

The Curse of the Technical CEO - iseff
http://www.iseff.com/post/49861932184/the-curse-of-the-technical-ceo

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dasil003
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.

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atwebb
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.

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jusben1369
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.

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iseff
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.

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ChuckMcM
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.

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comrade_ogilvy
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.

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zwieback
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.

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

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orangethirty
Or maybe, just maybe, work on becoming better.

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joshuak
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?

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orangethirty
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.

~~~
nickpinkston
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.

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

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ttrreeww
Promote from within.

