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Have you ever been excited to start a new job only to find out after a few months that it is not for you? Well, do not fret, you are not alone.

Discovering you are not the right fit for a job or organization is a common occurrence in job-searching and one that can cost both you and an organization valuable time and money. However, there is an easy way to avoid this emotional rollercoaster, and that is by assessing your fit for a job before you even begin to write an application.

Oh, and there is a big bonus to what I am about to detail for you. If you go through the process I describe below and find out you are passionate about the job, you will have set yourself up to be a prime candidate; talk about a win-win situation!

Before we get started, if you are not quite at a stage where you are actively job seeking within a field you are confident you are going to thrive, you may want to read: 3 Steps For Finding Your Passion and Make It Your Job.

1. Start with Self-Reflection

Before you can assess whether a job is a good fit for you, you have to be self-aware of what is going to ensure you can thrive in a position. So, take a moment (or a year) to reflect on what constitutes your ideal job.

Below I have listed some common indicators you may want to consider during your self-reflection:

  • Are you interested in a collaborative or independent working culture?
  • What is your preferred management approach: top-down or horizontal?
  • How important is equity, diversity, and inclusion to you?
  • What size of an organization are you interested in a small team or a comb in the beehive?
  • What does work-life balance mean to you? How will you know if a position can meet this?
  • How important is job flexibility, such as being able to flexibly schedule around your life?
  • How important is a social work environment for you  team lunches and drinks after work?

 Of course, you should definitely also consider more standard indicators of job fit, such as pay, benefits, commute time, etc. , but these are the things people usually consider without thinking about the topics above.

As such, do not simply dwell on these surface-level indicators of fit. You will spend a significant amount of your waking time at work, so go the extra mile and really reflect on what an ideal working situation looks like for you.

Once you have taken some time to self-reflect, it is time to start assessing your fit!

2. Do Online Research

The fastest and lowest barrier way to assess your fit is to turn to our old friend, the internet, and dive into publicly available information on organizations you are interested in. I recommend starting with an organization’s “About” page and paying specific attention to sections that discuss “Why Work For Us,” “Mission,” “Vision,” “Values,” or “Culture.” 

These pages will provide you with a superficial glimpse of what an organization strives to publicly be. For example, see what Amazon’s “About” page looks like to get an idea of what to look for. Based on your self-reflection, do you think Amazon would be a good fit for you? Perhaps, purely based on their stated values, the answer is yes. But of course, there is more to the picture than meets the eye.

It is important to recognize that the information posted on these pages is what an organization publicly strives to achieve. This is powerful because they can and should be held accountable for these statements.

However, just because something is stated on an organization’s website does not necessarily make it accurate in reality. So, if you feel like your values align with what is publicly said by an organization, that is an excellent sign to dive a bit deeper into really assessing your fit!

3. Read Available Reviews

The next place to take your online sleuthing is to publicly available employer review websites. Explore what former employees have posted on sites like Glassdoor, Indeed, and LinkedIn.

If the reviews are all negative, this can be a pretty clear sign of issues within an organization. However, it is far more likely that reviews are mixed, which is more symbolic of human diversity and workplace preferences than it necessarily is about the fit of an organization for you personally.

So, I recommend reading reviews with your self-reflected values in mind, and seeing if there are conflicts with your priorities. If you are interested in a collaborative workspace, and many reviews indicate that the work culture is like working in silos, you may have found a significant red flag.

Depending on the context and availability, it can be prudent to explore consumer reviews of an organization as well (say, through Google). What is the public’s perception of an organization, and what are the typical problems or highlights? Evaluate if any of these reviews clash with your workplace needs.

A quick note: if you have found a red flag – a clash with your workplace priorities – consider that a good thing. You may have saved yourself significant time applying, interviewing, or even starting a job you do not want to do!

4. Time For a Coffee Chat!

Unless you discovered a significant red flag in the first two steps, connecting with a current or recent employee of the organization you are interested in is by far the most effective way to assess your fit for a job.

But how do you find this person? There is a myriad of ways! The first and most impactful approach is to search within your network? Do you know any acquaintances that already work for the organization you are interested in? If so, because they know you, they are more likely to sit down for a coffee with you.

