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Dealing with bosses you don't understand

righan

Active Member
One of the biggest challenges I face is working with my boss. I've been a web designer working for the same company for 13 years. There were problems from the very beginning. Its a small company and there are no written down rules or protocols for pricing or customer service or written down expectations for what my boss wanted from me ... yet he clearly has expectations and rules and he expects me to know them and follow them but he's never told me what they are ... or rather, he tells me but not in a way that makes sense and when I ask for clarification he gets frustrated and tells me he's already explained it.

For instance, we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer. He seemed to think that was clear enough. In all the years I sold that product to people, I never figured out what made it more expensive. As far as I could tell there was no actual advantage to it.

Also when ever we talk he uses a lot of jokes that don't make sense. Like he says my name with 'dot com' after it when he greets me ... and he likes to say a lot of things that aren't true but are sarcasm I guess ... and I always react like its true. Which frustrates him because i don't get the joke.

After all this time, I have mostly learned how to get along by avoiding him and mimicking things I see he does ... I've taken copies of the things he writes and says and I parrot them back to our customers (and to him) so that he'll be happy with how I deal with people ... but I often don't understand what he wants or why ... I just try to keep my head down and not get noticed ... and whenever I run into a situation where I haven't dealt with it before so I have no script I just do the best I can but live in fear that I made the wrong choice and he's going to be pissed...

Does anyone else have these kinds of issues with their boss and how do you deal with it?
 
One of the biggest challenges I face is working with my boss. I've been a web designer working for the same company for 13 years. There were problems from the very beginning. Its a small company and there are no written down rules or protocols for pricing or customer service or written down expectations for what my boss wanted from me ... yet he clearly has expectations and rules and he expects me to know them and follow them but he's never told me what they are ... or rather, he tells me but not in a way that makes sense and when I ask for clarification he gets frustrated and tells me he's already explained it.

For instance, we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer. He seemed to think that was clear enough. In all the years I sold that product to people, I never figured out what made it more expensive. As far as I could tell there was no actual advantage to it.

Also when ever we talk he uses a lot of jokes that don't make sense. Like he says my name with 'dot com' after it when he greets me ... and he likes to say a lot of things that aren't true but are sarcasm I guess ... and I always react like its true. Which frustrates him because i don't get the joke.

After all this time, I have mostly learned how to get along by avoiding him and mimicking things I see he does ... I've taken copies of the things he writes and says and I parrot them back to our customers (and to him) so that he'll be happy with how I deal with people ... but I often don't understand what he wants or why ... I just try to keep my head down and not get noticed ... and whenever I run into a situation where I haven't dealt with it before so I have no script I just do the best I can but live in fear that I made the wrong choice and he's going to be pissed...

Does anyone else have these kinds of issues with their boss and how do you deal with it?
I have those kinds of issues with EVERYBODY!!
 
I have those kinds of issues with EVERYBODY!!
This. People in general. For example, a student wants to tell me he is cancelling the lesson, but what he actually says is, "I'm going to Rome next Thursday."

Going to Rome on Thursday means just that, that he's going to Rome on Thursday, it doesn't mean that he can't make it to the lesson. He has the lesson on Thursday morning, and it is quite conceivable that he might have the lesson in the morning and then travel to Rome in the afternoon or evening.

For instance, we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer. He seemed to think that was clear enough. In all the years I sold that product to people, I never figured out what made it more expensive. As far as I could tell there was no actual advantage to it.
Perhaps he doesn't have an answer to that. You put him on the spot with your question and he couldn't handle it. Perhaps it is arbitrarily more expensive and given the title of 'designed hosting' to make the customer think that they are getting something really special, when they aren't. A marketing ploy.

As a customer, I would definitely want to know what this 'designed hosting' is, and what it is that I'm paying extra for. I would ask such questions via email in writing - say that a customer asked you this and with what should you respond? Asking in writing gives him a chance to think up a reply.

