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Career 101: Your Job Questions Answered

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Welcome to the final installment of our month-long Career 101 series. Many thanks to those of you who left thoughtful questions about your job hunt (ranging from entry-level college grads looking to gain experience, to moms who want to re-enter the work force). Here’s Jenny to give us answers to your most pressing questions. Read on to see if yours was included.  


Q: “This is probably one of the more helpful posts I've read on this topic in a while! You have an awesome friend! My question is: If you have an unstable work history (jumping from job to job in a short amount of time - less than a year) how do you address that in your resume, cover letter, and most importantly, interview? Thanks!!”

A: Addressing your decisions for moving from job to job is super important because if you’re unable to speak to your trajectory, you can end up looking like someone who jumps around and is unable to make a commitment. I'd suggest addressing your tenure (or lack thereof) authentically.  

I wouldn't knock out a relevant candidate purely based on tenure, but would instead try and understand the rationale behind their moves. You don’t need to lie, because there is a way to talk about it positively. For instance, don’t throw your previous employer under the bus, but instead talk about why you made the decision to move on, what you learned from your experience there, and how the next opportunity was (or seemed to be) in line with your goals. You could say something like, “The reason I left XYZ company was because of THIS REASON PHRASED DIPLOMATICALLY, I learned THIS from the experience and will take it into my next role. I’m looking for a good fit / a home / a long-term commitment in my next role.”

Examples of reasons you may have left a previous job:

-“I really enjoyed the experience but there was limited growth potential in my role and I wanted to continue to push myself.”

-“The direction of the company shifted and was no longer aligned with my personal goals.” 

-“The company went through a lot of organizational changes while I was there. And while I am comfortable adapting to several different styles of leadership, I felt like I was lacking the mentorship I needed to grow.”

Do not say:

-“I wanted to make more money.”  

- "I hated my boss."

-“I was recruited away.”  If your last company wasn’t providing something compelling for you, or there was something really attractive about the new opportunity, I want to know about that. I don’t want to know that someone waved an opportunity and you jumped ship.

Q: "What are some tips you would give someone on writing a cover letter who has been a stay at home mom for a couple of years?" 

A: My recommendation in this situation (and almost any situation), is to be transparent. Whether you took time off to have a baby, take care of a sick parent, or to travel, address the gap in your experience candidly. Regardless of what you were doing, don't you want to end up at a company that values your choices? In any case, your cover letter should be less about the gap in your resume and more about why you’d be a good fit for the company or the role. You can mention that you took time off, but you shouldn't feel the need to justify the decision. Focus on what you’re passionate about and what you’d like your next step to be. Your cover letter and resume should articulate how your skill set will be beneficial and add value.

Q: "Great tips! I will be graduating with my Bachelor's in Fashion Marketing and a minor in Public Relations in May so my job search thus far has been overwhelming to say the least. Both my major and minor are very broad fields, so it's been tough to nail down exactly what I should look for. All of the jobs I'm wanting to apply for want experience. I've worked 2-3 jobs for my entire college career and haven't had the time or financial backing to take unpaid internships, although I've been working somewhat in my industry. Do you have any advice on how to apply for jobs with virtually zero experience?"

A: I hate to say it, but it's kind of a crapshoot. Unless you get lucky early in your search, you'll likely have to knock on a lot of doors. With limited (or no) experience, you have to find someone willing to take a chance on you. The best thing you can do to improve your odds, is try to make a lot of meaningful connections. Refer back to the job search post. Get people on the phone who have gotten their foot in the door of your desired industry, pick their brain, and then stay on their radar. This will make you top of mind when they have an entry level opening.

Also, don't get discouraged if the job posts say that they want to see candidates with experience. That requirements section is a wish list. I've filled several roles with candidates who are "too junior" on paper, but there was something compelling about their cover letter or their aptitude that made me want to pull for them. 

Additional Thoughts on Entry Level Openings:

1. Consider targeting big companies: Large companies tend to be somewhat hierarchal, structured, and open to entry-level talent because they have the resources to train you. The potential downside here is that you might find that you have less visibility in a giant company. 

