Dear Bossy

Dear Bossy 7: Should I apply for a job I'm not qualified for?

Dear Bossy,

I saw a perfect job. I know I’d be great at this job, but I don’t have the experience they are looking for. Should I apply? What should I do about being inexperienced? I really want this job.


Searching for my dream job

Dear Searching for my dream job

Yes you should apply! I believe that job listings are often a list of guidelines, but not hard and fast requirements. Very few companies find the exact perfect person for the job AND you may have other qualities or experiences that knock their socks off.

A few things to consider:

  1. How far off from the qualifications are you? If they are looking for 10 years of experience and you only have 2 that is quite different than they are looking for 10 and you have 8. Truly evaluate how different your experience is from the job at hand. Can you do this job? Do you have enough experience, at the right level, in the right areas, to be a great hire. Then go for it.

  2. There is a highly quoted study that men apply for jobs when they are 60% qualified and women only apply when they are 100% qualified. I find this HBR analysis quite insightful. Women tend to follow the rules - they assume the job qualifications are required and men tend believe they are guidelines. I believe they are guidelines. As someone who has hired many people, I’d say - hiring managers want great candidates and job descriptions are poor representations of everything we are looking for. If you think you are being too critical of your match for the job, then definitely APPLY.

  3. Get the discrepancy out there early - even in your cover letter. If there is something you definitely do not have in a list of requirements or skills, you might get it on the table early. “I know you are looking for someone who has worked overseas before, and though I have not done that, I have experience…” or "Though I lack a formal engineering degree, I have xx years of experience that gives me even more applied engineering experience than most graduates.” This may or may not help, but it shows them you understand where you don’t match up, but have other talents that will compensate.

  4. Do your research. Network - find someone who knows someone and ask about the job. How long has it been open? Who does it report to? What is the reputation of the team? All of these things can help you present the best possible resume and qualifications. Information is power. If this job has been open for a long time, they may have unrealistic expectations and you can steer them towards something else. If you have a connection to someone there, ask for an informational interview and ask pointed questions about the team and the skills required and ask for advice about how to position yourself for a role on that team that matches your criteria.

  5. And most importantly - believe in yourself. Put your best foot forward. There are many dream jobs out there, not just one, so keep at it - if it isn’t this job it will be the next one. It may turn out you didn’t want this job after all!

Good luck!


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Dear Bossy #6: Should I customize my resume for each job I apply to?

Dear Bossy,

A friend who is a career coach mentioned that she thinks customizing a resume for each job you apply to is the new trend. It sounds like something that would take forever, and I’ve always felt job searching is partially a numbers thing. (The more you send out, the better chance you have of getting a response.) I’d love to know your thoughts on this topic. : ) thanks!

Job Hunting in Jersey


Dear Job Hunting in Jersey,

I don’t know if it really is a new trend. Customizing anything makes you appear like a good fit. Resumes are not a list of everything you’ve ever done, they are curated highlights. And the highlights really matter for the job. Especially with the increase of Automated Applicant Tracking Systems (ATS). These scan resumes and look for keywords that are listed in the job description and how high of a match rate they find on your resume.

So at the BARE minimum, you should grab some key words from the job description and pepper them throughout your resume (you can use some more than once). Don’t be haphazard here, but use their language. Different companies use different words to describe the same thing, so use the words they chose in their job description. Add a Skills Section and specifically list out any skills they are looking for. Know the computer programs they require, list those. Have 5 years managing staff, and that is part of the required skills, list that. You are trying to look like the person they are looking for and what better way than to say you have exactly what they are looking for!

LinkedIn has a handy new feature on their jobs pages - a “how you match” section, which is basically looking at skills they list in the resume and those you have on your LinkedIn page. Use this as your cheatsheet. I sometimes like to copy the entire job description onto my resume and grab exact phrases and paste them onto my resume. It helps to nail the wording and make sure I’m not missing important things.


When I hear someone say they have “applied everywhere” and aren’t getting any response, I often tell them to focus on fewer jobs they want/care about/could get. What are you good at, what do you love to do? You are more likely to come across in your application as genuine and passionate about something you really are genuinely passionate about. Give yourself a break - apply to fewer jobs! But tailor your resume and cover letter. Research the companies, network with people who work there or know who works there. Higher quality applications will pay off.

And - if you have a friend who is a career coach - listen to her. She is right on.

Good luck in your job search. Let me know how it goes.



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Dear Bossy #5: Should I remove my grad years from my resume because I'm older?

Dear Bossy

I am over 40. I am looking for a new job (scary), but reality. Do you think I should remove the year I graduated from college from my resume? It will definitely date me.


Elder Job Seeker


Dear Elder Job Seeker

I’ve been there, literally. And though you are older and wiser, you are also at risk of being seen as just older to prospective employers. This can hurt your chances. I do think somewhere around 40something, it makes sense to leave dates that could age you off your resume. This includes years of graduating as well as saying something like “I have 30 years of experiences in…”

This may be the time to switch to a functional resume instead of a chronological resume. Functional resumes highlight skills and experiences, but not chronological jobs. I would suggest this type of resume if you are switching fields or looking to make some sort of transition. If you are staying solidly in the same field and your work history and places of employment and titles are relevant, then you could just focus on that last 10-15 years of jobs, not your entire life history.

