Keep being productive with overworked boss?

Question

I joined a Japanese financial company N months ago and the expectations set forth by my manager and the reality is strikingly different. Let me give you a couple of examples:

• I was promised a Linux computer the first day I joined. Despite my numerous requests over several months and being flexible about Linux or Mac (unix), I am still locked on my Windows computer. This impacts my performance greatly.

• Every estimate from my boss for tasks that he has to make takes 3 to 5 times as long as he says (if they get resolved at all). I realized when I joked with the new recruiter from 1 month ago that he should expect things to take 3-5 times as long as promised, but then I actually measured my boss estimate vs the actual timeline and it was scarily accurate.

This has some issues:

• Estimating is already hard in software, but with these great external dependencies I feel totally clueless about estimating my tasks. I will still be held accountable for the timelines, which doesn't make any sense.

• I get greatly demotivated since all of the team members are ignored systematically. Anything we say or propose gets met with enthusiasm, but any follow-up email gets flat-out ignored or just met with a "sure, let's see about that later". My productivity is, as I estimate, 5-10% of the total I could be doing. Most decisions have to go through my manager as a company rule so we can also not do anything (though I learned a really cool trick here).

• Security is a joke, we are severely limited due to the nature of the company but then the boss doesn't follow his own rules. Oh, they are not written anywhere, but every rule I hear I memorize and follow it, which is making my work absurdly complex (but better than being liable!).

The issue is mainly with my manager being overworked and I've raised it several times with him but again he agrees and nothing gets done.

I have a secondary boss (also Product Owner) so I am considering raising these issues with him. Not sure if it's the best person, or I should go above my boss, or to compliance/HR straight away. I am also considering contacting a lawyer, since I don't want the huge security issues to touch me in case there's any trouble with the company.

What do you recommend me doing? Who should I be talking with and how?

Extra: my team and boss are not Japanese, so culture is quite mixed.

Extra 2: let's assume I cannot leave the company.

Clarification (from OP): I estimate my productivity to be 5-10% of what I could be doing if there were no external limitations.

Answer 1

Your boss is slowing down the rate at which you work. You resolve this be becoming less dependent on him to get things done.

You say the company requires you to escalate decisions to him. You can do this in a very efficient way. Instead of giving him a choice of options, you decide the best thing to do. Then tell him "I going to do this thing unless you tell me not to." Commander David Marquette describes delegating control just like this in the very top down hierarchy of US Navy submarine command in the book "Turn the Ship Around!".

In the example of the Linux workstation. Do all the work so that he must only answer a yes/no question. Find the source and model of workstation you want. Find out how such a machine gets ordered. Get a price for the workstation. Prepare a brief description of justification for ordering it. Then ask him "can I go ahead and submit this order?" Be prepared in case you are over budget with a backup option so any negotiation is also an immediate a yes/no question.

Your boss may react in two ways. He may be grateful that you are taking control of things, helping him out so that he doesn’t have to make all the decisions. Alternatively, he may feel that he should be involved in making decisions. You mentioned he already acknowledges that this isn’t working so talk to him. Explain, that you are not trying to talk anything away from him, you are just trying to make his and everyone’s life a little easier by moving decisions down when they don’t need to be escalated. Perhaps you can agree guidelines when you can decide and what you must bring to him.

Don’t ask him about things that don’t require his approval. Often employees ask managers for advice, peculiarly if the manager was a subject matter expert before being promoted. Many managers when asked questions like this take it as a request for help. This becomes one more thing the manager takes on even though they will never get around to it. If this sounds like your manager read "Management Time: Who’s Got the Monkey?" and get him to read it.

Think about those commitments you are held to. What are the consequences of missing the commitments? I doubt it will be a bad review because you all have the same problem so this brings you all to the same level. Usually in companies the cost of missing commitments is that you feel bad. Do you best to make good predictions, they try to meet them. If you don’t make, understand why, but don’t feel bad.

If missing commitments costs you money in the form of bonuses, this gives you power to tell him that he must give you more autotomy so that you can earn your bonuses.

If you take more control of decisions you will feel more motivated because you will stop feeling things are out of your control.

He doesn’t have time for security. Are they ways you can make the security requirements easer to work within. I don’t mean you become less secure, in fact the opposite. Is there technology or different procedures that would be just as secure but easer to work with? Bring him a proposal he can simply answer with "make it so."

Having an overworked boss is an opportunity for you to take on more ownership of the decision making in your own area, controlling your own destiny.

Answer 2

Bosses are normally bottlenecks. There's nothing unusual in your situation.

If I were you

• I would observe how other people, who have been with the company longer, deal with that. Maybe they just don't expect so much input from the boss? Maybe your boss has an assistant who deals with some topics?
• I would also talk to the boss directly and ask them how you should deal with situations when you need input from him urgently. Ask him and see what he replies.
• I would also have some real CYA strategy in place. When I contact the boss I would always write things like: "Could you please let me know what your decision is by April 25th? Otherwise it won't be possible for us to adjust the software by the deadline on April 27th".
• And of course I would always try to communicate with him as soon as possible to give him plenty of time to reply.