ask the readers: when clients complain that you’re too robotic

I’m in an all-day meeting, so I’m throwing this question out to you all for help. A reader writes:

I work in an event management role that is one part logistics, and the other part customer service. Most of my client calls are on the telephone, making it difficult to cultivate that personal relationship. Some calls I have one-on-one and others are with large groups. Geographically, in-person meetings are not likely as I am in a different time zone than most clients.

I have had several clients complain to my boss that I am robotic, abrupt and checklist-oriented.

I don’t want to take this personally, but I am offended because in real life I am a warm, fun loving, and personable individual, not a robot.

Please tell me, do I suck at my job because of this feedback? How can I improve besides starting each call with some chit chat about the weather and the news?

What advice do you have for this reader?

wee answer Wednesday — 7 short answers to 7 short questions

It’s wee answer Wednesday — seven short answers to seven short questions. Here we go…

1. Interviewer mentioned contacting my current boss

I was on a phone interview recently and was asked, “What 3 good qualities would your current boss say about you?” And then the interviewer proceeded to let me know if this goes further they may call him for a reference. I couldn’t imagine that was a serious thought, right? How can someone possibly think it would be OK to call someone’s current boss for information about a potential employee for them?

It’s typical for employers to either agree not to contact your current employee for a reference, or to do so only when they’re ready to make an offer. Either way, you should control whether or not it happens, and what the timing is. If you move forward in this hiring process, say something like this at the next contact: “When I spoke with Jane, she mentioned that you might be contacting my current manager for a reference at some point in the process. My employer does not know that I’m job searching and I need to be discreet at this point in the process. At what point do you typically reach out to a current employer? I’ll obviously need to speak with her before that happens.”

 2. Factoring overtime pay into salary history

I’m a little unsure how to answer the question about salary at my most recent job and hoped to get your advice on this subject. This position had a base salary, but it was a non-exempt position so I also received overtime. When a prospective employer requests my salary history, I’m unsure if I should give my base salary or my actual take-home pay … which was a bit higher than my base. The concern with providing my actual pay is a prospective employer potentially being given a lower number than I provided (ie = my base pay) if they call to verify my salary and this disqualifying me from a job offer, but I also don’t want to cheat myself out of a potentially higher salary by not providing my total compensation. My W2’s could serve as validation of the discrepancy if pressed, but I’d hate to think it would come to this.

If you choose to share your salary history at all — which I maintain is no one’s business but yours — just be clear about what the numbers are. Say something like, “My base salary was $X, but with overtime, I earned $Y.”

3. Asking a recruiter about a position in a different location

About three weeks back, I applied for a position at a certain company at location x. Today, I heard from a recruiter from their company who wrote me to see if I would be interested in a different position at location y. I feel unqualified for the position at location y. (They’re both creative positions but require different software experience, so I have experience relevant to x but not to y.) I would like to reach out to her to inquire about the position I originally applied for at location x. How could I politely go about turning her down and inquiring about another position at the same time?

Just be direct: “I don’t think Y is a great fit for me because it emphasizes experience in Z, which I don’t have, but I’m actually very interested in X, which I applied for a few weeks ago. I’d love to talk with you about that if you think it’s a good fit.” (However, keep in mind that software can be learned, so if you’re turning down Y only because of that, it might be worth rethinking.)

4. Declining to give a mandatory contribution for office holiday gifts

I have been employed at my current job three years. I was shocked my first year there when I was told I was expected to contribute to a fund for Christmas gifts for the physicians and PAs. I was hoping you may have some advice as to how to decline or defend against this “mandatory” contribution.

I thought that this year I may suggest I would do something on my own, such as bake cookies, but I don’t want to continue this tradition at all. My “gift” is working hard every day! And now there are more people employed at the top level but the support staff is the same or fewer. There is an extremely high turnover rate. I am tired of sucking it up and compromising professionalism on so many levels so much of the time. My manager is a nice person and has a big heart, but he may be the worst manager ever! Horrible communication, misdirected priorities, finger pointing, lack of confidentiality, there is NO line drawn between personal and professional, and on and on and on.

