The Job Hunt: When the Shoe Fits

An example of bar lacing on a stompy shoe
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Most everyone wants a job or role that “works:” sufficiently challenging to keep you engaged, room for growth, pays fairly (aka “well”) in the form of monetary or psychological (if it’s volunteer work) compensation, fits in your schedule, fits with your geographic preferences, and comes with a boss and co-workers that you like and respect.

In other words, we want to it all.

The reality is that you will likely settle for something less – and for some that are jobless (common in certain job fields and certain parts of the United States during the Great Recession) most any job looks great.

So what are the big ticket things you should track on your checklist to see if the shoe fits – or alternately, if you can wear it at all?

There are two big, broad framing questions that you should ask yourself – things I ask clients in my work an executive, career and team coach. One is “Are you likely to be successful in this (possible) job?” While it’s great to be employed, it’s better to be employed in a role that has a chance of sticking. I don’t know what the number is, but recruiters are going to give somebody only so many chances, so much slack for saying “the job was a poor fit.”  At some point that lack of judgement is your responsibility, not the responsibility of the folks who hired you.

The second is whether this job makes sense in the career narrative you want to tell when you’re 90 years old and looking back on life. Does it fit in – or at best, avoid taking you backwards?  Is it complementary to all the things you want to learn or experience – or opposite, is it totally antagonistic and will set you back significantly?

Here’s are the questions that make up the smaller job pieces you should think through:

Is the prospective boss somebody you can work with? If you like steady as you go and the boss changes their mind every hour (as has happened to me), sooner or later it will drive you craze – and degrade your performance. Are your values similar, are your styles compatible, and do you speak the same language (e.g. you talk in generalities, they talk in specifics and metrics). Do you – not that lots of affection is required – like them? Nothing like spending lots of time with somebody with whom you hate to spend time.

Are the other people in the workgroup, department, division etc. people who you can work with? Not exactly the culture question (but close), the reality for most people is that you spend a fair amount of time with people other than your boss, and it helps to feel that you can work with them. Many of the same questions above (values, styles, backgrounds, etc.) apply.

Is the overall culture of the firm something that fits you? This is a “Are your an entrepreneurial spirt in button downed corporate environment?” question. Culture counts; who want to be the swan hanging out with the ducks – and all their ways of behaving – if you can avoid it? Culture is the some of all the learned ways of acting, feeling and thinking in an organizations (or part of an organization) – it’s the “shoulds” and “we do it this way” that inform how people are supposed to operate.

Is it the right role in this firm? People can have the technical skills, but it may not be the right role for them because of where the role fits within the organization. If you’re a financial take charge guy in a firm that devalues those skills, the role for you may be a poor fit. If you’re more comfortable not being at the table (or even at the meeting), the role may not be a fit if being an active participant is part of the way the role works at this firm.

There also a roster of other things that albeit important, are less important to broadly determining right fit. These include:

  • Career track (if any)
  • Pay and benefits
  • Geographic location
  • Does the job fit into your lifestyle (long hours and you’ve got elder care parent responsibilities?)?
  • Any cache or stink to the role or company – will I have to explain to everyone why I worked at Enron, or alternately will association with the firm give me a leg up as I move forward?

While this list is ample, it may not be comprehensive. We all have personal career wars we fight (win some, lose some) and the danger is that we have our eyes out for what we know, and can be blind to what we don’t know. One of the reason it’s valuable to have a person career network, career mentors or people like executive coaches working with you is that they can help you vet poor jobs choices before you make them, and help affirm roles that you might otherwise be reluctant to take.


Life Back West is an occasional set of writings focused on ways people, teams and organizations can be both more effective (doing the right thing) and more efficient (doing the right thing well). More about executive, career and team / leadership coaching services can be found at the “About J. Mike Smith and Back West, Inc.” sidebar or the “Hire Me” tab above. You can also read an online interview with me at WhoHub, as well as participate in my learning community courtesy of KnowledgeCrush.


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