Very few people like buying cars. It is due to several factors, not the least of which is having a high-pressure salesperson hover over you.
-Do you want to finance this vehicle?
-What would it take for you to close this deal today?
It turns many people off. The same can be said about zealous Christians who always seem to be trying to "close the deal" when they evangelize. But, there is a better way.

I remember an experience in college when a beautiful young woman asked to sit with me at lunch. Not 1 minute into our conversation, she launched into a question, "do you know Jesus as your personal Lord and Savior?"

Now that isn't a bad question, in the right context and if you have earned the right to ask it. But, one minute after meeting someone is generally not that time. My defenses went up quickly (this was before I was a disciple) and I got out of the situation as quickly as possible.

So, how can we Catholics become better evangelists? One strategy, which we will explore in this post, is to customize your evangelization to each individual. It is more art than science and no art is mastered without practicing. Below are the principles that can guide you.
 

I would like to propose that when we evangelize, we ought to ask more questions than the other person. Jesus frequently used this tactic. What others thought would be a Q&A session was suddenly changed, when Jesus turned it into a Q&Q session.

Below are some questions I have found helpful in different situations. Note, not all questions are appropriate for every situation. You will have to learn to discern what you should ask and when. 

Questions about life’s meaning / purpose of life / identity / etc.

• Where do you believe humanity came from / what is our origin?
• Where do you find meaning in life?
• What is the source of power?
• How do you define “success”?
• What is your destiny? How do you know this?
• What brings meaning to your life?
• Do you believe in a Higher Power? If so, can you describe this power for me? If not, can you tell me why not?

Questions about truth / values / falsehoods / priorities

• How do you know what is true and what isn’t?
• What are you willing to give your life for?
• What are your highest priorities? How did you arrive at these priorities?
• What are you passionate about? What do you find yourself arguing for or against? Why?
• What do you find most persuasive?
• What are your dreams for life? What do you hope to accomplish?
• What do you mean by describing yourself as ____?

Questions about how to live / how should I act / what is right or wrong

• How do you know right from wrong?
• How do you determine how you ought to act?
• Are there any universal human rights? What are they? How do we determine them?
• Are some acts morally relative?
• Is there anything that is universally moral?
• Where do the problems of humanity / evil come from?
• What is the solution to humanity’s problems / evil?

Another way of categorizing questions is by understanding the different kinds of labels that people apply to themselves and trying to drill down on those labels, to get beyond them and see the person behind the label. One of my friends reminds me constantly to “never accept a label in place of a story”. The story tells you what the label doesn’t! But, the label can be a starting point for a conversation.

Questions for Non Believers (atheists, agnostics, etc):

• Can you tell me about the god you don’t believe in?
• Can you describe what you find most fulfilling about being _____?
• Tell me about God? How do you describe God to others
• What do you know about Jesus?
• If you have heard of Jesus, what do you know about Him?
• What do you think Christianity adds to the lives of others?
• Do you believe in any kind of universal or higher power?
• Have you believed in God in the past? If you did and don’t any longer, why did you stop believing?
• If you did believe in a god, what kind of god would you believe in?

Questions for those from Non-Christian Religions (Hindu, Muslim, Mormon, etc):

• What are the different ways you pray?
• Can you describe what you find most fulfilling about being _____?
• Tell me about God? How do you describe God to others?
• What do you know about Jesus?
• Is there anything about Christianity that you find attractive?

Questions for those Christians who are not Catholic:

• Could you describe what you believe about Jesus?
• Is your faith something your practice every day?
• How would you describe your relationship with Jesus?
• Is there anything about Catholicism that you find attractive?
• What do you know about the Catholic Church

Questions for those who are Catholic:

• Can you describe what it means to be Catholic, in your experience?
• Do you have a personal prayer life? If so, how do you pray?
• Is God someone you would say you have a personal relationship with?
• Have you had any kind of moment when you felt particularly close to Jesus? If so, can you tell me about it? If not, have you ever wanted to? 

What I have found works well when evangelizing others is to truly listen to where they are coming from. Not in order to prove them wrong, but rather to accept the person who is in front of you as a human, made in God's image and likeness, and uniquely made to glorify His name. When we are able to do this, we can marvel in their creation and truly love them where they are at, in order to help them grow closer to God. Evangelization takes the other person's consent to God's grace, if we are to see them converted. To put it bluntly, the one doing the evangelization is the least important party in the drama. It isn’t our job to convert anyone – we can’t! Only God’s grace, chosen through a free act of the other person’s will, can make faith happen. Thus, I am a limited instrument in the hand of God, who is called to love the other person and help them grow closer to God.

True love for another person means I will always seek their good, and asking good probing questions can help me understand how best to help them grow, but only if I listen to understand. 

Remember this principle - understanding does not always mean acceptance. You are listening to understand the other person, not necessarily accept what they believe or think!

Now, some tend to equate evangelization with having all the right answers. I certainly used to be one who had to be right all the time! My idea of evangelization was winning an argument or proving someone else wrong. It wasted a lot of time pushing people away, through my pride and lack of charity, to realize my mistake. Certainly, we ought to know the content of what we believe and be good at expressing ourselves. So, there is nothing bad about apologetics or a good argument. In fact, they can be great tools to help remove an obstacle toward someone growing closer to Jesus. Still, the truth isn't a hammer we ought to beat over someone's head. Furthermore, we have to slow down and work on relationships more than just having the right answer. Over-talking is a real problem with many evangelists, myself included.

Others believe that our faith is something very private that shouldn’t be shared, in order not to offend or seem too pushy. It is the Catholic version of “don’t ask, don’t tell”. This attitude comes from a culture that believes faith is something we do part-time or compartmentalize. Unfortunately, this attitude creates a culture of silence, where we don’t talk about our faith at all. As many others have responded to this – our faith is always personal but never private. Imagine if the Apostles had never talked about their faith. We wouldn’t have any Christians today.
  After we ask questions and listen, we need to start to assess where a person is on their spiritual journey. This is the hardest part for many people who are just starting to work on sharpening their evangelization skills. But, it might be one of the most important steps. If we don't know where they currently are, we don't know what they need or how we ought to respond.

I highly recommend you study the different thresholds of conversion, discussed in the amazing book “ Forming Intentional Disciples” by Sherry Weddell. These thresholds can help you determine which questions are appropriate for individuals who are in different places and with different needs. Furthermore, you can look at our Stages of Discipleship for those who are already disciples.

But, don't stop merely with knowing where someone is spiritually. Now you need to respond appropriately.
  A response is where you tailor evangelization to the individual. Some appropriate responses include:

• taking the time to build a long-term relationship, in order to build trust and earn the right to be heard.
• proclaiming the kerygma and inviting a response.
• radical hospitality and friendship.
• giving your testimony.
• casting a long-term vision of what it means to follow Jesus and helping them to "count the cost" of being a disciple.
• serving others, without expecting repayment.
• allowing them to walk away (at least for a time).

All of these (and more) are appropriate responses for different people. We won't know what another needs until we have asked questions, listened, and assessed where they are and what they need.

Response is a weak-point in many Catholic evangelists lives. We tend to stop short and think that living a good life or being externally disciplined is enough to attract others to Jesus. While living a virtuous life is indispensable, we cannot avoid going the next step, even if it pushes us to being a bit uncomfortable.

Finally, every response should include prayer.
  In Acts 8, we see Philip use this methodology. He encounters a eunuch who is reading Scripture and asks him if he understands what he is reading. He then listens for the eunuch's response, assesses where he is spiritually (in this instance ready to become a disciple), and then he responds by preaching about Jesus and baptizing him. 
Question -> Listen -> Assess -> Respond