How to Survive a Bad Boss

By Kevin Jennings, Founder and CEO, Junction 32

Kevin Jennings has done marketing and platform development with Orange, Tony Robbins, Oprah Winfrey, Dave Ramsey and many more. Kevin has also worked with me to help me launch much of what you read and experience—some of my books, my podcast and more. I’m thrilled to have him share some new insights on my blog today.  – Carey Nieuwhof

At 15 years old, I decided I wanted to be an entrepreneur.

Unfortunately, that decision doesn’t come with a cool story about my vision for the future or my natural entrepreneurialism. Instead, my first commitment to be an entrepreneur is a story about my first bad boss.

What most people don’t know is I got my first job at 15 years old working weekends at Chuck E. Cheese, an American entertainment center and restaurant for kids. To most people, I was another kid looking for money to spend on video games, but in reality, I was a kid searching for a way to make life a little bit easier for a single mother working five, 12-hour shifts each week and side hustling on the weekends to provide for herself and two sons.

When I started working at Chuck E. Cheese, I was greeted by a foreshadowing experience. Each weekend, my 23-year-old male supervisor would model leadership by smoking with underaged teenage employees, flirting with female minors, and having his young employees work until 2 a.m. Back then, Chuck E. Cheese closed at midnight on Saturdays, which still makes very little sense when most of the kids there are less than 12 years old and gone by 10 p.m.

So what was my response? I decided I’d one day work for myself.

I didn’t know what I would do, I didn’t know when I would do it, but I knew I did want to work for myself. Why? I felt deep in my inexperienced core that going to work should be and feel different than what I was experiencing.

Since then, I’ve worked with great organizations and served under great leaders who have pushed me and helped me to become a better professional and person. However, some of my professional ambition is attributed to my boss being a bad one.

With this in mind, I asked Carey if I could share the following three situations where my leader frustrated me and showed me how not to lead.

Note: Similar to the previous post I contributed to Carey’s blog, I’ve written this post with millennial leaders or new leaders in mind. My goal is to share what I’ve learned as soon as I’ve learned it to help my peers avoid the cynicism or disconnection that often affects leaders.

However, if you’re an experienced leader, I hope this reminds you of how valuable you are in the lives of the new and young leaders around you. Also, if you know you’re struggling with issues like cynicism, compromise, disconnection, or pride, you should pre-order Carey’s new book Didn’t See It Coming: Overcoming the Seven Greatest Challenges That No One Expects and Everyone Experiences.

I’ve already read some of it, and I felt like someone gave me a how-to guide on character development in critical areas of life and leadership.

1) When My Leader Chose Cash Over Culture

I was wrapping my first week at a new job, and my leader asked me to join him as he headed to his car. While we were walking together, he said, “Kevin, I believe you have potential, and I’m looking for a director to eventually lead this team. It’s too early to decide between you and your colleague. Whichever of you overtakes the other will become the director.”

Even typing the word ‘overtakes’ in relation to a teammate gives me icky feelings, but that interaction was an omen for the chaos to come. Over the next several months, I felt my relationship with my colleague shift from collaborative to adversarial, and I didn’t understand why.

I later learned my leader gave her the same speech about realizing her potential by overtaking me. Unfortunately, she responded literally by becoming guarded, working on projects by herself, talking over me in meetings, and taking credit for as many ideas as possible. A previously productive and energizing work relationship disintegrated.

As I was transitioning to a new role in another department, the cold shoulder of my teammate melted as I was no longer a threat; it’s how I learned what she was told. My last few days in that department led to me discovering my leader did this to two other members of the team that appeared to be adversarial as well.

Through my conversations with my leader, I learned he made a deliberate decision to use competition, secrecy, and the ambition of his team members to drive the performance of the department, even if it bred dysfunction.

Manipulating or coercing others to achieve a goal is gamesmanship, not leadership.

2) When My Leader Refused To Make Decisions or Disagree with Others

The new year is around the corner, and next year’s budgets are due. When I sit down to present my plan to my leader, I walk her through each line item and explain the purpose and desired result for each expense. Then, I wait for feedback.

I probe with questions like:

What do you think about the new initiatives I’m proposing?

Is it too much? Is it too soon?

Would our resources be better utilized another place?

Do my suggestions align with the leadership team’s vision for the next year?

The response: “Well, Kevin, it’s on you. If they have an issue with what you’re doing or how you’re spending money, be prepared to explain and defend your decision.”

That sounds like common sense, right? What’s the big deal?

Well, my budget comes from my leader’s budget, which makes her the first-line of defense against distracting or detrimental activities and the primary advocate for great opportunities. Essentially, she’s partially accountable for my decision being approved, right?

Consider this: There were many times when leaders from other departments would give me assignments or make requests of me that would take me away from my primary responsibilities, and my leader’s response was essentially the Nike slogan – “Just do it.”

In other situations, our team would come to a stalemate during passionate discussions about how to best achieve a goal or execute an initiative, then we’d turn to our leader only to be told “You must come to a consensus before we move forward.” (If you didn’t know, consensus kills courage.)

After seeing a smart, capable person consistently and intentionally elude decisions, disapproval, and conflict with redirecting questions or mirroring speech, I recognized my leader wanted to experience adversity-free leadership.

