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Re:A two-person startup already uses twenty-eight other tools by GordonS on Saturday February 29, 2020 @04:49AM (#22449849)
It sounds like a few simple rules would help - you don't need complex procedures and forms, it can be as simple as "if you want to buy new software, ask the CIO or CTO, and in most cases they'll say yes/no on the spot".

I can't help but think this is a symptom of being awash with VC cash - I can't imagine this happening in a bootstrapped business.

Re:A two-person startup already uses twenty-eight other tools by hef19898 on Saturday February 29, 2020 @07:13AM (#22450193)
I tend to agree. Bootstrapping, and small budgets, force discipline. Even without procedures. Practically infinite budgets tend to have the opposite effect. If senior management isn't forcing discipline things can get out of hand pretty quick.
Re:A two-person startup already uses twenty-eight other tools by afarrell on Saturday February 29, 2020 @08:35AM (#22450439)
> Bootstrapping, and small budgets, force discipline.

This is only true in the evolutionary sense -- Example: "parachuting forces people to be good at checking their gear."

Telling someone that they are going to jump out of a plane won't magically give them a skill like meticulousness.

Re:A two-person startup already uses twenty-eight other tools by ryandrake on Saturday February 29, 2020 @09:36AM (#22450735)
It’s a skill like any other, and requires study and practice. There is a reason why half of pilot training is checklists and drilling procedures until they are permanently encoded into your muscle memory.
Re:A two-person startup already uses twenty-eight other tools by afarrell on Saturday February 29, 2020 @11:12AM (#22451247)
Right. But I often see people ask "how can I learn to X" and get advice like "Go do Y. It will force you to X". But jumping into to the situation unprepared is not how pilots learn skill X. They learn it through particular methods of study and practice.
Re:A two-person startup already uses twenty-eight other tools by hef19898 on Saturday February 29, 2020 @11:57AM (#22451507)
Yeah, true. Frugality is a nice thing to have learned. And I agree, you don't learn it by bootstrapping your company. Rather your company will likely go bankrupt if you didn't learn it before.

If you have the basics already, so, bootstrapping forces you to build up that. No guarantees, so.

Re:A two-person startup already uses twenty-eight other tools by afarrell on Saturday February 29, 2020 @08:41AM (#22450462)
Note that the phrase "ask the CIO or CTO" hides an "obvious" skill: Concisely make plain the cost vs. value -- grounded in the CIO/CTO's understanding of value.
Re:A two-person startup already uses twenty-eight other tools by GordonS on Saturday February 29, 2020 @10:32AM (#22451021)
I think it's fair that if you want to spend company money, you need to justify it, especially so if it's on something that will be used by a whole team or across the whole company.

At a smaller company that values its devs, there hopefully shouldn't be too much ceremony around this, unless it's a particularly large spend.

But at larger companies, yes, you're likely going to have to know how to make your case in a more formal way, and get involved in company politics (ugh).

Re:A two-person startup already uses twenty-eight other tools by afarrell on Saturday February 29, 2020 @02:13PM (#22452358)
Agreed.

And there should be a good guide for junior devs on how to do that "justify it" step well in startups. Sounds like something that could piggyback off of https://www.kalzumeus.com/2011/10/28/dont-call-yourself-a-pr...