5 Extraordinary Lessons that I Learned from the Worst Boss I Ever Had

Bad Bosses Can Teach Us Great Lessons to Become Extraordinary Leaders

During our careers, we will interact with dozens of Directors, managers, supervisors, and whatever title another human named others to oversee your R&Rs (roles and responsibilities) in your organization; but let’s call them bosses in this story. Some will be great; understand their position and strive for your personal best to support your development and life-work balance, adding joy and purpose to your career. But everything can happen in a VUCA (volatility, uncertainty, complexity, and ambiguity) environment. ?Other leaders, well, you probably experience the misfortune of working with a bad one who misunderstood his R&Rs and thought he oversaw your life.?

Once upon a time, I believed I could only learn from the most outstanding leaders and inspirational bosses I encountered in my career path. Until I worked for Adolf, I realized I could take advantage and learn relevant, life-changing leadership lessons from even the worst bosses.

It may seem a paradoxical concept, but no. Learning from bad bosses was the inspirational method I used as the first aid kit to survive that uncertain time and maintain and keep track of my career and spiritual and mental health. I learned from his mistakes and what?I would not do to others as a leader.

Having that in mind, let me tell you what I learned from Adolf, the worst boss I ever had. Some of this storyline is narrated in the voice of Magno, the book’s main character: “ Magno: El Viaje al Corazón de un Líder” (Spanish Version).

This is Adolf, The Worst Boss I Ever Had

Before I began reporting to Adolf, I had never interacted with him. Nevertheless, I had heard good feedback about him. There’s such a good thing that I desired to work in his organization at some point.

Adolf was sociable, cracking jokes always; he sat at your site in the cafeteria to gain your trust, proposing exciting conversations. He was a natural storyteller with a beautiful sense of humor; he also was kind. Adolf has it all, guys, a genuinely “motivational” person.

Nonetheless, Adolf was the other side of the coin as a boss. He was terrible, disorganized, neglectful, and lacked attention to details about his actions and consequences.?In short, he was a total disaster in his professional aspect.

So, regardless of his “friendly personality,” his leadership competencies were subpar, to say the least – in correlation to how high he was on the organization ladder.?

I worked for Adolf for three and a half years. That period provided me with firsthand experience of working under a really bad boss's leadership.?There were moments when I would ask myself:

• “Am I responsible for this situation?”
• Why am I feeling so broken or incompetent in this situation?”
• “Do I act like this with?my?direct reports? I hope not.”

This work-life experience taught me many suitable leadership lessons and reaffirmed my virtues, work ethic, and leadership skills that I already knew I had but needed to believe more in me.

Here are those five things:

1. A Job Opportunity is not necessarily a Development Process; Not All Roles and responsibilities are Adequate for Everyone

Adolf used to be an upper management boss near his retirement. His performance was declining. Instead of providing genuine feedback to support him, Adolf Boss passes the ball and assigns him to another R&R at a lower management level. Nobody takes care of him to overcome his flaws. Probably it was easier to transfer the problem to other hands. With that demotion, however, Adolf suddenly became responsible for an organization ten times lower than the role he had held for the prior year.?

The results of this situation become apparent after just a few short months – because of that demotion, Adolf went from being an upper-level boss of a massive team to being an overwhelmed head of the smallest organization. The demotion was too far, too soon, without any feedback or support to manage that transition.?Perhaps with a Performance Improvement Plan (PIP), he would have the time to settle and learn from his setbacks to better adapt to the new R&Rs.?Although, after watching him struggle for three years, it is more likely that Adolf interpersonal, leadership skills and talents were not suited for the new endeavor.

Ultimately, watching Adolf’s situation demonstrated that not all people are fit for all roles, projects, or functional areas.?While Adolf had his strengths and talents, masterfully filling the new lower role was not one of them.?He has too many years in upper-level management that demotion at that moment of his career was just unacceptable for him.

