The Meeting That Happens in Every Company
You're in a meeting. Something's broken—a process, a product, a customer relationship—and you need to fix it.
Jake speaks first. He's already got three ideas. They range from "reasonable" to "where did that even come from?" He connects the problem to something he read last week about supply chains. He wonders if the issue is actually in sales, not operations. He mentions a tool he saw at a conference. He's genuinely excited.
Maria waits. When she speaks, it's specific: "The issue is in step four of the fulfillment workflow. We changed the vendor API integration on Tuesday, and the error logs show a 340% spike in timeouts since then. I can have a fix deployed by three o'clock."
Jake is a Cowboy. Maria is a Surgeon.
And here's what most business owners get wrong:
They try to turn Jake into Maria. Or they hire a bunch of Marias and wonder why nobody saw the disruption coming.
The deliberate organization doesn't choose between Cowboys and Surgeons. It deploys both—and knows exactly when to call in each.
The Cowboy: Problems Are Everywhere, and So Am I
Cowboys are generalists. They're wired to see problems—everywhere, all the time. Not because they're pessimists, but because they can't help connecting dots across domains.
The Cowboy reads an article about logistics and immediately thinks about your customer onboarding flow. They hear about a competitor's pricing change and start sketching product ideas on the back of a napkin. They notice that the warehouse team is frustrated, and somehow that leads to a three-slide deck on organizational culture.
Here's how to spot a Cowboy:
They volunteer for things outside their job description. Not because they're trying to impress anyone—because they're genuinely curious.
They reference things you didn't expect. "That's kind of like what Toyota did with their production system, right?"
They ask questions that feel lateral. "I know we're talking about sales, but has anyone talked to the support team about this?"
They get bored with deep repetition. Cowboys are energized by novelty and frustrated by routine.
They have hobbies you wouldn't have guessed. They collect records, run ultramarathons, rebuild engines, learn languages—often poorly, but enthusiastically.
Cowboys are often undervalued in traditional organizations. They look unfocused. Their career paths look more like pretzels than ladders. They're easy to dismiss as "scattered" or "not serious."
But here's what Cowboys bring that Surgeons can't: peripheral vision.
What Cowboys Do Best
Cowboys thrive in conditions where the problem isn't yet defined—or where the problem everyone's solving is the wrong problem.
Early-stage chaos
Startups, turnarounds, new product launches. When nobody knows exactly what needs to be built yet, you need people who can range widely and triangulate fast. This is why starting deliberately doesn't mean having all the answers—it means knowing which questions to ask.
Cross-functional translation
Cowboys understand enough of multiple domains to help marketing talk to engineering, or sales talk to operations. They're natural bridges—they can see how work flows across levels without getting lost in the details.
Innovation and disruption
The best innovations come from combining ideas from different fields. Cowboys are wired to do exactly this—seeing connections where specialists see boundaries. Ray Dalio built Bridgewater on the premise that diverse perspectives and independent thinking beat specialized consensus.
Leadership in uncertainty
Research consistently shows that leaders with broad experience outperform specialists in times of change. When the playbook doesn't exist, you need someone comfortable making it up.
A Cowboy can walk into a room, know just enough about everyone's job to ask the right question, and find the thread that nobody else saw.
The Surgeon: One Thing, Done Perfectly
Surgeons are specialists. They've gone deep in a domain—not because they lack curiosity, but because they're wired to master.
The Surgeon doesn't want to know a little about everything. They want to know everything about their thing. They've read the textbooks, done the certifications, spent the 10,000 hours. When you need precision, they're the call.
Here's how to spot a Surgeon:
They go silent until they have something definitive. Surgeons don't brainstorm out loud. They analyze, then speak.
Their answers have depth. Not just "the API is broken," but exactly which endpoint, which edge case, and which line of code.
They have a toolbox—and they know every tool intimately. Ask a Surgeon about their craft and clear your calendar.
They're frustrated by surface-level conversations. When others are still framing the problem, the Surgeon is already three layers deep.
They've often been doing this longer than you realize. That "junior" developer has been coding since they were twelve.
