Here Are Your Most Pressing Career Questions Answered

Career Enrichment, Get That Job
05/13/21 - Nicole Wood

We are all well aware that these are “unprecedented times” and that there is no playbook for how to navigate them. That has left many of our clients confused about how to approach next steps in their careers. How do I approach the job search in a pandemic? Can I still negotiate my salary? Do I have to go back to the office?

We’ve rounded up a list of the most common and pressing questions from our career coaching clients. Our amazing team of coaches have provided answers to these questions so that you can keep progressing toward your goals.

A woman looking up

Job Search Questions

I’m seeing postings for interesting jobs that I feel under/overqualified for. Should I still apply?

Yes. Why do you need anything else?  That’s the whole answer.  Okay, more seriously…

absolutely you should. You’re not always the best, most impartial judge of your own abilities, and writing qualifications for a job posting is far from a scientific process. The reality is that if you can create value, that’s the only real qualification – so don’t eliminate yourself!

John Roccia

How do I not submit applications 800 times? 

The unfortunate answer is being super intentional with networking and crafting applications. Use it as a test – if you’re not interested in the job enough to spend time on the application, skip it. Don’t treat it like a to-do list with prescribed checkboxes. There’s no “right” way to do things, only effective and ineffective ways.  Effective ways aren’t one-size-fits-all, they’re customized.  Make friends and conversations, not applications.

Throwing spaghetti at the wall to see what sticks doesn’t get you any closer to a job, especially a meaningful one. Those fire-and-forget applications drain your morale and energy but add nothing to your process. Don’t get pulled into the trap of thinking this is a numbers game – it isn’t. 

– John Roccia

Does anyone read my cover letter? 

Yes, your cover letter is getting read. And not only by the recruiter or hiring manager. Sometimes your cover letter has been forwarded to your potential boss, or another department altogether. It is important to include a cover letter as it gives the reader the basic information about who you are, why you are interested in the company and what you have to offer. In some instances, a cover letter makes you distinctive as other applicants won’t/can’t be bothered with it. Check out some cover letter resources here

Shari Santoriello

Does my resume format matter? 

Yes!!! If you are applying through a “apply now” button, just know that your materials are going through an applicant tracking system (ATS). The best format for any online application is a word document, void of graphics, column, tables and borders. Use of bullets and commas are okay. While the online application may say that a PDF file is okay, I would still avoid it, if possible. I know there are so many stylized resume formats to adopt and they look great, but unfortunately not all of them can be parsed through an ATS system. That puts you out of the running before you get started. Watch out for these resume mistakes

For those in a creative field, having two different-formatted resumes is a great idea. You can have one straight Word document for online applications. Then craft a second stylized, creative resume for sending directly to people, or highlighting on your website.  

-Shari Santoriello

I know I’m a skilled person. Why can’t I get a job? 

This is my least favorite yet most commonly asked question these days. 

The tough reality is it may be timing. The world is tough right now. Things are changing rapidly.  Companies that appear to be hiring may just be recalling laid off or furloughed employees back. Companies you see growth in may have formerly asked employees to take pay cuts and are finally able to increase salaries and grow their current staff. So even when you see growth out there it may not have the outwardly impact you’re expecting.

Patience is critical in these times. It may not happen overnight, or as rapidly as it has for you in previous booming employment years. It’s important to remember that a delay in hiring doesn’t mean you’re not a great, high-skilled employee. 


Make sure you take your time and apply for every job with intention, tailoring your resume and cover letter.  Work hard to find a connection in the company (six-degrees of separation) so you can get your name to them in multiple ways. Network, network, network, and when you are sick of networking, network some more.  Most jobs are being found these days through networking. This doesn’t mean tracking down a stranger on LinkedIn and asking them to get you a job. This means letting people in your network know you’re looking and asking them to help connect you with other people. Then, let it grow from there. 

Treat every conversation you have as a possible opportunity and just see where everyday life leads you! A high skilled VP client of mine recently was very frustrated with the job hunt process. She wasn’t getting any bites and was feeling very stuck in a job she was miserable in.  I told her to pause. Take a break from all the searching and applying. Just take a break, take a breath and when ready just have a couple simple networking calls with people you already know so the pressure is low. She did precisely this, and two weeks later at our next session she told me they had connected her with someone in their network. She had a job interview that week. No applying, no surfing the internet, just a simple conversation with someone she knew. Tap into that network, keep your head high and your confidence up. 

Jennifer Maynard

Should I negotiate my offer even in the midst of the pandemic? 

Yes! There may not be a budget for what you request, but you should always try. Even if they cannot increase your salary, you may be able to negotiate more vacation time, stock options, flexible schedule, or a better job title. Review your work and accomplishments and be prepared with examples to show your value and worth and how your contributions have made a difference for the company. Numbers and data don’t lie! 

Hayley Dennis

A dog raising its paw

Return to Work Questions

What if I don’t want to go back? Should I start looking for a new job? 

There is never a wrong time to browse the job market and see what opportunities are available. The first question I would ask myself is, “Why don’t I want to return to my current job?” If you find yourself wanting more out of your career or wanting to switch careers, then now may be a good time to explore new opportunities. 

