can I ask for an extra week of vacation, even though I’m entry-level?

A reader writes:

I work at a very small organization (less than 10 employees). I’ve been working here full-time for just over a year, though I was a part-time intern for the preceding year. I currently get two weeks of paid vacation. There is no rigid policy regarding approval or recording of vacation days.

This is my first full-time job out of college, my position did not exist before I started working here, and I’m essentially entry-level, so two weeks of vacation seems reasonable in that sense. However, the only other full-time employees here are two senior vice presidents and the CEO. They all get significantly more time off than I do. I am not sure exactly who gets what, but I know my boss’s vacations for this year will add up to at least four weeks. (She’s one of the two SVPs.) All the other employees are part-time with very flexible hours. They are paid on an hourly basis.

So here’s my dilemma: I would really like to ask for an additional week of vacation (paid or unpaid). Part of me is thinking that this is an unreasonable request, as I’m just out of college and have only been working here for a little more than a year. The other part of me is frustrated that over the course of the year, I spend much more time in the office than any other employee, since I’m the only full-time person without extensive vacation. Does this caveat make my request any more reasonable?

I would love to get your take on this. If you think it’s worth asking for another week, I’d also really appreciate your advice on how to approach this topic with my boss. One reason I’m hesitant to ask is that I’ve only used one week and one day so far this year, so I don’t know if asking for more time will seem silly given that I have four unused days.

I don’t think it’s crazy to ask.

That said, I also think you’re probably looking at through the wrong lens. It’s not unusual (in the U.S., that is) for entry-level employees to get two weeks of vacation a year while more senior people get four — or more — weeks. That’s pretty common, actually; vacation time is often based on seniority (with people earning more the longer they’re with a company) or is negotiated as part of an offer (with more senior people able to command more, just like with salary). So I don’t think that you should get frustrated that over the course of the year, you’re in the office two weeks more than SVPs; that’s a pretty normal thing.

If you were at a large company, I’d tell you to accept that this is how their benefits work and that asking for the same benefit levels as SVPs and the CEO wouldn’t get you anywhere. But you’re at a small company with only four full-time employees; that means that they likely have a lot of flexibility with PTO, and if you’re doing awesome work, they might be perfectly happy to give an extra week off each year. So I don’t think it’s outrageous to ask. (But again, that assumes you’re doing awesome work. If you’re not, all bets are off.)

And I wouldn’t worry about the fact that you’ve only used a week and a day of your time so far this year — in fact, you can even cite that when you ask for more, explaining that you find yourself hoarding your time and hesitating to use it at all, since there isn’t a lot of it.

However, if you’re asking for it to be paid vacation, you’re essentially asking for an increase in your compensation package. In that case, I’d approach this very similarly to how you’d ask for a raise. (You can find advice on that here.)

But if you’re willing to take it unpaid, which it sounds like you are, that’s often an easier sell. Just ask your boss if she’d approve it. I’d say something like: “Now that I’ve been here a year, I’d love to talk to you about my vacation time. Would it be possible for me to have three weeks of vacation a year rather than two? It’s okay with me if the third week is unpaid; I’d just like the flexibility of having that additional time off available.”

At such a small company, your boss probably has the flexibility to approve this. But if she doesn’t approve it, at least knowing that it’s not a horribly different arrangement than lots and lots of entry-level folks have* might help.

* In the U.S., that is. Everyone outside the U.S. finds this outrageous. As someone in need of a vacation, I lean toward agreeing.

how a 20-minute meeting after every project can help you do better work

When you wrap up a major project, do you most frequently (a) immediately turn your attention to other pressing items on your to-do list, (b) file away some lessons for next time in the back of your head, or (c) schedule a meeting to debrief with others who were involved with the work?

If you’re most people, you do (a) or (b). But doing (c) instead can make a huge difference in your work.

In reality, most people don’t debrief nearly enough after a project is over, particularly when a high workload makes you harried. But there’s enormous value in making the time for it, because research shows that simply talking through what went well, what could have gone better, and lessons from next time can dramatically increase the quality of your work in the future.

After all, even when things have gone well on a project, you’ve likely learned from the experience and picked out things that could be done differently next time to get even better results. Writing those up, even as just a quick bulleted list, can be an invaluable resource to have on hand the next time you conduct a similar project.

