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Puzzles and Riddles Help InfoSec Pros Solve Real-World Problems

A researcher shares the unexpected lessons learned in years of creating puzzles and riddles for his cybersecurity colleagues.

Security pros tackle tough problems every day, from breach investigations to niche technical issues to strategy and policy development. The key to maintaining and improving these critical problem-solving skills may be regularly solving different kinds of puzzles, one researcher found.

When PwC UK research lead Matt Wixey started sharing puzzles and riddles with a small group of technical colleagues, he didn't intend for it to become more than an informal practice. As he started to create puzzles of his own, however, the custom challenges gained a sort of "cult following" within the company and slowly grew more formalized and structured over time. 

Two years later, PwC's team of 300 cybersecurity pros has slowly joined in to solve them. Wixey's challenges, which now include technical challenges as well as logic, wordplay, and math puzzles. Colleagues have added incentives to finish first: prizes range from small awards for minor challenges to bigger rewards for multi-day puzzles or those part of company events.

But there is another benefit: while the puzzles are for fun, many of the people who do them say they've noticed improvement in the problem-solving skills they use in their day-to-day roles.

"As I did more and more of these puzzles, making them from scratch, it made me think about how we solve problems and how that can be applied to security," says Wixey, who separates puzzles into four categories: wordplay and cryptic, logic, math and probability, and technical. 

When he creates these challenges, he tries to keep a range of people and skillsets in mind. If a technical puzzle is focused on penetration testing, for example, he includes people from the business unit by requiring the pentester get input from the incident response or threat intel teams. Sometimes the puzzle is a standard capture-the-flag exercise in which participants have to decrypt or compromise something. Other times, he makes the puzzle a little more complex.

"Years ago, I did a three-part puzzle where people had to solve problems to get the location of 'away day,'" he says, referring to a company retreat. The challenge involved wordplay riddles, knowledge of morse code, and different kinds of steganography, including image and chess steganography.

Wixey has found people have the greatest success with math and probability puzzles; however, the wordplay and cryptic riddles are most popular. The key to creating a successful challenge is making it accessible. "You don't want [people] to look at it and think, 'I don't even know where to start with this,'" he says. Puzzles need to appear easy to solve, even if they're tough to crack.

How Solving Problems Sharpens Skills

The practice of tackling challenges like these over time can address biases in problem solving and logical fallacies while encouraging lateral thinking and curiosity in cybersecurity experts.

"When you solve problems on a regular basis, you become aware of how it can change your perspective on things," Wixey explains. There are several elements related to problem solving that can be addressed in puzzles: challenging assumptions, for one, or "sub goaling," which means not thinking about the end solution but focusing on the steps and avoiding "rabbit holes" along the way. 

Working to solve complex puzzles also addresses the self-serving bias, which occurs when people convince themselves they're making logical decisions when they're not. Employees in PwC's cyber business unit say the puzzles and riddles have helped them keep problem-solving skills sharp and consider the bigger picture when facing cybersecurity problems in their jobs.

People who are good at problem solving tend to test their own assumptions, Wixey says, and they're open to changing their beliefs. The creator of a puzzle or riddle will play on people having a dominant construct about something – a bias or perspective on the world – and the people who are strong problem-solvers are aware they have biases and think beyond them.

For organizations who want to implement a program like this, he advises starting with preexisting puzzles and riddles. "It's really hard to try and design puzzles for a group of really intelligent people and try to make sure those puzzles are going to be solved in a reasonable timeframe," he says. "That's something I still struggle with day to day." He advises using different formats to broaden appeal and drive inclusivity from technical and non-technical minds alike, which boosts collaboration among people who don't usually work together.

Wixey will share more puzzles, riddles, and observations made while creating this initiative in his upcoming Black Hat USA talk, "Breaking Brains, Solving Problems: Lessons Learned from Two Years of Setting Puzzles and Riddles for Infosec Professionals" on Thursday, August 6.

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Register now for this year's fully virtual Black Hat USA, scheduled to take place August 1–6, and get more information about the event on the Black Hat website. Click for detail on conference information and to register.

Kelly Sheridan is the Staff Editor at Dark Reading, where she focuses on cybersecurity news and analysis. She is a business technology journalist who previously reported for InformationWeek, where she covered Microsoft, and Insurance & Technology, where she covered financial ... View Full Bio
 

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