15 Questions To Determine If You’re Taking The Right Job

15 Questions To Determine If You’re Taking The Right Job

By Jim Jonassen, founder of JJA Venture Search


In short:

  • Jim Jonassen is an executive recruiter and talent acquisition expert who has spent decades reading through C-level resumes and evaluating candidates’ career narratives. 
  • He argues that a stellar resume alone isn’t enough to get you hired: You must also have a compelling “why” behind your search for a new role.
  • To determine your “why,” Jonassen recommends using his Career Diagnostic, a set of 15 questions meant to both win over recruiters and lead you to a fulfilling position.


Some resumes just “jump out” based on the individual’s pedigree: academic credentials, quality of employers, rapid progression, tenure in positions, awards and honors. But realistically, that describes 1 percent or less of the talent pool. So let’s assume your resume will not “jump out” and grab the recruiter. You need another edge.

You must go into a job search knowing who you are, and be prepared to reveal it.


It’s not the resume getting hired; it’s you. Everybody fuels their career with the “net energy” of their assets and liabilities: Your personality can be an asset in one company, yet a liability in another. 

Help a recruiter see your personality by using your resume, cover email and/or interview talking points wisely. Give them insight into what you love to do and how you assimilate to new circumstances. Maybe even reveal some of your shortcomings. This is the key to getting an interview: Make your total narrative a “hologram” of you that compels a CEO to meet the flesh-and-blood you. 

Of course, doing this requires knowing why you’re looking for a new role, and what you’re looking for.



Most people look back at their career arc as something that “happened to them.”


As a career headhunter, I interview candidates to understand how they have made career decisions. I’m amazed when I ask why they joined a particular company and hear replies like, “My old boss recruited me,” “A colleague felt I’d be a good fit,” or “It cut my commute in half.” In some cases, these scenarios led to short stints with really sketchy companies, which we refer to as “skid marks” on the resume. It’s startling how little introspection or due diligence many individuals put in before taking an offer. 

Every time you put yourself on the job market, you have an opportunity to shape your own career trajectory. Indeed, the moment you start working for an employer, you are the beneficiary–and likely also victim–of a blend of events that you either “make happen” and that “happen to you.”

However, the one moment you absolutely control is your decision to join. 


To make a smart decision, you’ve got to know why you’re searching for a new role, and what kind of role you’re searching for. Knowing this will, in turn, make you appear “real” on the flat sheet of your resume and more likely to score an interview. 

But how do you pinpoint this personal why and what? Here’s some help:

The Career Diagnostic Test



When my recruiting team and I first meet you, we look at your resume and ask you to complete a quick assessment called the Career Diagnostic. The Diagnostic forces you to ask yourself what you want out of your next career move, spotlighting what’s likely to satisfy you. Completing it will help you “know yourself” so you can burst off the resume or email page as an engaging, problem-solving leader that people simply have to meet.

The task is simple: Answer the below Diagnostic questions, with your ideal next role in mind. Then, keep your responses as a bulleted list of content that you can selectively include in a cover email or your interactions with recruiters, HR folks, career gatekeepers and hiring authorities. It’ll both help you get hired and ensure you land a role that you enjoy.

  1. What are the ROLES (range of titles) that you are both qualified for and interested in holding next?
  2. What are you really great at? What is your SUPERPOWER?
  3. What type of work or functional responsibility do you HATE TO DO?
  4. What is your “Achilles heel,” aka your weaknesses or areas primed for FUTURE DEVELOPMENT?
  5. SECTOR(S)? (Please provide the specific industry categories/markets where your experience and passions lie.)
  6. STAGE? (Indicate the ideal stage of your employer in terms of revenue, number of employees, customers or other key metrics.)
  7. TIME OF LIFE? (Where are you in life?)
  8. GEOGRAPHY?  (How far would you commute from home? Would you relocate? To where?)
  9. FAMILY? (Are there obligations on your time outside the office?)
  10. RISK APPETITE OR AVERSION? (Would you trade some current cash comp for equity upside?)
  11. TRAVEL? (What percent of the time can you travel?)
  12. PASSION? (What personal or professional interests would you like to make a part of your work life?)
  13. PATTERN MATCHING? (Which companies or positions have you been exposed to that are of great interest to you? We’ll use those as examples of good matches.)
  14. COMPENSATION? (Please explain your current comp package including base salary, on-target incentive bonus (cash), stock/equity and last two years’ W-2 earnings (excluding the sale of stock.)
  15. FUSE? (Where are you in your search: Are you just getting started? In play on multiple opportunities? Expecting offers?)

Voila! You’ve completed the Career Diagnostic. To prepare for your job search, also prepare a document (if necessary) containing:

--Links to writing samples (white papers, blog posts, killer Quora answers)
--Video interviews
--Code contributions or the equivalent
--Results to your DISC test (excerpted, of course)

Keep this content in a DropBox folder so you can share links or attach in an email as you get into the dialog. Oh, and:

Don’t be afraid to share what may be missing in your current situation. 


Before sending a candidate out on an interview, one of the things we look for is the “why” behind their decision to explore leaving their current employer. Of course, the long-held taboos about not talking negatively of current or previous employers still applies, but you can reveal your career wound while still taking the high road. Is the commute killing you? Is the company about to be sold? Are you not being challenged technically, creatively or intellectually? Do you feel you are way under-market on compensation?

Overall, the Career Diagnostic enables you to campaign for the next role that will shape your vocational arc, equipped to sell your strengths while being self-aware enough to humanize your weaknesses. Now, it’s up to you to send your career arc soaring and ensure you end it doing only what you love.

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