At 3 years old, I discovered magic by a roaring fireplace in the Catskills in the form of an intricately carved wooden chess set. By age 5, I was playing and gearing up for competition. By 12, I’d gone from placing nationally to finding my true calling: demystifying chess.
At 13, I became New York City’s youngest solo chess instructor, teaching in classrooms across every borough. My students were usually older than me and almost always taller; sometimes they were even adults. Yet, I never hesitated to command the attention of grown men, or even harder, teenagers! Over the next 25 years, teaching chess became my passion: a perfect blend of corralling, inspiring, directing and being challenged. In other words, leadership.
The connection between chess and leadership is indelible. Created in India in the sixth century and often used as a tool for military generals to practice strategic thinking, chess has shaped leaders throughout history—from Benjamin Franklin, who wielded chess as a political tool and penned “The Morals of Chess,” to Mahatma Gandhi, Queen Victoria and Rachel Reeves, currently the UK’s first female chancellor. Even Napoleon Bonaparte played chess, albeit poorly, attacking his opponent while neglecting the protection of his own pieces, thus proving that being a great leader doesn’t automatically translate to chess mastery or vice versa.
To bridge the gap between chess and leadership, I turned to chess player and strategist Ashley Lynn Priore. At 14, she founded Queens Gambit, a nonprofit using chess to forge tomorrow’s leaders, before building Queenside Ventures, a consulting firm transforming the chessboard into a canvas for strategic thinking. Now a 2025 Forbes 30 Under 30 honoree, Priore’s journey from young female player in a male-dominated field to leadership entrepreneur resonates deeply.
“Chess taught me to take that risk, try that move, and understand that each decision I make will lead to a world of possibilities,” she shares when I ask about how chess impacted her journey to early leadership. “[It’s] critical thinking at its finest. Chess teaches us that taking risks is the only way to make real change.”
Now, let’s explore those lessons in detail. Remember, these strategies only come alive when you put them into play, and the chess board, which chess great Susan Polgar calls “a miniature version of life,” is the perfect place to practice.
1. Think fast on your feet
Good leaders often make snap judgement calls in the midst of chaos. While it seems ironic that a seated game helps with quick decisions, Priore has seen this during her work with the Cleveland Browns. She calls chess “the sport that helps all other sports,” explaining that it helps slow athletes (and everyone else) down so that they can think fast. “Once we… understand all [the] possible moves, [we get better at] deciding what decisions to make very quickly.”
2. See the forest and the trees
Leaders must balance big-picture vision with minute details—like chess players thinking about their next move while tracking the whole game and pieces not currently in play. While “politicians playing chess” often carries negative connotations, Priore sees it as strategy: “They’re understanding that one big mistake or even small mistake can have a series of consequences. So it’s about thinking through every single decision that we’re making.”
A leader may also have to make a tough decision that won’t please everyone. “It might not help all the pieces on the board, but you’re thinking about the greatest impact that it can have,” Priore says.
3. Use empathy
Strategic thinking works best when paired with empathy. Good leaders care and are willing to consider other perspectives. “Originally [chess] was about war,” Priore says, “and now I think leaders are using it to strategize around ‘how can I make the best decisions for myself and my company and my employees? What can I do that’s going to make a huge impact?’” Chess players constantly put themselves in their opponents’ shoes, anticipating their next moves. I used chess in my teaching practice at special needs schools to help students consider other people’s points of views.
4. Everyone matters
In a game where pawns can become queens or even checkmate kings, each piece matters. Priore notes that “chess is …a practice,” helping leaders consider important questions like “What’s [each piece’s] role in this current position? What’s its purpose?”
Just as each piece has its value, every team member counts, like the NASA janitor who, when asked by former President John F. Kennedy what he was doing, replied, “I’m part of the team that’s going to put a man on the moon.”
5. Push beyond your comfort zone
Good leaders constantly look for new ways to grow, pushing beyond comfort zones, even in times of success. When Priore’s coach pointed out a missed attack during a tournament, it wasn’t in a game she’d lost, but one where she’d focused on maintaining her position rather than advancing it. He told her this was what separated good players from great ones.
I faced the same lesson competing successfully with my signature fourth-move surprise (switching from a defensive-looking opening to an attacking one). When my coach suggested expanding my repertoire, I resisted. Eventually, I realized I was winning, but I wasn’t growing.
People naturally seek comfort and a cessation of struggle. But we need some adversity to become stronger versions of ourselves. Good leaders know the right amount of pressure to apply to incentivize rather than destabilize their team, guiding them into their next phase, which brings us to…
6. Winning isn’t everything
When Magnus Carlsen, one of the strongest chess players in history, declined to defend his world chess champion title in 2022, he explained that he no longer felt motivated. This is a crucial leadership truth: Success isn’t reflected just by titles or maintaining rating points; it’s about knowing when to pivot toward a greater impact. Priore reinforces this perspective: “At the end of the day… the win or the success is… the people you’re impacting.”
No matter how great one game is, they all end with the pieces being reset. That’s where the growth lies, in continuing to show up for each match. Great leaders, like great chess players, understand that winning isn’t an end in itself. It’s about creating lasting value and meaningful change.
7. Be ready to pivot
“The board can change very drastically in one to two moves,” Priore notes. People famously hate change, yet it’s a part of life. Chess players must always pursue their current plan while simultaneously forming others, remembering that the plan (regardless of how great) is always in service of the game, not the reverse. Fixating on one plan means missing both threats and opportunities. Strong leadership likewise remains flexible, knowing that the best move is the one that works.
8. Mistakes are part of the process
Chess lets us practice making mistakes to build our practice around them. “Mistakes are just a part of our process,” Priore shares, adding that owning mistakes and allowing for all the uncomfortable feelings, then asking yourself what you’ve learned and how you’ll move forward, makes us more comfortable in leadership and in our own lives.
Brené Brown, expert on courageous leadership, reinforces this in her TED Talk: “If you’re not willing to fail, you can’t innovate. If you’re not willing to build a vulnerable culture, you can’t create.” Great leaders know mistakes don’t have to destroy the game. They’re opportunities to learn about what we want next time and what we need to do differently to get there.
9. Don’t give up after the first round
Good leaders don’t let present circumstances dictate their perspective. Chess players constantly study each position, looking for ways to make them better, and so do good leaders. Benjamin Franklin wrote that chess teaches “the habit of not being discouraged by present bad appearances in the state of our affairs, the habit of hoping for a favourable change and that of persevering in the search of resources.” Whatever’s happening now (good or bad) won’t last forever. Like chess players, great leaders know they might’ve lost this round, but there’s always another reason to keep fighting.
10. Know yourself
It’s impossible to lie on a chess board. If you handle frustration poorly there, it’s mirrored in your life. If you’re risk-averse in your life, you’ll play defensively on the board. Chess reveals who we are, which is the foundation of good leadership.
“The best leaders that I’ve seen are the ones who lead so much with their heart and they lead so much with their passions,” Priore says. Understanding yourself must come before understanding others, something intrinsic to building the strong relationships that good leadership demands. If you don’t understand yourself, Priori says, “I don’t think you can be successful in whatever area that you pursue because you’re not going to be happy.”
While these lessons from chess illuminate the path of leadership, the real challenge lies in living them daily. For Priore, it’s about building healthy routines. She plays a game of speed chess each day with the goal of making decisions and following through on them. She reflects on her moves—what went well, what didn’t—just as she does off the board, something she thinks all good leaders do. “Those moves happened,” she says. “That’s the truth. We can’t go back and change that…. But what we can do is say, ‘What can we get from it?’”
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