Even Good Leaders Get Derailed

Living and leading in challenging times can bring forth our best qualities.  But when experiencing stress, even good leaders can get derailed.  When the context changes, such as it did for many leaders when the pandemic hit, their strengths became their liabilities and things quickly began to fall apart.  

Take for example, Taylor, Simone and Andrea, each of whom were very seasoned and successful school leaders.  All three were admired and well respected for their work in their learning communities.  They all found joy in their life calling and were personally and professionally fulfilled…until March 13, 2020, when their worlds suddenly changed.  With the sudden onslaught of the Covid-19 pandemic, a new norm was upon them.  The skills and mindsets that brought each  of them much success throughout their careers suddenly weren’t working for them.  Under this stress, their leadership began to derail.

Taylor was a good thought leader for their school.  They were regarded as a good thinker and coach; able to bring people together around new ideas and careful consideration of new ways of doing things. They were soft spoken yet personable and supportive; well liked by their team and community.  But Taylor was tripped up by their inability to make quick decisions, such as were required under the Covid-19 circumstances.  The care and thoughtfulness they typically would take in leading their team and making decisions was derailed by the need for swift action.  The pivot to online learning and virtual engagement for their school’s students took much longer than what most parents, students and teachers needed.  As Taylor lamented and labored over what to do, their delays caused considerable frustration and a loss of trust in their ability to lead. When facing challenges, Taylor’s tendency was to take flight — delaying difficult decisions, avoiding uncomfortable conversations, and retreating to the safety of their comfort zone.

When facing challenges, Taylor’s tendency was to take flight

Compared to Taylor,  Simone was a bold and colorful leader.  She moved through her day quickly and decisively.  Her charisma, charm and warm smile quickly drew people to her and gave everyone a sense of confidence that she could lead the community, even in challenging times.  This was all true; except when the tables were turned and the pandemic changed the script.  Simone wanted immediate results and demanded that her direct reports change gears suddenly, without giving them thoughtful direction as to how to adjust.  Their fears of the unknown were quickly dismissed by her as weakness and ineffectual leadership.  Simone demonstrated little empathy toward those who were struggling. 

When things got tough, Simone’s tendency was to engage in a fight — failing to find the care and sensitivity necessary to lead people in the midst of their anxiety and uncertainties.

And then there was Andrea;  an excellent planner and organizer and as such, led their school with careful precision that resulted in a smooth running operation.  Everyone knew where to go, and what was expected of them.  Their handbooks were impeccable and their new teacher orientations were precise, thorough and punctual.  Their leadership strength served them well when things were running smoothly.  When the pandemic hit, Andrea’s leadership got derailed.  The perfectionism they demanded from their team sent everyone reeling.  With new information coming at them daily at a frantic pace, their inability to drink from the fire hose of data proved more than they could handle.  Andrea became not only demanding of their team, but personally agitated and was difficult to be around; listening less and less to their team and burning bridges along the way.  Andrea’s need to plan was derailed by the organizations need to adapt. 

Under stressful circumstances, Andrea needed to be right. It was their way or the highway and it led to the team’s declining trust in their leadership.

How can we as leaders, like Taylor, Simone and Andrea, avoid these derailments?  It’s more than simply knowing our strengths, as important as that is.  It’s equally as important to have a keen awareness of the aspects of our personalities and work styles that can knock us off course in times of stress. In difficult circumstances, strengths can become liabilities - Taylor’s thoughtfulness and affability got in the way of quick decision making; Simone’s charm and bold personality got in the way of her ability to be humble and empathetic; Andrea’s need to plan and organize got in the way of the need to pivot and be flexible.


At the end of the day, how will you avoid derailment in these difficult days?  

  • Can you find ways to avoid the flight from the challenge and resist retreating to your comfort zone? When confronted with challenges, it’s important that we find ways to lean into the difficult tasks and conversations and make them a priority.  

  • Can you find ways to deescalate the fight when things don’t go according to your plan?  Empathy, in stressful times, goes a long way in healing the pain people are experiencing.  It’s vital for leaders to be able to demonstrate this.  

  • Can you seek and listen to the wise counsel around you and avoid the need to be right? Humility is an essential attribute to nurture, especially in times of crisis when you are in charge. You don’t have to have all the answers.  Surround yourself with those who can help and generously and sincerely give them credit.  

Stay well…and keep on the rails.  We’ve a long journey ahead.  

Carter Hollinger