3 Things Young Leaders Need To Hear From Their Boss, But Almost Never Do

This is a guest blog post by Dillon Smith. Dillon is my content manager and is a member of my new Speaking Team. You can book Dillon to speak at your next event here.

By Dillon Smith

Knowing how to lead the next generation is not easy.

As a leader, you know that if you want to stay relevant to young people, you need them to have a seat at your table, which means you have to lead them.

The problem is, the young perspective also comes with a lack of experience. And helping them get that experience makes your job much more difficult.

For the last year, I have been the 20-year-old on Carey Nieuwhof’s team. It has been my first major career position and Carey has invested A LOT of time, money, and energy into my development. (I’m extremely grateful.)

As a result of Carey’s investment, I am 10-times the leader I was before I became his assistant.

So what specifically did he do to help me grow so fast?

As I look back, I see 3 major things Carey repeatedly said to me that made a massive difference in my development.

I think they can have the same effect on the young leaders in your organization as they have had on me.

If you have led young people (or been a young leader), you probably know that one well-timed statement can change the trajectory of their leadership. For the better, or for the worse.

So, here are 3 things every young leader needs to hear from their boss, but almost never do:

1. “How can I help you win?” 

When I started working for Carey, I had almost no clue what I was doing.

I had been at a ministry college for the previous 2 years. It was a bit more difficult than the average state college but was still a walk in the park in comparison to my new role.

I thought I knew what working hard was. I had no clue.

Once I started to have actual responsibilities, like running Carey’s calendar or helping launch his products, I became overwhelmed. Fast.

None of the overwhelm I felt was Carey’s fault. He was just holding me accountable to the deadlines I had made a promise to hit.

But I didn’t see that.

There was a small part of me blaming Carey for the overwhelm I was feeling.

What I didn’t see was that I was feeling overwhelmed and dropping tasks because I was living a lifestyle that was damaging my productivity.

My overwhelm was my fault.

Carey could have just told me that, but I might have gotten defensive and said my personal life was none of his business.

But he didn’t.

Instead, he asked me, “Dillon, it’s okay that you are struggling, but it needs to get better. How can I help you win?”

I didn’t have a good answer for him.

I didn’t have a good answer because none of the reasons for my failures at work were work-related.

It took him asking that question and me trying to verbalize an answer for me to see that nothing that was going wrong could be fixed by him.

I finally saw that I was the only one who could fix my problems.

This hasn’t just happened to me; many of my peers have had to learn the same lesson.

So why don’t young leaders see, and take responsibility, for our own faults?

My theory: growing up, we were rarely told that our success was up to us.

It was always the umpire’s fault we couldn’t pitch a strike, our teacher’s fault we don’t have straight A’s, or our parent’s fault we didn’t have any friends.

When the real cause was that we didn’t practice for 9 months, we never did our homework correctly, and we were a jerk to everyone who came close to us.

We were promised, “if you go to college and get a degree, everything will work out,” “you don’t have to move out until you are ready,” or my least favorite, “as long as you try your best that will be good enough.”

Those messages are doing more harm than good to the next generation.

I wasn’t able to lead anything until I took responsibility for my own, and our organization’s, success.

The young people on your team won’t either.

You might be thinking: “Okay Dillon, that’s great for you, but how do I apply this to my team?”

I’m glad you asked.

I think we all can agree that every young leader needs to grow before they reach their full potential.

When you ask this question, that young leader on your team sees that their boss is doing everything they can to pour into their development.

When they see that, it inspires them to take responsibility and do everything they can to develop themselves.

In short, when young leaders know our bosses are bought-in to our growth, we buy-in to our growth.

For your team to thrive, they need to be growing. Just make sure to show them that you are doing your part, and they will gladly do theirs.

2. “I trust you.”

Want to know how to make a young leader dislike you for the rest of their life?

Make it obvious you don’t trust them.

