Dealing with “small” issues when working for a senior person

Question

I'm reporting to a really senior person. Most of their direct reports are higher in the hierarchy than I am. 

At the same time, the culture of my organization is sometimes difficult to navigate. To give you just one example: for my work I need a tool A. There's no viable alternative to tool A. Fortunately, the tool is very cheap. So I write to my boss's report who's in charge of taking this decision (but who's from another area and is not able to understand or has ever used tool A). They reply: "I don't think you need tool A, I don't think you should have it". So I start an exchange on that, explaining why I need A urgently. I offer to discuss it. They ignore me. After several days or weeks I still don't have tool A. (Btw, I've worked in several companies before, never have I been denied tool A).

I don't want to waste my boss's time for such small things, but I'm not able to work without tool A. So normally I would write a short email to my boss and his report something like: "It would be great if I could receive tool A. The alternative is my needing 5 times as much to complete task B. What's the decision?"

My boss gets irritated when I turn to him with such topics and I think my doing so twice (within 2-3 months) has impacted our relationship. They think I should "just talk to people and try to solve issues". But I'm not sure what the alternative is. I do talk to people, I try to build a good relationship with them, which works with most but doesn't help with some requests. To get a tool for 5 USD/ month can take months and fail - at the same time the expectations towards me are high.

Do you have any advice?

HR is useless where I work, so please don't advise me to turn to them. Yes, my boss has an assistant, but normally they can only help to a very limited degree.

Answer 1

If you have a problem or blocker, it's not a waste of your boss's time, it's literally his job. Everywhere I've ever worked, if you want a tool to help with your work, you ask your boss first before anyone else with precise rationale.

Hi Boss, task X is taking up 5 hours of my time every week. I found Tool A that will reduce my weekly time on task X down to 1 hour per week. Tool A costs $5/month. Can I get your approval to requisition Tool A? Thanks, martel

If he approves, then you forward that to his other report. If he refuses, then that's that: he's made the decision. If he forwards it for approval to this other person, then their decision becomes his decision.

It sounds like your boss has offloaded this management responsibility to someone else on his team. You say,

So I write to my boss's report who's in charge of taking this decision (but who's from another area and is not able to understand or has ever used tool A). They reply: "I don't think you need tool A, I don't think you should have it".

If you know that this person is not able to understand the need for it, state the rationale in terms of something universal they can understand, like time or money.

At the end of the day, if you've been denied that tool after this, you just have to accept it. If your boss or anyone complains that you aren't completing work on time, remind them about this. Don't be snarky, but say that if you had this tool, that would free up your time to finish another task.

Answer 2

Sounds like you are seeing a pattern. I'm assuming this isn't really about Tool A, that the issues in this example, are something you are seeing multiple times, with multiple other directs of your boss.

The skill here is "influence without authority" - which is a tough one. You have a specialized job, you're supposed to do it, you're of a lower rank, but you still need be able to get what you need to do your job.

This tends to be a multi-pronged technique with a lot of minor failures before you work a workable pattern, there is no one right answer. Key elements of getting through it:

• actively build relationships with other staff outside of the direct request. For example, try to find some time for some 1:1s or even a friendly cup of coffee with that person that's saying "I won't approve $5 for tool A" and see if you can get inside his head. Not with a direct campaign for tool A, but to see why he begrudges the $5, and also to convey some of the value of what you do, so he can see why tool A is actually valuble.
• look at how the organization functions and see what power you do have. For example, you make some sort of output with Tool A. Who consumes that output? If it's not only the boss, find the other folks that benefit and get them on your side so THEY can ask the budget approver for Tool A on your behalf. They may have a much better connection to what you do, and therefore may be allies in all sorts of things. It probably also means adjusting your work so you serve their needs well, but that will make everyone a bit better off... so that's a good step too.
• look at what mechanisms exist in the company - is there some kind of crazy reason for not approving a very small budget? Is there a kind of leverage/risk/concern in the stuff you do that may make certain folks reluctant to be cooperative? Learning the lay of the land helps a lot.

I suspect there's other strategies out there if these 3 fail - it's usually a lot of trial and error, building on the failures as you build hopefully positive relationships.

If this sounds like a hell of a lot of work for a $5 tool... you're right. I'm not gonna lie. This is, however, the price of working for someone too powerful/busy/high level to have the time/energy/interest in helping you. You're likely right that less highly placed manager with more subject matter expertise in what you do would be more helpful on this one - mid level managers are supposed to be able to all this relationship building and organizational manipulation so that their individual contributors can hunker down and get something done.

Instead of thinking of it as a giant epic quest for a $5 tool, think of it as an investment in the organization. The knowledge and relationships you build for the first quest are usually useful in the next one and the next and the next, until it really isn't as big a deal to get stuff done.

Answer 3

"It would be great if I could receive tool A. The alternative is my needing 5 times as much to complete task B. What's the decision?"

You yourself said the above quoted text.

Tool A indeed helps you to perform this task, but you can also carry on with the task without tool A, so it's not impossible to do the task without A.

I suggest two things:

• Ask for tool A directly to your boss, not to any report of theirs. If having tool a will increase your productivity 5 times, I don't think it will be a waste of time for your boss.

• Start doing the task without tool A, as otherwise you will waste time repeatedly asking for tool A and not actually do the task you were given.

If you just keep asking for A and not working in the meantime, the due date will come, anyway. If they ask you for reasons for not completing the task, and your excuse is "It's because I wasn't given tool A", this scenario doesn't look good for you. So start your task ASAP without tool A to avoid this problem.