Three bad career questions people ask me all the time

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I’d like to tell you that there are no bad questions. But you know what? That’s not true. So here are the ways people ask me questions that drive me nuts:

1. You ask me a career question for your wife.
The first problem with you walking around in the world telling people you need help for your wife/girlfriend is why can she not ask for herself? I can only imagine that she does not see her problem the same way you do. And in that case you should butt out. Or, maybe she does not want to ask for help. And in that case you should butt out, too, because who are you to tell her she needs help when she doesn’t want it and then go get it for her anyway?

Newsflash: The guy who asks career advice for his wife sounds way more needy and off-track than his wife does. Because the guy is being so disrespectful in such a public way and he doesn’t even know it.

And hey, mister, how would you like it if your wife walked around telling people that you need career advice but won’t get it yourself, so she’s getting it for you?

2. You ask me a question when five people have given you an answer you don’t like.
I have some bad news for you. Five people who agree on anything are probably right. Especially since it’s likely that after three people gave you answers you didn’t like, you probably started asking people who are maybe a little bit crazy so maybe they’d give you a different answer. And they still didn’t.

So look, consider taking the advice when a small community accidentally comes together as synchronized advisors. You are lucky. These people all took the time to hear your problem and give you a thoughtful answer. Don’t spurn them if you can help it — they will not want to give you an answer again.

Cheat sheet: If you are thinking that your problem is very unique and difficult, or that people everywhere do not understand you, then the problem is you. Because you don’t want to face the reality that you are not special (none of us is, really) and the people around you are not idiots. (And if they are, who is the original idiot that aggregated the idiots?)

3. You ask me a question that requires more than two paragraphs.
Sometimes I get emails that are more than two pages long, attempting to explain a problem. I’m going to tell you something: All career problems can be described in under 100 words. If you are going over 100 words, you don’t know your problem. If you are going over 1000 words, it’s because your self-knowledge is really bad, so that is your problem.

Think about it. If your problem is that you don’t know a good way to answer the phone when it rings, that is a very concise problem. If everyone in the office hates you and you can’t figure out why (maybe you can’t narrow it down to the phone) then that is still a concise problem.

If you have to explain to me all the characters of your office and why they suck and I have to infer that everyone hates you and that’s your problem, then your problem is self-awareness. You lack it.

So try this: If you are writing your problem and you’re on the fifth paragraph, try to edit. Try to get it to one paragraph. And then try to get it to one sentence. That’s a good exercise in figuring out your own problems.

Being smart about your career is not so much about having good answers. It’s having good questions. You don’t need to have answers to everything. But you need to work hard at making your questions useful, for both you and your advisors.

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  1. Don B.
    Don B. says:

    Knowing what you need to know and framing a question is a key when already in a career. Trouble is when you do not know enough to know what you need to know or what to ask. So always find a on job or outside mentor. Someone you can ask any question and can help you formulate the questions you will need to ask others.

  2. Jon S
    Jon S says:

    You’ve already made a pretty terrible mistake the moment you even thought about asking PT for career advice. The “bad questions” have no real meaning here.

  3. W. Church
    W. Church says:

    I’m guilty of this – not two pages, but not one paragraph. Most times when I do write, I tend to write two pages and then edit edit edit until its closer to the point. But I’m indebted to your advice through your blogs and e-mails. So thanks for being patient with some of us :)

  4. Ian
    Ian says:

    I like the last 2 points, they are good reminders. (#1 is probably just passing on info that their spouse is looking for opportunities)

    Even though it could be harsh, all 3 gives us a good look of what a recruiter, hiring manager or executive could be thinking when we ask for advise.

  5. Mark W.
    Mark W. says:

    I can understand where you’re coming from on this post. I sometimes get questions about whatever that tell me the person asking the question hasn’t taken the time to sort through the various issues involved. The question is not well formulated or specific. Many times it’s just plain laziness – mental thought process as well as any possible “legwork” that may be involved. The person asking a question as described above does not respect your time. I have only so much time available in a day so I give it to those people that are most deserving. Concise and thoughtful questions give merit to them and will elicit the most complete and best answers.

  6. Beth
    Beth says:

    I think another way to think about no. 3: no one can read your mind.