One compelling example: Harvard Business School researchers studied a group of surgeons learning a new operating technique and found that those who discussed each case in detail and debriefed with team members after procedures managed to cut their operating time in half. Those didn’t discuss and debrief hardly improved their time at all.

Of course, in practice, it can be tempting to skip a formal debriefing when new projects loom. One way to make debriefs more likely to happen is to build them into your project plan from the start: When you’re scheduling out a project, include a 20-minute reflection meeting on your calendar at the end of it – either with the project team if it’s a multi-person project, or even just with your own manager if you’ll be working on it relatively independently. If you have it on your calendar as part of overall project schedule, you’re more likely to do it when the time comes, rather than racing on to the next thing.

I originally published this at Intuit QuickBase. 

how can I prepare my teenager for the workforce?

A reader writes:

My daughter has just reached the minimum legal age to get a job (13 where we are) and she’s very eager.

I of course want her to do really well in any industry — both the ones she wants to be in for a lifetime and the ones she’s in short-term for the money and experience. What can I do as a mum to foster good work ethics and reasonable expectations? What would/do you and the readers to to prepare younger kids for the workforce?

I’m going to throw this out for readers to weigh in on, but here are some initial thoughts from me:

* Talk to her about your own job and workplace. Talk to her about other jobs you’ve had and what those workplaces were like, what you liked about them and didn’t like, and what your coworkers were like. (In general, I think it’s great for parents to do this from the time kids are small, so that work stuff isn’t such a mystery. And this old post has a ton of interesting discussion about how people are helped by what they absorb about work from their parents when they’re growing up.)

* Talk to her about what makes someone a good employee in any job, but especially the sorts of jobs she’s likely to have as a teenager: work ethic, pitching in, being friendly, being reliable, following through on commitments, using common sense.

* Brainstorm with her about what she’d want from her employees if she were running a business. Also, what wouldn’t she want?

* Talk to her about mistakes you’ve made at work — why they were mistakes, why you made them, and what you’d do differently now.

* Talk to her about what it means to commit to a work schedule and what it means for the people who will be counting on her … and how to handle it if she needs to call in sick, has an emergency, or otherwise needs to alter her schedule.

* Warn her that on some days work might suck, and that on those days it helps to remember that you are getting paid.

* Educate her about workers’ rights. Also educate her about the fact that many employers aren’t up to speed on labor law, and it’s not uncommon for them to have practices that Aren’t Quite Legal.

* Talk to her about how people get better and better jobs — helping her to see that doing well at early jobs can lead to better and better opportunities.

This is too much for one conversation, of course, or even one week. But lots of it can be woven in when you spot opportunities.

Readers, what advice do you have?

I’m a bookkeeper for a company that doesn’t pay its bills on time, rejecting applicants who don’t meet basic qualifications, and more

It’s five answers to five questions. Here we go…

1. I’m a bookkeeper for a company that doesn’t pay its bills on time

I have been working for a small company for a few months now as their bookkeeper. They are a small retail store and money is tight. They never pay their bills on time and have their vendors calling and even sending rude emails requesting payments. My boss has been directing their calls and emails to me, but my hands are tied. There is no money to pay them and payments have to be approved by her.

I am currently studying for my CPA and working towards being an independent bookkeeper for local companies in my area. Some of these vendors are local and I may want to solicit my service to them in the future. I feel that this is reflecting badly on me as they may think that I am not doing my job in keeping up with payments. What can I say to them when they are requesting payment so that it doesn’t reflect badly on me? I do not think that my boss would be happy if I tell these vendors that we simply do not have the money to pay them. However, I feel that I need to give an explanation so that it is not jeopardizing my reputation in the future as a bookkeeper.

Well, to some extent, I’m not sure that you can get out of it reflecting on you if you stay there long-term. While you’re not responsible for your boss’s decisions or lack of payment, being associated with that kind of thing over the long-term can color the way people see you. I realize that you might not have the ability to instantly change jobs or might have other reasons for staying there, but I’d give real thought to moving on. What your boss is doing is crappy and might be directly harming other small local businesses. If her cash flow doesn’t allow her to pay on time, she should be up-front with vendors about that from the start rather than agreeing to their terms and then breaking those terms.

As for what to say to vendors meanwhile, I’d say: “I’m so sorry. I’ve spoken to the owner about getting you paid, and as soon as she approves payment, I’ll get it out to you immediately.” I don’t think it’s your place to say “there’s no money to pay you” unless your boss okays that, but it’s entirely reasonable to make it clear that the hold-up is coming from your boss, not from you.