2. Consider targeting mid-sized companies: The good thing about gunning for a mid-sized company is that your contributions are often visible, even at an executive level, and this can propel career growth for top performers. However, in my experience, these companies have fewer entry-level roles available (and fewer roles available in general). Companies of this size may or may not have the structure in place to onboard entry-level hires. 

3. Consider targeting small companies and startups: Sometimes, a smaller company is willing to take a shot on you. You are likely to get thrown into the deep end and will have the opportunity to wear multiple hats. However, you may have a hard time seeing the growth opportunities in a small organization. 

4. Considering taking a class that is related to your dream job or spend one day a week interning. This can help pad your resume with experience that is relevant. 

5. Look for executive assistant / receptionist roles in your field of interest. Even if this isn't ultimately where you see yourself, if you use this opportunity to learn as much as you can about the industry and the company, you'll be in a much better position to transition to another role.

Q: "Great post! How would you advise someone handle being unemployed in an interview? I lost my job a few months ago due to downsizing but I kept it on my resume to look that I am still working there. For me those few months make a big difference since I am quite new to the work force and was only at my previous work for 8 months before major downsizing occurred. Some people told me that I should continue to make it seem that I am still employed there since I know it makes you look more desirable to the employer. I am lucky I came out with some good references but I also don't want to make them lie on my account either! I also don't like being deceiving and I don't want it to somehow come out in the future if I do land the job. Would love some help with this!"

A: This is a common concern that causes stress for a lot of candidates. The problem with lying, obviously, is that if you are caught, you could burn bridges with both your previous and prospective employers. Trust that employers know that the downturn in the economy had a huge impact for many people, so it’s not surprising for them when they come across candidates who are unemployed. And there are benefits to an employee who doesn't currently have a job - they can start right away because they don't have to give notice.  

My recommendation is to explain how you’ve been spending your time and what you are hoping for in your next role. Spend more time focusing on the future, what you bring to the table, and type of role you are hoping to land, than worrying about explaining your unemployment.


 "It was really unfortunate when my position (or department) was eliminated, but I'm excited about the opportunity this situation affords me to really focus on finding a longterm fit in THIS AREA OF INTEREST." 

This technique is even more effective if you actually believe it. It will put you in a better headspace to interview.

Q: "This is super helpful! I have a question: What advice would you give someone looking for a job in a new city? A city one is looking to relocate to without having any connections there."

A: It helps if you're able to spend some time in the city you're considering. Book a trip.  Reach out to people. Network. Search for professional groups in that city and attend an industry-relevant meet-up. Making these local connections will not only help fuel your job search but will also help you acclimate once you make the move. Be prepared to talk about your motivation to move in your interview. Companies want to know that you aren't just kicking the tires.  And if you're committed to making a move and open to relocating yourself (without relocation assistance from a prospective employer), state that in your cover letter. 

Q: "Hello Jenny, should one "connect" with prospective LinkedIn employees, or simply seek them out? Thanks for this wonderful post, it's very helpful!"

A: LinkedIn recommends that you only link in to people you know. If you don’t know them, my suggestion is to message them first and try to establish a connection. Some people are guarded about their networks, and others are very open. I think sending an initial message, or articulating why you want to connect, is the first step. 

Q: "Love this article. I'm currently a young attorney (practicing for only three years and under the age of 30) working at a small Midwest law firm. I've come to the conclusion that I'm pretty miserable at my current job. I can't decide if I don't like being an attorney or that I just don't like working at my particular office. I am interested in so many things other than the law and don't always seem to fit into the "legal culture" in my area (i.e., upper middle class white men that have nothing better to do other than boast about some client or case they recently tried or sit around talking lawyer jokes that I don't find amusing). I also get paid zilch for how much time, energy, effort and degradation I go through on a weekly basis. How do you know when a job title is right for you or whether it's the workplace/work environment holding you back?"

