5 Security Lessons from Chess
Treston Wheat, PhD
Geopolitical Risk | Security Expert | Professor | Strategic Intelligence | Policy Wonk Extraordinaire
I took up playing chess in late 2022 and have become absolutely enthralled with the game! I regret not having started playing years ago when it would have been easier to learn. Obviously, I am still quite the novice and completely inexperienced, but what I find extraordinary is the important professional lessons I’ve gleaned from the game. “Chess is life” as the adage goes, and I didn’t realize its veracity until I started studying the game in more depth. I love the mechanics of the game, but I genuinely appreciate how each player’s personality can come through. For example, I am an incredibly aggressive player who almost always tries to be on offense, but I have learned from playing passive players who are more cautious in their approaches. I think all security professionals can learn quite a bit from this game.
Chess has its origins in India more than 1500 years ago, spreading throughout Asia, but the game as we understand it today started in 16th century Europe. Through its multiple iterations over the centuries, chess would evolve rather slowly before settling onto the contemporary version, which is why much of chess strategy is a later development. Ruy Lopez, one of the early masters of the game, published a book on strategy in 1561, and he had a common chess opening named after him (1. e4 e5 2. Nf3 Nc6 3. Bb5). Part of his strategic assessment was to play the game so the sun was in your opponents eyes! It’s obvious that chess strategy and theory have improved quite a bit since then. Now there are libraries full of strategic books to help players understand the game more effectively, and it can take a lifetime of education to master the subtleties.
As a game, chess is a useful trope in popular culture whenever authors or directors want to quickly convey that this character is brilliant or a strategic thinker. From President Bartlet in The West Wing to Nate Ford in Leverage to Professor Moriarty in Sherlock Holmes, characters that play chess exude a certain level of erudition. That is because chess offers many important lessons beyond immediate gameplay. In The West Wing episode “Hartfield’s Landing” (S3E14), President Bartlet plays chess with his subordinates while simultaneously resolving a foreign policy crisis, and he concludes one of his games by drawing the exact lessons from his gameplay to dealing with the Chinese. Similarly, there are many appropriate lessons for security professionals from chess that can help them improve their approach to problems they are facing.
So, here are five lesson from chess for security professionals.
1. See the whole board.
In chess, you can get so focused on a few pieces as part of your strategy that you miss a bishop coming “out of nowhere.” Except, the bishop didn’t come out of nowhere. If you’d taken the time to step back, see the whole board, and not be myopic, then you’d have seen that problem coming. This could be called the chess version of the black swan or gray rhino.
Security encompasses most aspects of the business: access control to buildings, protecting executives, background checks/due diligence, assessing possible threats from OSINT, processes for appropriate responses, site threat assessments, etc. etc. etc. There are a significant number of variables that impact security, but each group within the organization tends to only focus on their narrow area of responsibility. Obviously, specialization is useful, but security organizations must learn to see the entire board before making decisions. This would normally be the role of the CSO and directors, but analysts, protectors, and guards should also have that attitude because it will make their work more effective, especially when collaboration across security is so important. ?
2. There are so many variations that you can make your own path.
There are 10^43 legal positions in chess! That number is almost inconceivable, but that’s what makes it extraordinary. It’s important to study strategy and tactics, principles and theory, but the possible number of iterations and factors means that you get to make your experience and path all your own. Take the wisdom of others, but don’t become pigeonholed. You can have your own perspective and spin and be just as successful!
Every business is different, whether it’s technology, banking, oil, or airlines, and understanding the different needs of the business should guide security professionals to establish programs based on those needs. This could mean a greater focus on security guards used for detecting possible illicit entry or a larger focus on executive protection because there are few physical assets. This lesson applies not only to security programs but also the individual analyst or security professional. One most assuredly needs a shared foundational knowledge, but your own areas of study or approaches can greatly help give a broader or different perspective. Red teaming particularly teaches this lesson by forcing disagreement from other frameworks (see Micah Zenko’s Red Team and Bryce Hoffman’s Red Teaming). Do not assume that because you have distinct experiences or education that you cannot also contribute in profound ways.