You can simply say, “I can’t participate this year.” You don’t need to go into your reasons. If some of your coworkers feel the same way, you can also talk to them and suggest that you speak up and say you want to discontinue the tradition, since there are already so many demands on people at the holidays.

Read an update to this letter here.

5. Explaining why I’m going “back” to an admin position

I am currently applying for administrative/assistant positions. I have done this type of work for several years in the past, and I am well-qualified. The only concern that I have trouble explaining in a job interview is that I currently am not an administrative assistant. I left an admin role to work in a much more front-line sales position, and the question I am asked frequently is why I am interested in going “back” to a support position. The completely honest answer is that I just had a baby and I have an ill family member, so I am looking for a job with more consistent hours and where I can leave my office worries at the door come 5:00 pm. But if I said that in a job interview, I feel I would come across as unmotivated and possibly unreliable because I have admitted to these personal commitments. I am not unmotivated. I work hard, I take pride in doing a good job, and I take initiative. I am just looking for a better work-life balance. Is there any good/less concerning way of answering this type of question?

You shouldn’t get into a discussion of your personal commitments, but it’s completely reasonable to say that you found admin work more satisfying than the sales work you’d moved into and you’re eager to return to that career.

6. Can I apply without going through this recruiter?

A recruiter contacted me about a position I had not seen before, but I happen to know people at the company. The job is posted on the company website. So my question is, am I obligated to apply for the job through this recruiter, since I wouldn’t have known about the opening otherwise? Perhaps I’m being soft, as I feel the recruiter did me a favour by telling me who he’s recruiting for. It looks really promising, so I want to get my application in the best way possible.

Hmmm. The recruiter’s contract with the company might require that he get credit for the hire, if you’re hired — which isn’t your problem, but it could become your problem if it turns into a disagreement between the recruiter and the company. Realistically, if you were to tell the recruiter that you’d spotted the position and were planning to reach out to your contacts there, he wouldn’t know the difference … but it wouldn’t really be ethical to do that. The reality is that the recruiter earned his fee in this case, and you’d be interfering with that.

7. I want my boss’s job in 5-7 years

I am a hospitality manager at a nonprofit organization. I love what I do! I love the company I work for! I love everything about the job! Right now! I am way underpaid for what I do in the field that I am in. That is not a problem. I am more concerned about the limited advancement opportunites. Like I said, I love everything about my job now. However, I am worried that I am not going to be happy doing it for the next 25 to 30 years. If I were to move into my boss’s position when he retires (5-7 years), I believe I would be happy with the job and pay for the rest of my career. I fear that they may choose someone from the outside. Most of my peers would not want the position, but we all do work closely together. Human Resources may realize this as well and determine that an outside candidate would be best. That is where my boss came from.

I have asked multiple people about my future here and I have not had any real solid answers. I had applied for a similar position to my bosses and it was filled internally (seemed political). Which I am okay with. Should I consider other opportunities elsewhere? If I leave, would that open up that door when my boss retired?

It’s normal to not think you’ll be happy doing your current job for the next 25 years, even though you like it now. That’s the case for most people. You shouldn’t be getting anxious about the fact that you may eventually need to change jobs or companies; that’s normal and something you should expect.

You can certainly mention to your boss that you’d love to be considered for his job when he retires in 5-7 years, ask if he thinks they’d prefer external candidates, and ask what you can do now to start positioning yourself to be a strong candidate when that day comes — but keep in mind that that’s a long way off. I wouldn’t leave a job you love just because it might help you get a different job in 7 years — the odds aren’t good enough. Instead, just talk to your boss and get his advice.

5 myths about negotiating salary

Job seekers get more nervous about negotiating salary than seemingly any other part of the job application process. Negotiation doesn’t come naturally to most people, and they’re often not sure how hard to push for more money, or whether to push at all.

Here are five myths you might believe about negotiating salary, and why they’re wrong.

