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I enjoy my job, but my boss makes everything more complicated than it needs to be. Whether it's policy, planning, implementation or improvements, he tries to "outsmart" simple things and make them needlessly complex. For example, I am the only one on the team with previous experience in a specific system, and he asked me to implement it here, too. It's pretty simple stuff, but he keeps saying "We need System X to also do 123, make it do 123. Also, it has to be able to do HIJ. By the way did you get it working with 789?" Not only are those things completely outside the scope of the system, they're things it isn't designed to handle and, in all my Googling, it appears no one else has ever demanded it also do these things. I tried explaining that these kinds of requirements are really not suitable, so he started coming up with a ton of complicated hoops we could jump through just to satiate these arbitrary ideas, talking about deploying more new systems, involving other teams, tons of work just because he decided it needs to be extended in the wrong direction.

Or later, we tried to set priority for different projects on our list. When we agreed to a one hour meeting, it was just to establish a 1, 2, 3 style list. Instead he spent four hours explaining how to visualize priority as a three-dimensional matrix along three axes, defining each axis, then disregarding those definitions in order to place everything at the highest priority, then deciding we need to use a different program to track priority, then Googling around for that, and so on. We were just supposed to make a list! And later he started talking about how there are actually six factors we need to account for when prioritizing projects...

How can I respectfully ask my boss to rein it in, and stop trying to make everything so much more complicated than it needs to be?

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  • Did you ask your boss what problems he's trying to solve by extending system X to do 123, HIJ, and 789? – combinatorics Apr 23 at 21:45
  • Did you broach the subject with him already? Is he amenable to that kind of feedback? If he doesn't recognize that there is a problem, it will be very difficult to fix it. – Stephan Branczyk Apr 23 at 21:58
  • @combinatorics It's something orthogonal to the original purpose (we need to hack a custom API for this VoIP software so that we can forward call logs to Teams so that different call types are integrated), assumptions about user work flows (we need to write powershell scripts so that this email address can receive an email template and users can reserve rooms, then if it's already taken it sends this template in return), or odd security ideas (we need to make sure these laptops only boot during business hours so that if they're stolen they only boot when we are on duty). Stuff like that. – dgergefrsdfc Apr 23 at 22:04
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    @StephanBranczyk When he asks what I think, I will honestly answer "I think you're making it too complicated." Sometimes he will ask me to explain and sometimes he will accept that explanation, but most of the time he says that we just need to add it to the project list and we can talk about it in the future. We're a team of four and have over 75 projects like this already, just flights of fancy we will "discuss" but never do. – dgergefrsdfc Apr 23 at 22:18
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    I think a more productive question would be what strategies you can use to deal with people who over-complicate things - it is much easier to change our own behavior than try to get someone else to change theirs. In my experience, even if your boss wanted to accommodate your request to keep things simpler, they may have a hard time doing it. – ColleenV Apr 27 at 12:38
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+25

Your Boss is your Boss and you probably won't be able to stop him from being all over the place and wanting to have it all. But you can develop strategies so you can still deliver something.

You have solve two problems here:

  1. Protect your time
  2. Protect your backlog

Having long meetings where you discuss changes in strategy are bad for two reasons. First spend time on something that is immediately productive and second it might even lead to you course changes, that make you lose some of your progress.

Protecting your time
Don't let your manager occupy all your time. Try sticking to the scheduled time and agenda and defer new ideas to follow up meetings. When your manager changes topic to discuss new feature HIJ don't comment at all on its technical feasibility, but emphasize that it is currently out of scope, but you are happy to schedule a follow up meeting to discuss about how to integrate HIJ in the plan. Then schedule the meeting at least a week later, so you don't get distracted by the topic for a while. Schedule meetings at times where they cannot easily go overtime, by doing them late (this can work if they like to leave on time, or backfire if they don't) or schedule them before another meeting they have to attend. In my old job a team mate and would schedule fail-safe meetings with each other just to give us a reasonable excuse to cut another meeting short, we knew would go overtime. Do whatever it takes to make sure they don't hijack all your precious development time. People who habitually go overtime in meetings, are usually used to people interrupting them and bailing out.

