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> Being a "good boss" includes being able to draw a line in the sand somewhere. A "bad boss" is one who thinks "the company" can pay for everything "just because" is doing the themselves, their employees and their company a disservice.

I have never met an employee who would characterize a “good boss” this way. At the very least I would not expect these qualities to win you any favours with prospective employees.

No one looks at “free work lunches” as some negative reflection of their boss’ financial acumen. The closest complaint I could think of is that the employee would rather that money go directly into their pocket. Maybe there is a middle ground here where you could allocate $50/year for these sort of expenditures in order to prevent them from getting out of hand?

I’m not sure, but I would consider reflecting on what really makes a “good boss” and whether or not your employees would agree with you on it. To me the distinction between a good boss and a bad one is always decided by the employees, never the boss.

> Maybe there is a middle ground here where you could allocate $50/year for these sort of expenditures in order to prevent them from getting out of hand?

Here I would agree and indeed I think certain people misunderstood my original comment.

What I was trying to say originally is a bad boss is one who has an open-wallet policy to "but its just $10 a year", because that sort of policy will absolutely come back and bite them or their company in the backside one day once the numbers start adding up. So yes, absolutely, set a hard dollar limit per employee and we're in agreement.

Because yes, if you don't, things will soon get out of hand (as I posted in more detail a little further down).

Sorry, but if the employees have to worry about $10 a year because of nickle-and-diming from the boss, you're either not paying them enough or your process for small reimbursements suck. Why don't the employees have enough freedom to get the tools to do their job in an appropriate way instead of wasting your time and theirs discussing whether $10/yr for adblocking is an essential part of their job? That argument alone would cost you more than $10, not to mention the productivity loss from intrusive advertising.

Yeesh, I'd hate to work for a boss like you...

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I'm sorry but the "its only $10/year, the boss can pay for it" argument is complete BS.

That "its only $10/year" multiplied by how many employees ? It soon adds up.

Then we move into the same BS "only $10/year" argument that charities use when they are asking you to donate "only $5" or that Disney+ uses when it says its "only $10/month".

The "only $5" to the charity and the "only $10/month" to Disney+ is ON TOP OF all the other household expenses. So really, you are foolish to buy into the "its only" school of nonsensical argument.

So we soon find ourselves in an exponential situation. One day we say "yes, the boss will pay $10/year for this" .... roll forward a few weeks then its "oh, just another $10/year for that" ... etc. etc. ... multiplied by X employees .... soon equals $$$$.

That's why a good boss is one who is capable of standing their ground and putting that line in the sand.

Otherwise the overheads soon run away from you and you find yourself spending tens of thousands of dollars a year on "but its just $10" non-essential stuff.

Basic business good practice.

It's not so much the particular dollar amount, but that it sounds like your process for evaluating whether a tool is "essential" is basically "whatever the boss feels like in any given moment" instead of having a transparent evaluation process that weighs, say, $10/yr/employee vs the potential for risk for malware/ransomware or even simply lost productivity from intrusive ads. Is there ANYTHING an employee should be able to spend money on without your direct approval? Is there a process for evaluating what is an essential business expense, per position? How small a business is yours?

It's the lack of agency and trust in your people, rather than the specific dollar amount, that bothers me. If it was a $10,000 or even $1,000 purchase (such as buying that ad blocker for the whole company), yes, of course it should merit more evaluation, but is there really a need to micromanage every single transaction instead of having an expense account of some sort and a procedure for small purchases and reimbursements?

Not arguing that all your employees should be able to arbitrarily spend company funds willy nilly, just that they deserve some say in how they do their jobs, and the tools they need for it, instead of being simply being told "no, because if we scaled that $10 up to all the X employees it would be too expensive..." Did all the X employees even ask for that..?

What if you just looked at it as a cost for employee satisfaction? If I ask my boss for a license to try a new tool, or something to make my workflow better, it's a win for the company if it works out. If it doesn't work out, it's a win for my morale, because I don't have a skinflint of a boss.

When a manager evaluates what is "essential", it creates a dynamic where they either agree with me (which wastes both our time), or they disagree (which creates conflict). For $10/year, it's better to avoid the conflict and just buy the stupid tool that makes the ICs life better.

Yeah, the nickel-and-diming thing is really annoying from a bookkeeping perspective. I was assuming a corporate structure where people have a budget for small expenses. I had this when I worked at Oracle. We had a company credit card, and I'd just fill in these small expenses along with my timesheet.

It can cost more to get approval on some small amount than the actual invoice is. Some places don't require approval for amounts under $x.