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Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

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Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#11
post #8
post #7

The primary question is "why"? Where is your company struggling because you aren't technical? In my mind (as a technical founder), the things a CEO needs to know are at the conceptual / theoretical level rather than the implementation level. I've seen businesses fail because the CEO silos the technical side of house from the "business" side and then doesn't have enough technical knowledge to parse suggestions that ar…

"That problem is better solved by eliminating the silos and aligning incentives rather than gaining technical knowledge, in my opinion." How do you actually do that though? Employees typically have incentive to perform their own function to the best of their abilities. This manifests as things like compliance theatre, excessive/impractical IT policies, over-engineering the software, features/products built for the sa…

You talk to them. And even more importantly, you listen.

You'll quickly learn that strawmen such as features built for the sake of it don't actually exist. When you think you have found one, ask yourself why. Why did that engineer choose to rewrite a working piece of code? Could it be that there is no documentation and the person who wrote it left the company? Could the engineer be eager to prove themselves and nobody is giving them a bigger task? Did they want to learn a new technical area?

Or take security theater. Could it be an external regulatory requirement?

Of course sometimes the reason may be "a relative needed a job" but that is still different from "just because" :)

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#12
You can always use the phrase "explain it to me like I'm 8".

That usually gets a fairly jargon free answer. I've see those requests and replied to them, as have others.

Also: I'll answer anything I can if you email me. I check it every day or so.

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#13
First: I am technical, and there are still technical articles (or conversations) that leave me in the dust. I was reading about advanced memory management techniques the other day and it was very apparent I was out of my depth.

So it's a spectrum, not a switch. You will never understand all of them. But you can increase the proportion.

My suggestion would be to just give yourself permission to play around. Look something up on wikipedia---when it gets boring or hard, stop. Install python on your personal machine. Now install another version. Now you hate pip, and you too are a Real Engineer.

Trick is avoiding the temptation to work hard. "Courageous play" is the phrase to keep in mind.

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#14
There is no an easy answer to gaining technical familiarity. If there were then everyone would be experts. You are going to need an investment of effort.

Understand some basic concepts. Technical subjects can span many domains:

* Accessibility

* Transmission

* Security

* Usability

* Performance

* Data Storage/Analysis

* Legal

* Enterprise Architecture

Understand that various technical domains have competing concerns and goals. Learn about the basics of the domains that are important to you and your business. For example it’s my professional experience as a software developer and former security analyst that most software developers bring a net negative in terms security knowledge/applicability because they have no formal knowledge of the basics. They commonly have unverified assumptions and build upon that faulty premise.

Secondly, communicating anything technical well is a matter of good writing on top of domain knowledge. That doesn’t mean the author should slow down and allow the reader to pause for breadth if they have no formal knowledge of the domain. That said, get some basic domain knowledge and then just jump in. Reading technical publications gets easier as the domain knowledge becomes more familiar, as you become emerged in the subject.

Third, build personal relationships with knowledgeable people. The goal here is to build trust and confidence in advisors. This is better if the trusted sources are people that don’t work for you so that they are more open to tell you things that you don’t want to hear, things that may conflict with your business interests. Trusted confidants aren’t there to reenforce what you can learn independently, but rather to help you make more informed decisions by challenging your assumptions and guiding your future.

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#15
post #8
post #7

The primary question is "why"? Where is your company struggling because you aren't technical? In my mind (as a technical founder), the things a CEO needs to know are at the conceptual / theoretical level rather than the implementation level. I've seen businesses fail because the CEO silos the technical side of house from the "business" side and then doesn't have enough technical knowledge to parse suggestions that ar…

"That problem is better solved by eliminating the silos and aligning incentives rather than gaining technical knowledge, in my opinion." How do you actually do that though? Employees typically have incentive to perform their own function to the best of their abilities. This manifests as things like compliance theatre, excessive/impractical IT policies, over-engineering the software, features/products built for the sa…

If they are not engaged in discussions about business priorities, they won't have the context or motivation to align their actions appropriately. If you hire tech people with soft skills, you can have them do rotations on support (and even sales), involve them in higher level strategy decisions, and avoid the CEO -> product manager -> designer -> developer pipeline that makes everyone feel like a cog, and detaches them from anything but their own little area. You can also align their financial incentives with company success (ownership), and give them ways to actually influence it in tangible ways.

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#17
Yes, there is that gap. My gut feeling is that it is as genetic as other components of intelligence, so I'd say don't worry about it too much.

Yes, absolutely you can learn. A lot. But I doubt you can cross the schism. I know it's an unpopular opinion.

I am on the tech side of the "schism". Anecdata is from observing how my and others' kids approached tech stuff.

Re: Ask HN: I'm a non-technical CEO of 20M startup that wants to learn

#18
Thank you all. To synthesize: - learn what I want to learn, probably by speaking with team to prioritize - leverage team + online to structure learning, starting high-level, 'courageous play' - periodically look for current weaknesses, or future strengths, from [lack of] operational integration within company (likely a benefit of technical learnings)
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