14 Critical Job Search Question to Ask Yourself

Just starting a new job search? Congratulations! Or, my condolences.

Look, I know this is a scary, emotional time. I know you are probably on edge and worried about a lot of things. You might be worried how you are going to pay your bills in a month if you don’t land something soon. Or, you might be worried about jumping into a new role, organization, culture, etc. It’s okay to be scared and worried. While this might be new for you, it’s pretty common. You aren’t alone, even if you feel alone.

Enough with the pep talk. I want to share 21 critical questions you need to ask yourself in your job search. I know you have a lot of stuff you need to do but please take a moment and walk through these questions. Answer them honestly. A career transition is a great time to recalibrate and check in with yourself. Without further ado, let’s jump in (these are not in any particular order):

Job Search Questions to Ask Yourself About Where You Are At in Life

1. What is your financial runway? 

Or, another way to ask this: How much time do I have before my money runs out? This is called your financial runway.

job search financial runway

When I started my Big Fat Failed Job Search in 2006, my dad told me he expected me to be out of work for at least six months. He knew that getting a professional-level job was not something you just applied for and got. He was setting expectations for me (and himself, as he helped me out during that time). I kept hearing it took one month for every $10k you earned… so if I was looking for a $60,000 job I could expect to look for 6 months.

Things change all the time, including this figure. Maybe you’ll get a job in a week, or next month. But if it goes on for six months, how will you pay your bills (roof over your head, utilities, and food being three of the most important things)? Or will your money run out in two months?

The answer to this question might change how you approach your job search.

2. What roles are you most interested in moving towards?

This time of transition might be a great opportunity to sit back and admit that you really hate the path you’ve been on. Maybe you hate the industry, your role, etc. Even if you have studied for years to get the job you recently left, it makes sense to reevaluate and ask what you really want to be when you grow up.

job search what do you want to be when you grow up

I’m not saying the job search is the best time to make massive changes, but maybe the job search is indeed the best time to make massive changes. Take this time and recalibrate. Think about your satisfaction, happiness, attitude, value, opportunities for growth, fulfillment, etc., and keep your options open.

Maybe changing roles means you start at a lower level, maybe less pay, but if this reduces your stress and makes you feel happier, maybe changing direction is one of the best things you can do. This might even mean this job search, normally a yucky experience, will be one of the biggest blessings of your life. It will be the time when you got away from dreary and moved towards real happiness.

That’s what happened to me, although at the time I had no idea how good this new path would turn out.

3. What is the role you could get the fastest that will pay your bills?

The answer to #2 might change your life. Maybe it will put you on a course of education and skill building. But… if whatever that answer is means you are a few years out, you might still need to get a job now. Think: the path of least resistance.

job search path of least resistance

Maybe you were in sales and hated it, but you know you could get another sales job fairly easy. So, get that sales job, do a great job (be honest with yourself and your employer), and work towards whatever the answer to #2 was.

This might sound like you are going backwards but you have a very important task at hand: get yourself in a position to pay your bills and not rely on others to help you. You probably have skills, contacts, etc. that can help you get out of this job search and get that paycheck coming in. Do that, but keep in mind what path you want to be on, and work towards that. It might take you months, or years, but you don’t have to feel stuck. You do, however, have to figure out how to generate income.

4. Do you need to make changes to your lifestyle (or sell things)? If so, when, what, and how?

If you eat out a lot you might consider going to a “make it at home” menu. If you have a closet full of clothes you have been meaning to sell, maybe now is the time. Maybe you have a boat that either can provide a few thousand dollars of much-needed cash or, by selling it, you could eliminate a big monthly payment.

job search sell your boat

I don’t know your circumstances but this is a great time to take a serious look at your financial runway and perhaps add some time based on changes you can make. Whether you cut out some streaming services or you sell stuff, you have some decisions to make. This can be hard and it can be freeing. Remember why you are doing it, and whatever changes you make now might be temporary until you are in a better position.

Just be honest with this question and be brave enough to make some hard decisions.

5. Who can help you work yourself out of your job search?

I don’t want to scare you off by saying, “who can you network with?” but that is the same question. Don’t try to do this alone. Being in a job search should not be a time to feel shame or embarrassment. Tuck your ego away and let others know you could use their help.

job search ask for help

You need to let people know how you can help them. Please read this post twice, print it out, highlight it, and then start to use some of this language in your job search. There are many important parts of this post that can help you help others with your job search.

