawn or two. Kevin McGee, a Senior Vice President at Oracle once told my team “You are usually not going to get a customer to buy something when he doesn’t need it but you could get creative and escalate timeline”. I started trying methods like reverse timelining and developing interesting price structures.
“In business and in chess, you can beat your competition if you know your landscape better than your opponent.”(230). Both business and chess requires a combination of analyzing historical data and thinking of your own ideas on the board.
When I was at Rapid7, one of the action items was looking at current and lost business opportunities in the pipeline. There was one opportunity with a a gentleman who manages IT for a county in upstate New York. My colleague who previously managed the account, wrote that the guy was waste of a time with no budget; he confirmed this in person. However, I took what he said with a grain of salt and reached out to the prospect. We built rapport and a few months later I closed a deal with him after he received Cyber Security grant from New York State.
When students play openings and endgames they’ve already learned before, they will often rush and not pay enough attention. A few weeks ago I taught a private student a new line in the French defense (1.e4, e6.) I then had him regurgitate the line and purposely played a slightly different move order, testing to see if he would notice the change. As expected, he quickly played the same response as in other variation and ended up quickly getting a big disadvantage.
A player will also get a financial loss if they mishandle a threat. “Three scenarios can happen… [he] can underestimate the threat by not seeing it….nail the threat by understanding it and taking appropriate action to diminish any damage….[or] overestimate the threat by thinking the situation is the worst.” In each of these methods to respond to threats, a player can go wrong, whether in chess or business.
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