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3 Times My Leader Frustrated Me to Help Me (A Millennial’s Insights)

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 insights on my blog today.  – Carey Nieuwhof

It was five years ago when I first acknowledged to myself, “I am a leader.”

At the time, I was 28 years old and up to that point, most of my professional accolades were attributed to my success as a practitioner (in my case, a marketer). I had not yet had any direct reports, but I had successfully led a few project teams.

Still, I had never thought of myself as a leader even though, looking back, I was clearly in positions of leadership. Since then, I’ve had direct reports and led larger teams. I’ve also become much more intentional about cultivating my skills as a leader. However, I’ve still been in positions where I’ve been led.

Now, I’ve been blessed to serve under some fantastic leaders, Carey Nieuwhof being one of them. However, being led while acknowledging I’m an emerging leader hasn’t been easy for me.

Multiple times I’ve found myself frustrated with my leaders. All frustrations, however, are not created equally. I recognize a few times when my leader frustrated me to help me, and here are three such situations:

(Note: If you’re a millennial or new to leadership, this post is for you. I’d love to help you navigate the tension of being an emerging leader with grace, humility, and optimism. If you’re a seasoned leader, I hope this reminds you of the opportunity you have to leverage your new and young leaders’ ambition and challenges.)

When Carey Frustrated Me To Teach Me About Excellence & Follow Through

After nearly four years since the launch of the Carey Nieuwhof Leadership Podcast, Carey has never missed a Tuesday. Never.

Maybe a technical difficulty has forced an episode to be published a few hours later than usual, but it’s safe to say 90-95 percent of the episodes have been published between midnight and 1 a.m. Eastern on Tuesday morning. Now, as the original showrunner of the podcast, I wish I could take credit for this, but I can’t. The consistency we’ve come to expect from the Carey Nieuwhof Leadership Podcast is attributed to Carey’s fanatical focus on excellence and trust. For Carey, the podcast coming out on Tuesday morning is not a suggestion or goal — it’s a promise.

There were times early in the life of the podcast when we had to work through technical glitches, production processes or busy schedules, and Carey would intentionally, frequently, and thoroughly check in with me to verify the podcast would be published on time. Transparently, I would think to myself, “What’s the big deal? This is free content. These are incredible interviews. We should be allowed the opportunity to publish a few hours or even a day late.” Carey never wavered. He would press and press until the team I led responded and got things out on time.

Carey always communicated in a kind, respectful manner, but here’s the truth: I was annoyed. I was frustrated. I believed my hard work on the podcast with and for Carey earned me the right to be less intense about this tiny detail every now and then. In my mind, as long as the episode was released that week and it remained free, it would be fine.

Looking back, I’m grateful Carey never stopped pushing. He ultimately helped me understand our team’s ability to thrive is driven by the leader’s relentless commitment to setting high standards and holding everyone accountable. We will fall short, but the goal is to never give ourselves an excuse for not reaching the standard.

High standards are a necessary ingredient to thriving teams.

When A Leader Frustrated Me To Teach Me About Communication

My team at Junction 32 was busy serving a non-profit organization. We were launching a new website, online store, new products, and several backend systems. Needless to say, my head was down, and I felt like my team and I were doing incredible work that would move this great ministry and their mission forward faster. However, its founder wasn’t too happy with parts of our performance so she called a meeting with me.

When we sat down to chat, she explained her disappointment in my lack of communication. She felt out of the loop. When she emailed me with questions, my response time was slow. I knew everything she said was valid. However, I found myself frustrated because I was working long hours on all of the organization’s projects, and the work being done by my team was setting up the organization for long-term success. In that moment, I felt misunderstood and unappreciated.

Now that I’m a few years removed from that situation, I’m grateful she confronted me. I was making assumptions about what she knew and holding her accountable for information she didn’t possess, which was why she was contacting me in the first place.

My lack of communication wasn’t allowing her to lead her organization well. In addition, it was impossible for her to appreciate contributions she was unaware of. She taught me our busy, stressful, challenging seasons are where misalignment is likely to happen. Yet, it’s also the time when we need each other most. Communication is essential to our team’s ability to stay connected, collaborative, and supportive.

When A Leader Frustrated Me To Teach Me About Influence and Persuasion

I approached my leader about exploring a few new initiatives. After a few conversations, he appeared to be on board with these ideas. However, instead of giving me permission and a budget to proceed, he required I connect with my teammates to secure their permission and request portions of their budget.

At the time, I thought to myself, “If my idea is worthy of our efforts, why won’t you just make the decision to move forward and commission it to be done?”

I look back and realize he was helping me learn the importance of using influence and persuasion over authority and position. As I recently shared on the Carey Nieuwhof Leadership Podcast, people need to weigh in if you want them to buy in. Well, I didn’t learn that on my own. I’ve had other leaders model that for me, and, in this case, require I practice this powerful principle.