Protecting your backlog
Let's be clear. Your boss is still your boss and tells you what is the direction to go. If your boss wants System X to also to integrate with 789, it is your job to jump through hoops to get there. While you do not have the final say of what to deliver, you can make sure that you deliver something by focusing on one thing at time and keep working on them unless your boss very explicitly tells you not to work on them anymore. Following your example

System X to also do 123, make it do 123. Also, it has to be able to do HIJ. By the way did you get it working with 789? Either way you will have to first deliver System X, start working on it right away with a minimal set of feature.

Put features 123, HIJ and 789 on your backlog. Keep feature on your backlog in mind where you can, but don't worry too much about them if they will need rework. Most of them you will probably never work on anyways. Every time your manager comes up with a new feature, compliment him on his great idea for a new feature and put it in the backlog.
This a good time to remember him of all the other features that are already in the backlog: "Should I pick up features HIJ before feature 789 and feature 123 or should I do it at the end?"
Give your boss control over the backlog, usually he will like is latest idea best so it goes on top and his other ideas getting pushed to the bottom. Let it go on the top, something else will replace it soon.

Then you keep working on System X. After you delivered System X see what is the next item on your backlog and check with your boss again whether they still want that feature. By the time you are ready to have that discussion there probably is already a System Y that is more important and you will never actually deal with most of these features.

5

How can I respectfully ask my boss to rein it in, and stop trying to make everything so much more complicated than it needs to be?

Short answer is you cannot. This seems to be his style and you do not have authority or skills to change his working style.

What you can instead do is proceed on the project way you think is the best (simple approach). For any random request from your boss, just stall him and yet keep him happy by saying fancy things like

Great idea. I will explore this. In the meantime, I got the first MVP (minimum viable product) with simpler features.

Sure. I will look forward to your suggestions on that. I will attack the low hanging fruits first.

Most likely, your boss does not understand implications of his own requests (Most of them do not anyway). He just wants to show (maybe to himself) that he is being a true mentor to you. You make him feel exactly that but at the same time ignoring his request and progressing on the project which is for the larger good of the company.

For instances like he calls you for a meeting and eat up your 4 hours in googling for best project management styles, try to avoid such meetings. Try to get as much inputs for him over the email so that he wastes his own time and you can filter out what he wants. If meeting is unavoidable, make sure you have an exit plan. Like a "hard-stop" after 30 minutes or 1 hour due to "that other thing" which you have to take care.

Of course you may feel like you can 'pretend' this way to do your work and may decide to change boss (i.e. job!). My experience is larger the company gets, more and more this pretend play with overcomplicated terms goes on. You just have to learn to play the same game and give it back.

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    While I'm a little reluctant to encourage full scale "nod and smile" mode, I do think that often people with "big ideas" can be satisfied simply be listening and engaging with them, so +1. I've often found that being a good sounding board and asking questions can help them talk themselves out of some of their worse ideas. – ColleenV Apr 27 at 17:19
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    Another implementation of what I believe is the same idea, and made possible by the recent proliferation of Work From Home is as follows: minimize the conference window to 2x3 cm, Always On Top and at the lower right corner of the screen. And proceed working. If mentioned manager ever says anything useful, it's not too difficult to realize what is happening and immediately switch context thus joining the conversation. – Vorac May 3 at 7:02
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Suggest him to make things easy and show him some sort of solutions.

Something I learnt a time ago is that smart people make complicated things easy. For instance, instead of forcing a tool to do things that is not prepared to, why not use another tool and maybe integrate them with an API?

About that meeting you had for priorities, I've had some experience like that. What I did is re-ask something like: What should I start with? Just set first 2-3 tasks and meeting is productive.

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Sounds like his antics will likely catch up to him without you needing to do anything. His overcomplications will likely lead to decreased productivity and increased resignations in his department, which in theory should raise his bosses ire. And it is his boss whose ire needs to be raised because it's his boss that's going to be able to be the most effective in curbing this behavior - not you.

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    You would think, but I recently found out I was hired because his previous team already quit over this stuff. We have an average employment span of one year. – dgergefrsdfc Apr 23 at 22:19
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    @dgergefrsdfc see you back here in a year when you have questions about resignations :) – morbo Apr 24 at 9:36
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Memorize this phrase: Minimum Viable Product

Your goal should never be to develop, from the start, a hugely spanning product. Your goal should be to develop a minimum viable product - the bare minimum to satisfy a business need - while doing so in a flexible, expandable way.