Don't automatically assume that it is you who is at fault in cases like these... people very often are poor communicators, and it sounds like your boss is one of them.
 
I've taken copies of the things he writes and says and I parrot them back to our customers (and to him) so that he'll be happy with how I deal with people ...

This is generally how I get by at both of my jobs, and in general life. At my fun evening job I see myself as an extension of my boss - everybody seriously loves him, so if I make myself a kind-off replica of him, I won't go far wrong. I do this at work, and in my social life too.

At times I do feel like a bit of a chameleon, but thus far I haven't found a better option, so will keep an eye on this thread to see if there are better options!!
 
I imagine that 'name.com' greeting is a play on your name and profession highlighted in a friendly/joking way. It's considered amusing - people seem to really like jokes based on wordplay...

Do you make sure that you are both alone whenever you ask him a question? Did you try asking by email? Some deal better with that and also you have more time to give an answer to any issues he may have.

I definitely sympathise with your problem. Whenever I am in a new situation, especially at work, I have to analyse behaviour others to find a proper way to behave myself and to understand social order a bit more. It makes you feel fake but it's necessary to not become an outcast.
 
So he is a geek but he is probably bad at communicating which is a possibilty in geek world. This situtation you just slid by on the back of your pants. A lot of these types are intelligent but have no patience in talking in laymen terms. Your best bet is to parrot back what he said if you are seeking clarification. So am l correct in hearing that you said to charge for the tweaking of the input but don't charge for the final website banner since that was just updating? This way you are holding them to accountability without going crazy in the process. Your type of profession may mean every situation comes up different in charges we bill the customer. Perhaps everything is tailored to whatever a la carte services they customer designs. If you are up to it, try devising some type of cost sheet.
 
This. People in general. For example, a student wants to tell me he is cancelling the lesson, but what he actually says is, "I'm going to Rome next Thursday."

You could say 'I am going to have to charge extra to do the lesson there.'

;)
 
I used to have a boss that spoke with a very heavy accent which made him hard to understand at times. Which was not a good thing, because he was my supervisor in the hospital sometimes. He often gave me instructions I didn’t understand.
I remember working a night shift, having a patient who was circling the drain quickly. I called to ask him for advice and had to ask him to repeat it three times because I didn’t understand what he was saying. He became annoyed, told me to just follow the protocol. I reminded him there were three different protocols and I didn’t know which one to use and he told me to just figure it out and hung up on me. I tried calling him again and it went straight to voicemail. I really freaked out at that point and decided to call the intensive care physician to come pick up my patient, but his phone went straight to voicemail as well. Luckily the intensivist came into the ER five minutes later, because it turned out my supervisor had just called him to help me stabilize the patient enough to transfer her to the ICU. Still, stressful times and a dangerous situation.
 
One of the biggest challenges I face is working with my boss. I've been a web designer working for the same company for 13 years. There were problems from the very beginning. Its a small company and there are no written down rules or protocols for pricing or customer service or written down expectations for what my boss wanted from me ... yet he clearly has expectations and rules and he expects me to know them and follow them but he's never told me what they are ... or rather, he tells me but not in a way that makes sense and when I ask for clarification he gets frustrated and tells me he's already explained it.

For instance, we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer. He seemed to think that was clear enough. In all the years I sold that product to people, I never figured out what made it more expensive. As far as I could tell there was no actual advantage to it.

Also when ever we talk he uses a lot of jokes that don't make sense. Like he says my name with 'dot com' after it when he greets me ... and he likes to say a lot of things that aren't true but are sarcasm I guess ... and I always react like its true. Which frustrates him because i don't get the joke.

After all this time, I have mostly learned how to get along by avoiding him and mimicking things I see he does ... I've taken copies of the things he writes and says and I parrot them back to our customers (and to him) so that he'll be happy with how I deal with people ... but I often don't understand what he wants or why ... I just try to keep my head down and not get noticed ... and whenever I run into a situation where I haven't dealt with it before so I have no script I just do the best I can but live in fear that I made the wrong choice and he's going to be pissed...