In a demotion or a promotion, we need to be more critical and selective; we must be to ensure we hire the?right?talent. A genuine leader must support uncovering people’s purpose to unleash their potential. Purpose can unlock unique hidden talents and virtues. A work environment that supports and focuses on people’s purpose can lead to the following:

• Many improved outcomes: physically, mentally, and emotionally, by clarifying what matters most to the employees in alignment with business needs.
• A purpose approach pursues opportunities to discover the most meaningful and satisfying fulfillment that brings people the best in work and life.

I also learned from this particular that we need to be a coach and mentor for our people, no matter the management level you are on the organizational Ladder. Serves as a guide to people to unveil their:

• Identity: Who am I? What are my experiences? Where do I want to be in the future?
• Purpose: What things bring joy and meaning to my life? What is my purpose in the work and personal environment?
• Career: What meaningful objectives do you want to accomplish in alignment with your purpose? How can I experience an explicit purpose in my professional career? What is my compelling cost?
• Actions: You need to create your development plan, which is YOUR; own it. What resources or support do you need? What is your commitment to your development? Do you have a roadmap to guide you through uncertainty?

2. Be a Role Model, Whit High Standards to Generate Trustful Relations

After the first month of the new assignments, Adolf’s conduct becomes more and more evident. He was not present or accessible to the new team. He communicates with only his past upper management bosses and doesn’t make himself available to address team and project needs. Sometimes, in meetings, he expresses his misfortune and frustration with the new R&Rs, making the team feel inferior and nullifying their opinion and contributions. He doesn’t accept the demotion and the area and crew. It was just punishment, an anchor for his career path. In addition, he also demonstrates a lack of technical, compliance, and decision-making knowledge. His decisions were not assertive or in compliance. The team provided different alternatives, but rapidly, he stepped over by stating: “This is my decision, and at the end of the day, I’m not responsible for explaining them; by that moment, I will be retired.”

It doesn’t seem right that team members have escalated this situation to other bosses. Unfortunately, they are Adolf’s past partners or direct reports and don’t take the team’s feedback seriously. The following are some of the statements of other bosses after the escalation process:

• “Adolf has this in control; you must believe in him.”
• “This Team is just struggling with Adolf’s high standards, gave him a break.”
• “Hey, Team, you just need to surf the wave; we are on the right track.”
• “Forget about was his saying; he will be retired soon.”

But what I learned from this?

Be a Role Model:

• Your behaviors and actions have a direct impact, no matter whether you have a clear intention or unconscious bias.
• If somebody is in a leadership role, you must understand that your R&Rs are no longer only about you as an individual contributor or your development process. It’s about how your decisions support or negatively impact your team members; this is a critical responsibility.
• Your team will always try to demonstrate what is okay and what is not. Therefore, leaders need to separate quality times to provide individual guidance and present with active listening in the conversations.
• Remember, it’s not by what you say but by what you do or act.
• Modeling engagement, energy performance, and genuine care can significantly improve an emotional benefit to the team.

High Standards are for All:

• A leader needs to pursue high standards, with solid ethical conduct that backs up her character and standpoints, to achieve sustainable growth in the business, as well as people development and trustful relationships.
• Our responsibility is to create an environment of compliance and guidance for our team.
• Leaders should know the compliance requirements for their project and functional areas and create an environment that enables the team to achieve goals in a compliance parameter.
• Communicate regularly with team members about compliance, quality stage gates, and third-party checkpoints, which can mitigate risks and settle a good compliance foundation.
• Leaders must regularly assess key compliance metrics and efforts to monitor team performance and provide guidance and direction. A leader can hold the team accountable for delivering results by doing that.
• As leaders, we are responsible for following processes and policies.
• Leaders must conduct continuous and meaningful conversations to support team performance and ongoing development.

Generate Trustful Relations:

Leaders need to be coherent:

• With positive thoughts without hidden agendas
• In alignment with credibility in their words
• Reliable in their actions
• And authentic in their behaviors.