Surgeons are expensive, but they're worth it. When you need something done right—when precision matters, when the stakes are high, when failure isn't an option—the Surgeon is your person.
What Surgeons bring that Cowboys can't: depth. And depth is what separates working from excellent.
What Surgeons Do Best
Surgeons thrive when the problem is defined—when the work requires precision, expertise, and flawless execution.
High-stakes execution
When the surgery must succeed the first time—a product launch, a critical fix, a complex integration—you want a Surgeon holding the knife.
Quality and consistency
Surgeons don't do "good enough." They do it right. Every time. LEGO's manufacturing precision—tolerances within two-thousandths of a millimeter—is the ultimate Surgeon culture. Every brick must fit every other brick, and there's no room for "close enough."
Technical leadership
Junior team members learn from Surgeons. They set the standard for craft. Their presence elevates everyone around them.
Complex problem-solving within a domain
When the issue is deep—not lateral but vertical—Surgeons diagnose faster and solve better than anyone else. This is where AI often falls short: genuine expertise in ambiguous, high-stakes situations still requires human Surgeons.
A Surgeon can look at a problem that baffles everyone else and say, "I've seen this before. Here's what we do."
The Talent Spectrum
↑ Broad knowledge
↑ Connects dots across domains
↑ Thrives in ambiguity
↑ Sees the forest
Deep expertise ↑
Precision execution ↑
Thrives in clarity ↑
Knows the trees ↑
Most people fall somewhere along this spectrum. But the real magic happens at the edges—and, very rarely, from someone who lives on both ends at once.
The Cowboy with a Scalpel
Every once in a while, you meet someone who defies the spectrum.
They have the Cowboy's peripheral vision—they see problems everywhere, make connections across disciplines, and can't help but wonder "what if?" They range widely. They're curious about everything.
But here's what makes them rare: when they find the problem worth solving, they go deep. Really deep. They pick up the scalpel and execute with the precision of a Surgeon.
The Cowboy with a Scalpel is a polymath—
someone who doesn't just know a lot, but masters multiple domains.
These are the people who found companies in entirely new industries. Leonardo da Vinci was one. So was Benjamin Franklin. In modern business, consider Yvon Chouinard—Patagonia's founder started as a blacksmith making climbing gear, became a world-class alpinist, then built one of the most innovative outdoor companies on earth, then pioneered corporate environmental responsibility. He's genuinely deep in metalworking, climbing, product design, supply chain ethics, and environmental science. Or consider Charlie Munger, who combined deep expertise in law, investing, psychology, and business strategy into a unique synthesis that helped build Berkshire Hathaway.
Investor Jake Chapman describes the ideal team as "a group of rock-star polymaths with a single subject-matter expert as a resource." That's the Cowboy with a Scalpel, surrounded by Surgeons when deep expertise is needed.
How do you spot a Cowboy with a Scalpel?
→ They have multiple "past lives." They were a teacher, then an engineer, then a product manager—and they were genuinely good at all of them.
→ Their insights are both broad and precise. They notice the problem AND can implement the fix.
→ They have impatient curiosity. They're not content to just understand something at a surface level—but they're also not content to stay in one domain forever.
→ They ship. Unlike dilettantes who flit from interest to interest, the Cowboy with a Scalpel finishes things. Impressive things.
These people are rare. Don't expect to hire one. But if you have one on your team—or if you are one—recognize it.
The Cowboy with a Scalpel is your secret weapon. They're the ones who see the disruption coming AND can build the response.
But Wait—What About Systems?
If you've read anything else on this blog, you might be wondering: Isn't the whole point of Deliberate Work to build systems that don't depend on heroic individuals?
Yes. And this is where it gets interesting.
The McDonald brothers' Speedee Service System was designed specifically so you didn't need Cowboys or Surgeons to run it. Break the work into simple steps. Make each step learnable in hours, not years. Put the skill in the system, not the individual. Ford did the same thing with the assembly line.
That's not wrong. It's essential. Well-designed systems reduce your dependence on any single person.
But here's what those systems don't tell you:
Someone has to design the system. Someone has to know when it's broken. And someone has to build the next one when the world changes.
That's where Cowboys and Surgeons come back in.