1. You should always negotiate, no matter what. While you should usually try to negotiate, there are some cases where you shouldn’t. For instance, if you tell an employer the salary range you’re looking for and they offer you something at the high end of your range — or even higher than your range — asking for more would look make you look like you were playing games or not operating in good faith. Similarly, if an employer discusses salary with you earlier in the process and you agree to a range, you can’t really ask for more at the offer stage; you already agreed. In general, anything that makes you look like you’re operating in bad faith will turn off an employer.

2. Never name a number first. Negotiating advice generally says that whoever names a number first loses. But the reality is that many employers will insist that you discuss your salary expectations before they’ll allow you to move forward in their hiring process. Refusing or pushing too hard to hear a number from them first can make you look overly coy or like you’re playing games.

3. One good strategy is to take a lower salary now with the understanding that it will be revisited in a few months. Candidates sometimes suggest this, figuring it’s a compromise that will allow them to prove themselves once on the job, and then get rewarded for it later. However, it often backfires. Your negotiating power is strongest before you’ve accepted a job – it’s far easier to negotiate more money before you start than it is to get a raise once you’re already employed there. Don’t count on a hefty raise down the road; do your negotiations now, before you accept the offer.

4. Employers will be put off if you try to negotiate. Job applicants sometimes worry that simply asking for more money will cause the employer to pull the job offer altogether. But as long as you handle the discussion in a pleasant, professional, and non-adversarial way, and as long as you’re not asking for an unrealistic amount, no reasonable employer will pull an offer. That said, some employers do bristle when a candidate tries to negotiate – but that’s the sign of an unreasonable, dysfunctional employer, and you probably would have encountered plenty more dysfunction if you worked there. In other words, don’t worry about turning off an employer by reasonable negotiation – you won’t be losing any employer worth worrying about.

5. You can lie about your current salary in order to get a higher salary offer. Candidates sometimes figure that by claiming they’re currently earning more than they really are, they’ll get a higher offer from a new employer. But this is dangerous to do, because plenty of employers verify salary history, either by asking to see a recent pay stub or a W-2, or by checking with the previous employer directly. And they often do this after you’ve already accepted a job offer as part of their new hire paperwork, which means that you risk having the offer pulled over the lie – after you’ve already accepted it and resigned your current job.

I originally published this column at U.S. News & World Report.

how can I get a job telecommuting?

A reader writes:

I live in a smallish community (80,000 people) in a small state. While there are phenomenal nonprofit opportunities in our state capital, which is 2 hours away, the prospects in my city are slim. They are mainly local organizations with local boards and very tiny budgets. Don’t get me wrong, they do great things, but administrative opportunities don’t come along very often and when they do, it’s often who you know that gets you the job.

I know many national organizations have staff that telecommute within their region on a day-to-day basis with quite frequent travel. I’ve done this before and it worked quite well. A position that interests me was posted the other day for an organization that has an office in our state capital (the division headquarters is in the next state). Resumes are to be sent directly to the division CEO. Is it worthwhile to email my resume and cover letter with a note that says I understand the position is based in X city, but am curious if telecommuting is a possibility? I also wonder if I should/could ask her to keep me in mind for other opportunities that might arise.

You could, but be prepared for a lot of rejection.

In general, most organizations are loathe to hire telecommuters who they don’t already know and trust. Often people start telecommuting after working for an employer for a while, after they’ve learned their culture and expectations and after they’ve built trust around their competence and work ethic. At that point, it’s easier to convert into a telecommuting position; it’s much harder to do it right off the bat when they don’t know you and you haven’t proven yourself in their particular context and culture.

(One exception to this is when a position is designed to be done by a telecommuter, such as a position that must by its nature be based in X even though everyone else is based in Y.)

That said, your chances may increase if (a) you can find connections in your network who are also connected to senior-level managers at the organizations you’re targeting and can have them vouch for you, and/or (b) you have a very in-demand skill set and a fantastic reputation. But if you’re in a crowded field and without strong connections or something else to boost you up in the applicant pool, it’s going to be tricky — after all, if they have great local candidates who wouldn’t need to telecommute, there’s not a ton of incentive for them to take on the potential risk and inconvenience, especially if their organization doesn’t already have some experience with telecommuters.