A resume isn’t meant to be every job, it is meant to show you in the best possible light to prospective employers (and screening computer programs), so focus on relevant skills and experiences and don’t list everything you’ve ever done.

One caveat - those pesky applicant tracking systems will make you put a date (including year) for everything, so even if you leave it off your resume, it is likely going to be listed somewhere.

Remember - you have years of experience, so be proud and confident that you are a seasoned expert and the right next job will be one that values that experience.

Good luck!


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Dear Bossy #3: I'm pregnant, when should I tell my boss?

Dear Bossy,

I’m pregnant. it is kind of early in my first trimester. I haven’t told anyone at work (just our close family). I know that after the baby is born I don’t want to go back to work full time and I may not want to go back at all. When should I tell my boss I’m pregnant and when should we talk about my returning to work?

Baby Bump in Boston


Dear Baby Bump in Boston,

Congratulations! So excited for you. Big life change coming at you. This is a great question and one I think most women who have children grapple with. Here are my thoughts for you.

I wouldn’t tell your boss about the baby until mid-2nd trimester. Lots can happen in your first trimester and you don’t need to share this news so early. Once you are solidly in your 2nd trimester you will definitely start to show and I would disclose to your boss about your baby and your due date. That said - if you are suffering from any first trimester health issues that require some workplace accommodations, then I would tell your boss sooner. But if you are managing just fine right now, then keep it your business for a bit longer.

I assume you are a woman of child bearing age, so your boss (male or female) has probably already made the assumption that you are going to get pregnant some day. So the news you are having a baby shouldn’t be a huge deal or a big shock. When you are ready to tell your boss, I’d focus on the due date, the maternity leave policy and making sure there is a plan in place to cover your workload while you are gone. More time for the team to plan is good, so don’t wait to start this conversation for too long.

However, I feel very strongly that you should not plan beyond the maternity leave with your boss right now. You don’t know what adding a baby to your life is going to be like and I wouldn’t make life plans that far in advance in collaboration with your boss. You should make all these decisions together with your family (partner, etc). My suggestion is to plan for a regular maternity leave, taking advantage of whatever policies your workplace has to give you. You do NOT need to start negotiating about part-time or not returning at all right now. Give yourself the full pregnancy and maternity leave to make these plans known to your boss.

Again, most bosses, make assumptions about women and babies. They assume some aren’t coming back or aren’t going to be as engaged when they do come back. So instead of tipping your hand about that - tell them you are planning on coming back on xy date and at full time.

Then once you’ve made up your mind about what you want for your family (once the little one has arrived), you can begin the negotiation process with your boss. If you are planning on not returning at all, you still want the maternity leave coverage and benefits through your labor/delivery and post delivery phase (this stuff costs a lot of money) and you may have a better sense of your availability and needs once you know about this kid and your needs.

If you decide you want to return to work in some part-time capacity, this is a different negotiation and depending on your workplace and flex time policies it may be hard or easy to have that conversation, but I’d wait until you know what you want.

I have one other piece of advice I give to ALL women who want to have families and have jobs and I stole it from Sheryl Sandberg - lean in to your work before they know you are pregnant and/or before your maternity leave. Get the raise, the promotion, the interesting project before you depart. If you do want to come back to work right away or later, you want something interesting to come back to. Don’t assume you will be less engaged or less productive and don’t let your boss assume that either. Get the raise and if you leave, you will have little more in your pocket for your time with your family and if you decide to go back to work you will have a higher salary expectation.

Good luck with the pregnancy. When you are on your maternity leave and decide what you want to do, write back and we can talk about the negotiation!



Dear Bossy #2: I'm a teacher and want a new job

Dear Bossy

Quick note. I’m a teacher. have been for 20 years. I’m about to walk into a ed-tech career fair. Any advice??

Thanks for any advice

Teacher in NY

Dear Teacher

20 years as a teacher - you have experience. My advice

be upbeat - no one wants to hear how burnt out you are as a teacher or what little shits your kids are or how this new generation is lazy. Keep it upbeat and positive.

Remember your experience - you have 20 years of experience. Anyone building an EdTech solution would be lucky to have you. You know what actually works in the classroom and with learners. Lots of this will translate.

I truly believe that anyone who can get up in front of students and get their attention day in and day out can do anything. You got this!

- Bossy

Dear Bossy - my new advice column

I have been called bossy my whole life.

I take it as a compliment.

I’ve decided to share some of the advice I’ve given (and been given) over the years about being overworked, always on, dealing with co-workers, re-org’d (again), poor performance reviews, changing managers, downturns, promotions, crying at work… and share it in all in an advice column format.

Let’s learn from each other.

Please send me your letters at