How do I stop constantly having to ask my manager for permission?

Question

Context

I work in a small company where I build websites.

There are two owners. One is responsible for designing the websites and other things.
The other one is my direct manager and does all the techy stuff, from setting up mailboxes to building complete websites.

In total we are now 9 people, 2 of them just joined us.
3 designers, 5 developers and 1 office manager

The owners and office manager do 95% of the contact with our customers.

There's a very clear structure in the company that we as employees need to respect the amount of hours estimated on each project (by management) and we shouldn't do more than what our customers pay for.

This results in a lot of feedback loops, where we can't just do stuff, because we have to ask the management first, but they don't completely know/understand what we're doing.
Which results in everyone wasting a lot of time.

Project

My question is about a specific big project we've recently done and are now maintaining.

My direct manager (the tech owner) has done and is still doing all the contact with our customer.

The project also involves a 2nd party, who build an API with which we communicate.

My manager has done all the contact with them before starting the project.
During the project when problems came up, he regularly started asking me to contact them directly by e-mail.
Now that the project is mostly done, we still have a lot of work with bugfixes, I'm not doing most, but not all, the technical contact with this 2nd party.

When things become pricy or require some more thought/work, my manager steps in though.

This creates this (imo) really weird structure, where I'm supposed to manage this project, but I don't really know what our customer wants or what the 2nd party is thinking/doing, ...

If a bug is found in the website, the customer contacts my manager, who then asks me to look into it.

If it's easy to fix, I just fix it and done.

Often it's a bit more complicated though.
Our customer, of course, has customers of their own.
When I need to fix something that impacts the customers of our customer.

I would say I'm afraid to make mistakes when doing something like that.
Which results in me constantly asking my manager if it's ok to make a change or not.

My manager gets quite upset when something goes wrong with this project.
It's a big project for our biggest client.
A lot of stuff has gone wrong already, (again imo) because the project was just a bit too ambitious for us, which I've told my manager before I started on it.

There are a lot of issues with the 2nd party as well.
Their stuff just doesn't do what it should do a lot of the time, making it hard for me to do my job properly.

My manager, as a company owner, has a TON of work himself, always busy, doesn't like getting interrupted, but is constantly interrupted by everyone nonetheless.

I'm very guilty of this myself and it's something I've been trying to work on.
I've been told several times that I ask too many questions and should just "google" it instead.
And while I've been working on this very hard and I now always do my own research before asking something, my manager and colleagues still assume I haven't done much research whenever I ask something.

So on one side I want to figure more things out for myself, without having to interrupt/ask my manager.

On the other side, I don't really have contact with the client, so I can't just go around doing stuff without knowing the impact for our client and their customers.

The question

Is there something I can do to make this structure work better for me?

I'm often "stuck" because I need to ask something, but my manager is busy.

But if I wait too long or just do what I think is right, I often get the feedback that I should've just asked instead of "wasting time" doing something they didn't want me to do.
(Time I would've otherwise spent doing nothing anyway, but management doesn't seem to care.)

What I've tried

I've told the owners several times that I would like more contact with customers.

The reply here is mostly that this is not possible because they do not know who's going to be responsible for a project up front and they cannot have all of us join the meetings with the customers.

Trying to figure things out for myself has proven to upset them more often than not, because I did something in a way they didn't want me to do.
The argument here is mostly that I'm wasting time they're paying me for by taking too much time trying to figure it out for myself instead of just asking them.
Or by doing things the customer hasn't paid for.

I've suggested daily/weekly dev meetings, but haven't seen any of them yet.
Why share knowledge if you can just google stuff?

I've suggested my manager to regularly ask us if we need anything instead of us constantly having to come to him, but that just never happens.

Pretty sure I've tried a lot of other stuff.

I feel like management is requiring me to take more responsibility in everything, while they're refusing to take any themselves.

So what ends up happening is me constantly disturbing my manager with questions, because I know that's the option that will least upset him/them.

I hope this didn't turn out into too much of a rant, I'm just trying to give a good idea of the situation I'm in.
My goal is to find a real solution here, preferably something I can do that doesn't require my manager to change or do anything, because I feel like that has never worked and is not an option.

Answer 1

TL;DR

A core skill for effective project management is being able to clearly communicate “we can’t get there from here” when it’s warranted. If you can’t or won’t do that, the problem is you. If you’re correctly doing that, the organization’s failures are no longer your responsibility, even though you may still get blamed for them.

Analysis

Your question appears to boil down to a few fairly simple things:

1. There is clearly organizational dysfunction, regardless of the cause.
2. There appear to be communications and process failures in both project management and line management.
3. You and your peers/supervisors aren’t able to collaborate on a workable solution.
4. The higher-ups aren’t taking their share of responsibility.

The first three points can have many causes, including a lack of experience on your part and a lack of leadership within the organization. This is not uncommon in small companies, but the ongoing dysfunction serves no one.

The last point is what I would focus on, but not because you can change it within the current level of dysfunction. Rather, it is important to acknowledge that you can’t fix broken communication or organizational dysfunction from only one side.

The bottom line is that senior management at any company ultimately owns the process and the results. Whether the problem is a lack of ability or knowledge on your part, or a leadership failure on theirs, in the end they own the business results of failing to fix either the process or people problems.

Various Unpalatable Solutions

Once you acknowledge the basic premise that senior management owns the organizational process and business results, it seems to me that your best bet with the current level of dysfunction is to do a little soul-searching to see whether you need to do some self-improvement for your next job, or just find another job that’s a better fit. Either way, you likely need to move on.

It’s certainly possible to improve communications failures or organizational dysfunction, but theres’s no silver bullet. In general, I’d say that if you have to ask the question the way you’ve posed it, then you and the company’s leadership both lack the skills necessary to fix the problem internally. An external consultant or process/leadership coach might help, but only if the business is willing to acknowledge the problem, spend money on a solution, and is then capable of making effective changes.

At best, you can suggest those things; but if you aren’t willing to be replaced or fired over pushing for process improvements, then you’re not in a position to effect real change. Part of successful project management is having the skills to clearly communicate “we can’t get there from here.” You’ve identified to us that you aren’t able to accomplish the business’s goals within the current framework, but you need to accurately and successfully communicate that fact to senior management (along with a proposed solution) if you expect to stay in your current role at your current company. If not, dust off your resume and move along.

Answer 2

While not strictly a PjM question, and liable to be closed, the PjM aspect of the question is fascinating.

A rule I was taught as PjM - that may just solve your problem - is:

Solutions, not problems

IOW: Nobody wants to hear about your problems, not even about the work you've put into solving them. People - managers in particular - want to hear about the solutions.

So, either come up with 2 or 3 possible solutions and ask them for a decision or come up with a single solution and ask for their approval.

Does that make sense? No! But that's how managers get work done; by making decisions. They pay you to find them and then implement them.