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Home/Biblical and Theological/The Problem with ‘Winsomeness’

The Problem with ‘Winsomeness’

Why this strategy is failing the church.

Written by Brooks Waldron | Saturday, April 11, 2026

As many others have pointed out over the past several years, in critiquing some aspects of Tim Keller’s ministry and legacy, and of the Gospel-centered movement, there are real problems with the Keller-style “winsome” approach. This is an approach that sometimes, rather rigidly, says we must always seek to be winsome in our tone and approach, as not to cause offense.

 

Here are three simple observations regarding how this is an unbiblical and unhelpful approach.

The Wrong Starting Place

To begin with, being winsome as a philosophy of ministry is fundamentally a misguided approach because its starting place is wrong. Winsomeness starts with man, instead of starting with God. In other words, this philosophy of ministry starts with an orientation toward humans by asking, “How will saying or doing this make others feel? Will it offend them? Will they be turned off to our church or to Christianity if they hear this?”

Now, while none of these questions or concerns are bad in themselves, and, in fact, Christians should seek to avoid putting any unnecessary stumbling block in the way of an unbeliever (see 2 Cor. 6:3 ), using this as a rigid guiding principle for how we do ministry or to govern what we say or do is not the right approach.

The place to begin, for both pastors and laypeople, ought to be by asking what God would have us do. In other words, how can we first be faithful to Christ and to the truth of His Word? Then we can ask how we can communicate that in the most helpful way. If we start from a place of not wanting to cause offense, we might find that we sacrifice faithfulness in the name of love for others.

 

Now I’m sure there are many who have embraced this philosophy of ministry who would deny the claim that they are seeking to be winsome in place of faithfulness to Christ. As they would point out, when Scripture itself instructs us to be thoughtful of outsiders, to avoid causing offense, etc., how can we know they are starting with man versus with God? A few questions may help to clarify this.

Is the value of being “winsome” or having the right “tone” prioritized over matters of doctrine and truth? Are we refusing to discuss things the Scriptures speak about or refusing to make application of Scripture out of fear for how it will be taken by our hearers? Would we refuse to have a fellow elder or pastor who doesn’t consistently fall in line with a particular tone, even though he meets the qualifications of an elder laid out by Paul? I would suggest that if our answers to these questions are yes, then winsomeness might just be the fear of man operating as a philosophy of ministry.

A Subjective Guide

Now, the other way you know that winsomeness is an unhelpful philosophy of ministry is that, in addition to starting with man instead of with God, it is also an inherently subjective guide rather than an objective one. Rather than starting with the objective truth of God’s Word, which informs us both on the message and the manner of our words and conduct with others, it starts with the subjective feelings of people.

For those who embrace this approach in our country today, we could ask, “Be winsome to whom?” Of course, the typical answer, rarely acknowledged, is winsome to the cultural elite or the Progressive Left. Rarely does a person with this philosophy of ministry intend to be winsome to someone on the far right, or even the mainstream right. Rather, those who hold to this strategy are generally operating under what Joe Rigney has called “the progressive gaze” — a continuous leftward glance to see what the Progressives would think of what they are saying or doing. 

Read More

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