Living the Lord's Prayer

The Awkward Ask: How to Start a Mentoring Relationship

By Mark Sentell · November 3, 2026 · 9 min read ·

Most of what keeps us from investing in someone isn’t theology. It isn’t time. It’s one sentence we have to say out loud to another adult, and the sentence feels like this: I think I have something worth giving you.

That feels arrogant. It feels presumptuous. It feels like you’re appointing yourself somebody’s guru.

So we don’t ask. And a man sits in the same seat at church for six more years, and nobody ever opens the Bible with him.

This is the awkward part of discipleship. I want to tell you plainly: the awkward part is the whole part. Nothing starts until somebody asks. So let’s make it smaller, and then I’ll give you the actual words.

You’re asking for time, not authority

Here’s the claim. Nothing starts until somebody asks, and the reason nobody asks is that we’ve made the ask far bigger in our heads than it is in real life.

You are not asking someone to submit to your spiritual authority. You are not offering to be their guru. You are not announcing that you’ve arrived and they haven’t.

You are asking for time.

That’s the actual content of the ask. Can I have an hour of your month? People give an hour of their month to a fantasy football league. This is not an outrageous request.

The reason it feels enormous is that we picture the whole arc, two years of breakfasts and hard conversations and Bible reading, and then try to cram all of it into one sentence. Don’t do that. You’re not asking for the arc. You’re asking for coffee.

How Jesus asked

Look at how Jesus calls his first disciples in Mark 1:16–20. What strikes me every time is how little there is.

Simon and Andrew are working, casting a net into the sea. Jesus walks up and says, “Follow me, and I will make you become fishers of men” (Mark 1:17). Then Mark adds, “And immediately they left their nets and followed him” (Mark 1:18). A few steps later he does the same with James and John, and they leave their father in the boat with the hired men.

That’s the whole recruitment. No vision-casting document. No six-week trial. No explanation of the discipleship pathway. Levi gets even less. Jesus sees him at the tax booth and says, “Follow me” (Luke 5:27), and Levi gets up, leaves everything, and follows.

I want to be careful here. I’m not Jesus and neither are you. Part of why those asks land is who is doing the asking. We don’t have that authority and shouldn’t pretend to.

But the shape of it transfers. It was short. It was direct. And it included what they’d become. Not just “come along,” but come along and I will make you something. Here’s what you’ll be able to do at the end.

That’s a good template for us. Direct, short, and it tells the person what’s in it for their life.

What you’re really offering

The other passage I want in front of you is Paul, writing to a young church he had just been forced to leave:

So, being affectionately desirous of you, we were ready to share with you not only the gospel of God but also our own selves, because you had become very dear to us. (1 Thessalonians 2:8)

Not only the gospel. Our own selves. That’s the cost, and it’s the honest thing to know before you ask. What you’re offering somebody is access to your life.

Paul says the same thing in a different key elsewhere. He tells the Corinthians, “Be imitators of me, as I am of Christ” (1 Corinthians 11:1). He tells the Philippians, “What you have learned and received and heard and seen in me—practice these things” (Philippians 4:9).

Seen in me. Paul expected people to watch him. That’s a terrifying standard, and it’s the real ask. Not “let me teach you.” Let me let you watch.

The good news is that this takes the pressure off being impressive. Nobody needs you to be an expert. They need you to be a little further down the road and willing to let them walk next to you. If you want the bigger picture of what that looks like week to week, I wrote about it in You Don’t Need a Title to Disciple Someone.

What to actually say

Here’s a script. Steal it. Change the words so they sound like you, but keep the four parts.

Part one: name what you’ve noticed. Make it specific and true.

“I’ve noticed you’re around a lot, and you ask good questions, and I don’t think anybody’s ever really invested in you here.”

Specificity is everything. “You seem like a great guy” is noise. “You asked that question about Job three weeks ago and I’ve thought about it since” is a person who has actually seen them.

Part two: be honest about who you are. This is the part that defuses the arrogance problem.

“I’m not an expert and I’m not going to pretend to be. Somebody did this for me, and it changed my life, and I’d like to do it for somebody else.”

That puts you in the middle of a chain instead of at the top of a ladder. You’re not the authority. You’re a link. That framing is true, it’s humble, and it takes the weirdness right out of the room. It’s also 2 Timothy 2:2 in plain clothes: what was handed to you, you hand on.

Part three: make the ask small and specific.

“Would you be up for breakfast once a month for the next six months? We’d read a bit of the Bible together and talk about your life. Nothing formal. I’ll buy.”

Notice what that covers: how often (once a month), how long (six months), what we’ll do (read a bit, talk), and who pays. Every one of those answers a question they’d be too polite to ask.

Part four: give them an out. Say it out loud.

“And if this isn’t your thing, that’s completely fine. No weirdness, I promise. Think about it and tell me next week.”