However, there’s no harm in trying, as long as you’re up-front about it. (Just don’t go through their whole hiring process and then spring it on them at the end that you don’t want to move.)  Good luck!

should I alert my employer that a new hire was fired for theft at her last job?

A reader writes:

Without disclosing a very long back story, if someone gets hired where you work, and you know for a fact (100% positive) that they were fired from their previous position for stealing (money), should you alert your current employer? This “someone” could also be considered a friend…

If the person were only applying for a job with your employer and hadn’t been hired yet, I would say absolutely yes. If it later came out that you knew something so serious about the person’s integrity and recent past and hadn’t spoken up while she was being considered, it would reflect poorly on you.

However, the person is already working there now, so you can’t prevent the hire … which makes this murkier.

Frankly, if it were me, I’d probably give my manager a discreet heads-up — something like, “I feel really awkward about this, and I do think people deserve second chances, but I’d feel uncomfortable not mentioning this, especially if something went wrong.” Your manager can then decide how to handle the information, and you’ll have fulfilled any obligation you have by sharing it with her.

But I think a lot of people would argue it differently, so I’m interested to hear what readers think.

By the way, this should have come out in a reference check, so that means one of the following is true:

1. It did come up in the reference check (or the person disclosed it on her own), and your employer decided to give her a chance anyway. This seems fairly unlikely, since stealing money is a big deal and it happened at her most recent job, not in the far distant past, but it’s possible.

2. Your employer didn’t do a thorough reference check. They either didn’t check references at all, or they only relied on the references she supplied and didn’t check any further. This is dumb, but not uncommon.

3. The person deceived your employer during the hiring process in some way — either by leaving that job off her resume entirely so they didn’t know to check that reference, or by lying about why she left and they took her at her word without verifying it, or by lying about who her manager was there and putting them in touch with a fake reference who would say what she wanted. (The last two traps are avoidable by a company with thorough reference-checking practices, but many, many aren’t thorough — especially smaller organizations.)

In any case, since you say that this person “could be considered a friend,” one possibility is to simply ask her: “Hey, how did it go with talking to them about what happened at XYZ Company?” If she says, “Oh, ha, I didn’t even mention that job on my resume, so they don’t know about it,” you could certainly tell her that she’s put you in an uncomfortable position by expecting you to cover for her with your employer.

What do others think? How would you handle this?

tiny answer Tuesday — 7 short answers to 7 short questions

It’s tiny answer Tuesday — seven short answers to seven short questions. Here we go …

1. Current manager seems to have hurt me with prospective new manager

I have gone for an internal interview with my firm. My current manager had a meeting with my prospective future manager (also his manager) regarding his concern for my leaving the department and my future wages. My prospective manager then proceeded to call me in before my interview to tell me that the new job will not benefit me financially, and that perhaps if that’s all I’m interested in, I should cancel the interview.

I have to admit that I had hoped for better wages, but the opportunity to better my career was what had attracted me to the position. My current manager has made many comments on how I will hate the new job, etc. I’m sure he’s just a little nervous that I’ll leave, but surely he shouldn’t have spoken about what my prospective wages could/should be?

I don’t know what your manager said to the prospective new manager, but yes, in most cases it would be a little inappropriate for him to discussing your future wages with the other manager. (Not illegal, just weird.) However, if he’s come to genuinely believe through managing you that you’re primarily motivated by money and wouldn’t be happy in the new job, it would make sense that he relayed those impressions to the other guy, since this is an internal interview and it’s generally expected that managers involved in an internal move will be pretty candid with each other. Regardless, though, I hope you told the prospective new manager that your primary interest is in taking on new responsibilities, rather than allowing your manager to set the other manager’s impressions of you.

2. What to say under “reason for leaving” on job applications

In networking or in interviews, I’ve discussed my reasons for leaving past/current jobs (e.g. left job to go to grad school full time, or job was limited term appointment) at whatever length makes sense for that conversation. But in the inevitable employment application form that I fill out during the hiring process, what should I put in the little box under “Employment History” for “Reason for Leaving”? Do I need a detailed reason here, or do they just need to know whether I resigned voluntarily or was laid off/fired? I’m sure that conversations with humans count more than files in HR records, but I just wanted to check what is expected on such forms.