Building trust in a relationship takes time and massive effort. But it is achievable if the leader has a genuine purpose of delivering results through others. The following are some simple actions that I learned from Adolf, not because he does them, but because of the lack of them and my desire to have these experiences with him:

• Allow honest and open communication; feedback is not good or bad; it’s feedback, and leaders must provide it and allow team members to also provide feedback to them.
• Being transparent about your decisions.
• Getting to know your team as individuals, learning about their personalities, ideas, desires, struggles, and fears.
• Create an atmosphere of safety by communicating your vulnerabilities and how the team members can support you and the rest to become better professionals and teams.
• This feeling of safety will make your team more comfortable sharing experiences and ideas and provoke an innovative environment.
• Expect failure and stop micromanaging. Allow your team space to fail to ensure learning from setbacks. Any member’s failure is the team’s and leader’s failure. Be there for them for the lessons, not to pursue the responsibility.

3. Connect with Your Team and Delegate Efficiently

Regardless of how he became a lower-level boss, in Adolf’s defense, he never had the opportunity to present a performance improvement plan.?He was near to accomplishing the extraordinary milestone of retirement. He deserves better, a chance, and not to be discarded; what about their past accomplishments? Is this the way that organizations treat persons near retirement? Those are some of the reflection questions that I ask myself. Although he went to great lengths to show he could satisfy his new responsibilities, it was noticeable that Adolf was uncomfortable in the new role.?He struggled to keep on track with essential and critical things. Adolf’s conduct gradually affected the organization underneath him as time went by.?Eventually, it hurts team morale, and team members become frustrated by the lack of clear direction, misleading messaging, and the perception of total disorganization.

No matter how often team members offered support and new ideas, Adolf left us on the sidelines. I was frustrated seeing how Adolf made one terrible decision after another; the team felt overwhelmed, and there was no other place to escalate the situation. Genuinely Adolf tries to fulfill on-time commitments, but he’s stubborn and does not accept team members’ opinions and help. In desperation, he delegates critical activities to members without the knowledge or experience to complete the task and neither provide them coaching nor mentoring to ensure success. He wants to finish at whatever cost. One time, he expressed that if he finished before retirement, he would probably be eligible for a bonus. My God, are those genuine inspirations/compensation for a frustrated, demoted boss?

But what I learned from this?

Connect with your Team:

• Helping your direct reports to learn new things, grow, and maintain inspiration and motivation is not a punishment for more work; it’s the privilege and honor that provides you satisfaction as team leaders.
• If you want to succeed, you need a team. Get out of your office and know them. They are unique individuals with unique needs that require your attention. There is no strategy; one size fits all.

As a leader, consider this formula: Situation + Person = Leadership style. In other terms, you need to be a situational leader. ?The following are some leadership styles that can help you through the process:

• Authoritarian Leadership (Autocratic): Authoritarian leaders, also known as autocratic leaders, provide clear expectations for what needs to be done, when it should be done, and how it should be done. This leadership style is strongly focused on both command by the leader and control of the followers. There is also a clear division between the leader and the members. Authoritarian leaders make decisions independently, with little or no input from the rest of the group.
• Participative Leadership (Democratic): Participative leadership, also known as democratic leadership, is typically the most effective leadership style. Democratic leaders offer guidance to group members but also participate in the group and allow input from other group members.
• Delegative Leadership?(Laissez-Faire): Delegative leadership, also known as laissez-faire leadership, was the least productive style. Teams/groups can make more demands on the leader, show little cooperation, and cannot work independently. Delegative leaders offer little or no guidance to group members and leave the decision-making up to group members. While this style can be helpful in situations involving highly qualified experts, it often leads to poorly defined roles and a lack of motivation.
• Transformational Leadership: Transformational leadership?is often the single most effective style. This style was first described during the late 1970s and later expanded by researcher Bernard M. Bass. Transformational leaders can motivate and inspire followers to direct positive change in groups. These leaders tend to be emotionally intelligent, energetic, and passionate. They are committed to helping the organization achieve its goals and helping group members fulfill their potential. Research shows that this leadership style results in higher performance and improved group satisfaction than other leadership styles.?One study also found that transformational leadership improved group members' well-being.
• Transactional Leadership: The transactional leadership style views the leader-follower relationship as a transaction. By accepting a position as a group member, the individual has agreed to obey the leader. In most situations, this involves the employer-employee relationship, and the transaction focuses on the follower completing required tasks in exchange for monetary compensation. One of the main advantages of this leadership style is that it creates clearly defined roles.?People know what they are required to do and what they will receive in exchange. This style allows leaders to offer much supervision and direction if needed. Group members may also be motivated to perform well to receive rewards. One of the most significant downsides is that the transactional style stifles creativity and out-of-the-box thinking.
• Servant Leadership: From the Project Management Institute (PMI) perspective, a servant leader is a leadership style that focuses on serving and supporting the needs of the team members. It is a model where the leader's primary goal is to empower and enable the team to achieve their objectives rather than solely focusing on their own authority or control. In the context of project management, a servant leader understands that their role is to facilitate and remove obstacles for the team, ensuring they have the necessary resources, support, and guidance to deliver successful projects. They prioritize the well-being and growth of their team members, fostering a collaborative and inclusive environment. A servant leader also promotes open communication, active listening, and empathy. They encourage team members to share their ideas, concerns, and feedback, valuing their contributions and perspectives. By being approachable and supportive, a servant leader creates a safe space for the team to thrive and take ownership of their work. Furthermore, a servant leader leads by example, demonstrating integrity, humility, and a commitment to the team's success. They inspire and motivate the team members, encouraging them to reach their full potential and fostering a sense of trust and respect. Overall, the servant leadership style, as viewed by PMI, emphasizes the importance of putting the team's needs first and empowering them to achieve their goals. A collaborative approach fosters a positive work culture and enables project success.

