Many employees can tell you a story of the ‘wrong job’ – where they were miserable or barely making it and the struggle that results. One job search is tough enough, doing two in a year or less is worse. And getting fired always hurts.

How do you know if you will be able to be successful in a job when you get a job offer?  Usually, the red flags were there but you may have missed them – or thought you could overcome them.

You know companies often consider ‘fit’ in deciding who to hire, but making sure this is the right opportunity means you need to assess whether you fit too. Commonly, the big reasons for a ‘bad job’ are whether you are a good match for the organization, the position, and the boss.

Knowing what is important to you is vital to successful job search, so start there if you have not already defined a plan to guide your search. Create a ‘career desirables’ list of what you want next. Then list the deal-breakers, absolute ‘no’ issues, and any must-have needs. These can range from closely aligned mission and values to your core values, and long-term opportunity, position-specific items, even benefits of vital importance, and so on. Whatever would make you say, “No, not worth it.” This process will save you time and will help when facing a tough decision.

Am I a Good Fit?

Good fit has to do with whether the opportunity offers what you need to succeed.

  • Do they share values which match yours? A mission you want?
  • Do they offer growth related to your career goals?
  • Are you able to succeed in their environment? With this boss? On this team?

Many of us think of this as part of the ‘culture’ of an organization. Few understand how to evaluate these issues. Virtual interviews and remote work often make this more difficult.

1. Begin by thinking about the best and worst bosses you have worked for and what made each ‘best’ or ‘worst’ – this helps you understand what you are looking for in a boss. Make a list of each side.

2. Then think about your preferences, such as:

  • How much control do you want over your work?
  • Are you more comfortable in building something new or working within pre-set rules?
  • What’s your preferred work and communications style?
  • How much responsibility do you want?
  • Are you looking for growth opportunities or not? (Sometimes a job you can do while having time for self or family is most important, other times growth may be.)

Go through the things you know about yourself and assess what you need to succeed. Add in your goals for the job and longer-term career goals. These become your job search criteria.

All of the above tells you what is essential to learn and understand if the job is a good match for your needs and goals. Use it to find potential employers, to assess job leads and ads.

Organize all this information so you can use it in your search. You may decide to modify it later but either way, it helps in your research, interviewing and decision making.

I was recently talking with someone who had four options to consider. Like many, he had focused mostly on the money. That’s dangerous.

We talked about the differing roles and what each meant in terms of development and future career options. We discussed the hiring managers, each company’s hiring process, and so on. Suddenly there were only two potentials and one was clearly the better option than the other. No it was not the most lucrative. Fortunately, he had thought about what he wanted in this next step and had created a set of career goals. This made the discussion clear.

How This Works

Assessing Fit

1. Start assessing fit when you are selecting target employers. Which match your career goals? Offer paths forward of interest to you? Meet your job search criteria?

Look at any potential employer’s website in detail. What do they say about themselves? Do they offer any evidence of stated values in use? Look carefully at their career section – is it detailed or brief, fluff or evidence-based? If they make their employee handbook available, read it. While not many do, these documents tell you a lot about how a company treats its employees and its values. Talk is cheap—policies and practices are much more of a tell.

Check out the employer on sites like Glassdoor and Vault. Do recognize that unhappy people are more likely to write reviews than happy ones are. But read whatever you find and see if there are patterns of interest.

Then move to the people you know. Who does or has worked there? What can they tell you? If you do not know anyone who has worked there, ask for introductions to people who do. Check your connections on LinkedIn or other social media for those with experience at the employer too.

2. Pay attention to their hiring process. What does it tell you about the company? About the value of the position to the manager? Is the application process fairly easy or a pain? Is the whole process organized and positive, or not? Does it move reasonably quickly or is it dragged out? Stuff happens in companies all the time, so a few delays or errors is not a killer – but a pattern of them often is.

How responsive is the recruiter to your questions? Do they keep you informed of any changes or delays?

Find out who the hiring manager is and check them out online. Look for information that gives you an idea of what the person’s career has been so far, potential connections, and common interests. These help you prepare to interview effectively and to ask the right questions to see if you can work together successfully.

Some aspects to consider:

  • Does the hiring manager expect you to be immediately available at their convenience, or do they respect your time and needs?
  • How many people are involved in the hiring process? What roles are they in?
  • Do you get to talk with peers and team members directly?  Are they willing to answer your questions?
  • Do they give you a clear picture of the role and responsibilities? Of what it is like to work there?
  • Is the hiring manager clear about the role? Their timeline?
  • Is it a real conversation or an interrogation or talking over you?
  • Are they prepared for the interview?

3. You should have specific questions about the role. Below are some questions that help you assess the culture and fit, and to understand the employer. Add your own and carry a copy to any interviews. Think about what is most important to you and ask relevant questions. Don’t just ask your potential boss – some questions are great to ask everyone you interview with. Pick a few for each person you talk with, including company recruiters.

Adam Grant, the best selling author and Wharton professor, recommends a great question for assessing culture: “What is something that would only happen here, but would not at other organizations?” When you ask this, be prepared for some platitudes or for an ‘oh-oh’ look or some silence as the person tries to think about it. But if you can get specifics in an answer, it is highly valuable.

Questions About Culture and Values for anyone in the process

What have you learned while here that will influence your future work choices?
What about the environment here brings out your best work?
What core values add the most to the organization’s success?
Which core values are in name only?
If you could change anything in/about the company, what would it be?
What would 1-to-1s be like with my manager? What topics are covered? (Ask that of team members and others, ask the hiring manager the direct version – and see what matches.)
What common characteristics do you find among people who are successful here?
How do information and ideas flow upward in the work unit and the company?

Questions for the Boss

What do you expect a successful person to achieve in this job in the first 30-60-90 days?
Thinking of the most successful people who have worked for you, what made them so successful?
How do you prefer to manage people? What causes deviations from that?
What is the difference between being good in this job and being excellent?
How are goals set for this position and department?
What will others tell me about working with you?

Questions for the Next Level Boss (as possible and appropriate)

What is the difference between being good in this company and being excellent?
How are goals set for this position and department?
What type of person gets development opportunities here? Promoted?

As you ask these questions, look at how the person reacts to your question and the quality of their answers. While this is most vital with the direct boss, every answer can tell you a lot about the work environment and whether it is one you can succeed in. Compare the answers you get to one-two questions across all the interviews to see whether there is normal variety or big contradictions. Focus on the big differences to understand more.

I am a big fan of taking notes in interviews. Do that with each question you ask. This helps you decide if you can succeed in the organization with that boss.

The culture and values of an organization and your fit with them usually makes the difference between a short-term job and one that contributes to your future long-term. Invest your time in thought upfront for better success in getting and keeping the right job in the right place for you.