It’s fine to just indicate whether you resigned, were laid off, or were fired. You can certainly add additional explanation if you want (“left for new job,” “returned to school,” or whatever), but generally, if they want more information, they’ll ask for it.

3. How many interviews is too many for an assistant position?

How many in-person interviews would you deem excessive for an assistant position? I am heading to my third of what I was told will be four.

That’s slightly higher than normal, but that doesn’t mean it’s a bad thing. If the interviews aren’t particularly effective — not thorough, not probing the right areas, repetitive or rambling — then they’re just wasting your time and theirs. But if the interviews are good, it means they’re concerned about hiring the right person and are proceeding cautiously — which makes a lot of sense. Frankly, it’s pretty silly how many employers hire people after only talking to them for an hour or two.

4. Dealing with a negative, narcissistic boss

I’m dealing with a boss who is negative almost all the time. Every conversation I have with him starts out with a criticism of someone who sent him an email, someone he had a meeting with, something that happened in our firm that he doesn’t like. He overtly criticizes his peers to me and everyone below his level, but never his boss. He has favorites on our staff, and announces things like “Staff Member A or B is my favorite employee.” Alternatively, he will come back from lunch and he is happy, or as happy as he can be. The difference is so startling sometimes that I wonder if he had several cocktails at lunchtime. His reactions are hard to predict….sometimes he is amenable and will agree, other times he will say no and go off on a rant. He is somewhat of a narcissist — only his jokes are the funny ones, he doesn’t really like or pay attention to other staff unless he needs something or unless they are one of his favorites, he doesn’t even acknowledge staff with a “good morning” unless they are one of his favorites, etc. He has never given me a compliment on my work (which my former boss praised often and which other people in the organization acknowledge) and I have never heard him compliment others, except for his favorites.

I wonder sometimes if this is just his personality or if he is bipolar. Any suggestions on how to deal with this? I don’t see any signs of him leaving the firm anytime soon (unfortunately) even though the rumor circulating is that he is seriously job-hunting.

It doesn’t really matter if he’s bipolar or not since the end result is the same — he’s negative and difficult to work with. You need to decide how much you care, and whether or not this is a deal-breaker for you. Assume he’s not going anywhere and he’s not going to change. Do you still want to work there? If so, you’ve got to look at this as part of the package and be clear in your own head about what you’re getting in return.

5. Is there a point of diminishing returns for internships?

I recently completed a professional masters’ degree and am looking for full-time work in my field. Everyone in my field recommends doing internships until you can find an actual job, which I’m totally prepared to do, although, as someone in my late thirties, I have to admit that I’m a little unenthusiastic about working for free or very little for the forseeable future. Is there a point of diminishing returns when it comes to internships on your resume? I’ve seen statements from people who hire in my field stating that they are more interested in proof of a stable work history than fancy internships. But my very stable work history is clearly not getting me anywhere right now. Is there a point where it just looks bad for you that all you can get are internships rather than “real work”? I’m starting to get worried about competing against next year’s graduates at this point.

In general, regular (non-intern) jobs in your field are better than internships in your field. And yes, years of internships after you’ve graduated are going to raise questions. But even so, internships in your field are better than no work in your field, or unrelated work. Assuming your choice is between another internship in your field or something totally unrelated, and assuming you want to stay in your field, go with the internship.

6. Someone competing for the same job as me gave my name as a reference

I was laid off back in February, and I have had a hard time finding another role. I am currently a finalist for a position that I would really love. Today, I found out that a former colleague of mine is up for the same position, and without letting me know, he wrote me down as a reference. When the recruiter called me, she let me know he was one of their top candidates before she realized I was the same person who was also in the running. I was a bit upset and caught off guard that he had put me down. It came across as I was talking to her, and I felt terrible. I sent her an email afterwards, stating, “I am sorry I was caught off guard by your voicemail. I was unaware that Brian had put me down as a reference for the same job I had applied to, I would have politely declined if he did. Unfortunately I don’t think it would be right for me to be a reference for him for this position. I apologize for the confusion, I hope you understand. Thank you.” I also found out he found out about the position by looking on my LinkedIn profile and emailing someone I was connected to. He also lied on his resume, which puts me in a bad position.