Does anyone else have these kinds of issues with their boss and how do you deal with it?
I'm not sure if you've tried this but money people are motivated to make more money and don't really care about the details if they don't have to. So if you ask in a very concrete way that means he can make more money it could work. Like,
"Is there a reference I can use to understand this concept? If I can understand it I can explain it I will be able to be a better salesperson for the company. " something like that, maybe.

Formulaic approach:
Me + knowledge= improved sales

Then again maybe he's just a crappy boss who doesn't care if you understand or if the customer understands so long as you're pulling in enough sales to meet a quota.
 
we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer.
It sounds as though it could be compared to something like manual labour. (Which it isn’t.) This is just a random example that companies use and this is their way of making things more expensive. So, taking care of them is more or less a similar way of charging customers.
 
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For instance, we used to charge people extra for something he called "designed hosting" ... and so I asked 'what makes it more expensive' so I could explain that to people if they asked. He told me "Well, we take care of them" which doesn't really mean anything ... and he couldn't give me a better answer.

That sounds like what we'd have called, "Content Management". Meaning that there was an arrangement with a particular client to amend, correct, add or delete content (both graphics and text) in real-time as opposed to the client having to do it themselves.

Yes, he could have given you a more succinct answer. But in his mind, he probably has rationalized that he doesn't have to. So that's that. :rolleyes:

Does anyone else have these kinds of issues with their boss and how do you deal with it?

Unfortunately what you are talking about strikes me as more of a specific trait among some, but not all managers or supervisors. Something that reflects an autocratic or military mentality of those who simply expect you to jump at their beckoned call, and NOT ask questions about it. Even if what they say makes little sense.

Reminds me of a time when I worked in insurance and my supervisor told me to do something that made no sense to me. I asked him to explain it, and his only response was, "Because I'm the boss!" Luckily he said it not noticing that his boss (the operations manager) was standing right behind him at the time. Whereupon she invited my supervisor into her office for some choice words spoken rather loudly behind a closed door.

It happens. Where some people simply let their perceived authority go to their heads without any sense of accountability to subordinates. A personality trait with some in management where there's only "the Peter Principle" or attrition to solve the problem. Where they either move on, or eventually get fired.
 
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I didn't have to deal with him often, but one of the senior NCOs at a radar site I worked at was known for hardly ever speaking. I mean nary a word. People would go in and ask him something and he would just look at them and eventually they would leave befuddled. It really intimidated a lot of people. I thought at first it was somewhat contrived, that is done purposely to intimidate. Then one day my boss was gone and I needed a decision and had to go up the chain then to him. I went in and asked and he just looked at me as usual. I waited briefly, then nodded and left. I figured he was either thinking about it or expected me to decide. But about half an hour later as I was working on equipment he came by and stopping, said 'ok' quietly and walked away. I heard later he had always been that way, even as a brand new recruit. Just an odd communication style, that happened to work very well in an odd way in a military setting!
 
I didn't have to deal with him often, but one of the senior NCOs at a radar site I worked at was known for hardly ever speaking. I mean nary a word. People would go in and ask him something and he would just look at them and eventually they would leave befuddled. It really intimidated a lot of people. I thought at first it was somewhat contrived, that is done purposely to intimidate. Then one day my boss was gone and I needed a decision and had to go up the chain then to him. I went in and asked and he just looked at me as usual. I waited briefly, then nodded and left. I figured he was either thinking about it or expected me to decide. But about half an hour later as I was working on equipment he came by and stopping, said 'ok' quietly and walked away. I heard later he had always been that way, even as a brand new recruit. Just an odd communication style, that happened to work very well in an odd way in a military setting!

