I have trouble deciding when to ask management what to do when something does not go according to plan vs. making my own decision. On one side if it's something small I do not want to bother management but on the other hand I don't want to be held accountable for having made the wrong choice. Often times I do not physically work with any management and I would have to call to talk to them.

The details are complex, but here is a short example. I was given prepaid company credit cards to make a purchase with. The purchase was around $300. After paying, the teller realized she over charged and asked if she could pay me back in cash. I wouldn't feel right making a profit from this mistake but I don't think a prepaid credit card could be refunded to. Also things were already behind schedule and the person on my team I was working with was in a rush. Management did want copies of receipts so I thought it may be an important difference. So I called my manager (who was in another time zone) to explain the situation and ask what to do with the $10. He said just to let them keep it. Looking back, I probably should have just decided for myself.

I often over think things. Any advice on how to decide when it's appropriate to decide for myself without talking to management?

  • @JoeStrazzere I was thinking it's a good idea when working with a new manager, wait for about a month, then ask for feedback so they have something to compare it to when saying they would like more or less feedback.
    – BitFred
    Nov 1, 2021 at 3:43
  • @BitFred I'd approach it as a opportunity to define with them the parameters on when they need to be involved for similar circumstances where there's no policy defined. If its already defined you may want to notify rather than discuss. That said, I never think it's wrong to discuss financial issues like the example as this has the potential of causing unforeseen issues. due to tax/expense implications etc. To me, that makes sense that you're agreeing the correct way forward. Nov 1, 2021 at 15:25
  • Over time, as you gain credibility through your work and earn the trust of superiors, you will find yourself being given (or allowed to get away with) more decision-making authority. Hardly anything substitutes for experience in this regard, and experience is gained through trial and error. Early on, erring on the side of caution is the best strategy; later on, you can begin to take calculated risks and learn from the outcomes of these decisions and the management's reaction.
    – A.S
    Nov 3, 2021 at 14:12

7 Answers 7


Rather than call your boss over every little decision, it may be better to make decisions, but ensure that your boss is kept in the loop.

Regarding the example you gave, you should just keep the $10, but also send a quick email to your boss and let him know that you have an extra $10 in petty cash.

When it comes to balancing the books, if it looks like it's $10 out, then that can be explained.


This is one area where you need to be careful. Fiddling your expenses can easily get you fired. Purchasing a $300 item and charging $310 to the company card looks very fishy.

In this case, asking the manager may have been the safest option.


You send an email like "Hey boss, X happened, and because of that, I will be doing Y, unless you tell me not to do it". With enough time for the boss to react; at least to say "we'll have to think about that".

Obviously apply common sense. Avoid things that could cause legal trouble. Avoid situations where asking your boss is more effort than just doing something. And if you are unlucky enough to have a micromanaging nightmare boss, let him micromanage.


It's called using your judgement and you get good at it by learning from experience and getting feedback from your management. Talk to your manager to get an idea of how much autonomy they would like you to assume in various areas. They may not care about dollar amounts under $20. They may want to always be involved if you are giving an estimate for a project to certain people.

Find out what limits your management is comfortable with, then use your judgement to decide whether a situation is within those limits where you should make the decision independently. Every so often check in with your manager to make sure they feel that you are consulting them often enough but not too often.


Heard of RACI? Time to utilize it.

In the above example, I'd say, you're responsible and accountable for the usage on the card, so you can make the decision yourself. There's no need to consult anyone, but it's always advisable to keep your boss informed about any usage (usual expense) and cases like in the example.

I'd suggest, every time you use the card, or on a weekly basis (which is lesser frequent), send an email to the boss with a summary of the payments via the card. That way, even if that $10 is an issue, you'll not be in the odd spot, it'll be on the records.


For quick decisions, use common sense and think about what a reasonable person would do. If the cashier overcharged you and offered to give you the money back in cash, and then you went to your boss and said, "the cashier overcharged me and paid me back in cash, here's $10 to cover the difference", do you think your boss would be upset? Probably not. So do that. Maybe your boss gets mad at you, but in that case you know for yourself that you did the reasonable thing and it's your boss who's being unreasonable; if your boss is unreasonable too much, you may find yourself wanting to find a boss who is more reasonable. In any case, don't make a big problem for the poor cashier trying to do their best, just do the thing.

For larger decisions that have wider impact, then you should go to management. There is a saying, "it's above my pay grade". Sometimes, things are above your pay grade, and when it comes to those things, you should ask those people. Use your judgment to determine what is or isn't above your pay grade. A cashier giving you a $10 bill to cover an expense discrepancy is not above your pay grade.


If something deliverable is varying with a minimum and acceptable variation, make your own decision. Important here is to never let these decisions shine a bad light on you. So for your specific example: Do not take 10$ and pocket it. I'd take the 10$, add 5 from my own and buy something for the team's lunch break. Or let the store keep it. Let's call this a "green" deviation.

If something is significantly impacting the predicted output, but you have a way to make it "green" by changing something within your mandate - then go ahead, but at the first convenient moment inform your boss about the problem and your mitigation. They might come up with a different plan, if so, accept their suggestion.

If something is significantly impacting the predicted output, and you have no way of making it back to "green", escalate to your boss at your earliest opportunity, directly. Go to their office, call them, send a text, send a mail. Now, some bosses don't like visits to their office, and prefer mail only - so pick your path, but I'd err on the side of escalating too much. It is way worse being chewed out for ignoring a problem than escalating it too early, IMHO. And I prefer employees that are alerting me too soon than those that never seem to act at all. If you were my employee and ran around trying to find me over a detail, I'd worry about your stress level, not my own!

  • This is unauthorized use of company funds. A theft.
    – Xavier J
    Nov 4, 2021 at 7:03
  • @XavierJ Bullsh... it is. The hourly cost of getting something time sensitive EASILY surpasses whatever manual fidgetery you'd have to do recoup that 10$ overcharge on a prepay. It is saving the company time, and time is money.
    – Stian
    Nov 4, 2021 at 7:18
  • People here in the States have lost their jobs and been jailed for far less than $10.
    – Xavier J
    Nov 4, 2021 at 7:23
  • @XavierJ And children are forced to slave labor in Myanmar. I don't recommend having any illusions of a mandate for anything at all if you are indentured labor, or sufficiently similar. And I don't see how anyone can be jailed for explicitly creating a situation where they do not take any money at all in OPs example. Do not pocket it.
    – Stian
    Nov 4, 2021 at 8:47

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