Jason Webb

Who are you, and what do you do?

Hi, I’m Jason Webb. I am a pastor at a church in Kenosha, Wisconsin, and campuses in Racine, Wisconsin. I’ve been in that line of work for about 20 years. I also worked a lot with nonprofits. I’m also a father of four crazy kids.

What has been one insight or lesson that has been most helpful in your career?

A recent lesson I learned was about leading a team —and this is from Patrick Lencioni, who wrote about this not too long ago. In one of his newer books, he talks about looking for people to add to your teams and the three qualities you need to possess as a leader.
One is being humble. People often don’t follow leaders who have great skill sets but who are not humble.
Second, you need to be hungry. In other words, there’s a passion that leaders have that drives them. They know why they get out of bed each morning; they have a passion beyond just “This is a job that I need to do.” It’s “This is just about who I am, and I can’t not do it.”
And then, the third is being smart. It’s not so much intellect, although that’s helpful; it’s more emotionally smart and relationally smart. In other words, you know how to interact with people, you know how to engage with them, you know how to listen to them, you know how to challenge them.
You need all those three qualities as a leader, and you want to look for all those three on your team. So, hungry, humble, and smart.

What has been your favorite mistake? A mistake that in retrospect led to a great lesson and progress.

There’s a lot to choose from. But I would say one of the greatest mistakes I made—and I made this for years—was saying yes to many good things, but that meant saying no to the best things. I thought I could do everything and anything.
A book called Essentialism helped me rethink that and helped me understand that when I say no to things, it’s actually making me a better leader so that I can do only what I’m supposed to do and what I’m best at. Because otherwise, you just kind of burn out, and you actually end up not doing what you’re best at.

Project forward ten years. How will your industry or field be fundamentally different then? What opportunities do you see?

Well, I think this year has been a pivot in all fields; whether it’s in the church world like I’m in, or nonprofit world or businesses, the reality of COVID has flipped people’s paradigms upside down.
Specifically, to the industry I am in, the churches, people are engaging differently now, partly because of social distancing but also, I think they’re just rethinking things. So what we are finding is we really have to be on the cutting edge of digital engagement, engaging with people where they’re at in their living rooms, being on social media, connecting with them in new ways, and understanding that the ways we used to think aren’t necessarily the way things are going to work in the future. So ten years from now, I don’t see churches being the massive things that they are; I see them much more spread out in smaller spaces but with digital engagement.

What are some bad recommendations you hear in your profession or area of expertise?

That’s a good question. I would say this bad advice in general, it’s not even directly said this way, but it’s this notion that you should never stop, never just pause. We often believe we have to climb higher, faster, and we need more, more and more, we have to be more successful. But I actually don’t think life works that way. I think it’s important to pause in certain seasons and just appreciate what you have. And certain seasons do not push the gas pedal super hard because people need to breathe and organizations need to breathe, and churches need to breathe, and sometimes just appreciate where they’re at before they kind of take the next hill.

In the last two years, what have you become better at saying no to?

I’ve become better at saying no to things that I know are not in my wheelhouse, things that drain me, mundane tasks. In the church world, I do a lot of counseling. I do some of that, but it’s just draining on me if I do too much of it. And so I have to be careful about that. Otherwise, I’ll only lead myself to burnout.

What is the one book you recommend most often and why?

There’s a lot, but one that’s been particularly helpful for me in my o of leadership journey has been “Strengthening the Soul of Your Leadership” by Ruth Haley Barton. She’s a spiritual and nonprofit leader. She’s worked in churches and nonprofits for years. But really, the emphasis of that book is that if you’re going to be a leader, no matter the field, whether churches, businesses, nonprofits, you have to be holistic in how you approach your life.

So the best leaders aren’t just the ones who have a five-year plan and achieve these great goals, but the best leaders are people who are healthy vocationally, healthy emotionally, healthy relationally, healthy spiritually, and healthy physically. You have to view your life that way, and once you start to engage in healthy rhythms in all those areas, then your leadership becomes better.

What advice would you give a smart and ambitious recent college graduate? What advice should they ignore?

That’s a good question. I would say, don’t be in a rush to change the world and just learn. Find somebody you want to learn from and just be quiet and sit at their feet and listen. Follow them around everywhere they go. Ask them to take you on business trips or bring you into meetings you wouldn’t usually be allowed in because you just want to learn from them.

At least, this is my experience. When I was a recent college graduate, I thought I knew everything, and so I wanted to come in and tell everybody how to do it. But I think the best thing we can do is learn and realize some people have been in the industries you’re in for years. The way you actually gain credibility is by being humble and being a listener and a learner first. That will prove you very well for the future.

What is your favorite quote, one you aim to live by?

There are many. One that I like in leadership is one by a pastor named Andy Stanley. He has a huge church in Atlanta, GA. He says, “Do for one what you wish you could do for the many.” In other words, you can’t be there for everybody, but it doesn’t mean you should be there for nobody. So do it for one person or do it for a couple of people, and build that into your organization’s ethos. Then other people will be doing the same for individuals, and that kind of becomes contagious. So often in organizations, we tend to think as leaders, “Well, we can’t do that for everybody, so we don’t do it at all.” But rather no, you can do it for one person, or you can do it for a couple of people, so go ahead and do it.


Over my website at https://www.jasonwebbmilwaukee.com.