Job Search Motivation: Increase Your Odds of Finding Happy Work With These Questions

By Guest Author: Wallace

“I can’t be of much help to you Wallace unless you know specifically, what direction you want to take your career. Now, I have a few assignments that I think you’d be a great fit for…”

Recruiters are not professional Career Coaches. At least the vast majority of them that I’ve met aren’t. Now before I anger a lot of recruiters, yes, there are those with deep experience in the field who specialize in certain industries and may have a background in human resources who can offer you some thoughts about your career path, but in the end, it’s really up to you.

Nobody knows you better than YOU and maybe a select handful of close people in your network (friends, family, current and former colleagues/bosses, clients, etc.) despite knowing you relatively well, that select handful of people will only be working from a portion of the picture that is you.

From my experience, I thought I was pretty good at identifying the kinds of job opportunities that I would want and excel at. I was able to trim down the types of jobs that sounded interesting, along with the types of companies/industries. That as I learned, was only skimming the surface. I wasn’t taking into account ME – my work style, the balance I would need with my personal life, my professional goals, my belief system, and more.

The Recruiter I spoke to made a very valid point. She couldn’t possibly guide me in the direction I wanted my career to go in. She wasn’t me, and at the time, I wasn’t certain where I wanted to go next. I didn’t take the time to figure out what common thread ran through why I was looking and more specifically, what I was looking for. I decided to sit down and develop a list of questions to guide me to what my next “ideal” work opportunity would look like. I went through them all and kept drilling them down until I had a pretty good picture of myself and used that as a guide for the rest of the questions. The most important thing was to be honest with myself, and what I needed, in order to find the best opportunities for me. Once I had a more accurate picture and did the work to get the tools I need in place, I was able to begin my job search with confidence and let that Recruiter know precisely what I was looking for – saving myself and her a lot of time.

Wallace’s Questions to Ask Before You Embark on a Job Hunt:

(Questions for professional self-reflection to use in job hunt preparation.)

Q: Why am I looking?

  • Unhappy | not satisfied with my current job and need to look elsewhere (Why? List out specifics.)
  • I was fired (Why? List out reasons from employer, if known. List out your reasons, being brutally honest.)
  • I was laid-off (Why? List out reasons from employer, if known. List out reasons from your perspective.)
  • I quit without another job (Why? List out specific reasons.)
  • I quit with another job (Why? List out specific reasons.)

The goal here is to look for common themes. If you’re not happy in your current role, and you list things such as lack of flexibility and no room for growth, the last thing you should do is take a job with a company that has fixed/set hours from 8 to 5, and a position that doesn’t demonstrate the opportunity for an upward career path with the criteria for reaching them. (Example of a possible career path with titles: Software Engineer<Sr. Software Engineer<Director of Software Engineering<VP of Software Engineering.)

Now let’s say you were fired for tardiness, it’s a safe bet that you’ll need a job that offer some flexibility, or a remote working option. It’s even better if you recognize that you were fired for tardiness and not just chalk it up to the boss being an impractical micro-manager and workaholic who walks around to see who is at their desks. The best case would be that you understand you were fired for tardiness, but know that  your best work occurs at all hours – and you find a boss that tracks you on the work you’ve completed and what you contribute daily, instead of keeping track of when you’re sitting at a desk since there are no desks – the company is 100% distributed.

Drilling down to those exact details will help you figure out what you truly need to do your best work. You can also look back to other jobs you’ve held and look for themes there, too.

Q: My next work opportunity looks like:

  • Titles/industries (Be as specific as possible.)
  • Work environment (Open floor plan, private office, cubicle, shared space, home office – where are you most productive and comfortable?)
  • Work arrangement (Full-time employee, self-employed contractor, consultant/contractor for an employer, part-time/half-time?)
  • Salary (Hourly/yearly compensation, bonus, profit-sharing, commission structure, 401k/employer-sponsored savings plan, insurance coverage for health/dental/vision, insurance coverage for short/long-term disability, personal time off for vacation/sick time, company recognized holidays, professional development/education reimbursement, etc. You’ll want to list out everything you’ll need and want to have for bargaining/reviewing and comparing offers.)
  • Company culture (Is this important to you? Think of what makes a place to work enjoyable. Is it weekly team gatherings over lunch, off-hours events, company-wide/team trips, monthly company-wide meetings, open-door policy/information sharing, company philanthropy, etc. Try to list out what matters to you.)
  • Management style (Minimal supervision, Micro-manager – numerous styles here. List the ideal qualities you’d want from the person or persons you report to.)
  • The company (Start-up, small to medium sized business, large to Fortune 500 companies, yourself – list out the pros/cons to each to give yourself an accurate picture of where you’d do your best work)
  • Opportunity to advance (Is this the highest role until someone else retires, are there clear opportunities to grow and develop, is there an opportunity to move around within the organization, are certain degrees a firm requirement for advancement?
  • Does the organization do work that could or would conflict with my belief system? (Religious-affiliated institutions, branches of a government/government affiliations, CPG companies that sell products I wouldn’t use myself or object to, B2B companies that offer services I find questionable or objectionable, etc. Does the company have a reputation that makes question whether I could be proud to say I work for or with them?)

Think of answering this question like ordering from a fancy restaurant where you are the VIP and can get whatever you want. You could order a steak with some asparagus, salad and a dessert. Or instead, you could order a Wagyu Kobe Beef steak with shaved black truffles and maderia sauce, fresh grilled asparagus with hollandaise, spring green salad topped with fresh caught blue crab meat, parmesan crisps, in a lemon vinaigrette, and to finish – a lovely, made from scratch chocolate eclair. All prepared by a James Beard Foundation, award-winning chef. Makes a difference, doesn’t it?

 Q: Who are companies I would like to work for locally, nationally, abroad? (List out 10 for each. Include the ‘dream’ places.)

  • What common threads do they share?
  • What’s it like to work for them? (Research online/offline to get some perspective from current and former employees.)
  • Who are their competitors?
  • Are they hiring? If not, are their competitors hiring?
  • Are there recruiting firms they use? If so, who?

Q: What can I contribute to my employer/what problem can I help them solve and provide real value in the short and long-term?

  • Hard skills
  • Soft skills
  • Things I’m currently learning and can use in the workplace

Q: Is my professional house in order? 

  • Updated base resume to tailor to job/position I would want
  • Base cover letter to tailor to specific hiring manager/HR/talent acquisition
  • Social channels (Facebook, Twitter, Instagram, etc. does the material here convey how I want to be perceived by a stranger?)
  • Are my professional channels (LinkedIn,, personal website/blog, etc.) updated and depicting me authentically? (With professional and personal lives blurring, more professionals are finding it easier to align themselves with employers who share their interests/passions/style/voice/thinking.)

Preparing for a job search is like preparing to launch a rocket. You wouldn’t launch a rocket without first having a plan in place, and made sure you are prepared with the knowledge and tools needed for a successful mission. I hope the questions here inspire you to dig deeper and take the time to make sure your next search is one that will land you someplace where you can do your best work.


A Bit About Wallace:

Wallace is a writer, product hunter, tech appreciator, and casual observationalist of life who writes about the time that fills the hours between waking up and nodding off. Sometimes those hours are sponsored by an employer, and sometimes they aren’t. Whichever the case may be at the present, the words here are owned by Wallace and cannot be copied in whole or in part, and reproduced without permission. The views reflected in this post and other posts created by Wallace are Wallace’s alone and do not necessarily reflect the views of any entity that is sharing this or any other material authored by Wallace.