2. Should we bother sending rejections to applicants who don’t meet basic job requirements?

I know that you suggest that a hiring manager should always respond to every person who applies for a position, and I agree. However, if the applicant doesn’t meet the basic requirements, do I need to respond? For example, we require our applicants to have their own car, valid driver’s license, and insurance. This is stated in every job posting, but people without a car or license still apply. Do I need to send these applicants a response? I feel like I don’t need to because they are obviously not reading the ad and are applying anyway.

I suppose it’s not as imperative as sending rejections to people who did take the time to read about what you’re looking for, but … why not just send them anyway? It takes a few seconds to send a form rejection. Given how fast the process should be, it would actually add more time into most rejection processes to separate out some people into a “no response” group, rather than just putting everyone into the same system.

3. Reaching back out to an employer a few months after starting a new job with a competitor

I started working with my current company a couple of months ago and I’m thinking of changing jobs. Right before I got hired with my current company, I took an informational meeting with a competitor. I met with two of their partners and four other employees and I took a writing test; they loved me and said they would keep me in mind as positions opened up. Two weeks later, I got hired by my current company and received an email from the competitor congratulating me and saying they would love to stay in touch in case anything changes.

I would like to reach out to the other competitor again, flag that I’m looking to change jobs, and see if they’re currently hiring. Of course, the easiest way to do this would be to respond to a job opening, but this company does not advertise job openings. Could you give me some advice on how to best approach this? I’m worried about my current company finding out, I also want to avoid sounding negative about my current company and I’m having a hard time deciding whether I should include information about why I want to change jobs when I reach out to the company I’m hoping to work for.

Actually, even if they advertised their openings, it would be weird to just respond to a job opening when (a) you have a relationship with these people, (b) they know you accepted a new job a few months ago, and (c) they’ve encouraged you to let them know if anything changes. You should reach out to your contact there directly and explain that your new role isn’t turning out to be what you’d hoped and you’d love to talk if they think it would be worthwhile. Be prepared to be asked why you’re already thinking of moving on after only a couple of months; that’s unusual enough that you’ll need to have a fairly compelling explanation so that it doesn’t look like flakiness. Good luck!

4. How to handle lunch as a temp worker

The culture in my office is to have lunch at your desk while you work. However, I’m one of two temp workers and I am paid hourly – not for lunch. No one eats in the lunchroom, so the few times I have eaten in there have been awkward. I want to leave a good impression, but I’m also not paid to work through lunch. Is it ok for me to regularly leave the office? Mostly I go downstairs where there is a nice balcony, but is it ok to meet friends? I’m always back under an hour.

Sure, leaving the office for lunch is pretty normal in most offices. And even if no one else in the office does that, it’s still not something that would typically be frowned on. And it’s really up to you what you do with that time; it’s fine to meet friends if you want to, assuming that it’s not causing you to take a longer lunch break than you’re supposed to be taking. I suppose that it’s possible that there’s some office out there that would frown on you leaving the premises, but that would be pretty unusual. As long as you’re not getting signals to the contrary, head out for lunch without worry! (And if you do get signals to the contrary, just ask whoever is managing you about it: “Hey, is it okay for me to leave the office when I take lunch?”)

5. Resume wording when I’m applying for a position I used to have

I recently worked a contract position at a college. They have just re-posted this position and I’m planning to reapply for it. The new job description is identical to what it was last year.

I used a lot of the wording directly from this job description on my resume and cover letter. (I have been applying for similar positions with other organizations.) But now I’m not sure what to do about my application for this job because it is back at the college. Do I need to change the wording so that it’s not essentially copied and pasted from the job description? Or can I leave it because it is exactly what I had done while in that role? I’m nervous about changing the wording because I know it will be put through a keyword scanner.

You should change into your own language so that it doesn’t sound copied and pasted. Moreover, you should change it anyway because your resume shouldn’t read like a series of job descriptions; it should be far more about what you accomplished in a job than just what duties you were assigned.

Also, since you used to work there, you have contacts there. In addition to applying through the official process, you should also reach out to the hiring manager (who presumably you know) and let her know that you applied and would love to be considered for the role.

if everyone dresses casually at my new job, can I still wear a suit and tie?