So what’s the point of these stories?

I personally asked Carey if I could share these stories on his blog because I believe it’s important for emerging leaders to pass along the lessons we learn as we learn them. The sting of these situations is still fresh enough where I’m slightly embarrassed by them.

Why would these situations be embarrassing? Well first, none of these lessons are necessarily different from what my mother told me to do my entire life, so part of me is disappointed these leaders had to call me out.

Second, I’m a recovering perfectionist and people pleaser so making mistakes really hurts.

Lastly, and somewhat surprisingly, I’ve discovered I’ve occasionally used my calling to leadership and my appetite for learning to rationalize being arrogant or prideful as if my preparation and calling would guarantee that I flawlessly execute a job I’ve never done.

A call to leadership isn’t a video game cheat code; just ask Joseph or Abraham. Leadership is messy, complicated, lonely, and hard. Mistakes will be made. Therefore, humility is required.

Gratefully, His grace is sufficient. Did you know one manifestation of God’s free, unmerited favor in your life is an opportunity to serve under other leaders? It is! If you’re an emerging leader, take advantage of your season to be a follower. This is a priceless opportunity for you to prepare for the realities of leadership without the pressures of being the leader.

Carey and these other individuals are on an ever-growing list of leaders I appreciate more as time passes and my season to lead arrives, and I want to publicly thank each of them for leading me well even when it wasn’t convenient or comfortable.

What frustrating situations did you encounter early in your leadership that you now realize helped move you forward? What previous or current leaders do you need to thank for their example?

Scroll down and leave a comment.


  1. […] Multiple times I’ve found myself frustrated with my leaders.  Click here to read on. […]

  2. Kolawole on June 17, 2018 at 9:48 am

    Thank yoy for your boldness in sharing
    for me what triggered frustration then when I was new at following my leader(and I stilk am) was the fact that he will tell me his schedule and expect me to follow him up on it to make sure he does it. I sometimes got a query when I didnt. I didn’t see why then but im grateful I was followed through because it has taught me accountability.

    • Kevin B. Jennings on June 28, 2018 at 7:19 am

      Thanks for your story, Kolawole. Accountability is a big lesson. Kudos to you for taking the time to reflect and pull the lesson out of a tough situation. Feel free to text me (+1 (615) 455-3399) if you want to talk about more leadership stuff. All the best to you! – Kevin

      • Kolawole on June 28, 2018 at 7:38 am

        I definitely will
        Gid bless you sir

  3. Richard on June 14, 2018 at 11:46 pm

    Wow Kevin! Thank you for being so vulnerable and authentic. Your experience really speaks to me and I can see how my frustrations with my leaders are really just examples of my own failings. How I love to blame others when my shortcomings are the real issue! But when I look back honestly, I see my embarrassment is my own doing and actually an opportunity to grow. Thank God that help helps us grow and thank you for your example!

    • Kevin B. Jennings on June 28, 2018 at 7:24 am

      Amen, Richard! God loves us so much that He’ll use every opportunity to help us grow, including the workplace. However, with His help, we’ll learn to take ownership for our actions and release the things we have no control over. Thanks for taking time to read the blog and comment. Feel free to text me (+1 (615) 455-3399) if you want to talk about more leadership stuff. Take care! – Kevin

  4. Evangeline D.Simon on June 14, 2018 at 6:17 pm

    Hi Kevin,
    Thank you for sharing your experiences. The frustrations you’ve had brought you positive insights that are essential elements of being a leader. Communications, Influence and Humility these are major ingredients of leadership. Your post is very relevant to Millenials, because your generation will take over the baby boomers and will assume leadership roles.

    • Kevin B. Jennings on June 28, 2018 at 7:27 am

      Thanks for your encouragement, Evangeline. I want to be a great leader worthy of the calling God has given me. It means a lot to have more experienced leaders support you as you grow. Feel free to text me (+1 (615) 455-3399) if you want to talk about more marketing or leadership stuff. All the best to you! – Kevin.

  5. Don on June 14, 2018 at 1:14 pm

    Great stories and thoughts Kevin, appreciate you sharing this part of your life with us. I, too, have perfectionistic tendencies. I’ve swung to both extremes of it in my lifetime – sometimes always ceaselessly striving for perfection in what I’m doing, other times letting it go completely due to being told it was sinful or wrong. Where I’m at now comes from studying Jesus’ actions in scripture, and from a quote from the great NFL coach Vince Lombardi. He would tell his teams, “We will chase perfection, and we will chase it relentlessly, knowing all the while we can never attain it. But along the way, we shall catch excellence.” (Knowing we’ll never attain it is the key there.) I think that brings the balance needed to doing things the best we can. And excellence, after all, is just doing the absolute best with what we have. Thanks again!