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3. Each piece has value if you understand its strengths/weaknesses.
The Queen is the most powerful piece, but even she can be taken down by a well-placed pawn structure. Know the strengths/weaknesses of yourself and the people in your life, place them in roles that augment their strengths, and partner them with people who mitigate their weaknesses. When you understand how each piece operates alone and together, they become significantly more powerful.
Recognizing the different capabilities of people in your organizations relates to both hard and soft skills. Using myself as an example, my skillset is overwhelmingly around analysis and organization. Therefore, when I was red teaming, I was the one that focused on OSINT research before an operation, acted as C2 during an operation, and produced the written assessment for vulnerability analysis. My compatriots, on the other hand, were brilliant operators willing and able to climb 30 flights of stairs, pick locks, or pretend to be construction workers. The team was exceptionally effective because we deliberately played on each other’s strengths. However, soft skills also matter - I recommend the Clifton Strengths test to help your team get to know each other’s strengths and weaknesses. Unsurprisingly, my greatest strengths are Deliberative, Context, and Input while my greatest weaknesses are Harmony, Includer, and Empathy. Understanding those weaknesses really helped with projects because intentional steps could be taken to mitigate my weakest areas.
4. Sacrifices are necessary for success.
You can’t get to checkmate with all of your pieces on the board. That’s how it is in your life and career too. You will have to prioritize some things over others, but you need to carefully choose what you’re willing to sacrifice to achieve your objectives and goals. You might have to sacrifice time with friends, the gym, a project you really care about, or even a job. Just know when and what to sacrifice to make it worth it.
In security, this lesson is equally important. There are limits with budgets, personnel, and most importantly time. When security teams try to do everything equally well, they often fail at even basic tasks. Take for example training programs for security groups. Top performing teams will set aside time and resources each week (or month) to learn new skills or maintain existing ones. If your team is focused on executive protection, then you should prioritize certain hard skills like emergency medicine and effective driving. However, that means you will sacrifice time for more esoteric though useful skills like strategic thinking or program management. But it also means understanding what to sacrifice in your own life. No one can tell you what to prioritize or set aside, but you will have to make that decision (or it will be made for you). Relatedly, there is power in saying no. If you have your objectives and goals clear in your mind, then it becomes significantly easier to sacrifice and say no to anything that inhibits those objectives and goals.
5. Think through every step you’re taking.
Chess can train you to think before grabbing and to think objectively. Trying to move pieces in the wrong order can cause your entire strategy to collapse. Each step must be considered in the appropriate sequence to succeed, and that’s how security professionals need to approach problems. Take it step by step by step by step. It’s mentally tedious and taxing, but it is what will ultimately lead to success.
No book better explains this than Dietrich D?rner’s The Logic of Failure. The central thesis is that in complex systems you can’t just change one variable (handle one problem) because you have to understand how that variable interacts with all the other variables. Trying to fix one problem can actually create significantly worse problems. Analysts and security professionals should understand complex systems because forecasting requires them to understand those relationships. Once the complex system is understood, then analysts and security professionals can create a strategy that works through each step to achieve the goal. Connected to being able to put together a strategy for a complex system is the need to see the issues objectively. Do not get bogged down in negative emotions just because there are threats. Immediately shifting strategy incorrectly to deal with a threat without considering the subsequent steps or impact to the complex system can cause more harm than doing nothing.
October's Cocktail - The Gibson Martini
Chess's greatest pop culture moment occurred when The Queen's Gambit appeared on Netflix. Based on the 1983 book of the same name, this absolutely extraordinary series is about a chess genius struggling with her own brilliance and demons. Everyone knows she's the best, but what we don't know is if she can maintain her own sanity while being the best. Not only do I highly recommend this miniseries, but it inspires October's cocktail. The Gibson plays a prominent symbolic role in the series, so we'll be detailing the appropriate recipe for it.