Three Questions That Change Everything For Urban Discipleship
The SG500 Files Part 2 of 3
By S. Crawley
Photo by Anatol Rurac on Unsplash
Many good people are wrestling with how to reach their cities and how to disciple effectively. They're asking important questions about obstacles to engagement and discipleship. But there's a third question that doesn't get wrestled with as much.
The third question changes our answers to the other two.
Where the Questions Came From
Last September, urban discipleship practitioners gathered from cities spanning East to West Asia as part of SG500. These weren't theorists—they were people on the ground in the harvest, faithful over years and decades in difficult places. Over three days, we wrestled with how to see discipleship spread virally through our cities. The diversity was striking—different languages, cultures, religious contexts, political situations. As we processed together, three questions seemed to resonate deeply across the diversity.
Two of them are familiar to most people with a Great Commission mindset. The third one emerged as the question that transforms everything else.
The First Two Questions Everyone's Asking
"What are the biggest obstacles to effectively engaging people who aren't walking with Jesus?"
This first question gets significant attention. How do we engage them? What does it look like? We analyze cultural barriers, religious backgrounds, socioeconomic factors, institutional challenges. We look for ways to serve and connect.
The second question goes deeper:
"What are the biggest obstacles to discipleship in our context?"
It requires us to identify which aspects of God's Kingdom people are most deeply longing for, the voices in that context which are competing most loudly with the Father, and the forms of brokenness which are most common. Remember, our simplest definition of discipleship is "listen to God, trust Him, obey Him, and help others do the same." Not programs or curriculum, but life with God. This pushes beyond transaction conversion to personal and corporate transformation - to communities of disciples. This requires us to wrestle with how to create spaces where people can know God and His Word, and discern how to respond to Him practically in their lives and relationships.
Both questions matter immensely, and thoughtful practitioners across our region are wrestling with them seriously.
The Third Question That Changes Everything
"What are the biggest obstacles to discipleship that can replicate?"
A lot of good people are wrestling with the first two questions already. The third question is not wrestled with as much. Huge question. It actually feeds back into the other two. It changes our answers to the other two.
Here's why: complexity and expertise are the biggest obstacles to replication.
Complexity means that one size cannot fit all - each context has its own unique set of needs and circumstances. The most common solution to complexity is to look to experts, but relying on expertise creates bottlenecks in extremely complex environments like cities - no expert, no progress. It takes time to produce experts, and the city and the communities in them are continually evolving and morphing.
Once you ask how discipleship can not just happen, but replicate, we have to start seeing things differently. If it depends entirely on our personal direct involvement, it won't cut it. Approaches that depend on our gifts, your resources, our expertise suddenly reveal their limitations.
Viral social media content is something everyone is going for. What about viral discipleship?
Genuine discipleship has quality - substance and depth. Not easy!
But the question is a crucial one - how can we disciple in ways that can replicate? This is the tension that keeps practitioners up at night.
How the Third Question Transforms the First Two
Ask yourself: in the city, what obstacles prevent effective engagement with people who aren't walking with Jesus?
You might answer: lack of natural relationships, cultural barriers, time constraints. These are real obstacles.
Now add the replication lens: what prevents engagement that others could also do?
Now we have to start thinking about simplicity and complexity of our approaches. We need to think about culture and language. We need to think about how "core" are the things we are point people to? For example, are we pointing people to the Bible, which they can access directly? Or our preferred interpretation of the Bible, which requires us to function as interpreters?
If my engagement strategy requires me to be the bridge because of my unique background, it won't replicate. If it depends on my theological training to navigate conversations, it won't replicate. That doesn't make it wrong, it just limits its effectiveness in the complexity of the city.
The same transformation happens with the second question, "What are the biggest obstacles to discipleship?"
You might identify: lack of good curriculum, insufficient biblical knowledge, not enough time for deep investment. Add the replication question: what prevents discipleship that the disciple could do with someone else?