If you do not have any acquaintances working for the organization, what about through their acquaintances? Having a friend or co-worker connect you with someone in their network is likely to yield you a coffee chat because there is an established relationship of trust mediated by your mutual connection. Oh, the power of networking!

However, sometimes you just do not have access to a connection at a given organization. At this point, it may be helpful to read 5 Tips for Writing Cold Emails to Prospective Employers for insight into how to appropriately “cold email” people.

If this is the case, not to fear, LinkedIn is here! Use LinkedIn to search the organization you are interested in working for, and you will find employees that work there.

The next step is to find the best employee to talk to, which is probably someone who works in the same department or field that you are interested in. If it is a big organization, you will want to find someone who meets the above description as workplace experience can vary significantly across departments in big organizations (think IT vs Customer Service).

Once you have found an employee that you think can give you accurate information about the workplace experience at a given organization, it is time to connect with them. Now, most people are happy to help others while having a coffee purchased for them, but sometimes that is not enough. What is vital in setting up a coffee chat/informational interview with someone through LinkedIn is telling letting them know you are interested in hearing their experience.

In other words, do not make the coffee chat about you, make it about them and their experience. People genuinely like talking about themselves, especially if free coffee is on the table. So, ask if the person you want to connect with is interested in talking about their experience so you can evaluate if you are a good fit for the organization.

Even if this goes “bad” – as in you discover you are not a good fit for the organization – you can count this as a great success. You will now have narrowed your search and won’t have to consider future opportunities from that organization. That is a great thing!

5. Be Prepared to Ask Good Questions

The absolute worst thing you could do in a coffee chat is to ask poor questions to someone who works in the organization. Why? Well, if you go on to become enamored with the organization, but one of their employees does not think highly of you, this information could get passed on to the hiring manager of the job you are interested in and seriously impair your chances of getting a job. Imagine a scenario where an employee says to a hiring manager in the office kitchen one day:

 “I went for coffee with this guy named Simon, who reached out to me because he was interested in XXXX job.” Says the employee.

“Tell me more, what did you think of them?” Says the hiring manager.

The employee responds, “To be honest, they asked generic questions and did not seem like they knew why they wanted the job. I am not sure they would be a good fit.”

Boom! Your chances of getting that job are now swirling down the drain.

However, and importantly, the script can just as easily be flipped the other way. If you ask good questions and impress upon that employee, you can vault yourself straight to the top of the application pile with a positive referral from that same employee you met for coffee.

That is the beauty of this approach. If you do it well, not only might you discover the job is a good fit, but you might have also firmly positioned yourself as a strong candidate for the job!

So, what do good questions look like?

Good questions during a coffee chat/informational interview show that you have done some research about the organization (hello steps 1 & 2). When you can ask specific questions about the organization, you become more relatable to the person you are speaking with, and you get more accurate answers. Here’s an example:

“I saw on XXXX website that you strive to create collaborative and inclusive working spaces. Based on your experience, what do these things look like in the organization?”

By asking someone who works/worked for the organization you are interested in these kinds of questions, you can see tangible examples of what it is like to work for that organization. In conjunction with your self-reflected workplace priorities, you can begin to clearly evaluate whether you can seriously see yourself working in that organization.

If there are things you are particularly worried about in a workplace context or about a specific job, you have a direct source for asking specific and detailed questions. You cannot beat that!

Asking good questions shows that you are seriously interested in working for an organization and can impress highly upon the person you are talking to. This is important if you want to get a positive referral!


 If you take the time to seriously consider if a job is a right fit for you, you can begin applying to jobs with a high level of confidence that it is worth your time.

Not only will you be saving your future self time by not continually going through the job seeking and application processes, but you will also give yourself an enormous boost on the competition by having knowledge and personal referrals that they lack!

If you have gone through this process and think you are now ready to apply for a job, consider reading the author’s blog on how to write an effective resume, you won’t regret it!

Written By
Simon Erlich, MA, is a Career Advisor and founder of Simple Simon’s Education, an educational services business that specializes in career advising, job searching support, and resume and cover letter writing. While he runs this business, Simon cycles around the world on his touring bicycle.

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