I am not sure if I handled the situation correctly and I am hoping to save face. I know she is in the process of contacting my references as well, but is there a better way to handle this? Should I just walk away?

Why would you walk away? You’re a finalist for a position that you think you’d love. You were candid with the recruiter about the fact that you didn’t feel comfortable providing a reference for this guy, and that’s all you need to say. As long as you weren’t inappropriately emotional or negative when you were speaking to her, you shouldn’t need to worry.

7. How much work history do you need to include on a job application?

I’ve heard lots of conflicting advice regarding the “work history” section of a job application. Some say you need to include your complete working history since you’ve started working; others say you only need include your most recent 3-5 jobs or most relevant jobs. What’s your take on this issue?

If the application doesn’t specify how complete a history it wants, then give whatever casts your candidacy in the strongest light. For most people, that’s roughly the last 10 years of work history, but that can vary depending on your specific situation. However, many applications ask for a complete work history; in that case, you need to decide if you’re willing to play that (often ridiculous) game or not.

can you recommend your boyfriend for a job?

A reader writes:

I review intern applications in my university’s department A. An intern in department B, Jane (not real name), said her boyfriend Steve is interested in an opening in my department. She approached me to ask how Steve should submit his application materials. Jane then emailed me, saying she personally recommended Steve for the position, talking about his previous experience, and saying she wanted to make sure his name stood out.

This struck me as weird and unprofessional; I’d note that Jane has not worked with or supervised Steve before. If anything, Jane’s proactiveness makes me question Steve’s judgment. I know people can personally recommend candidates for openings, but I’m curious if is what Jane did considered normal in the “put a good word in” process? More generally speaking, is it appropriate for someone to recommend his/her significant other? Would you consider the situation different if Jane were recommending her friend Bob, rather than her boyfriend?

I agree with you that it’s bad judgment, but I’d attribute it to the fact that she’s an intern and thus (I’m assuming) is fairly inexperienced in how this stuff works.

But yes, you’re assumed to be biased where your significant other is concerned — far more biased than you’d be with a friend — and as a result, you really can’t serve as a reference for a significant other, even if you worked with them or even supervised them at some point.

There’s certainly nothing wrong with saying, “Hey, I wanted to give you a heads-up that my boyfriend is applying for X and I think he could be a great candidate” … but you really can’t push beyond that without making everyone uncomfortable. That’s where your intern veered off course.

A version of this is true for platonic friends, as well. If you’ve never worked with a friend but are suggesting them for a position, you need to state clearly that you’ve never worked with them. You can mention why you think they’d be well-suited for the position, based on your non-work knowledge of them (for instance, you might note that the person is smart/well-connected/diplomatic/a great writer/fantastically knowledgeable about X/or whatever else might be relevant), but you should always be clear that you don’t have experience working with them … and again, you can’t be pushy without making everyone uncomfortable. But you do have a bit more leeway with recommending a friend than a significant other, simply because there’s not the assumption of blinding bias.

update from the reader who wanted to help young coworkers learn professionalism

Remember the letter from the reader who wanted to help his coworkers, who were new to working in a professional setting, and who came from disadvantaged communities without many professional role models? He was especially concerned because their manager was violating all sorts of boundaries with them — from going to nightclubs with them (despite a 30-year age difference) to taking them shopping for clothes and alcohol.

(This was the post that sparked the later discussion about how your parents’ level of professional achievement influenced you.)