    • Kevin B. Jennings on June 28, 2018 at 7:29 am

      Thank you so much for your comment, Don! Hearing about your progress of recovering from perfectionism is very encouraging. Also, I love that quote. I’d never heard it before. It’s going into my notebook right now. Feel free to text me (+1 (615) 455-3399) if you ever want to talk about more marketing an dleadership stuff. All the best to you! – Kevin

  6. Rodney on June 14, 2018 at 12:21 pm

    Truly enjoyed the post. I think the learnings are very applicable especially for a follower of Christ. Excellence, communication and influence are exampled throughout scripture. Further, your intent of why these learnings hit home is evident in my opinion based on your summary.

    • Kevin B. Jennings on June 28, 2018 at 7:33 am

      Thanks, Rodney! I appreciate your encouragement. I’m just want to become who God wants me to be. Thank you for taking the time to read and comment. Feel free to text me (+1 (615) 455-3399) if you want to talk about more marketing or leadership stuff. All the best to you! – Kevin

  7. Carlin on June 14, 2018 at 11:03 am

    This is about as good as a gut punch could ever feel… THANK YOU!

    • Kevin B. Jennings on June 28, 2018 at 7:36 am

      Haha! Thanks, Carlin. None of these experiences were fun at the time, but it’s life-giving to know my mistakes could potentially be your warning sign. Keep going, my friend. Feel free to text me (+1 (615) 455-3399) if you want to talk about marketing or leadership stuff. All the best to you! – Kevin

  8. Corey on June 14, 2018 at 10:11 am

    So good…

    •”…one manifestation of God’s free, unmerited favor in your life is an opportunity to serve under other leaders.”
    •”…take advantage of your season to be a follower. This is a priceless opportunity for you to prepare for the realities of leadership without the pressures of being the leader.”

    Thank you Kevin for taking the time to share your thoughts. I am one of Carey’s readers/listeners that consume a ton of materials (books, podcasts, conferences) each year in an effort to grow personally. I will have to sit with the two statements above for a while to take them fully in. Thanks again!

    • Kevin B. Jennings on June 28, 2018 at 7:37 am

      Thanks for reading and commenting, Corey. I’m glad you got something out of it. Don’t hesitate to text me (+1 (615) 455-3399) if you ever want to talk about marketing and leadership stuff. All the best to you! – Kevin

  9. Jeremy Mahood on June 14, 2018 at 10:10 am

    Kevin, I really appreciate the podcast and this blog. I think Jesus is an excellent example of excellence. In the stores he told he fanatically left his flick and dilligrntly and relentlessly searched for a list sheep, same idea in the list coin. The wonders of a God designed universe work with fanatical perfection. I’m thankful gravity operates every day, every moment and in time and without exception what goes up must come down ( loved that song written well before your time) . God rarely violates the natural order ( when he does we call it a miracle) He works best withing the order he has established…that order is perfect. He even desires perfection ( completeness) from us! Thanks for calling leaders to the high standards of Jesus Christ. His word and the gospel.

    • Jeremy Mahood on June 14, 2018 at 10:12 am

      Sorry for the auto correct.. certainly not an example of an excellent post!!!!

      • Kevin B. Jennings on June 28, 2018 at 7:39 am

        Amazing, Jeremy! You’re so right! There are lessons in excellence all around us. I needed your comment today. Thank you for taking the time to read and comment. Feel free to text me (+1 (615) 455-3399) if you want to talk about marketing or leadership stuff. All the best to you! – Kevin

  10. Mike on June 14, 2018 at 7:22 am

    Kevin, I’m pleased Carey has seemed to make a difference in your leadership qualities. As a young millennial, we often encounter those who seem to make a difference in our life and offer a beacon for our focus and admiration. This is a great thing. However, I don’t see or understand the connection to Jesus. As you so beautifully and truthfully wrote about disappointment in yourself and shame you felt, I would like to invite you to explore those truths once again. A fanatical focus on perfection more simply put is simply sin. Yes, the old ugly stuff even filters into a drive for perfection. While you or Carey are busy building as wall of Jericho of sorts, you’re hurting others that may never tell you. The Apostles were lots of things but leader is never mentioned in scripture. As the text more accurately points out they were shepherds. I would invite you to go to something as simple as YouTube and watch a shepherd and his flock. I think you’ll find a shepherd is generally lots of things but as far as out front leading that is a rare encounter. Again, I understand the need for a lighthouse in this wilderness of raging sea but I think you’ll find possibly guidance better addressed in scripture than another human infected with the same sin problem all us Earth dwellers suffer. Much grace and peace to you.

    • Kevin B. Jennings on June 14, 2018 at 9:09 am

      Thanks for taking the time to read my post and share your feedback, Mike! Other perspectives are always valuable. — Kevin

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