A reader writes:

I’ve been interviewed by a company that has a very interesting role which I think would help develop me further and also grow in my career. Assuming I get the role and I start with them, would it be an issue if I don’t align myself to their dress code right away? I noticed that most of the employees wear casual, but I’ve been wearing shirts and ties (since I work for a big bank) over the years and admittedly have not been able to update my casual wardrobe. Would that create an issue with potential coworkers or direct reports? The role I’m applying for is a senior manager anyway. What do you think?

In general, if an office has a pretty specific dress code, it’s good to fit into it. Of course, going more formal is generally better than going less formal, but it’s still not ideal.

Clothes send signals. In this case, you risk signaling “I’m not quite a part of this team,” “I’m removed from the rest of you,” or even “I’m not quite a culture fit.”

At least lose the tie.

how to get along with your most annoying coworkers

Unless you’ve worked alone for your whole career or you’re extremely tolerant, you’ve probably had your share of annoying coworkers – the busybody who peppers you with intrusive questions, the slacker who does no work but somehow takes all the credit for yours, and a whole cast of annoying others.

Although it can feel like frustrating coworkers are just part of having a job, often there are ways to deal with them more productively and minimize how much aggravation they add to your day. Let’s look at some of the most common types of irritating coworkers and how you can neutralize their most annoying characteristics.

Meeting monopolizers

Good luck trying to have a short meeting or even stick to an agenda when you’ve got this type in the room! They’ll monopolize every meeting with long, rambling tangents, comments on every item even if just to explain (at length) why they agree, and have never heard a rhetorical question they don’t want to answer.

How to deal with them: Speak up! Meeting monopolizers get away with their behavior because no one feels comfortable redirecting the conversation. Be the one who saves the rest of your colleagues (and rescues the meeting) by saying things like:

  • “I want to be sure we get through all the items on the agenda, so let’s move forward to the next topic.”
  • “We only have 30 minutes scheduled for this meeting, so I’m going to ask people to hold comments until the end unless they’re crucial.”
  • “That’s great input, but it’s outside the scope of our meeting today, so let’s come back to Topic X.”

You might also consider talking to your coworker privately after the next meeting where it happens. Say something like, “I’ve noticed that we’re having trouble getting through all the topics we need to discuss and sticking to our scheduled time. Can you help me make sure that we stick to the agenda and the time we’ve set aside?”

Busybodies

Busybodies want – and feel entitled to – more information about your life than you feel comfortable sharing, and they can be incredibly persistent when they want details about your love life, your salary, or even your reproductive plans. They’re the ones who will ask if you’re pregnant (or trying), scrutinize your lunch choices, and demand to know why you’re not bringing a date to the holiday party.

How to deal with them: The most important thing you can do when dealing with a busybody is to remember that you’re not obligated to share personal details if you don’t want to. People often reward busybodies with answers because they feel rude not responding, but there’s nothing rude about declining to share overly personal information. It’s fine to say, politely but firmly, that a topic is off-limits. For instance, you might have these phrases loaded up and ready to use:

  • “That’s awfully personal!”
  • “Why do you ask?”
  • “I’m not comfortable talking about that.”
  • “I would rather not talk about my dating life / my birth control choices / my upcoming surgery.”
  • “That’s not something I’d like to discuss.”
  • “That’s between me and my husband/wife/accountant/doctor.”

Slackers

While you’re hard at work, slackers spend their time in hours-long texting sessions, running a fantasy football leagues, and watching every available YouTube video on cats. It’s obvious to you and the rest of your coworkers that they’re not pulling their weight, but somehow they’re getting away with it.

How to deal with them: You’ve got two choices here: You can ignore it or you can speak up about. In most cases, ignoring it is the better choice. For one thing, while it’s possible that your boss is just overlooking it, it’s also possible that she’s addressing it behind the scenes – and you usually wouldn’t know about it if that’s the case. Moreover, if it’s not affecting your work, it’s ultimately not your business. However, if it does affect your ability to do your job (for instance, if you’re dependent on your coworker to finish her work before you can do your own, or if you’re routinely having to do extra work to cover for her), then it makes sense to speak up. Ideally, you’d first speak up to the coworker directly, and then if that doesn’t work, bring your manager into the loop, keeping the focus on how it’s affecting your own productivity.

Chatterboxes

Chatterboxes talk .. a lot. They’re often particularly talented at roping you into long conversations when you’re on deadline or about to leave the office, and they tend not to take cues that you’re trying to end the conversation. They’re also often kind people, which makes you feel guilty that you’ve started cringing when you see them approaching you.