    I have heard people ask questions that were so long, they would forget what the point was by the end. I am convinced that they do it just to hear themselves talk out loud. There is no way to possibly answer such a question! Unless, of course, you are a mind reader.

  7. Editormum
    Editormum says:

    PT said “If you are writing your problem and you're on the fifth paragraph, try to edit. Try to get it to one paragraph. And then try to get it to one sentence. That's a good exercise in figuring out your own problems.”

    THIS IS GOOD ADVICE! Seriously. I cannot tell you how many times I have sat down to write to someone to ask about a problem, written pages, realized that no one was going to read all of that, and edited the heck out of the thing … only to realize in the middle of chopping it up that I’d suddenly understood the problem and didn’t need advice after all.

    Blaise Pascal once wrote “I have made this letter longer than usual because I lack the time to make it short.” Making things shorter requires time, and often we’d rather not bother. But PT is right: to get good advice, you need to be able to identify the problem concisely and accurately. Thanks for the reminder!

  8. Jason Alba
    Jason Alba says:

    Good points Penelope… as I started to understand my career better, and career issues, I get all kinds of questions. I’m sure you went through this years ago, but I’m finding that most of the questions I get are Career Management 101 things… stuff I think is so obvious and clear, but really, many people have never really thought about.

    Because we haven’t had to…. we were coddled by our company until we were kicked out on our butts.

    Jason Alba

  9. Jane Greer
    Jane Greer says:

    Ian: “(#1 is probably just passing on info that their spouse is looking for opportunities)” — telling a Person In The Position of Hiring that someone is in the market for a new job (or “opportunity,” if you must) is vastly different from saying that someone needs career advice. “A” might make me consider helping; “B” would make me run in the opposite direction.

    To me, what all 3 bad questions boil down to is FOR GOD’S SAKE DON’T WASTE THE TIME OF A TOTAL STRANGER YOU’RE ASKING FOR A FAVOR–something our mothers should have taught us, but….

  10. blink
    blink says:

    RE: Point 3 (two paragraph max)

    One important tip I learned long ago was to try and cut the “story” out of your questions, and just get to the point. This includes the tangents, the reasons, the background info, the gossip, the opinions, etc. If the other person really needs to know to answer, they’ll ask.

  11. Jenflex
    Jenflex says:

    OK, I’m on board with the comments’ content, but the snark tone seems a little crafted-for-buzz. Or else a little stoned-in-a-glass-house-ishEspecially the comment about being disrespectful to a significant other in a public environment.

  12. emee
    emee says:

    I don’t think her tone is snarky, it just seems honest to me. IMO there’s too much warm fuzzy feelgood crap in HR right now and sometimes people need to hear the reality. Like an earlier commenter said, “so cold… and so true.”

  13. Susan
    Susan says:

    You’ve jumped the shark. Is that to the point?

    Simply put, people look for affirmation and explain to avoid later doubt. You’re guilty of it, so why the ‘tude?

  14. jeremiah
    jeremiah says:

    “being so disrespectful in such a public way”

    Really? That’s hilarious. This from a woman who has more concern for faceless readers than her family and friends. One marriage down and a farmer to go. Great entertainment. Oh, Gen Y are complete pantywaists. Keep ’em coming P.

  15. Shawn
    Shawn says:

    I’m also not a fan of the incredibly broad career question like “Can you tell me how to find a job in finance” without any information on what area of finance they’re interested in. Of course that’s in contrast to the 17-part question that is virtually impossible to respond to in 500 words or less.

  16. Ian
    Ian says:

    @Jane Greer
    I don’t see it as Not to ask for favors from strangers, instead I see 2 & 3 as Don’t turn personal crap into advice request?

    Although #1 is different, if someone want to bring up that the spouse need a job but don’t have access to the advisor. Then he/she could either ask ‘Do you know any opportunities for my spouse’ OR ask for advice. The advice approach can:
    – Letting the advisor talk about themselves
    – Inform advisor the spouse is looking
    – Having a meaningful discussion, it become a bit memorable
    – Sliding in more spouse’s details for the adviser to narrow down some opportunities
    – Getting some actual advices
    – It’s not aggressive, yet it forces the advisor to answer anything but no
    With so many pluses, wouldn’t he/she be stupid not to use this polite approach?

    Although I guess people use this so often that others has now see right through it.