A: First and foremost, I'm sorry you're not loving your job. Before we dive into this specific scenario, I think that this highlights another important question: should one go to grad school? I don't have an answer, but it's a good question. If the industry you are passionate about requires an advanced degree in order to progress, then it's probably a good idea. But I often see candidates who get a graduate degree because they don’t know what to do next, or what to do when they graduate from undergrad. Do your due diligence on grad school. What kinds of jobs do graduates get? Do internships in the field. Do you like what you're doing?

To answer your question, there are three approaches below that might help you determine whether it’s your company or your role that is making you unhappy.

First, you could explore similar roles in different companies. Consider other law firms. Ask around in the industry: where do people like working? Initiate conversations, submit your resume, and go through the interview process. Do you like the people interviewing you? Do you get a good vibe when you're in the office? Are people smiling / seem fun / look engaged? Or do people seem frazzled / irritated / fried? Ask strategic questions that will give you more insight on the company culture. 

Secondly, you could consider looking for roles that are outside of your industry. When you’re interviewing for a role outside of the legal field, ask the interviewer to describe what a typical day looks like. Would it make you happy to spend your days that way? Make similar observations about the people you meet and office culture - do people seem inspired / creative / interesting (or whatever else you deem to be important)?  

Lastly, and this may or may not be the case, but if you want to see if there is a way to make your current job work for you, consider what tasks you could delegate, what kind of support you'd need to be successful, or what kind of rapport you'd want with coworkers. Are these things that you can alter or influence? For instance, is there a mentor who can help you find more meaning in your day-to-day tasks? If you want to try this approach, I recommend writing out a list of the things you'd like to change. Identify which things are feasible, and which ones are not. For example, making an effort to get out of the office for lunch with coworkers periodically is probably attainable. Zero interaction with your boss is probably not... Be realistic about what you can control, and set a timeline for yourself. "If in X months I'm still not happy, I'm going to initiate a job search." Then, you can launch into a new job search knowing you gave it your best shot. 

It's possible that you're unhappy in both the role and company, but this way you’ll have a better sense. I applaud you for acknowledging that your job is making you unhappy. Lots of people would stick around for an extended period of time even if they’re unfulfilled.

Q: "Thanks for the great tips! I have been sending several "cold" e-mails lately and I don't always receive responses back. What is your advice on the amount of time to wait to send a follow up e-mail and what should that e-mail entail?"

A: It's a fine line between being proactive and persistent versus pestering and overzealous. I get that this can be an awkward thing to navigate. I think one follow up a week later, and maybe one the week after that, is appropriate. And then calendar to reach out in 3-6 months. The more job search activity you put out, the more irons you'll have in the fire, the less painful the radio silence will feel when you're waiting for a response. 

Q: "Jenny great tips, thanks! My question: If a candidate has already interviewed with a company and did not get the job, can he/she apply again to the same company for another position? Would you recommend applying again to the same company (once you have been rejected by them)? What's the norm?"

A: The short answer is “yes" (potentially even for the same position).

Some reasons to reapply may include:

You didn’t have enough experience for the role, and now you do.

You want to apply for a more senior (or more junior) role that you think is a better fit for you.  

If your job experience wasn’t relevant for the company at the time but now it is.

If the company satisfied their initial need, but they have since landed a big client or project. 

When you apply, save the recruiter some time by explaining that you applied once before. Say that it was a positive experience and you’d like to catch up to let them know about what you’ve been working on. Think about what has changed in the interim and how you can benefit the company as it stands currently.

Q: "This is great, thank you - my question for the Q&A:
 What are some of the most important questions you can ask, if you get 10 minutes of an HR professional's time through the use of the cold HR email approach? Since you are probably not seeking a specific open role, what are the key questions that show you have researched the company & prepared for the conversation, but that keep the speaking points focused on you and your strengths?"

A: First and foremost, I can’t stress the importance of having an organized conversation. Having a structure to the call can show drive, great communication skills, and your sensibilities in one fell swoop. 