Your network wants to help you. They want you to be out of pain and in a good place. They want you to be financially well and have fun in life. People want to help. They just don’t know how. Learn how to help them help you (hence, this post). Make a list of people you should talk to and start talking. It really helps, though, if you know who you are and what you are looking for.

6. How do others perceive (or, talk about) you?

The other way to ask this is, “What is your personal brand?” But I want to be specific on this: You need to understand how others talk about you, professionally, right now. You need to understand your personal brand and have a personal branding strategy.

job search epiphany you have a personal brand

When I started My Big Fat Failed Job Search of 2006 I had no idea what a personal brand was. Worse, I didn’t realize I had a brand. You do too. I want you to think about your brand, and how you can intentionally craft or recraft it to be what it should be. I have a course on that, of course: Developing Your Personal Brand

The key takeaway here is that yes, you do have a brand, and yes, you could change and influence that (or, you could change and influence how others perceive and talk about you). This is something you should seriously consider for the duration of your career (not just this job search).

7. Are you going to do other things in addition to this job (for money)?

I’m a nut for multiple streams of income. It is so empowering to have other money coming in… money you can’t lose if you lose your job.

Seriously: empowering.  Please read this post: I Got Laid Off Again. Why Losing 1 of 4 Income Streams Left Me Empowered.

Of course, you don’t have to work on other income streams. Maybe it’s just too much, or you have way too many personal things you are working on after work. Your life, your season, etc. I respect that.

job search different circumstances

Having said that, if you create other income streams, and you are excited about them, maybe the job you need is a temporary gig to pay the bills while your other stuff ramps up. This might mean you need to make less, or work less, or not work evenings or weekends, etc. Working on other streams of income should impact what you choose to do in your job search, what companies you go after, how you network, etc.

I guess the related question is, SHOULD you work on other income streams?

Job Search Questions to Ask Yourself About Your Next Job

8. What kind of boss do you want to work for?

This is not a trivial question. When you are just starting your career you have no idea how important this question is. Work for a handful of bad bosses and you’ll learn that the bosses you have can have a massive impact on your career, how happy you are, and can impact your time outside of work.

job search toxic boss

I have worked for some amazing bosses. I’ve had bosses that were good. And I have a short list of bosses that, when I think about them, give me bad physical reactions. Might sound petty but I remember going to lunch a few years back and seeing the guy who laid me off years earlier. I was so uncomfortable and couldn’t wait to finish my meal and leave the restaurant. I could barely stand to be in the same building with him.

When I worked for that boss I thought, I can do this. I need the job, I need the money. I like the title and the prestige, so I’ll just suck it up and work through the toxicity.

I’ve matured since then. My physical, mental, and emotional health is more important than sucking it up. It’s hard to leave a bad boss when everything else seems so right, but if you are in a job search right now it’s a great time to stop and seriously think about this. What type of boss do you want?

My last boss was so good with and for me. In addition to being such an excellent person, he gave me lots of room. I need lots of room to do what I do. I don’t like being micromanaged… I like room. If I ever have a boss again that, and a few other criteria, will be on my list of what I’m looking for. What is on your list?

9. What kind of coworkers do you want to have?

I’ve worked with cool people and I’ve worked with crude jerks. Just as the job search is a great time to pause and ask the question about the boss you want, it’s a great time to ask what kind of coworkers you want.

job search consider coworkers and colleagues

Do you want to work around young, recent graduates? That can be invigorating and exciting (or super frustrating). Do you want to work with a more seasoned team, perhaps giving you plenty of opportunities to get mentoring and learn from them? Do you want to work with industry experts, hustlers, Type A people, or a super chill group of coworkers?

The answer to this might change throughout your career. You might want a fast-m0ving group of over-achievers who are working lots of hours earlier in your career, but later you just want a chill, happy, drama-free office environment. Neither are wrong… look for what is right for you.

Remember, you will spend an inordinate amount of time with these people! You can’t necessarily choose your family but you can choose your friends and, to an extent, you can choose who you work with!

10. What growth opportunities do you want to have?

Some people love going to work, doing their job, clocking out and going home. Day after day, month after month, year after year. They know what to expect, they know they are good, and hope their employer doesn’t fire them or go out of business.

Just leave me alone and let me do my thing. And then I’ll retire and go fishing.

job search rather be fishing

Other people want to be more challenged at work. They want opportunities to excel, they want to know when they excel, they want to feel rewarded for their contributions, they want to learn and improve and grow.