How to deal with them: Remember that you’re not obligated to let someone cut into time that you need to be spending on something else, and it’s perfectly okay to explain that you can’t talk. Try any of these:

  • “I’m actually just in the middle of finishing something. Can I stop by your office later, when I’m at a better stopping point?”
  • “I’ve got to run to a meeting that’s about to start.”
  • “I’m on deadline, so I better get back to this.”

You can also try setting a time limit for the conversation at the very start,by saying something like, “I’ve only got a minute to talk.” And if the interruption is in person, you can physically signal an end to the conversation by standing up with some papers in your hand and saying, “I’ve got to run these down the hall.”

Grumps

If you’ve ever worked with someone who exudes negativity, you know how draining it can be to interact with them. Suggestions, new projects, new hires, and especially new managers – all are terrible in a grump’s eyes, and they’ll make sure that you know it.

How to deal with them: If you’re the grump’s manager, you should address the negativity head-on. Otherwise, it can have a corrosive effect on your team over time; negativity has a way of spreading, and people may become reluctant to bring up new ideas or even share their enthusiasm. But if you’re not in a position of authority over your office grump, one of the best ways to respond is to have a sense of humor about it. If you can see this coworker as your own office Eeyore (or Stanley from TV’s The Office), it can make the constant negative remarks easier to tolerate.

It’s also worth remembering that happy people don’t behave like this, and trying to cultivate sympathy for what’s clearly a troubled mindset can sometimes make dealing with difficult people easier.

Loud talkers, music crankers, speaker phone abusers, and other noisy coworkers

You’re trying to concentrate but your coworker’s penchant for loud gales of laugher and shrieking make it tough for you to focus – every day. Or you’ve got a coworker who believes in taking all phone conversations on speaker phone or who cranks the radio or sings loudly or won’t stop whistling – or any other ongoing distraction that makes you yearn to work in a silent monastery.

How to deal with them: When you have noisy coworkers who make it tough for you to focus on your job, the best response is to simply be direct. Most noisy coworkers don’t realize that they’re causing a distraction, so rather than stewing over it, speak up!

Say something like, “Jane, do you think you could turn your music down? I’m having trouble focusing. Thank you.”  Or, “Bob, you  probably don’t realize how much the sound carries from the speaker phone, but it’s making it hard for me to hear my own calls. Would you mind taking calls off speaker phone, or closing the door if you need to use it?”

If you’re hesitant to speak up, keep in mind that if you were distracting someone else, you’d presumably want them to tell you so that you could correct it. And sure, not every coworker will feel that way, but most will – and it’s a very reasonable request to make in a professional setting.

Know-it-alls

Know-it-alls have an opinion on everything, informed or not, and love telling you how to do your job better, where you went wrong in today’s meeting, why the client won’t like your presentation, and even what kind of raise you’re likely to get this year.

How to deal with them: Know-it-alls’ power lies in the attention you give them, so your best response here is to let their unsolicited opining go unacknowledged as much as possible. Let their unwanted opinions and advice roll right off your back. If you have to reply with something, don’t gratify them by getting drawn into a discussion; instead, just say, “Thanks, I’ll think about that.”  You can also look for ways to cut them off before the get started. If you sense a know-it-all is about to launch into an unwelcome soliloquy, change the subject or excuse yourself from the conversation.

my manager keeps complaining to me about her own boss

A reader writes:

I just got a new job – a job I am SUPER excited about.

My boss, who I share an office with, is great on all accounts so far except she has one major problem that makes me feel very uncomfortable: She complains and talks horribly about her boss as soon as her boss leaves the room from having a meeting or conversation with us – two or three times a week so far. My boss’ complaining will range from saying petty and belittling remarks under her breath (I am the only one there to hear it), or she will vent to me, sometimes for 10 or 15 minutes, about how incompetent her boss is.

Being new (only two weeks), I feel like I should pay attention and be respectful when my boss talks to me. So, thus far I have listened and paid attention during these venting sessions, but I know she wants me to “agree” with her and be on “her team.” Honestly, her boss seems pretty normal and reasonable to me, but either way I don’t want to be on either team – I just want to do my work and not get caught up their problems.

Would it be better at this early stage in the game to say something polite and direct or just let it go and try to fly under the radar for a while, hoping she will get the hint? (For the record, I know it’s totally inappropriate for her to do this at all, but I like this job and need to figure out a way to deal with it.)