I'd recommend that you have an opener: “I appreciate you jumping on the phone with me and I don’t want to take much of your time, but I’d love to pick your brain about XYZ.”

You should also have a closer: “This was helpful, do you mind if I use you as a resource down the line?”

Ask thoughtful questions:

“What kinds of entry level talent do you tend to hire?”

“What are the kinds of things you look for on a resume that compel you to extend a phone screen?”

“What are the common personality traits that help team members in my dream role succeed?”

“How can I make my resume feel relevant to your industry?”

"How long have you been at the company and what do you like most about it?"

Q: "This is invaluable advice! Thank you so much for putting this together. I have a question (or multiple questions I should say): Aside from the traditional 2-week notice (in the form of a resignation letter), how should one go about resigning from a current position with grace? Do you speak to your boss first? Also, how do you go about letting the rest of your team know?"

A: Your direct manager will probably appreciate knowing first, but it's also appropriate to go to HR. It varies from company to company. 

You could say: “I’ve enjoyed my time here, but I've made the decision to move on. I’m grateful for the opportunity and I'm happy to help with the transition in whatever way possible.” And then really commit to tying up loose ends and leaving your team in a good position. You never know who you'll run into again.  

Some employers may ask you to leave ASAP (if you are going to a competitor) and you should be prepared for that. Help tie up loose ends, help make it easy for data to be transferred, and give some thought and attention to the place that has positioned you for your next opportunity. It’s nice to leave and not feel like you’ve burned a bridge. You can feel free to give more than 2 weeks if you are tied into a project, but be mindful of time (ie, if you tell a new prospective employer that you can't start for 4 months, this might not work for them). 

Q: "Hi! Questions for Jenny - When an interviewer asks you what your biggest weakness is during a job interview, what is the best way to answer? I feel like it's a bit of a trick question and it's always so awkward to answer.

Also, another question - If you're interested in applying for a position that you have never worked in before (such as applying to work as an Executive Assistant for a company when your background is mostly in Personal Assisting at someone's home), what's the best way to explain why you think you are still a great fit for the job?

I love this series! It's so helpful! Thanks for all of your great tips so far! :)"

A: While I don't ask prospective employees this question, the answers I wouldn't want to hear are the BS ones like saying you’re a perfectionist or you're too organized. This is an opportunity to give a genuine answer, but to phrase it showing finesse and good sensibilities. If your genuine answer, phrased diplomatically, doesn't make sense for the company, then it’s good that you bring it up at this point in the process. 

Maybe you have a lack of experience in the space. You can share this and then explain how you will compensate or what you bring to the table. Or, maybe you get anxious public speaking, but you can explain that you have taken a Toastmasters to practice and improve these skills. More than being a “gotcha” moment, you can make this tricky question about problem solving and positioning your “weakness” as a growth opportunity. 

Q: "I've referred a few friends to openings at my company because I think they'd be great fits and so far, so good (one has been hired and others are talking to recruiters). On the flip side, how do you handle a referral gone wrong, especially if your pick gets hired and doesn't meet expectations? I love my company and enjoy talking about it and I'm also happy to pass along openings to friends who are qualified and looking but I feel bad (and selfish!) for worrying about how their performance might reflect back on me."

A: First and foremost, I’m sorry to hear that. It’s awkward. But, a lot people are usually involved in making hiring decisions. And just because you think the candidate you referred might be a good fit, doesn't mean that you are solely responsible for the hire. There is usually buy-in from a variety of people.  

You shouldn't feel the need to do damage control, but it's probably good reminder to soft sell the next referral you pass along to your company. I suggest that you don’t overstate your referrals. Something like, “I’ve enjoyed working with this person and I don’t know how their skills will translate, but if you think their resume is relevant I think it may be worth your time to talk to them.” You’ll feel less anxious because someone else is qualifying your referral.

Don’t worry. A bad referral is not a direct reflection of you and your judgment because in order to make the hire, other people must have agreed with your assessment. 

Job Search, Resume and Cover Letter, Interview and Follow-up

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