Therefore, the best way to apply leadership styles and demonstrate competencies is by getting to know each team member and recognizing them as unique individuals. These questions will allow you to understand people better:

1. What motivates them?
2. How do they like to be recognized?
3. In what areas do they want/need to develop capabilities?
4. What is their current/ongoing workload?
5. What are their current/ongoing levels of stress?
6. What is their current/ongoing Job satisfaction?
7. What strengths do they bring to the team?
8. What motivates and drives each person?
9. What are they passionate about?
10. What strengths do they bring to the team?
11. What kind of problems have they wrestled with in the past?
12. What did they learn from setbacks?

Delegate Efficiently:

Adolf’s desperation to complete his project duties lead him to delegate to the incorrect persons. But how can we delegate efficiently? The following are some questions that can support you in the delegation process:

1. What is the task/objective?
2. Why did you select this for delegation?
3. What is the goal of the task/objective?
4. What does a good job look like?
5. When does it need to be done?
6. What level of direction and support do you think this person will need to be successful?
7. What assumptions are you making that you need to verify?

After you have a clear answer to those questions, you can now plan a conversation not to throw more work onto your direct reports’ plates but to have a meaningful and engaging partnership conversation. Follow the following steps to prepare yourself in advance before the meeting date, and avoid improvisation:

1. Describe the task/objective
2. Provide clarity
3. Check your assumptions
4. Determine the level of support, urgency, etc.
5. Define a plan
6. Explain the success performance index to your team member and how he will be recognized to celebrate success.

4. Provides Genuine Feedback

Adolf has a misconception about what feedback is, what coaching is, and what mentoring is. He tries to do it, but as a result of his conversation, the team feels more like he is communicating an order, a punishment, or just pointing out the team’s flaws without a clear description of the behavior, impact, or path forward. Nobody is a minded reader. If a leader wants his team to perform well, he must give feedback to them clearly and regularly. If the team doesn’t know your standards or expectations, it's doubtful that the person or group satisfactorily completes an objective. Unfortunately, Adolf tends to use the most common way of feedback; it is something called?the sh*t sandwich.??How the sandwich works:

• Before you give critical feedback
• Start the conversation with something positive about the team/person.
• Then, provide critical feedback.
• Close the conversation with something positive, hoping that the person takes it clearly and positively.