Cowboys see the opportunities and threats that the current system isn't built for. Surgeons execute the critical pieces that can't be systematized yet. The system handles the 80% of work that's predictable and repeatable. Your talented people handle the 20% that requires judgment, creativity, or precision beyond what the system provides. This is what happens when you stop choosing between developing people and designing systems—and do both.
Accidental hell isn't having Cowboys and Surgeons. It's having them in the wrong places—or worse, having them spend their valuable talents on work the system should be handling.
The Deployment Question
Talent isn't just about who you have. It's about where you put them.
If you're familiar with the AAAERRR Framework, you can see how different talent types shine at different stages. Cowboys excel in Acquisition and Activation—exploring new opportunities, making connections, translating value across contexts. Surgeons excel in Engagement—the actual delivery of value where precision matters.
Here's a broader framework:
| Situation | Deploy |
|---|---|
| The problem is undefined | Cowboy |
| The solution requires precision execution | Surgeon |
| Teams aren't communicating | Cowboy |
| Quality is slipping in a core function | Surgeon |
| You need to explore a new market | Cowboy |
| You need to dominate an existing one | Surgeon |
| You're building a new product from scratch | Cowboy (then Surgeon) |
| You're systematizing repeatable work | Surgeon (then system) |
| The whole game is changing | Cowboy with a Scalpel |
The mistake most organizations make is hiring for one type and expecting them to perform like the other.
A Surgeon in a chaotic startup will be miserable—and probably ineffective. A Cowboy assigned to the same repetitive task for three years will quit, or worse, disengage and stay.
Building a Deliberate Team
In a Deliberate organization, you design your team around the work—not the other way around.
That means asking different questions:
When hiring:
Don't just ask "Can this person do the job?" Ask: What kind of work will this person be doing—and is their wiring a match?
If the role requires steady, precise execution of defined tasks, you need a Surgeon. If the role requires ranging across the organization, solving ambiguous problems, and connecting dots, you need a Cowboy. Most roles, honestly, need some of both—which is why T-shaped people (deep in one area, competent across many) are so valuable.
When developing existing team members:
Stop trying to turn Cowboys into Surgeons or vice versa. Instead, ask: How can I put this person in a position where their natural wiring is an asset and they're empowered to be great?
Your Cowboy might be struggling because they're stuck in a narrow role. Your Surgeon might be underperforming because they're being asked to do too many things at once. The fix isn't training—it's positioning. This is what it means to become a deliberate operator: you stop solving every problem yourself and start seeing patterns in how problems get solved.
When structuring work:
Use Cowboys to define problems and explore possibilities. Use Surgeons to execute solutions with precision. Build handoffs between them.
In a workflow, this might look like: Cowboy scouts the opportunity → Team refines the approach → Surgeon executes the critical path → System handles the repeatable parts → Cowboy checks for what everyone missed.
The Real Test
Look at your team right now. Can you identify who's a Cowboy and who's a Surgeon?
More importantly: Are you deploying them accordingly?
The goal isn't to value one type over the other. It's to value each for what they uniquely bring—and to build a team where Cowboys and Surgeons reinforce each other, supported by systems that handle the predictable work.
And if you're lucky enough to have a Cowboy with a Scalpel? Point them at your hardest, weirdest, most important problem—the one where no existing system or specialist approach quite fits.
Great teams aren't built from identical parts.
They're built from different talents, deployed deliberately.
Further Reading
- On generalists vs. specialists in team composition: Harvard Business Review research by Teodoridis, Bikard, and Vakili found that generalists outperform in slower-changing fields, while specialists excel when the pace of change is rapid. The ideal is often context-dependent.
- On polymaths and deep generalists: David Epstein's Range: Why Generalists Triumph in a Specialized World makes the case that broad experience—not early specialization—predicts success in most complex fields.
- On T-shaped employees: The concept originated at McKinsey and was popularized by IDEO—describing people with deep expertise in one area and broad competence across many. Most high-performing teams benefit from this shape.
- On team design and systems thinking: For more on how to structure workflows around different types of talent, see Chapter 14 ("Designing for Humans") of Deliberate Work. Sign up for early access.