Photo credit: Kari Shea,

Your level of success in any career transition may depend on your “fit” in relation to your boss and the organizational business culture. How can you tell if you’re going to be thriving, growing, and effective or despairing, disengaging, and diminished?

Sometimes we’re so eager to take a new job, close the deal, and “win” the offer, that we may ignore signals that predict whether the next opportunity will be a great career move or a regretted choice. Perhaps we may even make a good choice, only to find our department is soon disbanded; the boss we had great chemistry with leaves; or our work description, project assignment, and role changes.

Given most of us will make several career and job transitions, it’s important to “sniff out” problems that can derail us. Since no situation is perfect, be prepared to pivot and be flexible, but we should also become more discerning in judgment.

Don is a finance executive in mergers and acquisitions in the technology sector. He attended top undergraduate and graduate universities in finance, and specializes in evaluating companies and making deals. He has worked both as a deal broker and within a large, multi-national corporation in acquisitions, so he has good experience on both sides of deal negotiation. Satisfied in his career choice, Don is very good at what he does and wants to be on his way to an upper management position.

Yet, Don has had widely different experiences in how well he fits and works with his bosses. He attributes this to the character and style of his respective management teams. He also recognizes that he resonates with certain work styles and personalities, and considers that over the years, he has become far more attuned to his own work inclinations and success factors. Self-awareness — based on lived-in experiences — becomes the first necessary component to measure one’s potential comfort level in a new position or circumstance.

Reflecting on his past experience, Don recognizes that his unhappy situation with one boss could have been anticipated had he listened to his own “little voice” (that internal gut check) that recognized the signals. However, he was so eager to leave his previous position that he just wanted to plow ahead.

So what did he perceive that warned him of a bad match?

Don interviewed former clients and current workers about the boss who owned the firm, the same person that would be his direct report. Clients who had contracted deals said they would never do another deal with him. Current employees said he exaggerated and had a huge ego. The firm was a “revolving door” for past professionals who left after a year or two.

Don heard and saw trouble ahead, but suppressed his concerns. Soon he experienced a toxic relationship with his boss that he had to “manage”. Don became angry, resentful, and disdainful, but stayed for years in the hope that he could just “stick it out”; however, he recognized his contempt for the boss was diminishing his engagement with the work itself and his interest in his career.

With some coaching, Don started to look outside the firm for his next opportunity. He carefully cultivated relationships with some managers at a large multi-national corporation he had done business with, and let them know he was interested in a move to their company. He was attuned to the style, culture, and the character of the CEO, who modeled humility, collaboration, and competence.

Don astutely asked the HR manager, “Are people scared of the CEO?” Great question! While almost all decisions were made from the top, the managers wanted to perform their best so they could impress and earn the confidence of the CEO.

Don communicated he believed they were a great team. He wanted a position that he could grow into over the long term. After some negotiation and discussion, the firm created a position for Don, because he was a good match for them and they saw his potential to be a great, next generation C-suite executive.

Don is now thriving, happy, and growing in his newfound position. He has expanded responsibilities, believes he is being groomed for an upper management position, and has great relationships with the CEO and his peers.

There was nothing “wrong” with Don in his unhappiness in previous positions. He did not need to change industries or make a transition into another area of expertise. Finding the right “fit” for him, with a team he could trust and who was invested in his career development, made the transition easy. And Don was able to perform in a better human environment.

What are your values? How do you best collaborate with others? What kinds of relationships do you wish to have with your teammates? Comment below and perhaps you’ll have an “ah-ha” moment of your own!