The sh*t sandwich feedback can generate adverse outcomes because:

• There is no clear situation definition: the impact of the conduct involves the reflection process that the person/team is not addressing to ensure an action plan for a future state. In addition, Adolf’s feedback looks improvised, lacking facts and technical data to back up the conversation.
• The feedback isn’t clear: A potential disadvantage of the sandwich feedback method is that it can cloud the message and make it unclear. It can also generate cognitive confusion in the person/team: “So, did I do a good job or not?”.
• Using terms such as “but” can undermine positive performance: Have you ever been in a “feedback” conversation with a boss that stated: “You did this great but…”. Or you’re doing an excellent job, however…”. The usage of “but,” “however,” generates a negative outcome, because you will be leading people to defensive thinking; distrustful of praise, feeling like it will always be followed up with a?but?statement. It can be better for everyone to eliminate those terms from the conversation and include a reflection connection: “Perhaps,” “In addition to,” etc.

But what I learned from this?

Plan My Feedback Conversations:

• Before calling somebody for feedback, prepare yourself, collect all data, confirm assumptions, and challenge your bias with information, interviews, and facts. Lacking preparedness could lead you to lacerate a relationship by pointing out a non-confirmed situation.
• Ask open-ended questions to gather information and genuinely understand people’s and team’s points of view. Asking closed questions will only lead you to a “yes” or “no.” As a leader, you need to explore and generate powerful reflexive questions. Remember, you need data; ask from curiosity, not from an accusatory platform.

Once you confirm the conduct, non-conforming, or whatever other reason leads you to provide feedback, you can prepare yourself to follow these steps:

1. What is the subject to be addressed: Be clear that you provide feedback and focus on validated behaviors or conduct, not the individual. Remember, you don’t want to hurt people or team morale.
2. Describe actions observed and confirmed, provide specific examples, forget about your opinion or judgments, and stick to the facts.
3. What is the impact of the behavior or conduct? This is critical; you need to allow space for reflection so that team members have the opportunity to evaluate the magnitude of the situation.
4. After the reflection process, elevate your team members' morale and help them to build a remediation plan. Continue asking open-ended questions to ensure a reformative and reflexive plan.

Feedback, Coaching, and Mentoring are not the same:

Feedback: is the communication of a well-intentioned evaluation derivate from correction about an action, event, or situation that does not comply with the expected results.

Coaching: The International Coaching Federation (ICF) defines coaching as partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential. The process of coaching often unlocks previously untapped sources of imagination, productivity, and leadership.

1. Coaching is not therapy: because it doesn’t treat medical pathology and hasn’t worked in the past.
2. Coaching is not training: Coaching is based on a process of co-creation with the guidance of the coach, but the coach does not “impose” their agenda and, in a strict sense, should not give orders or prescribe what the client should do.
3. Coaching is not mentoring: The mentor is a subject matter expert in a specific topic and guides the steps of the mentee because they have already lived through similar situations and, therefore, have the knowledge and experience to know what is the most appropriate in each case.

Mentoring: This is a beneficial relationship and should also be sought for career and personal growth, yet it is more directive and is different from coaching, where the coach aims to help you find your answers so you can take ownership of your path forward.

5. You can Learn in a Chaotic Environment

Certainly, Adolf has his own situations to overcome. I think that he just was a victim of the system. It is a pity that he had to experience all those situations in the twilight of his career. In my reflection conversations with Leví (Leví is the 2nd main character that interacts with Magno; in the book: Magno: El Viaje al corazón de un Líder (Spanish version)), I put myself in Adolf’s shoes and start thinking in the following:

• “I am a good leader?”
• “How will people remember me after retirement or transitioning to another role or organization?”
• “Do I have the right resources, mentors, and coaches to evolve into a continuous improvement as a leader?
• “Am I in the right organization?”
• “Do I add value to my organization and nation?”
• “What else can I do to support other leaders?”

I am still in the reflection process about it. Another boss left behind Adolf; he did the same with his team, but their partners took a long view of this critical situation. At some point, Adolf retired, and I feel wonderful for him; I understand he is living an extraordinary life with his family; well deserved, Adolf.

But what was the cost of this situation?

• A team with hurt morale. After the facts, another boss was assigned to the area; the new boss did not want to manage the past and provided a good healing environment to lift team morale. Instead, he moved forward with a “Kumbaya” activity to override what happened, and the cycle started over again. Lifting team morale requires commitment and time, which some organizations typically lack.
• The healing process hurts: we need to be open to ruthless feedback to recover people’s trust.
• Cause and effect are universal laws. If you make a wrong decision, you will have bad results that lead to re-work, delays, and non-conformances and cost you more.