  17. Frieda Dietrich
    Frieda Dietrich says:

    great tips no matter how “cold” someone might describe them…I plan to use a variation of the ideas with parents who ask for advice on college selection after not hearing the answers they want from other “experts”….I am known as a “no BS” counselor…most parents appreciate hearing honest feedback-HS counselor

  18. Norcross
    Norcross says:

    While there is a gray area with #1 (there’s a difference between advice and actual job opportunities), #2 and #3 are dead-on. Asking enough people, you’ll eventually hear what you want. I’ve never understood that, though. If you want to do something, and you’re willing to both ask AND ignore any advice about it, then why not just go do it in the first place?

  19. Andrea Rice
    Andrea Rice says:

    I’m with Shawn on the incredibly broad question that either communicates “Do my work for me” or “I haven’t given it enough thought to know what I really should be asking”. The real problem here is that people don’t know how to effectively engage others around their career questions. As a result, they don’t ask and make unnecessary mistakes, or they ask the wrong/inappropriate questions and don’t get what they need.

    I loved what you said at the end: “Being smart about your career is not so much about having good answers. It's having good questions. You don't need to have answers to everything. But you need to work hard at making your questions useful, for both you and your advisors.”

    Andrea R

  20. Neil C
    Neil C says:

    I agree very strongly on point #3. We are all busy so get to the point when you have a question. Self awareness & objective self analysis is so important (which is why I have a distaste for Gen Yers who in general believe that they are worth so much more than they are to a company)

    Penelope-I have always been impressed how responsive you are to emails. I totally understand why you would need to have a post like this-some people need to hear it.

  21. Tim2
    Tim2 says:

    I haven’t even come close to agreeing with you in such a long time that I had to read your post again. #1–not so sure about.
    Numbers 2&3, however, you’re so on target.

    I’m still worried, though, that I agree with you at all.
    Must sit down for a while.

  22. prklypr
    prklypr says:

    Maybe this post cuts a little too close to the bone?? Commenters seem esp rude. IMHO #3 is dead on: edit, edit, edit! Wish more people did it in their emails, their conversations, their lives. Best class I ever took in college (eons ago)’technical writing’, how to edit down to the simplest, most basic communication. No fluff. Wish more people knew how to do it.

  23. hallie
    hallie says:

    I haven’t agreed this much in a long time. I also don’t see P’s tone as particularly snarky. Just true. Not everyone wants to be babied. I for one prefer hearing things straight.

  24. Jane Greer
    Jane Greer says:

    Ian: If you re-read my original comment, you’ll see that I didn’t say you shouldn’t ask strangers for favors–I said that you shouldn’t waste their time when you do so.

  25. Jennifer Lynn
    Jennifer Lynn says:

    Love the post, especially number two.

    My sister has a great way of dealing with people who ask for her advice/opinion when they already know the answer or are clearly looking for people to agree with them. She sighs, looks them dead in the eye and asks, “Do you want the truth or a lie?” When they inevitably get defensive, she says, “Don't get me wrong, I'm happy to validate you if that's what you're looking for. I just think we should be clear.”

    Oh, btw, Penelope is snarky sometimes, people. Why the surprise? Snarky is fun.

  26. Eve
    Eve says:

    “I have some bad news for you. Five people who agree on anything are probably right.”
    For the most part, these are very true, and they even made me chuckle, as I hear them all the time…but this part, quoted above….that is something to watch out for and I do beg to differ. I can name 5 people who agree its Ok to cheat on your spouse, have kids you don’t intend to take care of, cheat, lie, steal, etc….but that does not mean they are “right”. I guess what I am saying is, look at all of the “bad career advice” you hear the general public give, such as, “A degree guarantees you a decent paycheck”, or “lawyers are rich”, blah, blah, the list goes on, and tell me if you would base “good” career advice on anything they say!

  27. Liz
    Liz says:

    Whoa. People who get on here to yell, “you suck,” while complaining that the problem is PT isn’t nice enough for them, so she deserves it, are kind of sending a mixed message.

  28. Ian
    Ian says:

    Oh..then I totally agree: Go ahead and Ask, but don’t waste others’ time on useless discussion. (Like what I ‘m doing now with this confusion)

  29. John
    John says:

    As a 3rd party recruiter every once in a while I’ll get the rogue spouse on the phone that has to tell me how their spouse is the best engineer/salesperson/manager etc. and how any company should want them..yada, yada yada.