You may find that working from home permanently will allow you to have more of a work/life balance and that is something you wish to continue. Or you may discover that you are anxious about what the new normal will look like when you return to the office or your role may change when you return back to the office. Doing an honest self-examination will assist you in identifying what your core values are. You can decide if your current job still aligns with those or if a new role will provide better alignment and in turn bring your greater happiness and success.   

-Hayley Dennis

I’m having a lot of anxiety about going back to everything in person all at once. How can I ease some of the stress? 

Examine where the apprehension/fear may be coming from and what that outcome will mean for your personal well being. Examples…you may live with a spouse who has a compromised immune system or have elderly persons living in your household. Or you’re concerned what exposure you could bring back home for those family members and the risk involved. Another may be just the fear of what the new environment will look like. 

I encourage you to have open conversations with your manager about that and share your career concerns and questions so you can make an informed decision that will make you feel safe and secure. 

-Hayley Dennis

Career Management Questions

The pandemic made me rethink a lot of things. How do I make time for what’s important while being ambitious in my career?  

Identify what’s gotten in the way up until now and what needs to change/be put into place to prioritize those things! Set boundaries or schedule time to spend on what you’ve identified as important and share it with at least one person you trust so they can help you stay accountable! 

Natalia Tamburini

When should you be doing career planning? I end up making decisions under stress versus thinking about long-term plans when things are going well. 

People are almost always on the “back foot” when it comes to career decisions.  They make the most important decisions when they’re the most stressed – got laid off, industry changes, etc.  Stress leads to short-term thinking, but when things are good they’re also usually busy.  Breaking the cycle means being intentional NOW, no matter what your current circumstances are, and making planning the priority. I recently published this article on how to manage a successful career which discusses this concept in depth.

-John Roccia

I want to feel like I’m making a tangible impact. How do I find a company that’s aligned with my values and where I can make a difference? Does that have to be a non-profit?

Making a tangible impact means different things to different people. Define for yourself what that means. It could mean being an effective account manager so that you are decreasing any roadblocks for your clients to being a direct-service provider to creating opportunities for underserved populations or raising funds for a not for profit. Determining your personal meaning of “tangible impact” will help you find out which companies align with your values. 

It is also important to identify which values you want represented at your next company. To help assess this, think about what are your negotiables and non-negotiables, then prioritize which ones are most important for you. Which companies exhibit those same characteristics? Explore those companies and what types of roles they give that appeal to your sense of making a difference. There are a few ways to “make a difference” without working for a not-for-profit organization. Check out corporate social responsibility jobs, B Corporations, development and service-oriented roles.

-Shari Santoriello

Am I too old to switch industries? Do companies want to just hire younger people so they can pay them less?

The simple answer is a resounding: NO!!!! You are never too old to switch industries! While some companies prefer a younger workforce, many companies value the experience and work ethic that an older worker brings to the table. Ideally, a company will mix its workforce up with both older and younger workers to maximize all perspectives.

Switching industries is a great way to leverage your skills in a new way. Humans change regularly, and your professional life can and should reflect those changes. Some people make a slight change to an adjacent industry, and some will make a 180 degree pivot to something brand new. A successful way to handle any career change is to do your research, both role and company. Take an inventory of your strengths and skills. Identify if you have any gaps that need to be filled. Work to make connections and build relationships that can support your new direction.  

-Shari Santoriello

If I change jobs will I be starting over from the bottom?

First, your past experiences always teach you something; it’s all about being able to communicate what that something is and how it’s impactful to your next career move. While it might depend on the type of change you’re making, proactive career management is about planning in advance what it is you need to make a change that you’re looking for. 1) Define your non-negotiables, 2) Assess your skills and how they align to the new job you want 3) Fill in the gaps and build relationships that can guide you in making the change.  

-Natalia Tamburini 

What do I need to be thinking about regarding my finances if I leave my current job?

Remember three important things:

  1. The salary you commanded in your last job isn’t your rock-bottom price.  People often get hung up feeling like they’re going “backwards” if their next job offers them 5% less money than their last one.  But what if it’s 100% better?  You don’t need a job you hate to give you money to buy things that make you happy.  You can cut out the middleman and just be happy directly.
  2. There is absolutely nothing, nada, zilch, zero wrong with transitional “survival” jobs.  They won’t hurt your professional reputation, they won’t clog up your work history, and they aren’t going to damage your self-worth.  If driving for Uber or waiting tables for a few months takes the financial pressure off of you, then you buy the freedom to choose your next major career step on your own terms, instead of from a place of desperation.
  3. Good career moves are an investment in yourself.  You may have to tighten your belt during a transition, and while that may be unpleasant it doesn’t have to be painful.  But at the same time, your five-year financial health almost always looks better in a job where you’re happy versus one where you’re miserable.

-John Roccia

A woman looking up in confusion

I hope this has helped to answer some career questions that are top of mind for you. If you are interested in more personalized support, simply click here to schedule a consultation with us to be paired with the perfect coach for you.

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