The Curse of the Technical CEO | Hacker News Reader

The Curse of the Technical CEO

iseff.com

50 pointsiseff19 comments

To me the conflict is not just time allocation, but it's the mentality. When you put your engineer hat all you can see are flaws, but when you put on your CEO hat, especially in the context of fundraising or biz dev you need to spin things positively. I find it difficult to make this mental switch.

Great point. Engineers sometimes like to see the broken in the world. Leaders need to have the tendency to see the possibilities. Emotional Intelligence is so, so hard (and something I struggle with consistently).

That's a really great way of putting it.

I think another issue is "birds of a feather" related. Unless you've got a wide personal circle (or force one) the people you're talking with most with have the same engineering view and can form an echo chamber of flaws and technical issues. They may be valid but they probably aren't that crucial.

Reminds me of this: https://news.ycombinator.com/item?id=2545823

Per the article I think the trick is to know when to make the switch. At first, if you're the technical CEO, it means you're the guy who maybe talks to prospects and angels (if applicable) That might be two half days a week over time. So clearly coding adds a boat load of value. The trick is to determine when you really need that Fred full time CEO.

Totally true. In our case, it was after our seed round, once we were able to start selling and we felt as though we have proved the initial idea as being worthwhile to customers.

When that happened, we started hiring, and me coding turned into more of a detriment than an advantage. It was approximately a team size of 7-8 for us/e.

This is definitely a challenge, but its also a challenge for engineers who are new to management as well. Rather than lead their team into becoming a problem solving group, they can jump in and just fix things to keep stuff moving along. The line between too 'hands off' and too 'hands on' is hard to navigate. Easier when there are other things taking your time but hard when you're in a hiring lull or there aren't any upper level things calling on you.

As one goes higher up the hierarchy, one's primary responsibility is to see a bigger and bigger picture, while delegating an ever larger portion of the problems to the right people.

Under pressure and suffering uncertainty, the Can Do attitude of a good engineer encourages falling back into the comfort zone of doing engineering. It is understandable. But whether manager, director, VP, or CEO, the urge must be resisted approximately always.

It is probably forgiveable at the manager level. But this is still what I call a "Good Skill, Bad Habit", even for managers.

When I read stories about "CEO"s in startups I mentally compare the description to my CEO Meg Whitman. I think it just doesn't make a lot of sense to use the same label for a founder trying to get a startup off the ground and someone running a large company.

Maybe it makes more sense to have different names for the early positions and ask the question when's the right time to hire a CEO.

Or you need to accept that you're not a very good CEO, and find someone more suited for the job.

Or maybe, just maybe, work on becoming better.

Yes, but to be more clear I mean you should do what you love. If you aren't good at being a CEO but you are at being an engineer it's probably become you enjoy being an engineer more. Why force yourself to become better at something that other people could be great at, and you don't want to do anyway?

You should never do what you love. You should do what works for you. I love fishing, but I would never hold it as a job. Programming works for me. I like it, its fun, challenging, and allows for a good lifestyle. Two different things.

We love those things that bring us pleasure, we like those things that allow us to do the things we love.

It's not a dichotomy - some people do make a living fishing and love their lives. Will you love everything all the time - no, but you'll still essentially be doing what you love.

Life is the thing that goes by while we try to make a living.

Even though I'm from a technical background, I'm finding that I really enjoy the business side of things, enough that I would (and will) happily cut programming responsibility loose whenever I can find a technical CTO, or even a good lead programmer. But when there's no one you can trust with the work, and you know how to code, it's very easy and very tempting to spend an evening up to your elbows in code. It's safe and comfortable.

But if I wanted safe and comfortable, I wouldn't be trying to start a company, now would I?

Sometimes, you just aren't having a perfect view on what you are doing, and what you should be doing.

It is OK if you are sometimes not sure about something, or if you find that you have focused on the wrong thing. It doesn't follow that you should find a different job.

It does mean that you are capable of self reflection. It probably means that you are learning.

Reminds me of this: https://news.ycombinator.com/item?id=1266444

Promote from within.

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