    Guess which candidate I never want to work with again!?

    And by the way, it’s usually the wife heralding the virtues of her husband, not the other way around.

  30. Jim
    Jim says:

    Here’s the problem:

    What if my spouse is the greatest UNIX Systems Administrator that ever lived?

    A lot of technology people have a very hard time communicating and have very poor people skills. That doesn’t make them a bad technologist though. That is probably why they are in the field already, they can just bury their head in the computer. But maybe the Spouse is just trying to help them along by going to bat for them?

    I know programmers should have great people excellent communication skills. But remember, if they did, there would be no need for Technical Writers. And if everyone had excellent communication skills, it wouldn’t be a requirement on most job postings, it would be a given.

  31. John
    John says:

    This comment is addressed to Jim.

    Jim, it’s wonderful that you want to help your spouse (at least I presume it’s your spouse we’re talking about), especially if she asks for assistance. The best assistance you can give her, however, is to help her craft her marketing and presentation skills, identifying her strengths to puthem in the best light possible and then letting her sink or swim with the new skills you helped her achieve. To paraphrase an old worn out saying “Give a man a fish and feed him for a day, teach him how to fish and feed him for the rest of his life”.

    It might be tough for her, but life is tough. We all have to do things we don’t like to do, but once we do them a few times guess what, they do get easier. Help her, but in the end let her stand on her own 2 feet.

  32. Phreaked
    Phreaked says:

    You could not be more right!! I felt a personal connection to number one. I had a boyfriend try to solicit his company to hire me to write for their marketing department. I was still a bit cautionary about working in the same building as him and he was so pushy! I met up with him for lunch in the park and he purposely brought me over to the side where his “co-workers hang out” hoping to establish some impromptu interview… as I was wrestling for control of my dog mind you. So inconsiderate.

    I am so unbelievably HAPPY to be out of that relationship on SO many levels.

  33. Joe S
    Joe S says:

    OK, fair observations. Perhaps all three point to how insidiously we prop up our delusions. Begs the question: What are some really good career/life questions to ask (oneself) to help cut through delusions.

  34. Shefaly
    Shefaly says:


    I think these problems plague not just career-related questions but – since you write about work and life – also people’s general approach to seeking advice.

    For my sins, I get a lot of people – including random strangers – from my native country seeking relocation advice from me. The questions usually come on email and say things like “I want to pick your brains wrt to location, costs etc where I should look to move to”.

    If I see no evidence of either clarity of problem definition or an iota of work done by the person asking for help, I send them on their way with some pointers. I usually say that in the absence of info re your budget, familial situation, lifestyle preferences, anything I say will be a waste of my time and theirs. So they need to use Google to find some real estate aggregator sites and look up what locations suit their budget and then if they want qualitative info, I am happy to help.

    The crux of the problem lies in intellectual laziness. This means people do not even define problems for themselves and expect someone to, first, define the problem for them and then to solve them for them. That is just crap.

    I use the same patient approach the first time with grown-ups (purportedly, since someone gave them a job and is paying them) and with youngsters (who usually have a more open mind and therefore teaching them how to think is a joy in itself).

    Oh if I see continued signs of laziness, I usually refer them to professionals who charge. End of.

  35. Phil
    Phil says:

    I agree with the 2nd comment posted by Jon S. It still ceases to amaze me that people come here for career advice. I especially love it when “CEO’s” or other big wigs chime in with agreeance. I would be scared as hell to work for that person. Show me one PT success story that would want to make you take advice from her? I especially love her annoyance with point #1, asking advice for a spouse. So a husband asking advice for his wife makes him look needy??? Come on, where do you get these “theories”? The last I checked, badmouthing your husband and publicly destroying a marriage on a blog that is linked to so-called professional articles is pretty tactless and might one say, needy? I needed this weekly read to reaffirm my sanity and to keep me sharp. The comments here prove there are still plenty of crazy people out there. I still have about 2000 acres of prime lunar real estate if anyone is interested. It is a great investment for the future.