Here is what I have noticed about myself and other driven young leaders. Driven young leaders rise to the level of the expectations set on them.

I have had highly capable, highly driven friends and classmates work for organizations that have little expectations for them. Do you know what happens?

They do nothing impressive because they aren’t expected to do anything impressive.

That same leader will then go to an organization with lofty expectations that I wasn’t even sure that leader could handle, and they crush it!

Here is the shocking part: they took a pay cut going to the new position, but they still produced 10-times the results.

The only thing that changed from one job to the next was the level of expectation and freedom given.

When I started working for Carey, he put some extremely high expectations on me and said: “I trust you.” Not only did he say “I trust you,” but he acted on it.

He let me work from wherever I wanted, trusted me to track my own work hours, and trusted me to manage my own tasks. That is a lot of trust, and that is a lot of responsibility.

One major way he placed higher expectations on me was trusting me to lead the launch for his most recent, bestselling book Didn’t See It Coming at 19 years old.

I was the opposite of qualified to do this. The most significant thing I had led before working for him was a parking lot team at my church, and I had never even met a publisher.

With Carey’s help, I successfully rose to the level of expectation.

So will the young leaders that work for you.

One HUGE Caveat:

The level of trust you put in a leader should be based on their character, not on their competency. If the young leader on your team has given you reasons to not trust their character, this will not work.

Honestly, if you can’t trust their character, don’t keep them.

Obviously start with talking to them about their character, and ask for them to improve.

But if that doesn’t work, demote them, cut their residency, or fire them. Tell them why, and get rid of them. If someone is morally corrupt, they don’t need a place at your table, no matter how “qualified” they are.

In my experience, leaders with less than great character will only learn to change the hard way.

If you want help on how to handle this conversation, Henry Cloud has a great talk on dealing with the 3 types of leaders in your organization.

3. “I want you doing what you were made to do. (Eventually…)”

My bachelor’s degree is in pastoral ministry. I have never been described as organized, and I hate spreadsheets. I was not made to be an executive assistant, and yet, God put me into the role of executive assistant to Carey Nieuwhof. And I survived.

Sure, Sarah, Carey’s assistant of 10 years that went on maternity leave, would have done a much better job than I did, but everything still turned out relatively well over the year I was his assistant.

There were 2 major reasons I survived being Carey’s assistant for a year:

A. Anyone can do any job for a year if the “why” is big enough.

For me, the “why” behind working for Carey has always been helping the Church reach more people on a massive scale.

That “why” outweighed the “what” of doing a job I’m not naturally wired for. I couldn’t do it forever, but I could do it for a year.

If you have someone in a role they aren’t a great fit in, make a note to positively remind them of the “why” often.

B. Carey kept saying “I want you doing what you are made to do.”

Carey would often say this when we were talking about the future roles I could play in the company after Sarah returned from maternity leave.

This mindset did lead him to change a few minor things about my role in the moment, like having a much more detail-oriented co-worker book his flights, but the major thing it did was show me that he cared about what I am passionate about and made to do.

If Carey wouldn’t have shown me that he cared about my gifting, I might not have kept working for him.

Now that Sarah is back, I am in the much more content-based role of “Content Manager.” This role is a much closer fit with my natural gifting and one I can see myself doing for a long time.

If you have young leaders in your organization, you need to be showing them you care about their gifting.

3 Things Young Leaders Need To Hear From Their Boss, But Almost Never Do


  1. Jenna Berthoud on October 12, 2020 at 1:01 pm

    This is excellent info. As a 41yo I can say that gen-z and millennials need this but this is good leadership regardless of age.
    As someone who has never had a boss or leader that showed they cared about my development until just this year, I can say this is what everyone needs in a boss/leader.