Ooooh, that’s a sticky situation. On one hand, you’re new, you want to stay on your manager’s good side, and this is clearly a major sticking point with her. On the other hand, you rightly don’t want to get drawn into this and you definitely don’t want your listening to ever get twisted into her telling someone else that you agree with her.

I think the answer is totally dependent on what your boss is like and what your relationship with her is like. With some managers and some relationships, you could say, “Hey, I feel a little awkward hearing this! Can I be Switzerland?” and it would be fine. With some, you could even say, “Huh. You’ve got context I don’t have, but I didn’t think what she was saying sounded horrible.” And with others, you’d be planting a poison pill in your relationship to even approach saying anything near either of these, especially if you said it while you’re so new.

So until you have a really solid sense of which of those is the case, I’d go with listening politely, staying non-commital, and changing the subject as soon as you can.

And unfortunately, I’d be pretty wary of your boss. At a minimum, she’s showing horrible judgment in saying this stuff to you. But her horrible judgment might go beyond that — extending to her assessment of her boss, and potentially even to the quality of her work (which is sometimes the case when someone hates their reasonable-seeming boss with such vitriol). So keep your eyes open for problems with her beyond this situation.

I found an ad for my own job, my manager tells us to bill for hours we didn’t work, and more

It’s five answers to five questions. Here we go…

1. I found an ad for my own job

I’m supposed to have a team of four, but one of my employees transferred to another team/office three months ago. I put in a job requisition request for his replacement right away but have had no movement on this front. My team is struggling to meet all of our deadlines and doing a decent amount of overtime, but we’re making it work. I’m getting frustrated that HR has not forwarded me any resumes or set up any interviews for me. I checked our online careers page to see if the job was listed and it is, and I also happened to see that my job is listed too! (At least I’m 95% sure it’s mine because there are particular terms that only relate to my department.)

We just had our annual reviews in July and I was given a great review and a small but better than average merit increase (average was 3% and I got 3.5%). My direct supervisor also told me that I received the largest bonus out of everyone in my practice area (which is about 80 people). I met all of my bonus metrics goals, plus I received a large discretionary bonus, for a total of almost 9.5% annual bonus based on my income.

If they are unhappy with my performance and looking to replace me, why would they give me such a large bonus and praise me during my recent annual review? Why else would they put my job online unless they are looking to replace me? What should I do now?

Ask your boss about this, right now. While employers do sometimes seek to replace someone who doesn’t know it yet (although it’s generally a pretty crappy thing to do), they generally don’t do it by openly advertising the role on the company jobs page. It’s much more likely that this is a different role, or that it was posted by mistake, or some other explanation.But rather than wonder and stress about it, go talk to your boss. Say something like this: “I was just looking on our jobs page to see if the X role is listed yet and I saw a position that looks like it could be mine.”

It’s highly likely that your boss’s response will set you at ease.

That said, I’m being given a tiny amount of pause by the fact that HR hasn’t sent you any resumes for the job you’re hiring for. If they were planning to replace you, they might cut you out of the loop on hiring for that role, or even put it on hold until your replacement is hired. But there are also lots of other explanations for this (including just having a kind of lame HR department, the same kind that would accidentally post a role that sounds so much like yours). But there’s no point in speculating when you can just go ask your boss what’s up.

Read an update to this letter here.

2. My manager tells us to bill the company for hours we didn’t work

My manager has employees record extra hours, and I’d like to know what the possible repercussions to the employees could be.

I work part-time, as does every other member of our department, with the exception of management. To help out the employees, our manager has established the following pay scale:
Task A = 4 hours
Task B = 6 hours
Task C = 8 hours

If we work in excess of the hours assigned to each task, we record the full amount of hours we actually worked. But if we work less, we get a freebie, since we’re told to record the additional time. My manager says that this is to compensate for low hourly wages and vastly varying workloads, and to make everything stay under the radar–if everyone gets the benefit, no one will rat him out. What are the repercussions for the employees for doing this, if any should questions arise from upper management?

Well, you could all get fired. But it’s more likely that your manager would be the one who gets booted. He’s basically defrauding the company, unless he’s doing this with the knowledge and approval of the company’s management (which it sounds like he’s not, given your reference about him doing it for everyone so that no one will report it). And telling you to report extra hours “to compensate for low hourly wages” is pretty outrageous — the company sets the pay scale and if he takes issue with it, he should advocate for higher wages, not enlist you all in fraud.

