The Comb-Shaped Generalist

I've been on several podcasts now, and one question always comes up: what makes a great generalist?

Valid question. Let's explore it.

My personal definition of a generalist: a person who bridges many different domains, adapts quickly to new circumstances, and has an insatiable curiosity.

Note that this describes what a generalist is – not what makes one great. Plenty of people tick all three boxes and still end up as "dabblers": they know a little about everything, but have never truly entered the arena.

(Think of the people who call themselves "startup enthusiasts" on LinkedIn but have never founded anything themselves.)

The great ones look different. They're not the infamous "T-shaped" generalist with one deep skill and a bit of breadth on top. They're more like a comb: several areas of depth, built one after the other.

So how do you build a comb? It starts with something you don't actually get to choose.

You don't choose to be a generalist

Most people don't choose to become a generalist. They're just inherently turned off by the idea of spending their life doing one thing and one thing only.

When I started university, I didn't know what the term "generalist" meant. I had no idea the word existed. But the degree I found most attractive was the one that mixed disciplines: TUM-BWL, with a major in business and a minor in computer science. Later, I did my first internship in business development at Flix – arguably the most generalist department out there (today, we'd call it venture development).

So the question isn't really whether you should become a generalist. I think it's already inside of us: either we enjoy going deep on one or very few things, or we enjoy going broad.

Being a generalist isn't really a choice. But becoming a great one is.

Stage one: breadth

The first step is breadth: knowing enough about many domains to act as a connector and "translator" between them.

"You don’t have to like baseball, but you should understand the concept of what a pitcher’s ERA means. Approach life similarly." – John LeFevre

Know enough so you can ask the right questions. I don't know how to write really good software, but I understand how code works. So when I speak to developers, I can ask the right questions and check my own assumptions.

Build this by trying lots of things early in your career. Take a generalist role that throws different challenges at you right away, start your own business early, or rotate through departments.

In a startup, a few months each in sales, product, marketing and finance will give you a pretty good understanding of how the company works. You might not be a great product manager, but you'll be infinitely more qualified to interface with one than someone who's never worked in product.

So go down rabbit holes. Work in different fields. Follow your strengths and curiosity.

But breadth is also where most generalists get stuck. It makes you a good conversation partner – and being conversational isn't what makes you indispensable in a company.

Look at how I actually learned to code. I didn't just read about it. I took a minor in computer science and built my first website in HTML myself (in middle school – that was fun). I went from being able to talk about it to developing a small spike.

And that's the next step on the path to becoming a great generalist.

Stage two: the comb

What makes a generalist great is the ability to get good fast. Knowing a bit about everything helps, but the true value lies in repeated depth.

Can you walk into an undefined problem, work out what matters, reach competence in the necessary domain(s), and then build a solution?

Think of a special forces operator (Navy SEALs, KSK, Kampfschwimmer, SAS, …). They have to be good at everything, not just average. Their baseline is higher than the average soldier's, and they usually add one or two specialties on top.

But what they're really good at is operating in the most extreme, unknown circumstances. Hostage rescues, recon behind enemy lines, counter-terrorism – high-stakes ops where the playbook isn't necessarily clear. They can do it because they've been trained to adapt.

Good news for all of us: nothing we do in business is as high-stakes as what these guys do.

Great generalists operate similarly, though: you give them a problem, they solve it. They become interim experts in it. And, as much as I hate to say it, this is exactly the skill set consultants develop: gathering information quickly and distilling it into what matters.

Then they put everything into practice and execute.

Want to see what that looks like in action (without praising myself too much, haha)? Take my last job, running international expansion for a company called Sdui (now, Seven Education). That meant:

1. Developing a high-level international expansion strategy
2. Building lead lists of Swiss elementary schools and cold calling them (quite tricky in itself – raise your hand if you know what a "Znüni" is)
3. Realizing that closing Swiss schools might have VAT implications, so briefly becoming an expert on Swiss VAT
4. Entering the Turkish market and building the local team while renting an office
5. Thinking "s**t, I think I need to learn Turkish" and getting private lessons
6. Turkey's currency crashing, so looking into financial instruments to hedge it
7. Exiting the market, thinking Ukraine might be a good choice – but war was brewing, so becoming a regular reader of the Military Times
8. CEO calls: "Hey, let's try to buy a company"
9. Figuring out how buying a company works
10. …

… and that was just the first 8 months.

Each tooth of the comb adds another perspective for solving problems – taking ideas from one discipline and applying them to another.

Take "The Checklist Manifesto". Atul Gawande, a renowned surgeon, was trying to cut the number of people dying from surgery. So he looked at an industry that had already solved a version of his problem: aviation.

Part of the reason flying is so safe is the relentless use of checklists. Pilots go through all sorts of them before taking off, landing, and whenever something goes wrong. And Gawande wondered: why don't we do this in the operating room?

So he tested it: before, during and after every surgery, the team went through a simple checklist. Confirm the patient and the procedure. Introduce everyone in the room. Count every swab and instrument before closing, so nothing gets left inside the patient (yes, that happens).

In a pilot across eight hospitals around the world, deaths dropped from 1.5% to 0.8% and complications from 11% to 7%. Who would've thought a simple checklist could save so many lives?

Great generalists are able to understand what's needed, go deep on it for a while, then come back up and do the next thing. And with every tooth of the comb, their ability to solve problems gets better – until eventually, it feels like they've seen it all.

And once you have enough teeth in your comb, something interesting happens: you can start combining them. (Pun not intended, I swear.)

Stage three: recombining

Recently, a new set of professions began emerging: Marketing Engineers. Forward Deployed Engineers. Deployment Strategists. Roles that barely existed a few years ago.

Those are generalist positions!

A Marketing Engineer, for example, is part engineer, part marketer: thinking in systems matters, and so does great taste. But you can't just be mediocre at both. To be a great Marketing Engineer, you need to excel at both.

Can this be learned? Absolutely. And the more expertise you've built previously, the easier it gets. So a generalist who already has the "systems thinking" tooth and the "taste" tooth in their comb would be very well suited to become a Marketing Engineer.

Apply the same logic to other emerging professions that either combine 2+ "old" disciplines or require completely new ones. Either way, generalists who are good at adapting to something new have a huge edge here.

Which brings us back to adaptation: even that can be trained. If someone's moved 10+ times in their life, their adaptability is likely higher than that of someone who never left their hometown. Changing jobs and getting excellent results fast is a great indicator as well.

You only get better at adaptation by constantly exposing yourself to new environments, topics and challenges.

Luckily, that's what we're wired to do as generalists anyway. :)

In the end, what separates ordinary generalists from great ones is getting into the arena.

Reading about something is one thing; actually doing it is completely different.

In a way, that's also what separates consultants from operators. Consultants have the raw ability to become instant experts, but they don't have to implement anything. Once you combine the ability to acquire knowledge fast with the ability to act on it, you become truly dangerous.

And, most importantly, future-proof.

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