Give them a week. Somebody who says yes on the spot out of politeness will ghost you in March. Somebody who thinks about it for a week and comes back is in.

That’s the whole thing. Four parts, ninety seconds, one cup of coffee.

Setting expectations: how long and how often

Six months is the number I’d give you. Long enough to be real. Short enough that it isn’t a life sentence. And it builds in a natural exit for both of you, so nobody has to “break up.” At the end you sit down and ask, “Do we keep going?” Most of the time the answer is yes. When it isn’t, nobody’s embarrassed.

Once a month is the floor. Every other week is better if both of your lives allow it. But I’d rather you promise once a month and keep it than promise every week and quietly stop in February.

Here’s the habit that matters most: you own the calendar. Don’t leave “we’ll figure out next time” hanging in the air. Before you stand up from the first breakfast, put the next one in both phones. Every time. This one habit will double your success rate. It isn’t spiritual. It’s logistical. And logistics is where most good intentions die.

When I wrote the sentence I’d use to ask people into The Investors, it came out like this:

“Someone poured into you. I think you’re ready to do that for somebody. It’s forty-five minutes a month for two years, and it will cost you a relationship’s worth of time. Will you come?”

Same four parts, more or less. What I’ve noticed, why it matters, what it costs, and a question they’re free to answer either way.

When they say no

Let’s talk about the no, because the fear of it is what’s actually stopping most of us.

First, a no is a real outcome, not a failure. If you ask somebody and they say no, you’ve done the obedient thing. The result is not your department.

Second, most no’s aren’t about you. There are three common ones, and only one of them is a real refusal.

“I’m too busy.” Usually true. Usually a season. Say, “Totally understood. Can I ask you again in six months?” Then put it in your calendar for six months out, and ask again. The second ask lands very differently than the first, because it proves you meant it.

“What exactly would this be?” That’s not a no. That’s a request for clarity, and it usually means your ask was too vague. Answer concretely: “An hour, first Saturday of the month. We read a chapter and I ask you how you’re actually doing.” About half the time, that turns into a yes.

A real no. Sometimes somebody just doesn’t want it, or doesn’t want it from you. That’s allowed. Receive it graciously. Don’t campaign. Don’t get weird at church. Say, “No problem at all. I’m glad you were straight with me,” and mean it.

Then go to the next name on your list. This is why I’d always have you pray over three names rather than one. If you ask one person and get a no, you feel rejected. If you’ve prayed over three names for weeks and one says no, you say, “Okay, so it’s not him,” and keep going.

When they say yes and then don’t show up

Nobody warns you about this one, and it’s more common than the no.

They say yes. You’re encouraged. You meet once and it’s good. Then the second one gets rescheduled, the third one they forget, and by month four it’s dead and you feel foolish for trying.

One no-show is not a verdict. Text them like a friend, not like a disappointed teacher: “Missed you Saturday. Everything alright? Same time next month?” People’s lives are chaotic. The guy who flakes twice and comes back the third time is often the guy who most needed somebody not to give up on him.

Three in a row is information. At that point, ask directly and kindly: “Is this a season where this works? I’d rather you tell me straight than both of us feel bad about it.” Sometimes they’ll re-commit. Sometimes they’ll tell you the truth. Either way, it’s cleaner than a slow fade.

“Shouldn’t this just happen naturally?”

I hear this a lot, and there’s something real in it. Nobody wants a friendship that’s secretly a recruitment funnel.

But look at the New Testament. Jesus chose. Paul took Timothy along. Barnabas went and found Saul. None of it was accidental. Intentionality isn’t the opposite of a real relationship. It’s what helps a real relationship survive contact with a calendar.

Here’s what “it should happen naturally” usually means: I would like the benefits of this without the risk of asking. I’ve said it myself. It’s not a principle. It’s a hiding place.

And practically, the things we leave to happen naturally are the things that don’t happen. Nobody accidentally reads the Bible with somebody for six months.

Your practice this month

Ask one person. Take the name that’s been standing out as you’ve prayed. Use the four parts: what you’ve noticed, who you are, the small specific ask, and the out. Give them a week to think.

Then bring back the yes or the no. Both count.

I mean that. If you ask and get a no, you’ve done exactly what this step requires, and you have my full respect. The failure isn’t the no. The failure is a whole church full of people who agree with discipleship and never once open their mouths.

One more practical note. The holidays are coming, and they’re the easiest season of the year to do this. Everybody’s calendar is a little strange, everybody’s a little more sentimental than usual, and “Can I buy you breakfast?” is the most normal sentence in the world between Thanksgiving and New Year’s. Use it. In February that same sentence feels heavier.

Write the name down. Pick the day you’ll ask. Then ask.

Nothing starts until somebody asks. Go ask.


This article is part of The Investors, a two-year leadership track at Living Faith Church for people who are ready to pour into someone else the way someone poured into them.

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