Whatever it takes to maintain authority...or the illusion of doing as such. :rolleyes:

Though I suspect intimidation is still a part of that equation. ;)
 
My current supervisor is a strange man. He doesn’t communicate very well, talks to himself and has a habit of repeating himself or over explaining things. And he might be even more of a perfectionist than I am. I write all my reports exactly the way he wants them to be written, because otherwise he’ll have me sit as his desk while he rewrites everything (with spelling errors, to my dismay) Still, every time he reads one of my reports he’ll exclaim that the way (his way) I write my reports is great. As if I haven’t been doing the same thing every day for the 16 months I’ve worked there. But oh well.
He’s also made it a point to repeatedly tell me he doesn’t want to know anything about my personal business or my health, which is tricky since I’ve repeatedly had to take a few months off work because of my mental health issues. I don’t necessarily want to tell him about my mental health, but it does make it a little tricky when he asks how I’m doing and I’m not allowed to say anything other than ‘fine’ because otherwise he’ll throw up his hands and say it’s none of his business and he doesn’t want to know.
Working with him isn’t all bad, as he’s very enthusiastic about his work and about me as an employee, but I’m always walking on eggshells and doing everything just so, so he won’t get on my case.
 
My current supervisor is a strange man. He doesn’t communicate very well, talks to himself and has a habit of repeating himself or over explaining things. And he might be even more of a perfectionist than I am. I write all my reports exactly the way he wants them to be written, because otherwise he’ll have me sit as his desk while he rewrites everything (with spelling errors, to my dismay) Still, every time he reads one of my reports he’ll exclaim that the way (his way) I write my reports is great. As if I haven’t been doing the same thing every day for the 16 months I’ve worked there. But oh well.
He’s also made it a point to repeatedly tell me he doesn’t want to know anything about my personal business or my health, which is tricky since I’ve repeatedly had to take a few months off work because of my mental health issues. I don’t necessarily want to tell him about my mental health, but it does make it a little tricky when he asks how I’m doing and I’m not allowed to say anything other than ‘fine’ because otherwise he’ll throw up his hands and say it’s none of his business and he doesn’t want to know.
Working with him isn’t all bad, as he’s very enthusiastic about his work and about me as an employee, but I’m always walking on eggshells and doing everything just so, so he won’t get on my case.

Since you work in the medical profession, the degree of professional liability is inherently very high compared to other types of work. Making the issue of being micromanaged by a superior more "par for the course". Where even the smallest detail can indeed count.

I like your strength in being able to stick with such daunting work, even with mental and physical health concerns. But quite honestly that's a "tightrope" I'm not sure I could even walk. I had to routinely deal with very high amounts of corporate assets and liabilities, but that's not the same in terms of human lives and professional medical liability. And in most cases I was able to avoid managers who micromanaged much of anyone.

I just wish that I could have avoided people in general in terms of most jobs I've held over the years. But that never happened. :oops:
 
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My boss is not a geek, despite the fact that he works in the tech industry. He is a jock turned coast guard turned paramedic who burned out and decided to start a tech company with a few friends. They know enough about servers and web design and things like that to use off the shelf installable plug-n-play technology, but if its in any way technical they usually have no idea what is going on.

I very often find myself trying to explain things to him that I'm doing as a designer and I know he has no idea what I'm saying ... and he usually just makes a decision about what I said and goes with it ... which is often not what I was saying at all.

I actually primarily communicate with him by email. I work from home. Due to health and mental issues I almost never leave my house. We do talk on the phone sometimes. He usually communicates better that way.

In emails he says almost nothing. In fact, one of the things we disagree about a lot is how wordy I am and how many questions I ask and how much information I give. He wants things to be simple and succinct. - summarized ... simplified. And I tend to be bad summarizing things ... I have a hard time not putting down all the details. I have a hard time even knowing which details to remove and which to keep. They all seem necessary. When it comes to communications from other people, I like details. As many as I can get.