There are lots of reasons for this, such as:

  • The time period you know the least about what the product will require is at the beginning of the project. Why try to plan out every technical detail during this period, when your knowledge is at its lowest?
  • It reduces the likelihood of overdesign/overscoping. If you're developing an MVP, you don't run much risk of developing a feature that won't be used. Programming a feature that isn't used is a complete dead waste of time.
  • It allows the possibility that some features may be essential but others are merely nice-to-have, and it makes more business sense to work on other projects instead of fleshing out the nice-to-haves.
  • It allows features to be prioritized in terms of when they're delivered
  • It allows faster return on investment - the client area gets something to use quicker, instead of having to wait for every aspect to be finished.

In short: try to continuously push to your boss: quick delivery, small scale, get-it-out-there-and-go-from-there. If it helps, get them involved with Agile, which naturally lends itself to this sort of product delivery.

Also, something else you need to consider: your boss seems to be the one delivering project requirements. But... they're probably not the one that's actually generating the requirements for the project - your boss isn't the end user of what you're working on, right?

You might need to forge a better connection with the business areas that are requesting what you're working on. Ideally, your boss shouldn't have to be a liason between you and the business area - they should be able to tell you directly what they need/want.

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To answer the question

How can I respectfully ask my boss to rein it in, and stop trying to make everything so much more complicated than it needs to be?

I will refer to a comment you wrote on the answer:

When he asks what I think, I will honestly answer "I think you're making it too complicated."

I think that's the best you can do. Do it over and over again. Whenever he asks what you think.

From what you wrote about his 4-hour lecture on his ideas about "three-dimensional priority", to be blunt, your boss lacks a normal sense of perspective. Thoughts move in his head according to some rhythm comprehensible only to him.

Sometimes he will ask me to explain and sometimes he will accept that explanation,

That's a good sign. In my experience, that is not always something you get when you work with someone whose thoughts move like this.

but most of the time he says that we just need to add it to the project list and we can talk about it in the future. We're a team of four and have over 75 projects like this already, just flights of fancy we will "discuss" but never do.

Fortunately, an icebox full of "nice to have" user stories is an easy thing to ignore.

Instead, work on the important things.

Unfortunately, to find those things, you need to prioritize mercilessly. But that is, of course, made quite a bit more difficult when the boss has deeply unconventional ideas about what "prioritization" really means, and insists on expounding on them.

The only solution I can think of for that is to just let him talk, and when he's finished talking, ask, "So, what do you want me to work on first?"

-5

Could be you're really overthinking it and worrying too much.

he spent four hours explaining how to visualize priority

Fantastic!

Give me a boss like that!

You got paid for four hours to do nothing. Sweet. Better than sweet!

How can I respectfully ask my boss to rein it in, and stop trying to make everything so much more complicated than it needs to be?

  1. Your boss is your boss. Unfortunately in work life we always have one and only one option - leave if you don't like it. Otherwise, unfortunately, they are the boss. They are paying. That's it.

  2. The situation is not harming you in any way. Try working for some super-efficient bastard who has no flim-flam and has you grind 8 hours a day!

  3. Politely listen to whatever the boss says. More paid time for you!

I tried explaining that these kinds of requirements are really not suitable...

Deal only in concise specifics. Never deal in generalities.

After your boss has spoken for the six hours, say something SPECIFIC and BRIEF, such as:

  • "Interesting. Should I try Google Docs?"

  • "Make sense boss. Should I start with the spreadsheet?"

  • "Great stuff. I'll get started on the PDF."

Keep it SPECIFIC. Do NOT say anything like

  • "Can we simplify"

  • "Are we using too much time"

  • "I don't understand"

  • "We are spending too much time on planning"

Deal only in SPECIFICS.

Do not say anything conceptual, strategic, analytical or philosophical.

If "you're so smart", after you have been (incredibly lucky enough to get paid to sit through) a four hour vague-fest, in under 8 words say something concrete that should be done next, and do that.

How can I respectfully ask my boss to rein it in, and stop trying to make everything so much more complicated than it needs to be?

Leave him alone! Take and enjoy the incredible experience of being paid for hours to smile and nod. You cannot change someone who likes to "think out loud for hours." And, unfortunately, he's the boss - that's life - leave the company if you want. Come back only with simple specifics, never offer anything conceptual or strategic. Everything will be great!

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    It feels like you're the boss OP is taking about. – Aventinus Apr 26 at 21:58

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