Some organizations cater towards the first while other cater towards the second. If you need to grow, and want to improve, make sure you find an organization that let’s you.

11. What hours and flexibility do you want?

Do you want to ever work on weekends? Do you want the night pay differential some roles offer? Do you want to be able to work from home, ever? Do you want to work four days a week (10 hours a day) and have a three-day weekend every day? Do you want to unplug at 5 or 6 every day, or are you okay to work into the evening? Do you want to have to start at 8am, or have flexible to start at 9 or 10?

job search sleep in or get up early

These are all important questions that, if left unanswered, might leave you miserable.

Imagine a job where you need to start at 7am, work until well past 5pm, and be expected to be available over the weekends. Fun? Not for me.

My last job was very flexible. They were really big on “get your work done,” and not as big on “you weren’t in your office at 8am, you were late. You are always late.” No one kept track of that (that I knew).

Also, even though my boss’s boss could work from home almost every single day, she required us (or at least me) to be in the office. I didn’t appreciate that, and if I was there longer I’m sure I would have tried to get that changed. I had a 24 mile commute, each way, which felt extremely wasteful (time, gas, energy, etc.) when I could have worked during those commute times, or at least been more relaxed about what I wore and my schedule.

Think about this during your job search because you may have some opportunities that look better, or worse, depending on how they think about your schedule, time, and productivity.

12. What is the commute like?

When I was a teen I commuted, as a high school “intern,” into a big city for three summers. It was miserable. It was the thing that turned me off of commuting. The people I commuted with were cool and accomplished but couldn’t talk about their work (confidentiality issues).

I was bored out of my mind and wondered if the rest of my life would involve commuting.

job search commute considerations

Thankfully my career has rarely required me to commute. Nowadays it’s better since you aren’t beholden to whatever is on the radio. You can get some great books and podcasts in, and get smarter during your commute. But I still despise the idea of spending hours and hours each week driving to and from work.

That’s just me. Whatever you like, you like, but you need to ask yourself what you want to tolerate. I knew people who chose three and four hour commutes each way. Sounded crazy to me but they seemed to be good with it. Mix the commute requirements with the flexibility of remote work and schedules and you’ll be on your path to figuring out a plan that won’t leave you miserable.

13. Are there travel requirements?

Many postings will say things like “50% travel,” to give you an idea of how often you can plan to be meeting with prospects or going to conferences. Traveling can be a lot of fun. It can also be extremely boring and tiring.

job search air travel

I remember the first time I got on a plan representing an organization I worked with… I was so proud! It was fun to have an expense account and eat wherever I wanted. I felt important.

The next time I went on a similar trip was exciting until my butt hit the airplane seat. At that very moment, at the beginning of my trip, the romance was gone.

I love to travel but if I had to get on a plane every week and leave my wife and kids all the time I know I’d get worn down. On the other hand, if you get a per diem that you can keep (if you don’t spend it), being on the road can be financially rewarding in a huge way. There’s no right or wrong answer for everyone but you need to ask yourself what you are up for during your job search so you can target the right opportunities and avoid the wrong opportunities.

14. How important is organizational prestige and company size?

Do you need to work for a big, name-brand organization? I’ve had neighbors who were super duper proud of where they worked. It was their identity. Moving to a smaller, no-name company, even with better pay and benefits, would have crushed them.

I know plenty of people who work for small companies I’ve never heard of, and they do very well. They love where they are and are treated very nicely.

job search company size ego dream job

There are pros and cons and really, it probably doesn’t matter in the long run. But it might matter to you. You just need to be honest about it and let the answer guide you to the right target companies in this job search.

Or, maybe the smaller company is a startup with lots of growth opportunity. Maybe you can get equity and have a more diverse role. Working in a bigger company you might be a cog, which could be great or it could be boring.

Things to consider. The whole point is to go into this job search with purpose, strategy, and intention, instead of just biting at everything that comes your way.

Job Search Questions to Ask Yourself About ____

I’m sure there are other questions you could, or should, ask yourself. Don’t get hung up on imposter syndrome questions like “why even try” or “can I even do this?” In your job search it’s easy to forget who you are and the path you have been on that builds your credibility. Self-exploration is one thing but beating yourself up is not a good job search strategy.

What other questions should you, or have you, asked during a job search?