“Your Baby is Ugly”: How to Challenge a Customer Without Telling Them They’re Wrong
Have you ever had a customer tell you how they solve their problem today and thought to yourself, “That’s crazy! I can’t believe they’re still doing that!”
Or maybe they’re clinging to some old, outdated feature, report, or process that they think they can’t live without because “that’s the way they’ve always done it”?
Meanwhile, you’re sitting there thinking:
I can’t believe they still do it like that!
Don’t they know there’s a much better way?
Why do they think yesterday’s solutions will solve today’s problems?
In other words, what you’d really like to do is tell them their baby’s ugly!
But trying to change your customer’s mind by telling them their thinking is old and outdated rarely works. Because you’re not just challenging a feature, process, or way of working. You’re challenging a deep-rooted belief they hold or a position of safety they’ve likely spent years cultivating. So if you want to transition your customers into the future, the trick is to stop correcting and start connecting.
Start by Making Them Right
Your customers will be much more open to considering a different perspective once they feel their current one has been respected. That’s why, in Sell The Way You Buy and in my training practice, one of the first steps in the powerful objection handling framework I teach is to acknowledge and soften the concern. This lowers your customers’ defenses and creates a sense of psychological safety.
For example, suppose you had a customer who was concerned that your product doesn’t offer a key feature they think is important. You might say something like:
“I totally understand why you’d want that feature. That way of doing things was very common a number of years ago and made perfect sense when you implemented your last system.”
Notice what you’re doing here. You’re not telling them their thinking is outdated. You’re supporting them emotionally by making them right.
You’re acknowledging that their thinking made perfect sense given what was true at the time.
Then Show Them What Changed
Next, you give them a reason why the thing that they believe to be true has changed:
“But about five years ago, there was a shift in the industry because of [ABC forces], which caused people to start moving away from that standard. Eventually, companies realized that doing it that way no longer made sense [because of XYZ reasons], which is why today, most of our customers [do it this way].”
Now you’ve given them a face-saving path to a new conclusion.
Another powerful way to make this transition is to invoke the authentic voice of customers who once believed or behaved the same way. This is especially useful when customers talk about solutions they’ve used in the past or competitors they’re considering today.
Instead of saying, “Here’s why your approach doesn’t work anymore,” or “Why that competitor’s solution won’t work for you,” you might say:
“We’ve worked with a number of customers who were doing exactly what you’re doing today. What they told us was that as [ABC] started to change, they began struggling with [XYZ]. That’s ultimately what caused them to rethink their approach.”
Notice that you’re not telling the customer they’re wrong. The narrative is rooted in the real experiences of customers like them, who are sharing what they learned.
That makes the message feel less like a correction and more like useful perspective from people who’ve already gone down the same road they are.
This easy one-two approach, acknowledge and soften, then evolve, helps you reposition the conversation without forcing customers to admit they were wrong in the first place.
A Story from My Startup
My third startup, Rypple, was acquired by Salesforce. Our product was a feedback, coaching, and recognition platform designed to replace the traditional annual performance review.
The HR leaders we sold to had built their entire performance management process around that once-a-year meeting. It was familiar and established. For decades, it had been the gold standard for employee feedback. So when we showed up talking about continuous feedback on a social platform, their reaction was predictable:
“We already have a review process in place. It’s not perfect, but moving away from it would be a pain.”
Now, we could have said:
“Are you kidding? ‘Not perfect’ is a bit of a stretch. That ancient process is outdated! “In fact, research on Fortune 1,000 companies found that 66% of employees were strongly dissatisfied with their performance evaluations!”
But that would have immediately put them on the defensive. Instead, we’d make them right by saying something:
“It’s true. Performance reviews were the gold standard for many years. They worked when organizations were structured more like military hierarchies and feedback flowed from the top down, often just once a year.”
Then we’d bridge to the future:
“But the world has changed a lot in the last little while. With the rise of social media, people are used to getting feedback in real time: likes, thumbs-up, DMs, swipes left and right. So at work, when they only get meaningful feedback once a year, the experience feels broken and inconsistent. In fact, exit interview data shows that lack of feedback is one of the biggest reasons people leave their companies. That’s why we’re seeing organizations move away from the traditional annual review.”
Notice what happened.
We didn’t tell them they were wrong for adopting the old approach. We showed them why the old approach was right for the old world, and why a new approach made sense for the new one.
By validating their past decision before showing them what had changed, we made them part of the evolution instead of the obstacle.
So the next time you come face-to-face with a buyer clinging to their old ways, try this approach:
- Acknowledge and Soften: “That approach made total sense at the time.”
- Contextualize the Shift: “But times have changed, and here’s how.”
- Bridge to the Present: “That’s why today, people do it differently.”
You’ll notice that when you do this, the tone of the conversation changes. Instead of defending the past, your buyer starts imagining what the future could look like.
The Bigger Picture
Like almost all objections, the ones that sound old-fashioned usually aren’t about what they appear to be on the surface. They’re about something much more human: Nobody wants to feel like they were wrong.
Your job isn’t to prove that your customer’s old way of thinking is outdated. It’s to show them that it made sense at the time, help them understand what changed, and give them a safe path forward.
Because when you handle objections this way, you’re not arguing with your customer from across the table.
You’re sitting beside them, helping them move into the future.
PS – Did you find this approach helpful and want to learn more powerful tactics for handling your customer’s toughest objections? Check out the popular Cerebral Selling Sales Academy training program.
