Ask YC: Better to be a Specialist or a Generalist as a CEO?

Neither.

I think you want to be "angular", which (not surprisingly) is what the Ivy's are looking for too.

Angular means having a few elements of true specialization and mastery, but being a reasonable generalist everywhere else.

That answer could also be phrased as "both".

And I agree. You need to be ok at most things and really amazing at a couple.

My specialties are technology/coding and writing, but I'm also a competent consultant with the associated skills in management, negotiation, presentation, networking and business analysis, and since quitting my job have also acquired decent skills in online marketing.

Not everyone in your company needs to be competent in so many areas, but I'd suggest the CEO needs to be. At the same time, there needs to be at least one thing the CEO brings to the table that others aren't as amazing at as he or she is. Later on, when the company becomes larger, who the CEO attracts to work at the company becomes more important than what skills they bring in, but at the early stage everyone in the company needs to be amazing at something, and be involved in using that skill to create an amazing version 1.0.

Daniel

I have been a Founder/CEO for the last fifteen years which in my experience is different from being the CEO of an established company. Founder/CEO for a startup is an entrepreneur whereas a CEO is a professional manager. But I assume entrepreneurship is what you have in mind and the following is what I wrote in my post.

http://www.lovemytool.com/blog/2007/10/vc-worst-enemy.html

"Anyone can be an entrepreneur but they must not have the mindset of a lawyer, an engineer or a doctor.

First of all, there are always more than two sides to an issue and often the right place is to be is in the middle - an option that a lawyer does not have. Also, there is not always an answer to every question; or if there is an answer, it might not be unique. So waiting for perfect data to arrive at a perfect solution is a luxury that I don’t have as an entrepreneur. If that bothers me, then I should go back to being an engineer. Finally, as an entrepreneur, I often have to shoot my patient (and I have)."

So my experience is that it has a lot less to do with skills and a lot more to do with mindset. In the end, it is about attracting people (a good Founder/CEO is one who is a "talent magnet" regardless of his/her professional training). Hope it helps.

Is that url nsfw? lol - I'm scared to click a link to "LoveMyTool.com"

Sorry about that. I get this a lot. The primary site (which also hosts my own personal blog) is my new startup which is an online marketplace for network TOOLs.

If you have to look at it in the context of a team. If you are hiring folks for your management team, select people with skills that will complement you, i.e. people with great depth in Technology, operations and marketing in your case.

If you are getting hired, understand the gaps and fill them accordingly.

This isn't really an answer to your question, just food for thought: Two of the most successful entrepreneur CEO's, Steve Jobs and Larry Ellison, both started out as specialists in engineering who eventually (it seems) realized that they weren't and would never be the best engineers. Their strengths have been in finding the best ways to apply existing technology, not inventing it or writing its code. So, they slid into leadership roles by finding the best engineers who weren't necessarily interested in management (Steve Wozniak is a great example) and giving them room to be brilliant.

Meanwhile, someone like Richard Branson has never been a specialist in anything specific to his businesses. He's basically a professional manager who has a crazy ability to find and retain the best people in various fields. His original strength (according to his book) was that he was willing to do anything to succeed, including bluffing, lying, and (on one occasion) breaking the law. (Most of that was ultimately harmless, except the last part!)

He also works really, really hard.

I've worked with people in various leadership positions and seen all sorts of examples. I've seen a well-paid manager of a programming team voluntarily step down from his leadership position because he wasn't comfortable telling people what to do. I've worked for a well-known duo in the game industry where the charismatic designer became the manager and the programmer had no interest in doing so (with a team of 30 while I was at the company, probably 40 now).

So maybe the specialist/generalist question doesn't matter as much as your mindset. Successful people work hard, seek out information, and are willing to take risks. Some CEO's are more respected for their abilities than liked for their personalities, but obviously if you're just putting a team together and not starting from scratch you've got no room to be unlikable.

Whew, long rant.

Given the other posts, there's a mix needed, and a startup CEO might need to be very different from a scaling company CEO.

In a startup, who's on your team matters. Are you a two man show? You (the generalist) and your co-founder/CTO (techie)? The two of you alone probably don't have what it takes to promote/market your product after it's built. However, if you're good at managing teams and can pull in people who can fill gaps (marketing, sales, etc.) and coordinate all the people in the initial phases to make things hum. However, if you can't find these people, you may need to be kick-ass (a specialist) in biz-dev to get things going.

In a scaling company, your curent skill-set may be perfect. There may already be enough boots in your team to fill all the critical roles, and you, as a generalist can both coordiante AND help out in any one area, as needed.

At the end of the day, it comes down to this: your confidence in your self.

You're already a generalist, and though it sounds unintuitive, becoming a generalist is not something that's simple--people tend to become good at just one or two things (coders, carpenters, paineters, etc...). Do you have the passion for the idea? Are you willing to work hard to get from a startup phase to a growth phase? Given that you're asking the question above to a forum, you're probably already thinking about these questions--and these questions are good ones for you to ask.

Specialist people don't always make the best CEOs. If you are able to create a kick-ass team ad share the vision, make things happen, and get things done, then I am sure you will be fine and do well.

I don't believe one is necessarily better than the other, though different businesses at different stages of their lifecycle will definitely need different style CEOs.

Broadly, I tell CEOs I deal with that there are only three things they need to focus on:

Managing in Context (ie, the bigger purpose)

Coach don't Play

Managing the Energy in your Business

You sound like you are natural CEO material. The daily life as CEO of a startup doesn't require you to be deeply immersed in any one particular subject (unless the company is so small that you have to do a lot of stuff yourself) but it does require you to have a broad overview and an operational knowledge of a lot of disciplines.

Good luck mr. CEO.

The skill that you must be a specialist at is leadership. You can hire finance specialists, IT specialists, legal specialists, etc. The ability to lead during the peaks and valleys of any business, not just a startup, is what you are being hired for as a CEO.

"can offer no deep, astonishingly insightful commentary"

So what?

Can you ask "deep, astonishingly insightful questions"?

I thought so.

You'll be fine.