Imagine you have to choose between two job offers: both have good commutes, the salaries are similar, and you could see yourself in both positions. How do you decide? First, you might want to go out and buy yourself a lottery ticket (because it’s clearly your lucky day!). After that, though, it’s time to put your thinking cap on.

We asked executive leadership and career transition coach Mark Federman to walk us through some considerations.

Don’t make it about the money or title

While our default may be to think about money and title, what Federman calls “proxies for status,” he warns that such differences are far less important than how you feel in the job. Unless the salary difference is one that could blast you into another tax bracket and be truly life changing, it’s not worth considering a small separation in these categories.

“If I had to choose between two jobs, one with 10 to 15 per cent more money, or one with an environment that allowed me to shine, I’d take the shine. Because in the long term, when I shine, that will allow me to get more opportunities, more promotions, and end up with a better-looking resume, which over time will allow me to make up any difference in salary,” says Federman, adding that when his clients base their decision on money or title, they are often unhappy with the result.

Picture yourself in the job

Instead of dreaming about expensive vacations and fancy job titles, think about what motivates you at work. Federman says everyone wants to be their best at work: to perform well, to feel good about going. So, the first step is to look at your previous employment and identify what that means for you. “Think about what work conditions, interactions with employees and potential managers that have allowed you to do your best in the past,” says Federman.

Since supervisors are such an important factor, look back over your history to identify qualities of past managers who inspired you. “Think about manager who gave you internal motivation to excel and do your best, what were their attributes?” says Federman. He adds that younger workers can think back to education or part-time jobs. Also think about the opposite: managers who may have made you feel bad or fearful.

Consider too what workplace conditions helped pull the best from you, from employee interactions to opportunities for autonomy or collaboration. “Then when you’re looking at offers, ask what environment will provide those sorts of inspiration and enablement for you to bring the best,” he says.

Get the insider scoop

Research can help you find the right fit. Once a hiring manager is hinting at offers, ask to speak with potential colleagues, including ideally a direct report to your prospective manager. If the employer dodges the issue, consider that a red flag. If they do agree, ask probing questions, and in an environment off site where employees can speak their mind. Consider not only what they say, but how they answer.

Sample questions might include:

  • What do you like about this place?
  • What did this job allow you to do that previous jobs did not?
  • If your best friend was thinking about working here, what would you advise them?
  • What do you wish you would have known before starting in this role?

Pay close attention to how they answer your questions. Or they avoiding anything? Are their answers curt and unhelpful? That might be a red flag.  “On other hand if they get excited, know you might be onto something,” says Federman.

Think about your career as a whole

Federman says he leads his coaching clients through an exercise whereby they picture themselves as an elderly person telling your grandchildren about what you’re most proud of accomplishing in life. The thought experiment can help clarify both career and life path, and while the job may not bounce you ahead in time, it should be a step towards that imagined future.

On a related note, think about what you want your effect on the world to be – what Federman calls your “tactility”? Again, the notion should bring clarity to your thinking about the two offers.

“These things speak to enabling the human spirit, and clarifying your intrinsic motivation, so that all things can end up being right,” he says.