At a minimum, I’d keep very careful documentation of his instructions to you on this, so that if/when it’s uncovered, you can show that you were following his instructions. But ideally you’d also speak up about it — either to him (if there’s a chance that the company does know, since he could clarify that for you) or to someone above him.

3. How can I ask for regular one-on-one meetings with my manager?

I work for small organization. I sometimes feel disconnected from the rest of the office. My boss and I usually exchange greetings when/if we see each other in the common areas, but some days I don’t see her at all. We rarely discuss what I’m doing unless I’m in her office to ask her a specific question, and she asks, “how are things?” I understand that she’s a busy person and she doesn’t have time to chase me down, and that I need to go to her if I need anything. So I think I want to set up some sort of weekly short one-on-one meetings with her where I could give her a lowdown of what’s going on, ask her questions, ask her if she needs me on any other projects, and also where she can give me a lowdown on things on her end that she feels I should know, but how do I politely bring this up? It was brought up as a good idea at one point a while ago, but it hasn’t been mentioned since. Could I approach her office and ask in person? Or should I send her an email to preface it?

This is a totally reasonable thing to ask for, and even more so since it’s actually been suggested in the past! Asking in person or via email is fine. I’d say something like this: “Would it be possible to start scheduling short weekly check-ins with you? I’m realizing that I don’t have a great mechanism for updating you on my work, getting your input on things, and making sure I’m in the loop on anything you need from me, and I’d love to get short weekly meetings on your calendar (or even every other week if that’s easier on your schedule).”

4. I’m going to start telecommuting, but my employer wants to change me to a contractor

My husband recently received a once-in-a-lifetime job offer that requires relocation. My employer – a nonprofit organization – is allowing me to work remotely, but they want to change my status from a full-time employee to a full-time contractor. The expectations communicated to me so far would be that I’m available during business hours and that my job would not change, except for my location. The only reason I received from my employer about why my status would change is a fuzzy answer about liability of some kind (something about insurance the employer would need to carry for having employees in another state). My organization is about 70 people, and I would be the only full-time remote employee.

As I think about this, and as I’ve learned more about the distinctions between contractors and employees, I feel pretty strongly that what I would expected to do would be in the realm of an employee. Obviously, the change has a lot of implications for me personally (taxes, benefits, etc.). I’d like to go back to my employer and discuss keeping me on as full-time remote employee, as I think their expectations of me are going to be more in line with that of an employee.

Do you have any advice on how I might handle this, or what the merits of being a contractor v. employee might be (particularly from an employer standpoint)? I know lots of people work remotely as employees (instead of contractors), so I’m trying to understand my footing of how I might approach my employer on this matter.

It’s true that having an employee based in another state will sometimes require your employer to get additional workers compensation insurance (even if you’re working from your own home), which they might not consider cheap. But it’s also true that your employer can’t just decide to treat you as an independent contractor because it will be more convenient to them; whether or not you qualify to be treated as a contractor is a matter of law, not of preference. It’s possible that your role could meet that test with a few minor changes, but they shouldn’t take it as a given.

And yes, there are disadvantages to you in that arrangement: You’ll presumably lose your paid time off, health insurance, retirement contributions, and other benefits, and you’ll be responsible for paying self-employment tax, which is about 12% of your income (although that can also be offset by your ability to deduct more business expenses). That said, if you’re the one pushing to work remotely, you might decide that those trade-offs are worth it to you. But go into it with your eyes open.

5. Following up on networking emails when you haven’t received a reply

My question is about networking. After you reach out to a new person you want to connect with professionally and they don’t respond, is it appropriate to follow up in two weeks to see if they would be interested in connecting or is that just pushy and annoying? And what’s the most appropriate way to frame that email?

I just moved to a new city and have been emailing a lot of professionals who work in the area I’m interested in (nonprofit and government work). Most of the emails I send are because another connection of mine recommended I get in touch with that person. Thus I start off all my emails with some sort of line like “X recently suggested I reach out to you,” and then give a brief explanation of who I am and why I want to connect with them. I have a very high response rate to these emails (maybe 1 out of every 10 or 15 people I reach out to do not reply) so I don’t think the problem is that I’m sending a lame networking request.

