We caught up with the brilliant and insightful Trevor Olesiak a few weeks ago and have shared our conversation below.

Trevor, looking forward to hearing all of your stories today. What was the most important lesson/experience you had in a job that has helped you as a business owner?

Aside from my coaching practice, I have been on staff at a church for 13 years. As an organization, we’ve had a lot of ups and downs, including a really challenging leadership transition a couple of years ago of the senior leader. I can’t go into all of the specifics, but suffice it to say that it was not an enjoyable place to work over the few years leading up to the transition and the two years during. There were many times I wanted to quit (and once where I almost did but was talked out of it by a friend on staff).

Thankfully, we are now well clear of those challenges and in a much healthier place. As I reflect back on that time, I learned how incredibly important leadership and culture are to any business. Organizational culture is built by what you create and what you tolerate. And there is no such thing as a culture-neutral action; everything someone in your organization does either takes you a step closer to or a step further from the culture you want.

In most organizations, culture is built by accident. This can work sometimes (aka you can get lucky), but more often produces an undesirable result. What I’ve learned is that if you want to build a thriving organization, you have to be incredibly intentional about building culture.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

This is one of the most challenging questions for me to answer. I’ve always been a jack of all trades and had my hand in a little bit of everything. Spending the last 13 years in vocational ministry as a pastor at a church, it sort of comes with the territory. While my “day job” involves leading our People & Culture efforts, you’ll find me in any number of roles on a Sunday morning, from playing bass guitar with the worship team to taking photos to praying with congregants.

A few years ago, there started to be a demand for the work I was doing in the church (coaching and developing leaders) outside of the church. And since I love being up to lots of different things, I’ve since jumped into that space with both feet as well.

Fast forward to today, and my life’s work takes on three different expressions:
1) pastoring in the local church
2) coaching and training leaders through my executive coaching practice
3) creating content

On the pastoring front, as I mentioned, I lead our People & Culture team. We have about 80 on staff, and my team not only handles all the traditional HR tasks like payroll, benefits, and compliance, but we also are responsible for coaching and developing our team. This is a BLAST and I love the impact I get to make through this work.

My role at the church is actually how I feel in love with the coaching work. I’ve coached solo outside of the church since 2017, but I recently partnered with an incredible coaching organization called Novus Global. I realized that I love working in the context of team, so in 2022 I knew I needed to pivot away from the solopreneur coach life. And while I still lead my own practice and team, getting to build my business alongside other incredible coaches is a gift. We’re better together.

The newest arm of my business is the content creation side. I have always seen myself as a creative, but I really only related to that side of myself as “fun hobbies.” I’ve played music and been a photographer for as long as I can remember. I knew I didn’t want to make either of those pursuits my full-time gig, but what I didn’t realize is that I was missing an opportunity to use my creative skillsets to improve my existing business. So this year in 2024 I’m working on my first book and have a YouTube channel that will be debuting soon focused on equipping the next generation of leaders.

All of that said, what I’ve ultimately learned about myself is that the “what” I do is constantly evolving and in flux. But the “who” I’m committed to being in the world is unwavering, and that’s a builder of leaders and cultures. So, call me whatever you want; be it pastor, executive coach, or content creator. They’re all true and they’re all me.

What’s a lesson you had to unlearn and what’s the backstory?

Through the early part of my leadership career, I prided myself on being the “answer guy.” When someone had a question or a problem to solve, I always had an answer for them. I was often first to speak, last to shut up, and was addicted to being “right” about things.

After more than a decade of leading teams and developing leaders now, I’ve come to realize that always having the answers gets in the way of greatness on a team. I’ve learned that leadership is not about having the right answers, but about asking the right questions.

Practically, here’s how I’ve trained myself to unlearn this behavior. Before I ever offer a solution, opinion, or answer to someone’s question, I always begin with at least one clarifying or thought-provoking question of my own. This does a few things: (1) it invites me into a more curious way of being, (2) it ensures I have a better understanding of the problem we’re solving, and (3) it trains people to begin to think critically about their own problems.

Being Curious > Being Right

Do you have any insights you can share related to maintaining high team morale?

I love the sentiment of the question, but I actually think there is a flaw in the premise. It is very difficult to “manage” a team into high morale. Think about your spouse or close friend or family member. How well does it go for you when you try to “manage” their mood or feelings for them? The reason so many leaders don’t get the results they want in the morale department is because they see themselves as managers only, and behave accordingly.

To build a great team, there is a paradigm shift that has to take place within the leader. They have to shift from seeing themselves as a “manager” to seeing themselves as a “servant.” And I fully recognize that some of you reading this are rolling your eyes right now. But I want to invite you to hear me out.

If we go back to the example of a spouse or friend again, it is way easier to “serve” your way into a happy and thriving marriage than it is to “manage” your way into one. The same is true with teams. If you wan’t a thriving team with consistently high morale, learn to serve your team. Give it a try, and I think you’ll be pleasantly surprised with the results.

Contact Info:

• Website: www.trevorolesiak.com
• Instagram: https://www.instagram.com/trevolesiak/
• Linkedin: https://www.linkedin.com/in/trevolesiak/
• Youtube: https://www.youtube.com/@trevorolesiak

Image Credits
Trevor Olesiak, Becca Egger