Unfortunately, leading without risk or responsibility is faux leadership.

3) When My Leader Put Power and Position Over the Team and the Mission

I once served under an amazingly gifted leader. Unfortunately, he wasn’t gifted at or interested in leadership. He was gifted at a particular discipline that led to him being elevated to leadership.

Who am I to make such claims? How do I know this? He told me. That’s right! My leader directly said, “I don’t like managing people; I’m not interested in it; I’m not very good at it; and I wish I didn’t have to do it.”

Sounds simple, doesn’t it? However, Solomon is clear about what happens when we excel in our work and what our gifts do for us.

My leader was talented, hardworking, and creative. He’s just not, well, a leader by his own admission, but it would be hard for most people (myself included) to turn down a promotion, especially one that comes with the status of being a leader. Being offered a leadership position is also validation of the potential others see in you, recognition of your achievements, and it typically comes with increased compensation. That’s a lot to walk away from.

For my leader, leading simply because he was selected or promoted made him a reluctant leader, and he often felt misplaced. However, he didn’t walk away from the position. He accepted and struggled. I have witnessed multiple situations where he’s been frustrated or when he’s frustrated others. He has decided the validation of the position is more important than the achievement of the mission.

How do great organizations prevent talented, skilled practitioners from being miscast as leaders? They respect and reward craftsmanship as much as leadership.

The Value of Being Shown How Not to Lead

These are three different stories of leaders I’ve worked for who have hurt their influence by manipulating others, abusing power, or prioritizing themselves over the team and mission. However, most of them made their decisions with the hope of enhancing or maintaining their influence, but, as a young team member, it didn’t take long for me to observe (or hear) the way people felt about these leaders.

I know there are blind spots and hidden factors that affect our abilities to lead well, and I have a lot left to learn.

As an emerging leader, these situations solidified the value of an anti-role model, a person looked to by others as an example to be avoided. As Carey has written here on his blog, “our problem often isn’t what we believe as an organization, it’s how we behave.”

So if you’re currently serving a leader that feels like an anti-role model, continue to work hard, serve him/her with excellence, and view every experience as a learning opportunity.

Discovering what leadership is not is as important as discovering what it is.

What’s something we can do to more intentionally learn from the decisions of other leaders?

Scroll down, and share your response in the comments.


  1. Kathy M on June 29, 2018 at 12:38 pm

    Thank you, Kevin, this post gave me insight into leadership problems I’ve encountered (and caused!) in past organizations. In one case the managerial team often filled open positions with people who were “available” and who had good intentions, but weren’t necessarily gifted for the role. I was one of those people. I had some skills that carried me to a point but eventually I felt I was being held accountable for results I wasn’t qualified to produce and decided to resign. Now I think one of the keys to discerning good leadership is evaluating whether they are systematically creating good leaders underneath them.

    • Lyn on June 29, 2018 at 7:23 pm

      “Now I think one of the keys to discerning good leadership is evaluating whether they are systematically creating good leaders underneath them.”
      I agree. It shows they are looking for new leaders and are willing to train them up into higher positions.
      It shows they are caring for whom they are working for and thinking of better ways to do things.
      It shows they care for and are encouraging the people around them. They are positive and caring.

  2. Dan on June 29, 2018 at 8:13 am

    Great thoughts, thanks it reinforced something my mom said “you can always learn something from anyone” even if it is how not to do something.

  3. Mark on June 29, 2018 at 7:05 am

    It was hard when I was a young leader sometimes to discern what was bad leadership when so many people with more experience assured me it was good leadership. Like some of the situations you describe above everything seemed to fall back on me and it didn’t feel right. Finally after years of struggle because I loved the ministry I got a leadership coach and a seminary degree in leadership. Outside perspective was very helpful in discerning the leadership in the culture. I spent many years trying to help leadership improve and came to the conclusion that you can’t change what doesn’t want to be changed. The leadership culture and theology of the organization was developed unintentionally to keep a particular leader in power and protect him from his wounds and non strengths. My coach helped me as I decided to leave to journal what I had learned about leadership on my way out. Much like what you’re suggesting here it’s a good exercise to prevent one from repeating what you just experienced. Thanks for sharing, it was helpful to me.

  4. Mike Duke on June 28, 2018 at 8:34 am

    Kevin, although I see no connection to ministry, you make some great points. I think most have had “that” boss. It’s quite difficult to see any good in them at the time as they loom over your subordinance, lie, manipulate and desperately want to make you more like them. It’s looking back do we discover that they help form our current being. Shining examples of what we don’t want to be and what we hope to be, all help to bring us to present day. What’s more incredible as we put our lives into perspective as a grain of sand, the very ones we perceived as persecuting us soon become a comfort as we realize they were simply a grain of sand as well adrift on the beach of a great wilderness. We all anxiously await the great wave to cleanse us, sort us and move us to a new place. Personally, looking back, I failed to see the reality of great suffering in “that” boss always reaching for something in the air or on Earth to help bandage the temporary sore of never having enough.
    Enjoyed the post. Thanks

    • Kevin B. Jennings on June 28, 2018 at 10:21 am

      Thank you for your poetic and thoughtful response, Mike. You’ve definitely given me so food for thought. I appreciate you taking time to read and comment. All the best! – Kevin

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