However, the people who haven’t replied are some of the people I am most interested in connecting with. I really want to send a follow-up email to those people, but I don’t want them to label me as that annoying person who keeps harassing them. I was thinking that maybe I should contact the person who originally recommended I reach out to the non-responders, but I also don’t want to harass that group of people since they are also new connections and I don’t want to appear like I can’t even email someone without help. Please advise on what the best way to handle this situation would be.

It might not be a coincidence that the people you’ most want to connect with are the ones who haven’t replied. The people who others are most interested in connecting with are often the people who are especially busy and who field a lot of these requests. That means that you might need to resign yourself to simply not getting a response from them. There’s nothing wrong with one polite follow-up after a few weeks have gone by (so a total of two emails to them) — but after that I’d move on.

And I wouldn’t try enlisting the original referrer for help — that’s too much like saying “can you please nag this person who has already had a clear opportunity to respond to me but who has chosen not to,” and that’s way too big of an ask for anyone who you don’t know extremely well and where the stakes aren’t more urgent than just wanting to make additional contacts.

is it rude to call out an employee’s name when I want them to come into my office and they’re nearby?

A reader writes:

My assistant and three other staff members’ desks are just outside my office door. From my desk, if I look up, I can even make eye contact with one person. If I call someone into my office to discuss something, sometimes I will call on the phone, but since they sit five to eight feet from my door and I have my door open, sometimes I will just call out the person’s name.

Is it disrespectful to call out a name? Should I call them via the phone even though they can still hear me? We are the only ones in this area behind glass doors.

Eh, I don’t think it’s a big deal if it’s every once in a while, but I’d try to avoid it most of the time.

While it’s your prerogative to simply call out when you want someone to call to your office, it’s a bit of a … well, not a power play exactly, but it’s not the most respectful way to approach people. Think of them doing it to you, after all; if something about that rubs you the wrong way, that’s the respect piece. And while certainly being their manager means that you can ask things of them that wouldn’t go over the same if they asked them of you, it’s a nice gesture to be thoughtful about it when the circumstances allow it.

Plus, I’m a big believer that you most of the time you should be asking people if they have a minute, rather than just interrupting them. And if you just call out someone’s name, you’re basically summoning them to appear in your office right then and there. But if you call or instant-message, you give the person the opportunity to finish their train of thought if they’re writing something, or to reply that they’re about to get an important phone call that they scheduled for one minute from now but will come by as soon as it’s done, or whatever.

That said, it’s something that will take on a different flavor depending on the dynamics of the relationship. If you have a gruff or very top-down relationship with them, it’s more likely to come across as a rather ungracious summoning. But if the relationship is warm and respectful on both sides, people might not even think twice about it.

how can my resume demonstrate initiative, problem-solving, work ethic, and other qualities?

A reader writes:

I’m currently a college student studying engineering. I keep on reading lists with titles like “Top 10 Skills and Qualities Employers Seek in College Grads.” All of the skills listed there are fairly subjective. For instance, a list might include words like teamwork, leadership, written communication, problem-solving, work ethic, initiative, and other good qualities that most people think they’d possess.

Apart from having work experience and joining clubs, are there any specific ways to show an employer at the resume stage that I am good a problem-solving or any other trait? Furthermore, how do employers who are scanning resumes at the pace of one every dozen seconds, recognize those skills?

Yeah, those lists of skills are often remarkably unhelpful, for exactly the reason you name: Most people think they possess those qualities, whether or not they actually do. Few people think, “Oh, work ethic, that’s not me” or “ha, initiative — as if!”

But many job-seekers just load up their resumes with those types of words, which is incredibly ineffective. Self-assessments from relative strangers count for basically nothing in hiring (and probably in life, too). I mean, I could proclaim that I’m brilliant and enormously charismatic, but you’d be right to be skeptical.

Instead, the key is to find ways to show that you have those traits. Employers want to see actual evidence of those things, not just proclamations. And the way you provide that evidence is to talk about what you’ve done that illustrates your work ethic, or your written communication skills, or your initiative, or whatever is that you’re trying to demonstrate. For instance:

  • “In first month, cleared out previous eight-month backlog of cases” (work ethic, productivity)
  • “Devised and implemented faster process for X” (initiative, problem-solving)
  • “Published op-eds in the WinterfellTimes and the Westeros Tribune” (written communication)

… and so forth.

The principle with resumes is always: show, don’t tell.