  2. Scott on October 11, 2020 at 8:01 pm

    As an almost 50-year-old, it is really hard to stomach the reality described in this article. I don’t disbelieve it. I just remember how, when I joined the workforce, I understood the job as a simple transaction: I give you my time and work hard, and you pay me a fair wage. That was the deal. But now, as a team leader in today’s world (America, at least), you have to love and care for your young employees…or you will lose them. (Actually nothing wrong with that, IMO.) Also this article is hugely ironic to me in that Carey N teaches pastors to be managers/leaders, but as a manager, he promotes being something that looks suspiciously like a pastor.

    • Steve Miller on October 12, 2020 at 8:50 am

      4. I was recently given some “gifts cards”.
      Let me share some of them with you..

  3. Travis Wright on October 11, 2020 at 12:35 pm

    Dillon – fantastic article.

    I am a Lead Pastor (38 Years Old) leading an entire church staff of Millennials and GenZ rockstars. Your words and insight were such a great encouragement and affirmation of them and the impact I pray they will all have for The Kingdom (inside or outside of my organization).

    In November, I am preaching a three part sermon series on the NY Times Best Seller ‘The Coddling of the American Mind’ and attempting to give a strong biblical case against the ‘Three Untruths’ in the book. I am going to quote YOU and this article in that series, because it has given me such great hope for your generation.

    Thank you for serving The King.
    I can’t wait to see all that you accomplish for His glory!

  4. David L. on July 19, 2019 at 10:34 am

    Great openness and sharing real situations that others can identify with and learn from.

  5. Kitti Homan on July 11, 2019 at 7:24 pm

    I’ve been in church leadership for nearly 40 years and my only comment is, “These are excellent leadership principles regardless of age.” One of my greatest joys is the development or emerging leaders. Unfortunately, it seems encouragement and coaching take an investment of time many are unwilling (or unable) to make. Thank you, Dillon, for a well-written piece and Carey, for taking a risk on a young leader. If our Heavenly Father can trust humans with His Gospel, surely we older leaders can trust young adults to rise to the challenges that face the 21st century Church.
    Kitti Homan
    Kansas City Missouri

    • Dillon Smith on July 12, 2019 at 4:58 pm

      Thanks Kitti!

      So glad to be able to help however I can. 🙂


  6. Sheila Jansen on July 11, 2019 at 6:53 pm

    Nice job Dillion
    So proud of you
    Totally agree what you wrote in your article
    Love and God Bless
    Sheila Jansen

  7. Colby Jenkins on July 11, 2019 at 12:42 pm

    This is Spot on Dillion. Being 28 years of Age before I found an amazing Boss that cared about my development, I can say the Trust Factor is huge. I was a lower level employee and the CEO ask me to join a leadership team with the CFO, and other Managers. He said “I value your opinion and what you bring to the table” From that day on, I was sold and have never been happier with my job. But it came because our owner was a secure leader and much like Carey new the next generation has much to offer. Keep it up guys!

  8. Nate Combs on July 11, 2019 at 12:07 pm

    Great words Dillon! You did a fantastic job taking care of all the emails over the past year on top of everything else you were doing.

    In regards to Carey’s email prefacing this post, I’ve actually not had to deal directly with a boss that thought I (or maybe even more young people) was lazy. Perhaps that’s just because my wife and I usually get far more things done than whoever the last young person was, so we get compared in a positive light (for us at least).

    However, I have seen a gap of understanding between generations in ministry moreso than other places. It’s true that the perspective of “You need to help me win (and stuff your own ideas),” as opposed to the leader asking what they can do to help us win drives away young people in great numbers. I’ve sadly seen so many friends and peers leave their positions, often in the church, over these 3 topics.

    But the good news is many out there are fighting to keep learning and growing and changing even at 60 or older rather than taking the position of all-knowing and peaked out. And your team has so much to do with those results and encouragement in many of the great leaders out there!

    • Dillon M Smith on July 11, 2019 at 12:43 pm


      Thank you so much for the encouragement! I also see this disconnect having a massive impact on the next generation.

      I hope more and more leaders begin to work together across generations in the future.


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