Is He or She the “Right Supervisor?” – Connect Some Dots 

One of the exercises we encourage people to go through as they consider where they would like to next work is to reflect on 3 jobs. What was their first job? What was their worst job? And finally, what was their best job? 

As you can imagine, over the 18 years I’ve been doing this exercise, I’ve heard some incredible answers! Some inspiring, some funny, some sad, and some predictable. One of the predictable outcomes, which happens with all too much frequency, relates to the worst job scenario. As the story unfolds, a common root cause which led to the worst job situation is the person’s supervisor. All too often, what started out as a good, or even neutral, relationship turns bad and leads to a really bad work experience. 

Why do I refer to it as predictable? Because years of research and literature has consistently shown the number one reason people leave positions is due to their relationship with their supervisor.   

Relationship with Supervisor

How does that happen? After all, it’s almost unheard of for a supervisor not to directly interview a candidate. It’s the supervisor’s decision to hire the candidate. It’s their choice to make the offer, and it’s the candidate’s choice to accept the offer. So how do two consenting adults agree to enter into a working relationship that later on doesn’t work? 

The answer to that question doesn’t take much thought, actually and unfortunately. “Human beings are the trickiest mammals on the planet,” stated Matthew McConaughey, and while I agree with that statement and it’s latent outcomes, a more tangible root cause answer is given in various Scriptures. 

Jeremiah 17:9 “The heart is deceitful above all things and beyond cure. Who can understand it?” tells us that our flesh isn’t naturally good, and that due to the Fall, we can’t expect human efforts to create lasting relationships. Proverbs 17:9 states, “Love prospers when a fault is forgiven, but dwelling on it separates close friends.” As most of us have experienced, love and forgiveness are difficult. For some reason, even more so with working relationships. Proverbs 18:19 explains, “An offended friend is harder to win back than a fortified city. Arguments separate friends like a gate locked with bars.” I could go on and on with quotes and stories throughout Scripture about broken and failed relationships. 

Ok, so that all sounds like a huge downer! We have to work with others, so how can you find a supervisor with whom you can develop a healthy, positive relationship? This question is what we’ll be dealing with for this month, as there are various ways to appropriately investigate whether you’ll be the right fit for the supervisor and vice versa. 


As with many complex situations, the first step is to begin with some fundamentals. For me, the first fundamental is alignment. Is the supervisor’s personal mission and values aligned with the organizational mission and values? Here are some questions to ask your potential supervisor that will give you some insights into this question: 

  • How do you put into practice the organizational mission and values? 
  • What are your personal values?  Personal mission? 
  • Why are the organizational mission and values important to you? 

Within a supervisor’s answers to any of those three questions will be some significant signals for you to take note. Much of a relationship depends on the foundation, and if the supervisor is aligned and personally wedded to the organizational mission and values, whenever conflict arises (and it inevitably will), you will have a solid grounding to base your reconciliation upon. 


Another fundamental for me is clarity. How clear will the expectations be that the supervisor outlines? Here are a few questions to consider to get after that: 

  • What are the initial expectations you would have for me to accomplish in the first 30 days of my employment? 
  • When you communicate new expectations to me going forward, how have you found it most effective for me, as your direct report, to be clear and aligned with you on the path forward? 
  • If I’m not clear on your expectations, how would you like me to bring that to your attention? 

Too many relationships crater because expectations are not clearly set or executed upon. So why not lay out the groundwork to figure that out before you start? 

Work takes up too much of our life to go through it with unhappy relationships. And if you’re unhappy with your supervisor, life won’t be enjoyable at all! 🙁 Take the time to go through a sound due process to connect some dots with your potential supervisor. You won’t regret it! 

Dave Sparkman currently serves as the volunteer Crossroads Career board chair and local ministry leader. He is also the founder and managing director of Spark Your Culture, a corporate culture consulting firm. Prior to that he worked at UnitedHealth Group, a Fortune #5 public company, serving in the role of Chief Culture Officer. His unemployment experience came from the implosion of Arthur Andersen, where he served as the West Region Managing Partner, People. 

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