But what is the most extraordinary thing that I learned?

Simple, is called ETHIC, do the right thing regardless of if the results affect me or not. Is every leader ready for this? Probably not. The ego intervenes in human behaviors, and individuals seek personal benefit.

Life will always present situations, challenges, and problems that will put our values to the test. What should we do? Unwaveringly, we attend to those issues without negotiating the values that define us as individuals. In our lives lies the law of cause and effect; every decision we make, depending on where our foundations lie, will have a consequence. It is not necessarily the case that making decisions consistent with our values will lead us to the green pastures of happiness and peace.

This was the case with Martin Luther King Junior, Gandhi, Malcolm X, and Joan of Arc. They defended their values until death. This makes me reflect: Am I a person who thinks, acts, and behaves according to my values regardless of the consequences? Or do my values give up during adversity?

Seneca, Epictetus, and Marcus Aurelius tell us about four pillars that makeup a morality from a Stoic philosophical perspective. This foundation constitutes the virtues that every human being should consider in their walk-through life:

Wisdom: we need it to know what is coherent with our being and what is not; in this way, we will be able to choose the values that best represent us. Wisdom helps us to place ourselves as observers in certain circumstances or situations in which we have to see ourselves from a general point of view. The Stoics divide wisdom into:

• Mental acuity
• Astuteness
• Discretion
• Ingenuity

Justice: it is the second pillar of Stoic morality. Justice, as understood by the Stoics, is not to comply with the law but a mixture of ethics, equity, and honesty. It is to respect, give every one what is theirs, and practice wisdom in the face of injustice. Justice is divided into four subcategories:

• Piety
• Fair treatment
• Honesty
• Fairness

Courage: this is the third pillar. It can be called courage and is the act of doing what is right in unfavorable situations, such as danger or pain. According to the Stoics, courage should be manifested both physically and mentally. On the physical level, it protects us from the harshness of the external elements, and on the mental level, it builds strong willpower that makes us comply with our values when life takes us out of the path we had established. Courage is subdivided into:

• Resistance or resilience
• Confidence
• Positive mentality
• Cheerfulness Ability to work alone and in a team

Temperance: the fourth and last pillar. Temperance is the control we have of our emotions and ourselves. Equanimity and wisdom in the face of passions and vices. It constitutes self-confidence and autonomy in the face of life's setbacks. The Stoics divide temperance into:

• Discipline
• Decorum
• Modesty
• Self-control

The subject of moral and ethical values is a hot topic and a good one to discuss with a good group of people who have leadership in academia, churches, organizations, and communities. As leaders, Let’s reflect on these questions:

• What are the three most important values in your life?
• Mention a situation in which you have used your values to make decisions.
• Were the decisions you made based on your moral values the right ones?
• What would you have to change or integrate?
• How would you achieve these changes?
• Considering your values, what would you rely on to create unwavering behavior?
• What are you tolerating in your life, and what would you not like to tolerate anymore?
• What resources do you need to achieve your well-being?
• What are the most critical pillars in your life?
• On whom or what do the results of your life depend?
• How will you know that you are achieving unwavering behavior?

If we all asked ourselves these questions from time to time and genuinely respected others, this world would be a better place. Let’s spread love instead of fear. We are all beings of light, living a mortal human experience. May our lives not be wasted, pointing fingers at each other. Adolf, you were the perfect teacher the universe sent me to make me a better person and professional; I owe you a lot.

Magno,

Magno: El Viaje al Corazon de un Lider

?Reference:

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Additional Reading

• Hersey P, Blanchard KH.?Management of Organizational Behavior: Utilizing Human Resources . Prentice Hall, 1969.
• Adapted and extracted from the internet: 10 Things I Learned from the Worst Boss I Ever Had; https://www.managersresourcehandbook.com/lessons-from-bad-boss/
• Story adapted from Alexander Carrasquillo. Magno: El Viaje al Corazón de un Líder”. La Pan House; 2021Bad Bosses Can Teach Us Great Lessons to Become Extraordinary Leaders