Career Decision – Stay or Leave

One of the most important decisions a leader can make in their role is “stay or leave.” Still, it is amazing how many otherwise very competent, seemingly successful people make a terrible decision. Be strategic with this decision. Is the feeling of career crisis due to a:

  1. Struggling business model?
  2. Bad boss?
  3. Acknowledge bosses change?
  4. Leadership void or crisis?
  5. The business model is under stress?
  6. Glass ceiling?
  7. Organizational perception of your capabilities or worth?
  8. A wrong decision or judgment error is putting you at risk?

You feel you may be at a fork in your career path. Maybe you’re not enjoying your work, culture, climate, or opportunity. Every role with every company has peaks and valleys, so the “stay or leave” decision should not be a knee-jerk to an isolated occurrence. Whether to stay or leave should be made as this valley persists or deepens. Let’s analyze each of these eight decision points.

  1. Struggling Business model – Is it temporary or long-term? Does the organization have a plan to get out of a bad situation? Are there milestones to improvement? If there are no plans and ways to measure growth (milestones), then it is time to take steps to leave. If there is a plan without milestones or if the company is continually missing the benchmarks, it is time to take steps to go. Continual progress toward an improved situation is essential to stay.
  2. Bad boss – A lousy boss 
    1. Blames others without accepting responsibility
    2. Fails to coach for improvement
    3. Seeks scapegoats for his or her failures
    4. Is over his or her head and as a result
    5. Manages to the lowest tactical level (micro-managing)
    6. Is disrespectful or abusive
    7. Fails to communicate organizational goals, milestones, and work purpose.
  3. Acknowledge that bosses change, and this might be a temporary situation. It is not uncommon bad bossing is seen from the top-down as well as bottom-up. Are there subtle indications that his/her boss is coaching the lousy boss? Is it likely the bad boss will leave or be reassigned shortly? If the answer to both of these is no, it is time to take steps to go.
  4. Leadership void – Is this due to a temporary management change or a long-term cultural problem. Leadership void is very similar to a bad boss but is more systemic to the organization and its culture. Does it seem the work and direction are rudderless, and this derelict wandering by the organization or department is continual? If so, it is time to take steps to leave.
  5. The business model under stress – We work in a very disruptive, competitive world today. New competitors enter daily with new offers and value propositions. Is the organization aware of these seismic shifts, or are they just doing business as usual? Are they monitoring and measuring the impact of disruption on their revenue, product adoptions, consumer expectations, or profits? If not, it is time to take steps to leave.
  6. Glass ceiling – Are you prevented from advancement because of your gender, sexual orientation, religion, or race? It is time to take steps to leave.
  7. Organizational perceptions of your capability – It is not uncommon for an excellent employee to be typecast after one mistake or miss-step. We all make mistakes or have a learning curve in the job that may result in an isolated and temporary performance issue. Can this perception be changed? Have you taken appropriate steps to change this perception, but it persists? If leadership cannot see you for your potential and continue to typecast you unfairly, it is time to take steps to leave.
  8. A decision or judgment error – If you make decisions, some are going to be wrong. You will make mistakes managing situations and people. Does your boss or the organization hold a grudge? Do you get appropriate coaching/training when you make mistakes and are allowed to learn from them and correct them? If the culture is to hold a grudge or not let errors to be opportunities to learn, it is time to take steps to leave.

This list of eight is representative of different forks in your career path. But there is another often overlooked situation where a natural leader makes a stay or leave decision. Have you ever been in a role that no longer inspired you, challenged you, or where you became complacent? Have you ever been in a position where your impact turned from significant to incremental? Have you ever gotten to the point where you have taken the department or organization as far as possible, and it was time to bring in the next person to take it to the next level? Are you not getting the trust and support you need to make the significant changes required to take the organization to the next level? This decision point is subtler, personal, and feels riskier, but when you get to this apex of the impact curve, it may be the best time to take steps to leave.

Once you decide to leave, build a bridge, don’t burn a bridge. Do the necessary work to set your tasks, projects, department, and direct reports up for success. Create a job description and skills inventory that your replacement will need to succeed. In some situations, you can be very transparent with your decision and offer to help hire a successor; this is rare but brings excellent value to the organization. You are leaving voluntarily, so be gracious and generous with your bosses, the company, and direct reports; don’t throw anyone under the bus. In your exit interview, be honest but respectful as to why you are leaving; always try to provide them with your insights to help them improve their situation.

In business today, everyone needs to own and manage their career. Thinking the company will return your loyalty or take care of you when times get rough is a grave career mistake. Hanging on just because that feels safer sets the stage for failure and low self-esteem. If we acknowledge these fundamental facts, we begin to make better stay or leave decisions.


Rich Jones is the Founder/Principal of Leading2Leadership LLC. Before starting his strategic planning agency, he spent over 20 years in leadership roles in the financial services sector. Before becoming an executive in the financial services sector, Rich was an entrepreneur, building and selling two businesses and working for early-stage start-up companies in executive roles in marketing, business development, and seeking investment partners. With more than three decades of experience, he brings innovative thought to companies and executives. Rich published “Leading2Leadership, a Situational Primer to Leadership Excellence.” The book is available on and was designed to be used as a book study for leadership development programs; it breaks leadership skills into manageable situations for discussion and reflection. Rich works with credit unions, CUSOs, and vendors, designing digital, data, culture, marketing, and branding transformation strategies. In 2014, Chosen as a Credit Union Rock Star by CU Magazine, and in 2018, Rich received the Lifetime Achievement Award from CUNA Marketing and Business Development Council. A Marine and graduate of Colorado State University, Jones shares his expertise at

Leave a Comment