If our discipleship approach requires access to resources the disciple doesn't have, it creates dependency. If it needs our level of biblical knowledge before they can help someone else, we've built in a massive delay. If it's so complex that even after months they couldn't guide someone else through it, we may not have made a disciple—we've made a dependent.
The Dependency Test
Here's a simple diagnostic: if we remove ourselves from the process, what happens? If everything stops, we've built dependency.
We often confuse quality with complexity. We assume that depth requires expertise, that substance needs sophistication. But what if the deepest things—listening to God, trusting him, obeying him—are actually simple enough that anyone who's learning can help someone else learn?
Not simplistic. Simple. There's a difference.
Understanding Cultural Wineskins
The third question forces us to distinguish between what's essential and what's just our cultural wineskin—the non-essential forms and methods we've attached to the gospel.
These cultural wineskins are often mistakenly linked to "quality" or "control." We convince ourselves that our particular way of doing things ensures depth or faithfulness, when really it just ensures our ongoing involvement. We require prerequisites not because they're necessary for following Jesus, but because they give us confidence we're maintaining standards.
Consider what's actually essential. Is theological precision in explaining justification essential for someone to begin trusting Jesus? Or is "you are seen, you are known, you are invited by the Father" enough to start? Doesn't precision come over time as we walk with God? Is a comprehensive curriculum essential? Or is "listen to God, trust Him, obey Him, and help someone else do the same" sufficient?
We add layers that we think ensure quality, but often they just make things complicated. We require prerequisites that we think guarantee depth, but often they just guarantee delay.
Quality That Can Go Viral
This is where most practitioners get stuck. We've been taught that quality requires expertise, that faithfulness means maintaining complex standards. But what if that's backwards? What if quality discipleship is demonstrated by its ability to reproduce—not despite its simplicity, but because of it?
The third question exposes a hard truth: if we're not careful, the things we associate with "quality" can actually build dependence. Much of what we call "depth" is actually complexity that disempowers disciples as harvest workers and prevents reproduction. Sometimes our "faithfulness" is more to our religious preferences than our Lord, and this can get in the way of what He actually wants to do.
This doesn't mean going shallow. It means identifying what's truly necessary for someone to listen to God, trust Him, obey Him, and help someone else do the same. It means being prepared to acknowledge that anything beyond this—no matter how good it is or how meaningful to us—may be a cultural wineskin that needs to be released to allow the Gospel to go viral in our cities.
From Dependencies to Disciples
The third question isn't just about methods. It's about releasing our personal control and trusting that the simple core of following Jesus can reproduce under His leadership without us managing every step. When we're honest about what prevents replication, we often discover we've been building dependencies rather than disciples.
The question changes everything because it exposes our assumptions about what's essential and what's just our cultural preference. It reveals where we're holding on to control and calling it quality.
God's vision for our cities is massive—knowledge of His glory saturating everything like waters cover the seas. That kind of saturation can't happen through dependencies or complex systems that require expert management.
It requires disciples who make disciples who make disciples, viral reproduction that doesn't need us managing every generation.
This article is one of three based on conversations that came out of conversations between a diverse gathering of urban disciple-makers at SG500 in September 2025. SG500 has an initiative to pray for the 500 biggest cities of Asia this year. You can pray alongside here.
Getting Practical
As you think about God's vision for your city:
1) Look at your current discipleship approach: What elements require your ongoing involvement or expertise? What would happen if you removed yourself from the process?
2) Of the three questions (obstacles to engagement, obstacles to discipleship, obstacles to replicable discipleship), which one challenges your current practice most? What would it cost to address it?
3) Consider one person you're currently helping follow Jesus. If that person were to help someone else follow Jesus in the same way you're helping them, what would need to be simpler? What's Biblically essential and what's cultural?
Discipling the Urban Harvest provides practical insights and encouragement to walk with God in multiplying discipleship in an increasingly urban world - growing as children of the Father, serving the communities He has called us to, and discipling those hungry to know Him.