I mentioned that there seems to be rules and he expects me to know them but doesn't tell me what they are ... things like when writing a proposal for a client ... he'll read what I wrote and then send it back to me and tell me he doesn't like it ... but not why or what ... and if I ask he'll act like I asked him him why water is wet ... like its perfectly obvious and he doesn't know why he has to explain it to me ... sometimes he'll end up giving me a little bit of an answer ... but its usually short and vague and not really very informative (at least from my perspective). He seems to think that what makes a good proposal is perfectly obvious and should be perfectly obvious to anyone with a brain and he shouldn't have to explain it.

In fact, a lot of rules and expectations and protocols I have trouble figuring out get that same response ... like he thinks it is perfectly obvious ... the kind of thing that everyone should just know ... and I never really know how to deal with that.

I think the assessment that its a military mentality might be possible since he's x coast guard. He uses a lot of military phrases like 'SOP' and 'comms' for communication ....
 
My boss is not a geek, despite the fact that he works in the tech industry. He is a jock turned coast guard turned paramedic who burned out and decided to start a tech company with a few friends. They know enough about servers and web design and things like that to use off the shelf installable plug-n-play technology, but if its in any way technical they usually have no idea what is going on.

I very often find myself trying to explain things to him that I'm doing as a designer and I know he has no idea what I'm saying ... and he usually just makes a decision about what I said and goes with it ... which is often not what I was saying at all.

I actually primarily communicate with him by email. I work from home. Due to health and mental issues I almost never leave my house. We do talk on the phone sometimes. He usually communicates better that way.

In emails he says almost nothing. In fact, one of the things we disagree about a lot is how wordy I am and how many questions I ask and how much information I give. He wants things to be simple and succinct. - summarized ... simplified. And I tend to be bad summarizing things ... I have a hard time not putting down all the details. I have a hard time even knowing which details to remove and which to keep. They all seem necessary. When it comes to communications from other people, I like details. As many as I can get.

I mentioned that there seems to be rules and he expects me to know them but doesn't tell me what they are ... things like when writing a proposal for a client ... he'll read what I wrote and then send it back to me and tell me he doesn't like it ... but not why or what ... and if I ask he'll act like I asked him him why water is wet ... like its perfectly obvious and he doesn't know why he has to explain it to me ... sometimes he'll end up giving me a little bit of an answer ... but its usually short and vague and not really very informative (at least from my perspective). He seems to think that what makes a good proposal is perfectly obvious and should be perfectly obvious to anyone with a brain and he shouldn't have to explain it.

In fact, a lot of rules and expectations and protocols I have trouble figuring out get that same response ... like he thinks it is perfectly obvious ... the kind of thing that everyone should just know ... and I never really know how to deal with that.

I think the assessment that its a military mentality might be possible since he's x coast guard. He uses a lot of military phrases like 'SOP' and 'comms' for communication ....
There are a lot of executive level people with no or little practical experience who surround themselves with people who are more experienced and competent and build their business in that manner. The worker is a tool they buy to achieve their own success. You, as a tool, simply need to do as you're told for him to get his desired result. Whether or not that is milliary, he does not seem capable of taking into account that you are a human being with thoughts and that your thoughts have worth not only because you are a human deserving respect but because your job performance could improve if you were able to have your questions answered. This will continue to be his management style. He does not, and will not, care about communicating with you more than he thinks is necessary, the minimum. "You're a tool, now do your job". It sounds terrible, but some people are like this. It's not that they're intentionally trying to be disrespectful, emotion just doesn't enter their equation. What you're asking about may not feel like a matter of emotion, but you are asking because you care enough to do your best job. There would be other employees who ask nothing and do the minimum because they just don't care. Maybe imagine him as a machine with a very simple, limited ability to process data. He can only accept specific input and he can only produce specific output. He does what he is designed to do, but any other functions are impossible because it just isn't his design. We can't program a simple toaster play music, but damn does it make good toast. You can try dropping a thumb drive into one of the toaster slots, but it's not going to work out well. You put in bread, you get toast. That's it. And conversely that's what he expects from you.

Wondering how the other employees feel about him.
 
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