Here’s his update:

I wanted to update you on the situation with my non-profit and the new-to-the-workplace Neighborhood Liaisons that were being poorly managed. Things with the obnoxious manager and the NLs were getting a little bit worse, but because of a serious bout of community violence and some pretty scary death threats, we had to pull the whole team out of there (that included relocation of the NLs and their families; it was an incredibly stressful time, but thankfully none of our team members or their families were hurt, and now they’re in a safer location). Once they were safe, our admin wasn’t sure what to do, and I suggested we create an internal internship-style program so they could test out different pieces of the business and see if there was a fit in a new department. Folks loved the idea, and one of the former NLs is working with me now, and while we still struggle with certain workplace norms and office culture, she’s crazy intelligent — she speaks four languages fluently, for crying out loud — and it seems like there’s a lot of potential for a brighter future for these guys. It’s really exciting!

I also wanted to say thank you to you and your readers for the thoughtful follow-up conversation about disadvantaged communities and the workplace. The folks in the NL program came from families where not one family member had ever had a job, as in EVER. In my current “intern”‘s family, no one had ever held a job for three generations back. It’s amazing how much these young adults have had to learn, and it’s amazing how much knowledge we take for granted when we come from families with professional backgrounds. I am a firm believer in social justice — it’s our nonprofit’s mission — and this is an issue at the heart of it, and it involves lots of factors — money, race, education, opportunity, privilege, culture … all kinds of fascinating stuff. I think it’s an issue that we should continue to raise and talk about. Thanks so much for doing so!

how can I tell a job applicant that her behavior is inappropriate?

A reader writes:

I’ve been hiring for a few different positions since mid-summer and have one applicant who I now recognize by name, as she applies for every position. However, she just isn’t qualified and I’m starting to get a bit irritated, especially when her emails come to me with statements like these in them: “This is my fourth time applying and I really believe I’m the best person for the job and I won’t stop trying! Please give me the chance to wow you!”

She has also called me a couple times and once stopped by to visit during an inconvenient time without an appointment and waited for an hour while I was in a meeting.

I do feel a bit bad for her, as she seems new to the field and possibly just misguided job-search-advise-wise. I feel she’s doing herself a great disservice by being so persistent. I would really like to give her feedback in a kind way to tell her this isn’t an appropriate way to land a job. What are your thoughts?

You’d absolutely be doing a service by giving her feedback, as long as you do it in a kind way.

I might say something like, “I’ve noticed that you’ve applied for quite a few positions with us and I wondered if it would be helpful for me to give you some feedback about your application. I’d be glad to set up a time for a phone call if you’d find it useful.”

If she takes you up on it, you could then let her know that (a) you’re generally looking for qualifications X, Y, and Z when you hire, and that you don’t typically consider candidates without that; (b) she’s making her cover letters less effective when she cites how many times she’s applied and says that she won’t stop; and (c) showing up without an appointment will alienate far more employers than it will please.

By the way, be prepared for some defensiveness, which isn’t an uncommon reaction to feedback in this context — but trust that even if you encounter defensiveness, your feedback may sink in and make a difference later. It’s still a kind thing to do, even if it seems unappreciated in the moment.

One last point: Don’t be irritated. This applicant is probably frustrated and maybe a little desperate, and simply doesn’t understand how this stuff works. Yes, her behavior is inappropriate (especially the stopping by without an appointment), but not knowing how to job search appropriately isn’t exactly a character flaw like dishonesty or jerkiness. Give her some help if you’re willing, but either way, don’t let it irk you.

why would my former boss invite me to lunch?

A reader writes:

Why would my former boss invite me to lunch?  Haven’t seen or heard from him in over a year.  My position was eliminated due to budget cuts.

There are all kinds of possible reasons your boss might invite you to lunch:

1. He simply wants to catch up. Did the two of you have a good relationship, and was he a generally social guy? If so, this is possible.

2. He has a job opening or knows of an opening somewhere else that he thinks you might be interested in, and he wants to feel you out about it.

3. He wants something for himself — he’s interested in a job that you somehow have a connection to, or wants advice on something you’re an expert in, or who knows what.

But you won’t know which of these it is until you go. Unless you really hate the guy, there’s no reason not to go and catch up and find out what’s up. And if nothing else, it’s worth maintaining the connection for its own sake; they tend to be useful in all kinds of ways you might not anticipate (to say nothing of references, etc.).