  36. Jim
    Jim says:

    Reply to John:

    John, I am a Technical Writer, and as such I work with a lot of people with very poor communication skills. They might be great programmers / technologists, but they have little or no social skills.

    Being around these people all the time, I can see how someone else might have to provide assistance as not only do they not have the skills, some of them do not have the means to even develop these skills.

  37. JC
    JC says:

    “As a 3rd party recruiter every once in a while I'll get the rogue spouse on the phone…”

    I agree that this is obnoxious behavior, and could be handled more tactfully by the candidate.

    However, on the other side of the coin, one of the most successful and competent 3rd party recruiters I know asks a lot of pointed questions about one’s friends/ex-co-workers/significant others when he’s on the lookout for skilled positions.

    This is how I scored my current job; an ex-bf recommended me to the recruiter. The ex-bf had knowledge of my job skills because we met at work (!). Note: that is not usually how I go about networking.

  38. Adunate Word & Design
    Adunate Word & Design says:

    Uh, Phil, actually the fact that you and hundreds of other people read PT is an example of her success. And when you add comments, that provides yet another example – she has successfully promoted conversation, which is what brings success to blogs.

    PT is an excellent example of good marketing and branding. Google her and you come up with pages and pages. Of course, people are going to buy her book, media is going to hire her, and organizations will pay her to speak.

    As a small business owner, I read PT for advice, awareness, and entertainment. Her world is very different than my own, yet it’s important for me to know what’s going on out there, because, hey, that’s the world I need to do business with.

    Thankfully, I’m open-minded enough, I can sort through what’s applicable to me and off-handedly disregard what isn’t. Interestingly, often what I think isn’t, later down the road, is. Discussions from PT’s blog always come back to mind.

    So, ouch to you Phil. Maybe you should open your mind a bit too. If not, why irritate yourself with all us crazy people?

  39. Anne Botha
    Anne Botha says:

    I believe that people struggle to be concise for four basic reasons:

    * Firstly, they know something is wrong/amiss/confusing but they don’t know where to start figuring it out. So, they end up taking a “shot in the dark” approach.
    * Secondly, they are not task focused. Task focused requests tend to have far less emotional intent (and content) in them.
    * Thirdly, people can be rather lazy and would prefer not to take the effort to understand.
    * Fourth, the person actually doesn’t want/need an answer, but would rather use the question to have a reason to engage with someone.

  40. Adunate Word & Design
    Adunate Word & Design says:

    #3 hits it right on. In my line of work, I see this two ways, both the way people write and the way they come to me for communication solutions.

    All of us are busy these days. We have very short attention spans, and no one wants to read anything overly verbose. In fact, if the paragraphs are too long, if they create too big a block of text, we automatically are scared away.

    Rule of thumb: Maximum sentence length: 15 words. Maximum paragraph length: 45 words.

    Secondly, you’re right when you say people want an answer before they’ve identified the problem. Businesses (usually start-ups, or wanna-be’s) frequently come to me for a logo or collateral before they’ve determined their business and marketing plans. They have no idea what is their mission, who is their market, or how they plan to promote their product. They say they’ll know the right logo when they see it. This just doesn’t work.

    Take the time to examine yourself, know what you want and determine plans to achieve that. Do the work yourself, don’t look for someone else to do it for you. People get paid big money for that job.

  41. hallie
    hallie says:

    Every time I say something bitchy online carma bites me in the ass… I can’t help but notice that I made some rather embarrassing typos while trying to dis Phil.

  42. Phil
    Phil says:

    I’m honored to be ‘dissed’. I guess it was bad KARMA (not carma). Thanks for making my day even more special!

  43. Jon S
    Jon S says:

    Good marketing and branding?? Hmmm… yea… I googled one of PT’s names “Adrienne Eisen” and it came up with some website with adult content. If branding is so good, why all the name changes?

  44. Shefaly
    Shefaly says:

    @ Hallie and Phil:

    On Carma:

    Looks like, someone’s Carma just ran over someone’s Dogma!

    Sorry, couldn’t resist. ;-)

    BTW the real word, karma, from Sanskrit, has nothing to do with the common usage in the west to mean some kind of comeuppance-type-divine-or-supernatural-accounting-system . It simply means ‘action’. :-) This action may set in motion a cause-and-effect cycle but per se, it means nothing more than ‘action’.

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